TY  - JOUR
AU  - Braun, Sebastian
AU  - Paskaš, Svetlana
AU  - Laube, Markus
AU  - George, Sven
AU  - Hofmann, Bettina
AU  - Lönnecke, Peter
AU  - Steinhilber, Dieter
AU  - Pietzsch, Jens
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6431
AB  - The presence of inflammatory mediators in the tumor microenvironment,
such as cytokines, growth factors or eicosanoids,
indicate cancer-related inflammatory processes. Targeting these
inflammatory mediators and related signal pathways may offer
a rational strategy for the treatment of cancer. This study
focuses on the incorporation of metabolically stable, sterically
demanding, and hydrophobic dicarba-closo-dodecaboranes
(carboranes) into dual cyclooxygenase-2 (COX-2)/5-lipoxygenase
(5-LO) inhibitors that are key enzymes in the biosynthesis
of eicosanoids. The di-tert-butylphenol derivative tebufelone
represents a selective dual COX-2/5-LO inhibitor. The incorporation
of meta- or para-carborane into the tebufelone scaffold
resulted in eight carborane-based tebufelone analogs that
show no COX inhibition but 5-LO inhibitory activity in vitro. Cell
viability studies on HT29 colon adenocarcinoma cells revealed
that the observed antiproliferative effect of the para-carborane
analogs of tebufelone is enhanced by structural modifications
that include chain elongation in combination with introduction
of a methylene spacer resulting in higher anticancer activity
compared to tebufelone. Hence, this strategy proved to be a
promising approach to design potent 5-LO inhibitors with
potential application as cytostatic agents.
PB  - Wiley-VCH GmbH
T2  - ChemMedChem
T1  - Carborane-Based Tebufelone Analogs and Their Biological Evaluation In Vitro
IS  - 14
VL  - 18
DO  - 10.1002/cmdc.202300206
SP  - e202300206
ER  - 

@article{
author = "Braun, Sebastian and Paskaš, Svetlana and Laube, Markus and George, Sven and Hofmann, Bettina and Lönnecke, Peter and Steinhilber, Dieter and Pietzsch, Jens and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "The presence of inflammatory mediators in the tumor microenvironment,
such as cytokines, growth factors or eicosanoids,
indicate cancer-related inflammatory processes. Targeting these
inflammatory mediators and related signal pathways may offer
a rational strategy for the treatment of cancer. This study
focuses on the incorporation of metabolically stable, sterically
demanding, and hydrophobic dicarba-closo-dodecaboranes
(carboranes) into dual cyclooxygenase-2 (COX-2)/5-lipoxygenase
(5-LO) inhibitors that are key enzymes in the biosynthesis
of eicosanoids. The di-tert-butylphenol derivative tebufelone
represents a selective dual COX-2/5-LO inhibitor. The incorporation
of meta- or para-carborane into the tebufelone scaffold
resulted in eight carborane-based tebufelone analogs that
show no COX inhibition but 5-LO inhibitory activity in vitro. Cell
viability studies on HT29 colon adenocarcinoma cells revealed
that the observed antiproliferative effect of the para-carborane
analogs of tebufelone is enhanced by structural modifications
that include chain elongation in combination with introduction
of a methylene spacer resulting in higher anticancer activity
compared to tebufelone. Hence, this strategy proved to be a
promising approach to design potent 5-LO inhibitors with
potential application as cytostatic agents.",
publisher = "Wiley-VCH GmbH",
journal = "ChemMedChem",
title = "Carborane-Based Tebufelone Analogs and Their Biological Evaluation In Vitro",
number = "14",
volume = "18",
doi = "10.1002/cmdc.202300206",
pages = "e202300206"
}

Braun, S., Paskaš, S., Laube, M., George, S., Hofmann, B., Lönnecke, P., Steinhilber, D., Pietzsch, J., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2023). Carborane-Based Tebufelone Analogs and Their Biological Evaluation In Vitro. in ChemMedChem
Wiley-VCH GmbH., 18(14), e202300206.
https://doi.org/10.1002/cmdc.202300206

Braun S, Paskaš S, Laube M, George S, Hofmann B, Lönnecke P, Steinhilber D, Pietzsch J, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Carborane-Based Tebufelone Analogs and Their Biological Evaluation In Vitro. in ChemMedChem. 2023;18(14):e202300206.
doi:10.1002/cmdc.202300206 .

Braun, Sebastian, Paskaš, Svetlana, Laube, Markus, George, Sven, Hofmann, Bettina, Lönnecke, Peter, Steinhilber, Dieter, Pietzsch, Jens, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "Carborane-Based Tebufelone Analogs and Their Biological Evaluation In Vitro" in ChemMedChem, 18, no. 14 (2023):e202300206,
https://doi.org/10.1002/cmdc.202300206 . .

TY  - JOUR
AU  - Kazimir, Aleksandr
AU  - Schwarze, Benedikt
AU  - Lönnecke, Peter
AU  - Jelača, Sanja
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6266
AB  - For decades, tamoxifen-based hormone therapy has effectively addressed oestrogen receptor positive (ER+) luminal A breast cancer. Nonetheless, the emergence of tamoxifen resistance required innovative
approaches, leading to hybrid metallodrugs with several therapeutic effects besides the inhibition of oestrogen receptor α (ERα). Drawing inspiration from tamoxifen metabolite structures (4-hydroxytamoxifen
and 4,4′-dihyroxytamoxifen), a phenyl ring was replaced by a bidentate 2,2′-bipyridine donor moiety to give
4-[1,1-bis(4-methoxyphenyl)but-1-en-2-yl]-2,2′-bipyridine (L), enabling coordination of bioactive transition
metal compounds such as copper(II) dichloride, yielding [CuCl(μ-Cl)(L-κ2N,N′)]2 (1). Notably, copper(II)
complex 1 exhibited remarkable activity within the low micromolar concentration range against ER+ human glioblastoma U251, as well as breast carcinomas MDA-MB-361 and MCF-7, surpassing the efficacy of previously reported palladium(II) and platinum(II) dichloride analogs against these cell lines. The pronounced efficacy of complex 1 against triple-negative MDA-MB-231 cells highlights its potential multitherapeutic approach, evident through induction of apoptosis and antioxidant activity. This study evaluates the potential of copper–tamoxifen hybrid complex 1 as a potent therapeutic candidate, highlighting its diverse mechanism of action against challenging breast cancer subtypes.
PB  - Royal Society of Chemistry
T2  - RSC Medicinal Chemistry
T1  - Exploring the potential of tamoxifen-based copper(II) dichloride in breast cancer therapy
DO  - 10.1039/d3md00344b
ER  - 

@article{
author = "Kazimir, Aleksandr and Schwarze, Benedikt and Lönnecke, Peter and Jelača, Sanja and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "For decades, tamoxifen-based hormone therapy has effectively addressed oestrogen receptor positive (ER+) luminal A breast cancer. Nonetheless, the emergence of tamoxifen resistance required innovative
approaches, leading to hybrid metallodrugs with several therapeutic effects besides the inhibition of oestrogen receptor α (ERα). Drawing inspiration from tamoxifen metabolite structures (4-hydroxytamoxifen
and 4,4′-dihyroxytamoxifen), a phenyl ring was replaced by a bidentate 2,2′-bipyridine donor moiety to give
4-[1,1-bis(4-methoxyphenyl)but-1-en-2-yl]-2,2′-bipyridine (L), enabling coordination of bioactive transition
metal compounds such as copper(II) dichloride, yielding [CuCl(μ-Cl)(L-κ2N,N′)]2 (1). Notably, copper(II)
complex 1 exhibited remarkable activity within the low micromolar concentration range against ER+ human glioblastoma U251, as well as breast carcinomas MDA-MB-361 and MCF-7, surpassing the efficacy of previously reported palladium(II) and platinum(II) dichloride analogs against these cell lines. The pronounced efficacy of complex 1 against triple-negative MDA-MB-231 cells highlights its potential multitherapeutic approach, evident through induction of apoptosis and antioxidant activity. This study evaluates the potential of copper–tamoxifen hybrid complex 1 as a potent therapeutic candidate, highlighting its diverse mechanism of action against challenging breast cancer subtypes.",
publisher = "Royal Society of Chemistry",
journal = "RSC Medicinal Chemistry",
title = "Exploring the potential of tamoxifen-based copper(II) dichloride in breast cancer therapy",
doi = "10.1039/d3md00344b"
}

Kazimir, A., Schwarze, B., Lönnecke, P., Jelača, S., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2023). Exploring the potential of tamoxifen-based copper(II) dichloride in breast cancer therapy. in RSC Medicinal Chemistry
Royal Society of Chemistry..
https://doi.org/10.1039/d3md00344b

Kazimir A, Schwarze B, Lönnecke P, Jelača S, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Exploring the potential of tamoxifen-based copper(II) dichloride in breast cancer therapy. in RSC Medicinal Chemistry. 2023;.
doi:10.1039/d3md00344b .

Kazimir, Aleksandr, Schwarze, Benedikt, Lönnecke, Peter, Jelača, Sanja, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "Exploring the potential of tamoxifen-based copper(II) dichloride in breast cancer therapy" in RSC Medicinal Chemistry (2023),
https://doi.org/10.1039/d3md00344b . .

TY  - JOUR
AU  - Richter, Stefan
AU  - Lönnecke, Peter
AU  - Bovan, Dijana
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Kaluđerović, Goran N.
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6265
AB  - The coordination behavior of three ligand precursors 2-[(2-pyridinylmethyl)amino]acetic acid hydrochloride, 4-[(2-pyridinylmethyl)amino]benzoic acid hydrochloride and 4-{[2-(pyridin-2-ylmethylamino)ethylamino]methyl}benzoic acid hydrochloride, HL1∙HCl–HL3∙HCl, respectively, in copper(II) complexes is described. The complexes were characterized by elemental analysis, ESI mass spectrometry and IR spectroscopy, as well as X-ray structural analysis. The reaction of copper(II) with HL1∙HCl in methanol afforded the polymeric complex [{Cu(µ-Cl)2(MeL1-κ2N,N’)}n] (1) featuring the methyl ester of L1 (MeL1). With HL2∙HCl or HL3∙HCl, the dimeric complex [{CuCl(µ-Cl)(HL2-κ2N,N’)}2] (2) or the mononuclear complex [CuCl2(HL3-κ3N,N’,N’’)] (3) were obtained. All complexes exhibited square-pyramidal geometries. In 1, polymeric chains are formed through bridging chlorido ligands without typical hydrogen bonding interaction. Contrarily, the COOH group in 2 is participating in the formation of intermolecular hydrogen bonding forming a supramolecular structure. In 3, intermolecular hydrogen bonding (Cl…O) leads to a 1-D polymeric structure. The copper(II) complex 2 diminished viability of human 8505C, MCF-7, 518A2 and SW480 cell lines. The tumoricidal effect of 2 was realized mainly through caspase-mediated apoptosis.
PB  - Belgrade: Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives
DO  - 10.2298/JSC230818072R
ER  - 

@article{
author = "Richter, Stefan and Lönnecke, Peter and Bovan, Dijana and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Kaluđerović, Goran N. and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "The coordination behavior of three ligand precursors 2-[(2-pyridinylmethyl)amino]acetic acid hydrochloride, 4-[(2-pyridinylmethyl)amino]benzoic acid hydrochloride and 4-{[2-(pyridin-2-ylmethylamino)ethylamino]methyl}benzoic acid hydrochloride, HL1∙HCl–HL3∙HCl, respectively, in copper(II) complexes is described. The complexes were characterized by elemental analysis, ESI mass spectrometry and IR spectroscopy, as well as X-ray structural analysis. The reaction of copper(II) with HL1∙HCl in methanol afforded the polymeric complex [{Cu(µ-Cl)2(MeL1-κ2N,N’)}n] (1) featuring the methyl ester of L1 (MeL1). With HL2∙HCl or HL3∙HCl, the dimeric complex [{CuCl(µ-Cl)(HL2-κ2N,N’)}2] (2) or the mononuclear complex [CuCl2(HL3-κ3N,N’,N’’)] (3) were obtained. All complexes exhibited square-pyramidal geometries. In 1, polymeric chains are formed through bridging chlorido ligands without typical hydrogen bonding interaction. Contrarily, the COOH group in 2 is participating in the formation of intermolecular hydrogen bonding forming a supramolecular structure. In 3, intermolecular hydrogen bonding (Cl…O) leads to a 1-D polymeric structure. The copper(II) complex 2 diminished viability of human 8505C, MCF-7, 518A2 and SW480 cell lines. The tumoricidal effect of 2 was realized mainly through caspase-mediated apoptosis.",
publisher = "Belgrade: Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives",
doi = "10.2298/JSC230818072R"
}

Richter, S., Lönnecke, P., Bovan, D., Mijatović, S., Maksimović-Ivanić, D., Kaluđerović, G. N.,& Hey-Hawkins, E.. (2023). Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives. in Journal of the Serbian Chemical Society
Belgrade: Serbian Chemical Society..
https://doi.org/10.2298/JSC230818072R

Richter S, Lönnecke P, Bovan D, Mijatović S, Maksimović-Ivanić D, Kaluđerović GN, Hey-Hawkins E. Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives. in Journal of the Serbian Chemical Society. 2023;.
doi:10.2298/JSC230818072R .

Richter, Stefan, Lönnecke, Peter, Bovan, Dijana, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Kaluđerović, Goran N., Hey-Hawkins, Evamarie, "Square-pyramidal mononuclear, dinuclear and polymeric copper(II) complexes with (2-pyridinylmethyl)amino derivatives" in Journal of the Serbian Chemical Society (2023),
https://doi.org/10.2298/JSC230818072R . .

TY  - JOUR
AU  - Braun, Sebastian
AU  - Jelača, Sanja
AU  - Laube, Marcus
AU  - George, Sven
AU  - Hofmann, Bettina
AU  - Lönnecke, Peter
AU  - Steinhilber, Dieter
AU  - Pietzsch, Jens
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5823
AB  - Targeting inflammatory mediators and related signaling pathways may offer a rational strategy for the treatment of cancer. The incorporation of metabolically stable, sterically demanding, and hydrophobic carboranes in dual cycloxygenase-2 (COX-2)/5-lipoxygenase (5-LO) inhibitors that are key enzymes in the biosynthesis of eicosanoids is a promising approach. The di-tert-butylphenol derivatives R-830, S-2474, KME-4, and E-5110 represent potent dual COX-2/5-LO inhibitors. The incorporation of p-carborane and further substitution of the p-position resulted in four carborane-based di-tert-butylphenol analogs that showed no or weak COX inhibition but high 5-LO inhibitory activities in vitro. Cell viability studies on five human cancer cell lines revealed that the p-carborane analogs R-830-Cb, S-2474-Cb, KME-4-Cb, and E-5110-Cb exhibited lower anticancer activity compared to the related di-tert-butylphenols. Interestingly, R-830-Cb did not affect the viability of primary cells and suppressed HCT116 cell proliferation more potently than its carbon-based R-830 counterpart. Considering all the advantages of boron cluster incorporation for enhancement of drug biostability, selectivity, and availability of drugs, R-830-Cb can be tested in further mechanistic and in vivo studies.
PB  - Basel: MDPI
T2  - Molecules
T1  - Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs
IS  - 11
VL  - 28
DO  - 10.3390/molecules28114547
SP  - 4547
ER  - 

@article{
author = "Braun, Sebastian and Jelača, Sanja and Laube, Marcus and George, Sven and Hofmann, Bettina and Lönnecke, Peter and Steinhilber, Dieter and Pietzsch, Jens and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "Targeting inflammatory mediators and related signaling pathways may offer a rational strategy for the treatment of cancer. The incorporation of metabolically stable, sterically demanding, and hydrophobic carboranes in dual cycloxygenase-2 (COX-2)/5-lipoxygenase (5-LO) inhibitors that are key enzymes in the biosynthesis of eicosanoids is a promising approach. The di-tert-butylphenol derivatives R-830, S-2474, KME-4, and E-5110 represent potent dual COX-2/5-LO inhibitors. The incorporation of p-carborane and further substitution of the p-position resulted in four carborane-based di-tert-butylphenol analogs that showed no or weak COX inhibition but high 5-LO inhibitory activities in vitro. Cell viability studies on five human cancer cell lines revealed that the p-carborane analogs R-830-Cb, S-2474-Cb, KME-4-Cb, and E-5110-Cb exhibited lower anticancer activity compared to the related di-tert-butylphenols. Interestingly, R-830-Cb did not affect the viability of primary cells and suppressed HCT116 cell proliferation more potently than its carbon-based R-830 counterpart. Considering all the advantages of boron cluster incorporation for enhancement of drug biostability, selectivity, and availability of drugs, R-830-Cb can be tested in further mechanistic and in vivo studies.",
publisher = "Basel: MDPI",
journal = "Molecules",
title = "Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs",
number = "11",
volume = "28",
doi = "10.3390/molecules28114547",
pages = "4547"
}

Braun, S., Jelača, S., Laube, M., George, S., Hofmann, B., Lönnecke, P., Steinhilber, D., Pietzsch, J., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2023). Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs. in Molecules
Basel: MDPI., 28(11), 4547.
https://doi.org/10.3390/molecules28114547

Braun S, Jelača S, Laube M, George S, Hofmann B, Lönnecke P, Steinhilber D, Pietzsch J, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs. in Molecules. 2023;28(11):4547.
doi:10.3390/molecules28114547 .

Braun, Sebastian, Jelača, Sanja, Laube, Marcus, George, Sven, Hofmann, Bettina, Lönnecke, Peter, Steinhilber, Dieter, Pietzsch, Jens, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "Synthesis and In Vitro Biological Evaluation of p-Carborane-Based Di-tert-butylphenol Analogs" in Molecules, 28, no. 11 (2023):4547,
https://doi.org/10.3390/molecules28114547 . .

TY  - JOUR
AU  - Useini, Liridona
AU  - Komazec, Teodora
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Schädlich, Jonas
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5826
AB  - Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most widely used
therapeutics against pain, fever, and inflammation; additionally, antitumor
properties are reported. NSAIDs reduce the synthesis of prostaglandins by
inhibiting the cyclooxygenase (COX) isoforms COX-1 and COX-2. As
nonselective inhibition is associated with off-target effects, strategies to
achieve selectivity for the clinically preferred isoform COX-2 are of high
interest. The modification of NSAIDs using carborane clusters as phenyl
mimetics is reported to alter the selectivity profile through size exclusion.
Inspired by these findings, isonimesulide and its carborane derivatives are
prepared. The biological screening shows that the carborane containing
compounds exhibit a stronger antitumor potential compared to nimesulide
and isonimesulide. Furthermore, the replacement of the phenyl ring of
isonimesulide with a carborane moiety resulted in a shift of the COX activity
from nonactive to COX-active compounds.
PB  - Hoboken: Wiley
T2  - Advanced Therapeutics
T1  - Isonimesulide and Its Carborane Analogues as Isoform-Selective COX Inhibitors and Antitumor Agents
DO  - 10.1002/adtp.202300117
SP  - 2300117
ER  - 

@article{
author = "Useini, Liridona and Komazec, Teodora and Laube, Markus and Lönnecke, Peter and Schädlich, Jonas and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most widely used
therapeutics against pain, fever, and inflammation; additionally, antitumor
properties are reported. NSAIDs reduce the synthesis of prostaglandins by
inhibiting the cyclooxygenase (COX) isoforms COX-1 and COX-2. As
nonselective inhibition is associated with off-target effects, strategies to
achieve selectivity for the clinically preferred isoform COX-2 are of high
interest. The modification of NSAIDs using carborane clusters as phenyl
mimetics is reported to alter the selectivity profile through size exclusion.
Inspired by these findings, isonimesulide and its carborane derivatives are
prepared. The biological screening shows that the carborane containing
compounds exhibit a stronger antitumor potential compared to nimesulide
and isonimesulide. Furthermore, the replacement of the phenyl ring of
isonimesulide with a carborane moiety resulted in a shift of the COX activity
from nonactive to COX-active compounds.",
publisher = "Hoboken: Wiley",
journal = "Advanced Therapeutics",
title = "Isonimesulide and Its Carborane Analogues as Isoform-Selective COX Inhibitors and Antitumor Agents",
doi = "10.1002/adtp.202300117",
pages = "2300117"
}

Useini, L., Komazec, T., Laube, M., Lönnecke, P., Schädlich, J., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey-Hawkins, E.. (2023). Isonimesulide and Its Carborane Analogues as Isoform-Selective COX Inhibitors and Antitumor Agents. in Advanced Therapeutics
Hoboken: Wiley., 2300117.
https://doi.org/10.1002/adtp.202300117

Useini L, Komazec T, Laube M, Lönnecke P, Schädlich J, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey-Hawkins E. Isonimesulide and Its Carborane Analogues as Isoform-Selective COX Inhibitors and Antitumor Agents. in Advanced Therapeutics. 2023;:2300117.
doi:10.1002/adtp.202300117 .

Useini, Liridona, Komazec, Teodora, Laube, Markus, Lönnecke, Peter, Schädlich, Jonas, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey-Hawkins, Evamarie, "Isonimesulide and Its Carborane Analogues as Isoform-Selective COX Inhibitors and Antitumor Agents" in Advanced Therapeutics (2023):2300117,
https://doi.org/10.1002/adtp.202300117 . .

TY  - JOUR
AU  - Useini, Liridona
AU  - Mojić, Marija
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey‐Hawkins, Evamarie
PY  - 2023
UR  - https://onlinelibrary.wiley.com/doi/10.1002/cmdc.202200583
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5432
AB  - Fenoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) against rheumatoid arthritis, degenerative joint disease, ankylosing spondylitis and gout. Like other NSAIDs, fenoprofen inhibits the synthesis of prostaglandins by blocking both cyclooxygenase (COX) isoforms, COX-1 the “house-keeping” enzyme and COX-2 the induced isoform from pathological stimuli. Unselective inhibition of both COX isoforms results in many side effects, but off-target effects have also been reported. The steric modifications of the drugs could afford the desired COX-2 selectivity. Furthermore, NSAIDs have shown promising cytotoxic properties. The structural modification of fenoprofen using bulky dicarba-closo-dodecaborane(12) (carborane) clusters and the biological evaluation of the carborane analogues for COX inhibition and antitumor potential showed that the carborane analogues exhibit stronger antitumor potential compared to their respective aryl-based compounds.
PB  - John Wiley and Sons Ltd
T2  - ChemMedChem
T1  - Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity
IS  - 5
VL  - 18
DO  - 10.1002/cmdc.202200583
SP  - e202200583
ER  - 

@article{
author = "Useini, Liridona and Mojić, Marija and Laube, Markus and Lönnecke, Peter and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey‐Hawkins, Evamarie",
year = "2023",
abstract = "Fenoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) against rheumatoid arthritis, degenerative joint disease, ankylosing spondylitis and gout. Like other NSAIDs, fenoprofen inhibits the synthesis of prostaglandins by blocking both cyclooxygenase (COX) isoforms, COX-1 the “house-keeping” enzyme and COX-2 the induced isoform from pathological stimuli. Unselective inhibition of both COX isoforms results in many side effects, but off-target effects have also been reported. The steric modifications of the drugs could afford the desired COX-2 selectivity. Furthermore, NSAIDs have shown promising cytotoxic properties. The structural modification of fenoprofen using bulky dicarba-closo-dodecaborane(12) (carborane) clusters and the biological evaluation of the carborane analogues for COX inhibition and antitumor potential showed that the carborane analogues exhibit stronger antitumor potential compared to their respective aryl-based compounds.",
publisher = "John Wiley and Sons Ltd",
journal = "ChemMedChem",
title = "Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity",
number = "5",
volume = "18",
doi = "10.1002/cmdc.202200583",
pages = "e202200583"
}

Useini, L., Mojić, M., Laube, M., Lönnecke, P., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey‐Hawkins, E.. (2023). Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity. in ChemMedChem
John Wiley and Sons Ltd., 18(5), e202200583.
https://doi.org/10.1002/cmdc.202200583

Useini L, Mojić M, Laube M, Lönnecke P, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey‐Hawkins E. Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity. in ChemMedChem. 2023;18(5):e202200583.
doi:10.1002/cmdc.202200583 .

Useini, Liridona, Mojić, Marija, Laube, Markus, Lönnecke, Peter, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey‐Hawkins, Evamarie, "Carborane Analogues of Fenoprofen Exhibit Improved Antitumor Activity" in ChemMedChem, 18, no. 5 (2023):e202200583,
https://doi.org/10.1002/cmdc.202200583 . .

TY  - JOUR
AU  - Kazimir, Aleksandr
AU  - Schwarze, Benedikt
AU  - Lönnecke, Peter
AU  - Jelača, Sanja
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2023
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5469
AB  - The luminal A-subtype of breast cancer, where the oestrogen receptor α (ERα) is overexpressed, is the most frequent one. The prodrug tamoxifen (1) is the clinically used agent, inhibiting the ERα activity via the formation of several active metabolites, such as 4-hydroxytamoxifen (2) or 4,4′-dihydroxytamoxifen (3). In this study, we present the tamoxifen derivative 4-[1,1-bis(4-methoxyphenyl)but-1-en-2-yl]-2,2′-bipyridine (4), which was combined with platinum or palladium dichloride, the former a well-known scaffold in anticancer treatment, to give [PtCl2(4-κ2N,N′)] (5) or [PdCl2(4-κ2N,N′] (6). To prevent fast exchange of weakly coordinating chlorido ligands in aqueous solution, a bulky, highly stable and hydrophobic nido-carborate(−2) ([C2B9H11]2−) was incorporated. The resulting complexes [3-(4-κ2N,N′)-3,1,2-PtC2B9H11] (7) and [3-(4-κ2N,N′)-3,1,2-PdC2B9H11] (8) exhibit a dramatic change in electronic and biological properties compared to 5 and 6. Thus, 8 is highly selective for triple-negative MDA-MB-231 cells (IC50 = 3.7 μM, MTT test), while 7 is completely inactive against this cell line. The observed cytotoxicity of compounds 4–6 and 8 against this triple-negative cell line suggests off-target mechanisms rather than only ERα inhibition, for which these compounds were originally designed. Spectroscopic properties and electronic structures of the metal complexes were investigated for possible explanations of the biological activities.
PB  - Basel: MDPI
T2  - Pharmaceutics
T1  - Metallodrugs against Breast Cancer: Combining the Tamoxifen Vector with Platinum(II) and Palladium(II) Complexes
IS  - 2
VL  - 15
DO  - 10.3390/pharmaceutics15020682
SP  - 682
ER  - 

@article{
author = "Kazimir, Aleksandr and Schwarze, Benedikt and Lönnecke, Peter and Jelača, Sanja and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2023",
abstract = "The luminal A-subtype of breast cancer, where the oestrogen receptor α (ERα) is overexpressed, is the most frequent one. The prodrug tamoxifen (1) is the clinically used agent, inhibiting the ERα activity via the formation of several active metabolites, such as 4-hydroxytamoxifen (2) or 4,4′-dihydroxytamoxifen (3). In this study, we present the tamoxifen derivative 4-[1,1-bis(4-methoxyphenyl)but-1-en-2-yl]-2,2′-bipyridine (4), which was combined with platinum or palladium dichloride, the former a well-known scaffold in anticancer treatment, to give [PtCl2(4-κ2N,N′)] (5) or [PdCl2(4-κ2N,N′] (6). To prevent fast exchange of weakly coordinating chlorido ligands in aqueous solution, a bulky, highly stable and hydrophobic nido-carborate(−2) ([C2B9H11]2−) was incorporated. The resulting complexes [3-(4-κ2N,N′)-3,1,2-PtC2B9H11] (7) and [3-(4-κ2N,N′)-3,1,2-PdC2B9H11] (8) exhibit a dramatic change in electronic and biological properties compared to 5 and 6. Thus, 8 is highly selective for triple-negative MDA-MB-231 cells (IC50 = 3.7 μM, MTT test), while 7 is completely inactive against this cell line. The observed cytotoxicity of compounds 4–6 and 8 against this triple-negative cell line suggests off-target mechanisms rather than only ERα inhibition, for which these compounds were originally designed. Spectroscopic properties and electronic structures of the metal complexes were investigated for possible explanations of the biological activities.",
publisher = "Basel: MDPI",
journal = "Pharmaceutics",
title = "Metallodrugs against Breast Cancer: Combining the Tamoxifen Vector with Platinum(II) and Palladium(II) Complexes",
number = "2",
volume = "15",
doi = "10.3390/pharmaceutics15020682",
pages = "682"
}

Kazimir, A., Schwarze, B., Lönnecke, P., Jelača, S., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2023). Metallodrugs against Breast Cancer: Combining the Tamoxifen Vector with Platinum(II) and Palladium(II) Complexes. in Pharmaceutics
Basel: MDPI., 15(2), 682.
https://doi.org/10.3390/pharmaceutics15020682

Kazimir A, Schwarze B, Lönnecke P, Jelača S, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Metallodrugs against Breast Cancer: Combining the Tamoxifen Vector with Platinum(II) and Palladium(II) Complexes. in Pharmaceutics. 2023;15(2):682.
doi:10.3390/pharmaceutics15020682 .

Kazimir, Aleksandr, Schwarze, Benedikt, Lönnecke, Peter, Jelača, Sanja, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "Metallodrugs against Breast Cancer: Combining the Tamoxifen Vector with Platinum(II) and Palladium(II) Complexes" in Pharmaceutics, 15, no. 2 (2023):682,
https://doi.org/10.3390/pharmaceutics15020682 . .

TY  - JOUR
AU  - Braun, Sebastian
AU  - Paskaš, Svetlana
AU  - Laube, Markus
AU  - George, Sven
AU  - Hofmann, Bettina
AU  - Lönnecke, Peter
AU  - Steinhilber, Dieter
AU  - Pietzsch, Jens
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey‐Hawkins, Evamarie
PY  - 2023
UR  - https://onlinelibrary.wiley.com/doi/10.1002/adtp.202200252
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5384
AB  - The selective inhibition of enzymes that catalyze the conversion of arachidonic acid to inflammatory eicosanoids represents a promising approach for cancer therapy. This study, therefore, focuses on the incorporation of metabolically stable, sterically demanding, and hydrophobic carboranes into existing dual cycloxygenase-2 (COX-2)/5-lipoxygenase (5-LO) inhibitors that are key enzymes in the biosynthesis of eicosanoids. Here, the first carborane-containing dual COX-2/5-LO inhibitors derived from RWJ-63556 are presented. The replacement of the fluorophenyl moiety by meta- or para-carborane resulted in five carborane-containing derivatives 3, 6, 9, 13, and 17 that show high inhibitory activities toward COX-2 and 5-LO in vitro. Cell viability studies on the A375 melanoma cell line revealed that meta-carborane derivative 3 shows higher anticancer activity compared to RWJ-63556 based on accumulation of lipid droplets in the cells due to blockage of the COX-2 and 5-LO pathways, indicating a promising approach for the design of potent dual COX-2/5-LO inhibitors.
T2  - Advanced Therapeutics
T1  - In Vitro Cytostatic Effect on Tumor Cells by Carborane‐Based Dual Cyclooxygenase‐2 and 5‐Lipoxygenase Inhibitors
DO  - 10.1002/adtp.202200252
SP  - 2200252
ER  - 

@article{
author = "Braun, Sebastian and Paskaš, Svetlana and Laube, Markus and George, Sven and Hofmann, Bettina and Lönnecke, Peter and Steinhilber, Dieter and Pietzsch, Jens and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey‐Hawkins, Evamarie",
year = "2023",
abstract = "The selective inhibition of enzymes that catalyze the conversion of arachidonic acid to inflammatory eicosanoids represents a promising approach for cancer therapy. This study, therefore, focuses on the incorporation of metabolically stable, sterically demanding, and hydrophobic carboranes into existing dual cycloxygenase-2 (COX-2)/5-lipoxygenase (5-LO) inhibitors that are key enzymes in the biosynthesis of eicosanoids. Here, the first carborane-containing dual COX-2/5-LO inhibitors derived from RWJ-63556 are presented. The replacement of the fluorophenyl moiety by meta- or para-carborane resulted in five carborane-containing derivatives 3, 6, 9, 13, and 17 that show high inhibitory activities toward COX-2 and 5-LO in vitro. Cell viability studies on the A375 melanoma cell line revealed that meta-carborane derivative 3 shows higher anticancer activity compared to RWJ-63556 based on accumulation of lipid droplets in the cells due to blockage of the COX-2 and 5-LO pathways, indicating a promising approach for the design of potent dual COX-2/5-LO inhibitors.",
journal = "Advanced Therapeutics",
title = "In Vitro Cytostatic Effect on Tumor Cells by Carborane‐Based Dual Cyclooxygenase‐2 and 5‐Lipoxygenase Inhibitors",
doi = "10.1002/adtp.202200252",
pages = "2200252"
}

Braun, S., Paskaš, S., Laube, M., George, S., Hofmann, B., Lönnecke, P., Steinhilber, D., Pietzsch, J., Mijatović, S., Maksimović-Ivanić, D.,& Hey‐Hawkins, E.. (2023). In Vitro Cytostatic Effect on Tumor Cells by Carborane‐Based Dual Cyclooxygenase‐2 and 5‐Lipoxygenase Inhibitors. in Advanced Therapeutics, 2200252.
https://doi.org/10.1002/adtp.202200252

Braun S, Paskaš S, Laube M, George S, Hofmann B, Lönnecke P, Steinhilber D, Pietzsch J, Mijatović S, Maksimović-Ivanić D, Hey‐Hawkins E. In Vitro Cytostatic Effect on Tumor Cells by Carborane‐Based Dual Cyclooxygenase‐2 and 5‐Lipoxygenase Inhibitors. in Advanced Therapeutics. 2023;:2200252.
doi:10.1002/adtp.202200252 .

Braun, Sebastian, Paskaš, Svetlana, Laube, Markus, George, Sven, Hofmann, Bettina, Lönnecke, Peter, Steinhilber, Dieter, Pietzsch, Jens, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey‐Hawkins, Evamarie, "In Vitro Cytostatic Effect on Tumor Cells by Carborane‐Based Dual Cyclooxygenase‐2 and 5‐Lipoxygenase Inhibitors" in Advanced Therapeutics (2023):2200252,
https://doi.org/10.1002/adtp.202200252 . .

TY  - JOUR
AU  - Useini, Liridona
AU  - Mojić, Marija
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Dahme, Jonas
AU  - Sárosi, Menyhárt B.
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey-Hawkins, Evamarie
PY  - 2022
UR  - https://pubs.acs.org/doi/10.1021/acsomega.2c01523
UR  - http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=PMC9301635
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/5075
AB  - Mefenamic acid represents a widely used nonsteroidal anti-inflammatory drug (NSAID) to treat the pain of postoperative surgery and heavy menstrual bleeding. Like other NSAIDs, mefenamic acid inhibits the synthesis of prostaglandins by nonselectively blocking cyclooxygenase (COX) isoforms COX-1 and COX-2. For the improved selectivity of the drug and, therefore, reduced related side effects, the carborane analogues of mefenamic acid were evaluated. The ortho-, meta-, and para-carborane derivatives were synthesized in three steps: halogenation of the respective cluster, followed by a Pd-catalyzed B-N coupling and hydrolysis of the nitrile derivatives under acidic conditions. The COX inhibitory activity and cytotoxicity for different cancer cell lines revealed that the carborane analogues have stronger antitumor potential compared to their parent organic compound.
PB  - Washington: American Chemical Society
T2  - ACS Omega
T1  - Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation.
IS  - 28
VL  - 7
DO  - 10.1021/acsomega.2c01523
SP  - 24282
EP  - 24291
ER  - 

@article{
author = "Useini, Liridona and Mojić, Marija and Laube, Markus and Lönnecke, Peter and Dahme, Jonas and Sárosi, Menyhárt B. and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey-Hawkins, Evamarie",
year = "2022",
abstract = "Mefenamic acid represents a widely used nonsteroidal anti-inflammatory drug (NSAID) to treat the pain of postoperative surgery and heavy menstrual bleeding. Like other NSAIDs, mefenamic acid inhibits the synthesis of prostaglandins by nonselectively blocking cyclooxygenase (COX) isoforms COX-1 and COX-2. For the improved selectivity of the drug and, therefore, reduced related side effects, the carborane analogues of mefenamic acid were evaluated. The ortho-, meta-, and para-carborane derivatives were synthesized in three steps: halogenation of the respective cluster, followed by a Pd-catalyzed B-N coupling and hydrolysis of the nitrile derivatives under acidic conditions. The COX inhibitory activity and cytotoxicity for different cancer cell lines revealed that the carborane analogues have stronger antitumor potential compared to their parent organic compound.",
publisher = "Washington: American Chemical Society",
journal = "ACS Omega",
title = "Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation.",
number = "28",
volume = "7",
doi = "10.1021/acsomega.2c01523",
pages = "24282-24291"
}

Useini, L., Mojić, M., Laube, M., Lönnecke, P., Dahme, J., Sárosi, M. B., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey-Hawkins, E.. (2022). Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation.. in ACS Omega
Washington: American Chemical Society., 7(28), 24282-24291.
https://doi.org/10.1021/acsomega.2c01523

Useini L, Mojić M, Laube M, Lönnecke P, Dahme J, Sárosi MB, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey-Hawkins E. Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation.. in ACS Omega. 2022;7(28):24282-24291.
doi:10.1021/acsomega.2c01523 .

Useini, Liridona, Mojić, Marija, Laube, Markus, Lönnecke, Peter, Dahme, Jonas, Sárosi, Menyhárt B., Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey-Hawkins, Evamarie, "Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation." in ACS Omega, 7, no. 28 (2022):24282-24291,
https://doi.org/10.1021/acsomega.2c01523 . .

TY  - JOUR
AU  - Buzharevski, Antonio
AU  - Paskaš, Svetlana
AU  - Sárosi, Menyhárt-Botond
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Neumann, Wilma
AU  - Murganić, Blagoje
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey-Hawkins, Evamarie
PY  - 2020
UR  - http://www.ncbi.nlm.nih.gov/pubmed/32179835
UR  - http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=PMC7076013
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3640
AB  - Owing to the involvement of cyclooxygenase-2 (COX-2) in carcinogenesis, COX-2-selective inhibitors are increasingly studied for their potential cytotoxic properties. Moreover, the incorporation of carboranes in structures of established anti-inflammatory drugs can improve the potency and metabolic stability of the inhibitors. Herein, we report the synthesis of carborane-containing derivatives of rofecoxib that display remarkable cytotoxic or cytostatic activity in the micromolar range with excellent selectivity for melanoma and colon cancer cell lines over normal cells. Furthermore, it was shown that the carborane-modified derivatives of rofecoxib showed different modes of action that were dependent on the cell type.
T2  - Scientific Reports
T1  - Carboranyl Derivatives of Rofecoxib with Cytostatic Activity against Human Melanoma and Colon Cancer Cells.
IS  - 1
VL  - 10
DO  - 10.1038/s41598-020-59059-3
SP  - 4827
ER  - 

@article{
author = "Buzharevski, Antonio and Paskaš, Svetlana and Sárosi, Menyhárt-Botond and Laube, Markus and Lönnecke, Peter and Neumann, Wilma and Murganić, Blagoje and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey-Hawkins, Evamarie",
year = "2020",
abstract = "Owing to the involvement of cyclooxygenase-2 (COX-2) in carcinogenesis, COX-2-selective inhibitors are increasingly studied for their potential cytotoxic properties. Moreover, the incorporation of carboranes in structures of established anti-inflammatory drugs can improve the potency and metabolic stability of the inhibitors. Herein, we report the synthesis of carborane-containing derivatives of rofecoxib that display remarkable cytotoxic or cytostatic activity in the micromolar range with excellent selectivity for melanoma and colon cancer cell lines over normal cells. Furthermore, it was shown that the carborane-modified derivatives of rofecoxib showed different modes of action that were dependent on the cell type.",
journal = "Scientific Reports",
title = "Carboranyl Derivatives of Rofecoxib with Cytostatic Activity against Human Melanoma and Colon Cancer Cells.",
number = "1",
volume = "10",
doi = "10.1038/s41598-020-59059-3",
pages = "4827"
}

Buzharevski, A., Paskaš, S., Sárosi, M., Laube, M., Lönnecke, P., Neumann, W., Murganić, B., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey-Hawkins, E.. (2020). Carboranyl Derivatives of Rofecoxib with Cytostatic Activity against Human Melanoma and Colon Cancer Cells.. in Scientific Reports, 10(1), 4827.
https://doi.org/10.1038/s41598-020-59059-3

Buzharevski A, Paskaš S, Sárosi M, Laube M, Lönnecke P, Neumann W, Murganić B, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey-Hawkins E. Carboranyl Derivatives of Rofecoxib with Cytostatic Activity against Human Melanoma and Colon Cancer Cells.. in Scientific Reports. 2020;10(1):4827.
doi:10.1038/s41598-020-59059-3 .

Buzharevski, Antonio, Paskaš, Svetlana, Sárosi, Menyhárt-Botond, Laube, Markus, Lönnecke, Peter, Neumann, Wilma, Murganić, Blagoje, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey-Hawkins, Evamarie, "Carboranyl Derivatives of Rofecoxib with Cytostatic Activity against Human Melanoma and Colon Cancer Cells." in Scientific Reports, 10, no. 1 (2020):4827,
https://doi.org/10.1038/s41598-020-59059-3 . .

TY  - JOUR
AU  - Buzharevski, Antonio
AU  - Paskaš, Svetlana
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Neumann, Wilma
AU  - Murganić, Blagoje
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey-Hawkins, Evamarie
PY  - 2019
UR  - http://pubs.acs.org/doi/10.1021/acsomega.9b00412
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3366
AB  - Ketoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) that also exhibits cytotoxic activity against various cancers. This makes ketoprofen an attractive structural lead for the development of new NSAIDs and cytotoxic agents. Recently, the incorporation of carboranes as phenyl mimetics in structures of established drugs has emerged as an attractive strategy in drug design. Herein, we report the synthesis and evaluation of four novel carborane-containing derivatives of ketoprofen, two of which are prodrug esters with an nitric oxide-releasing moiety. One of these prodrug esters exhibited high cytostatic activity against melanoma and colon cancer cell lines. The most pronounced activity was found in cell lines that are sensitive to oxidative stress, which was apparently induced by the ketoprofen analogue.
T2  - ACS Omega
T2  - ACS Omega
T1  - Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines
IS  - 5
VL  - 4
DO  - 10.1021/acsomega.9b00412
SP  - 8824
EP  - 8833
ER  - 

@article{
author = "Buzharevski, Antonio and Paskaš, Svetlana and Laube, Markus and Lönnecke, Peter and Neumann, Wilma and Murganić, Blagoje and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey-Hawkins, Evamarie",
year = "2019",
abstract = "Ketoprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID) that also exhibits cytotoxic activity against various cancers. This makes ketoprofen an attractive structural lead for the development of new NSAIDs and cytotoxic agents. Recently, the incorporation of carboranes as phenyl mimetics in structures of established drugs has emerged as an attractive strategy in drug design. Herein, we report the synthesis and evaluation of four novel carborane-containing derivatives of ketoprofen, two of which are prodrug esters with an nitric oxide-releasing moiety. One of these prodrug esters exhibited high cytostatic activity against melanoma and colon cancer cell lines. The most pronounced activity was found in cell lines that are sensitive to oxidative stress, which was apparently induced by the ketoprofen analogue.",
journal = "ACS Omega, ACS Omega",
title = "Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines",
number = "5",
volume = "4",
doi = "10.1021/acsomega.9b00412",
pages = "8824-8833"
}

Buzharevski, A., Paskaš, S., Laube, M., Lönnecke, P., Neumann, W., Murganić, B., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey-Hawkins, E.. (2019). Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines. in ACS Omega, 4(5), 8824-8833.
https://doi.org/10.1021/acsomega.9b00412

Buzharevski A, Paskaš S, Laube M, Lönnecke P, Neumann W, Murganić B, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey-Hawkins E. Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines. in ACS Omega. 2019;4(5):8824-8833.
doi:10.1021/acsomega.9b00412 .

Buzharevski, Antonio, Paskaš, Svetlana, Laube, Markus, Lönnecke, Peter, Neumann, Wilma, Murganić, Blagoje, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey-Hawkins, Evamarie, "Carboranyl Analogues of Ketoprofen with Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines" in ACS Omega, 4, no. 5 (2019):8824-8833,
https://doi.org/10.1021/acsomega.9b00412 . .

TY  - JOUR
AU  - Buzharevski, Antonio
AU  - Paskas, Svetlana
AU  - Sárosi, Menyhárt‐Botond
AU  - Laube, Markus
AU  - Lönnecke, Peter
AU  - Neumann, Wilma
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Pietzsch, Jens
AU  - Hey-Hawkins, Evamarie
PY  - 2019
UR  - https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.201800685
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3254
AB  - Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most common way of treating inflammatory disorders. Their widespread use helped reveal their other modes of action as pharmaceuticals, such as a profound effect on various cancers. Celecoxib has proven to be a very prominent member of this group with cytostatic activities. On the other hand, the highly dynamic field of drug design is constantly searching for new ways of modifying known structures to obtain more powerful and less harmful drugs. A very interesting development is the implementation of carboranes in pharmacologically active structures, mostly as phenyl mimetics. Herein we report the synthesis of three carborane-containing derivatives of the COX-2-selective NSAID celecoxib. The new compounds proved to have promising cytostatic potential against various melanoma and colorectal adenocarcinoma cell lines. Inhibited proliferation accompanied by caspase-independent apoptotic cell death was found to be the main cause of decreased cell viability upon treatment with the most efficient celecoxib analogue, 3 b (4-[5-(1,7-dicarba-closo-dodecaboranyl)-3-trifluoromethyl-1H-pyrazol-1-yl]-1-methylsulfonylbenzene).
T2  - ChemMedChem
T1  - Carboranyl Analogues of Celecoxib with Potent Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines.
IS  - 3
VL  - 14
DO  - 10.1002/cmdc.201800685
SP  - 315
EP  - 321
ER  - 

@article{
author = "Buzharevski, Antonio and Paskas, Svetlana and Sárosi, Menyhárt‐Botond and Laube, Markus and Lönnecke, Peter and Neumann, Wilma and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Pietzsch, Jens and Hey-Hawkins, Evamarie",
year = "2019",
abstract = "Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most common way of treating inflammatory disorders. Their widespread use helped reveal their other modes of action as pharmaceuticals, such as a profound effect on various cancers. Celecoxib has proven to be a very prominent member of this group with cytostatic activities. On the other hand, the highly dynamic field of drug design is constantly searching for new ways of modifying known structures to obtain more powerful and less harmful drugs. A very interesting development is the implementation of carboranes in pharmacologically active structures, mostly as phenyl mimetics. Herein we report the synthesis of three carborane-containing derivatives of the COX-2-selective NSAID celecoxib. The new compounds proved to have promising cytostatic potential against various melanoma and colorectal adenocarcinoma cell lines. Inhibited proliferation accompanied by caspase-independent apoptotic cell death was found to be the main cause of decreased cell viability upon treatment with the most efficient celecoxib analogue, 3 b (4-[5-(1,7-dicarba-closo-dodecaboranyl)-3-trifluoromethyl-1H-pyrazol-1-yl]-1-methylsulfonylbenzene).",
journal = "ChemMedChem",
title = "Carboranyl Analogues of Celecoxib with Potent Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines.",
number = "3",
volume = "14",
doi = "10.1002/cmdc.201800685",
pages = "315-321"
}

Buzharevski, A., Paskas, S., Sárosi, M., Laube, M., Lönnecke, P., Neumann, W., Mijatović, S., Maksimović-Ivanić, D., Pietzsch, J.,& Hey-Hawkins, E.. (2019). Carboranyl Analogues of Celecoxib with Potent Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines.. in ChemMedChem, 14(3), 315-321.
https://doi.org/10.1002/cmdc.201800685

Buzharevski A, Paskas S, Sárosi M, Laube M, Lönnecke P, Neumann W, Mijatović S, Maksimović-Ivanić D, Pietzsch J, Hey-Hawkins E. Carboranyl Analogues of Celecoxib with Potent Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines.. in ChemMedChem. 2019;14(3):315-321.
doi:10.1002/cmdc.201800685 .

Buzharevski, Antonio, Paskas, Svetlana, Sárosi, Menyhárt‐Botond, Laube, Markus, Lönnecke, Peter, Neumann, Wilma, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Pietzsch, Jens, Hey-Hawkins, Evamarie, "Carboranyl Analogues of Celecoxib with Potent Cytostatic Activity against Human Melanoma and Colon Cancer Cell Lines." in ChemMedChem, 14, no. 3 (2019):315-321,
https://doi.org/10.1002/cmdc.201800685 . .

TY  - JOUR
AU  - Kuhnert, Robert
AU  - Sárosi, Menyhárt-Botond
AU  - George, Sven
AU  - Lönnecke, Peter
AU  - Hofmann, Bettina
AU  - Steinhilber, Dieter
AU  - Steinmann, Sara
AU  - Schneider-Stock, Regine
AU  - Murganić, Blagoje
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2018
UR  - http://doi.wiley.com/10.1002/cmdc.201800651
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3225
AB  - 5-Lipoxygenase converts arachidonic acid into leukotrienes, which are involved in inflammation and angiogenesis. The introduction of carboranes can improve the pharmacokinetic behavior of metabolically less stable pharmaceutics. Herein we report the syntheses of several carborane-based inhibitors of the 5-lipoxygenase pathway. The isosteric replacement of phenyl rings by carboranes leads to improved cytotoxicity toward several melanoma and colon cancer cell lines. For the colon cancer cell line HCT116, the co-inhibition of heat shock protein 90 was observed.
T2  - ChemMedChem
T2  - ChemMedChem
T1  - Carborane-Based Analogues of 5-Lipoxygenase Inhibitors Co-inhibit Heat Shock Protein 90 in HCT116 Cells.
DO  - 10.1002/cmdc.201800651
ER  - 

@article{
author = "Kuhnert, Robert and Sárosi, Menyhárt-Botond and George, Sven and Lönnecke, Peter and Hofmann, Bettina and Steinhilber, Dieter and Steinmann, Sara and Schneider-Stock, Regine and Murganić, Blagoje and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2018",
abstract = "5-Lipoxygenase converts arachidonic acid into leukotrienes, which are involved in inflammation and angiogenesis. The introduction of carboranes can improve the pharmacokinetic behavior of metabolically less stable pharmaceutics. Herein we report the syntheses of several carborane-based inhibitors of the 5-lipoxygenase pathway. The isosteric replacement of phenyl rings by carboranes leads to improved cytotoxicity toward several melanoma and colon cancer cell lines. For the colon cancer cell line HCT116, the co-inhibition of heat shock protein 90 was observed.",
journal = "ChemMedChem, ChemMedChem",
title = "Carborane-Based Analogues of 5-Lipoxygenase Inhibitors Co-inhibit Heat Shock Protein 90 in HCT116 Cells.",
doi = "10.1002/cmdc.201800651"
}

Kuhnert, R., Sárosi, M., George, S., Lönnecke, P., Hofmann, B., Steinhilber, D., Steinmann, S., Schneider-Stock, R., Murganić, B., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2018). Carborane-Based Analogues of 5-Lipoxygenase Inhibitors Co-inhibit Heat Shock Protein 90 in HCT116 Cells.. in ChemMedChem.
https://doi.org/10.1002/cmdc.201800651

Kuhnert R, Sárosi M, George S, Lönnecke P, Hofmann B, Steinhilber D, Steinmann S, Schneider-Stock R, Murganić B, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Carborane-Based Analogues of 5-Lipoxygenase Inhibitors Co-inhibit Heat Shock Protein 90 in HCT116 Cells.. in ChemMedChem. 2018;.
doi:10.1002/cmdc.201800651 .

Kuhnert, Robert, Sárosi, Menyhárt-Botond, George, Sven, Lönnecke, Peter, Hofmann, Bettina, Steinhilber, Dieter, Steinmann, Sara, Schneider-Stock, Regine, Murganić, Blagoje, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "Carborane-Based Analogues of 5-Lipoxygenase Inhibitors Co-inhibit Heat Shock Protein 90 in HCT116 Cells." in ChemMedChem (2018),
https://doi.org/10.1002/cmdc.201800651 . .

TY  - JOUR
AU  - Kuhnert, Robert
AU  - Sárosi, Menyhárt-Botond
AU  - George, Sven
AU  - Lönnecke, Peter
AU  - Hofmann, Bettina
AU  - Steinhilber, Dieter
AU  - Murganić, Blagoje
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Hey-Hawkins, Evamarie
PY  - 2017
UR  - http://doi.wiley.com/10.1002/cmdc.201700309
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2789
AB  - The progression of cancer is accelerated by increased proliferation, angiogenesis, and inflammation. These processes are mediated by leukotrienes. Several cancer cell lines overexpress 5-lipoxygenase, an enzyme that converts arachidonic acid into leukotrienes. An early inhibitor of the 5-lipoxygenase pathway is Rev-5901, which, however, lacks in invivo efficacy, as it is rapidly metabolized. We investigated the introduction of carboranes as highly hydrophobic and metabolically stable pharmacophores into lipoxygenase inhibitors. Carboranes are icosahedral boron clusters that are remarkably stable and used to increase the metabolic stability of unstable pharmaceutics without changing their biological activity. By introduction of meta-carborane into Rev-5901, the first carborane-based inhibitor of the 5-lipoxygenase pathway was obtained. We report the synthesis and inhibitory and cytotoxic behavior of these compounds toward several melanoma and colon cancer cell lines and their related anticancer mechanisms.
T2  - ChemMedChem
T1  - CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway
IS  - 13
VL  - 12
DO  - 10.1002/cmdc.201700309
SP  - 1081
EP  - 1086
ER  - 

@article{
author = "Kuhnert, Robert and Sárosi, Menyhárt-Botond and George, Sven and Lönnecke, Peter and Hofmann, Bettina and Steinhilber, Dieter and Murganić, Blagoje and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Hey-Hawkins, Evamarie",
year = "2017",
abstract = "The progression of cancer is accelerated by increased proliferation, angiogenesis, and inflammation. These processes are mediated by leukotrienes. Several cancer cell lines overexpress 5-lipoxygenase, an enzyme that converts arachidonic acid into leukotrienes. An early inhibitor of the 5-lipoxygenase pathway is Rev-5901, which, however, lacks in invivo efficacy, as it is rapidly metabolized. We investigated the introduction of carboranes as highly hydrophobic and metabolically stable pharmacophores into lipoxygenase inhibitors. Carboranes are icosahedral boron clusters that are remarkably stable and used to increase the metabolic stability of unstable pharmaceutics without changing their biological activity. By introduction of meta-carborane into Rev-5901, the first carborane-based inhibitor of the 5-lipoxygenase pathway was obtained. We report the synthesis and inhibitory and cytotoxic behavior of these compounds toward several melanoma and colon cancer cell lines and their related anticancer mechanisms.",
journal = "ChemMedChem",
title = "CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway",
number = "13",
volume = "12",
doi = "10.1002/cmdc.201700309",
pages = "1081-1086"
}

Kuhnert, R., Sárosi, M., George, S., Lönnecke, P., Hofmann, B., Steinhilber, D., Murganić, B., Mijatović, S., Maksimović-Ivanić, D.,& Hey-Hawkins, E.. (2017). CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway. in ChemMedChem, 12(13), 1081-1086.
https://doi.org/10.1002/cmdc.201700309

Kuhnert R, Sárosi M, George S, Lönnecke P, Hofmann B, Steinhilber D, Murganić B, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway. in ChemMedChem. 2017;12(13):1081-1086.
doi:10.1002/cmdc.201700309 .

Kuhnert, Robert, Sárosi, Menyhárt-Botond, George, Sven, Lönnecke, Peter, Hofmann, Bettina, Steinhilber, Dieter, Murganić, Blagoje, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Hey-Hawkins, Evamarie, "CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway" in ChemMedChem, 12, no. 13 (2017):1081-1086,
https://doi.org/10.1002/cmdc.201700309 . .

TY  - JOUR
AU  - Gozzi, Marta
AU  - Schwarze, Benedikt
AU  - Sárosi, Menyhárt-Botond
AU  - Lönnecke, Peter
AU  - Drača, Dijana
AU  - Maksimović-Ivanić, Danijela
AU  - Mijatović, Sanja
AU  - Hey-Hawkins, Evamarie
PY  - 2017
UR  - http://xlink.rsc.org/?DOI=C7DT02027A
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2858
AB  - Three [(η6-arene)RuC2B9H11] complexes (arene = p-cymene (2), biphenyl (3) and 1-Me-4-COOEt-C6H4 (4)) were synthesised according to modified literature procedures and fully characterised. 2-4 were found to be moderately active against two types of tumour cell lines (HCT116 and MCF7), with IC50 values in the low micromolar range. However, viability of normal, healthy cells (MRC-5 cell line, MLEC and mouse macrophages) was not affected by treatment with 2-4, indicating high selectivity of the metallacarborane complexes towards tumour cell lines, compared to the unselective antitumour agent cisplatin and other potential RuII drugs. Moreover, flow cytometric analysis suggested that 4 induces cell death via a caspase-dependent apoptotic mechanism. DFT calculations of the frontier molecular orbitals showed that the HOMO-LUMO gap in 2-4 is smaller than in the corresponding cyclopentadienyl complexes 2-Cp-4-Cp (e.g. 5.47 (2) vs. 6.31 eV (2-Cp)). In order to assess the stability of 2-4, particularly the ruthenium-dicarbollide bond, energy decomposition analysis (EDA) of 2-4, together with the respective cyclopentadienyl analogues 2-Cp-4-Cp, was performed. EDA suggests that the ruthenium(ii)-dicarbollide bond in the three complexes is mostly ionic and far stronger than the ruthenium(ii)-arene bond.
T2  - Dalton Transactions
T1  - Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines
IS  - 36
VL  - 46
DO  - 10.1039/C7DT02027A
SP  - 12067
EP  - 12080
ER  - 

@article{
author = "Gozzi, Marta and Schwarze, Benedikt and Sárosi, Menyhárt-Botond and Lönnecke, Peter and Drača, Dijana and Maksimović-Ivanić, Danijela and Mijatović, Sanja and Hey-Hawkins, Evamarie",
year = "2017",
abstract = "Three [(η6-arene)RuC2B9H11] complexes (arene = p-cymene (2), biphenyl (3) and 1-Me-4-COOEt-C6H4 (4)) were synthesised according to modified literature procedures and fully characterised. 2-4 were found to be moderately active against two types of tumour cell lines (HCT116 and MCF7), with IC50 values in the low micromolar range. However, viability of normal, healthy cells (MRC-5 cell line, MLEC and mouse macrophages) was not affected by treatment with 2-4, indicating high selectivity of the metallacarborane complexes towards tumour cell lines, compared to the unselective antitumour agent cisplatin and other potential RuII drugs. Moreover, flow cytometric analysis suggested that 4 induces cell death via a caspase-dependent apoptotic mechanism. DFT calculations of the frontier molecular orbitals showed that the HOMO-LUMO gap in 2-4 is smaller than in the corresponding cyclopentadienyl complexes 2-Cp-4-Cp (e.g. 5.47 (2) vs. 6.31 eV (2-Cp)). In order to assess the stability of 2-4, particularly the ruthenium-dicarbollide bond, energy decomposition analysis (EDA) of 2-4, together with the respective cyclopentadienyl analogues 2-Cp-4-Cp, was performed. EDA suggests that the ruthenium(ii)-dicarbollide bond in the three complexes is mostly ionic and far stronger than the ruthenium(ii)-arene bond.",
journal = "Dalton Transactions",
title = "Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines",
number = "36",
volume = "46",
doi = "10.1039/C7DT02027A",
pages = "12067-12080"
}

Gozzi, M., Schwarze, B., Sárosi, M., Lönnecke, P., Drača, D., Maksimović-Ivanić, D., Mijatović, S.,& Hey-Hawkins, E.. (2017). Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines. in Dalton Transactions, 46(36), 12067-12080.
https://doi.org/10.1039/C7DT02027A

Gozzi M, Schwarze B, Sárosi M, Lönnecke P, Drača D, Maksimović-Ivanić D, Mijatović S, Hey-Hawkins E. Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines. in Dalton Transactions. 2017;46(36):12067-12080.
doi:10.1039/C7DT02027A .

Gozzi, Marta, Schwarze, Benedikt, Sárosi, Menyhárt-Botond, Lönnecke, Peter, Drača, Dijana, Maksimović-Ivanić, Danijela, Mijatović, Sanja, Hey-Hawkins, Evamarie, "Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines" in Dalton Transactions, 46, no. 36 (2017):12067-12080,
https://doi.org/10.1039/C7DT02027A . .

TY  - GEN
AU  - Gozzi, Marta
AU  - Schwarze, Benedikt
AU  - Sárosi, Menyhárt-Botond
AU  - Lönnecke, Peter
AU  - Drača, Dijana
AU  - Maksimović-Ivanić, Danijela
AU  - Mijatović, Sanja
AU  - Hey-Hawkins, Evamarie
PY  - 2017
UR  - http://xlink.rsc.org/?DOI=C7DT02027A
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2848
AB  - Three [(η6-arene)RuC2B9H11] complexes (arene = p-cymene (2), biphenyl (3) and 1-Me-4-COOEt-C6H4 (4)) were synthesised according to modified literature procedures and fully characterised. 2–4 were found to be moderately active against two types of tumour cell lines (HCT116 and MCF7), with IC50 values in the low micromolar range. However, viability of normal, healthy cells (MRC-5 cell line, MLEC and mouse macrophages) was not affected by treatment with 2–4, indicating high selectivity of the metallacarborane complexes towards tumour cell lines, compared to the unselective antitumour agent cisplatin and other potential RuII drugs. Moreover, flow cytometric analysis suggested that 4 induces cell death via a caspase-dependent apoptotic mechanism. DFT calculations of the frontier molecular orbitals showed that the HOMO–LUMO gap in 2–4 is smaller than in the corresponding cyclopentadienyl complexes 2-Cp–4-Cp (e.g. 5.47 (2) vs. 6.31 eV (2-Cp)). In order to assess the stability of 2–4, particularly the ruthenium–dicarbollide bond, energy decomposition analysis (EDA) of 2–4, together with the respective cyclopentadienyl analogues 2-Cp–4-Cp, was performed. EDA suggests that the ruthenium(II)–dicarbollide bond in the three complexes is mostly ionic and far stronger than the ruthenium(II)–arene bond.
PB  - The Royal Society of Chemistry
T2  - Dalton Transactions
T1  - Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines
DO  - 10.1039/C7DT02027A
ER  - 

@misc{
author = "Gozzi, Marta and Schwarze, Benedikt and Sárosi, Menyhárt-Botond and Lönnecke, Peter and Drača, Dijana and Maksimović-Ivanić, Danijela and Mijatović, Sanja and Hey-Hawkins, Evamarie",
year = "2017",
abstract = "Three [(η6-arene)RuC2B9H11] complexes (arene = p-cymene (2), biphenyl (3) and 1-Me-4-COOEt-C6H4 (4)) were synthesised according to modified literature procedures and fully characterised. 2–4 were found to be moderately active against two types of tumour cell lines (HCT116 and MCF7), with IC50 values in the low micromolar range. However, viability of normal, healthy cells (MRC-5 cell line, MLEC and mouse macrophages) was not affected by treatment with 2–4, indicating high selectivity of the metallacarborane complexes towards tumour cell lines, compared to the unselective antitumour agent cisplatin and other potential RuII drugs. Moreover, flow cytometric analysis suggested that 4 induces cell death via a caspase-dependent apoptotic mechanism. DFT calculations of the frontier molecular orbitals showed that the HOMO–LUMO gap in 2–4 is smaller than in the corresponding cyclopentadienyl complexes 2-Cp–4-Cp (e.g. 5.47 (2) vs. 6.31 eV (2-Cp)). In order to assess the stability of 2–4, particularly the ruthenium–dicarbollide bond, energy decomposition analysis (EDA) of 2–4, together with the respective cyclopentadienyl analogues 2-Cp–4-Cp, was performed. EDA suggests that the ruthenium(II)–dicarbollide bond in the three complexes is mostly ionic and far stronger than the ruthenium(II)–arene bond.",
publisher = "The Royal Society of Chemistry",
journal = "Dalton Transactions",
title = "Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines",
doi = "10.1039/C7DT02027A"
}

Gozzi, M., Schwarze, B., Sárosi, M., Lönnecke, P., Drača, D., Maksimović-Ivanić, D., Mijatović, S.,& Hey-Hawkins, E.. (2017). Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines. in Dalton Transactions
The Royal Society of Chemistry..
https://doi.org/10.1039/C7DT02027A

Gozzi M, Schwarze B, Sárosi M, Lönnecke P, Drača D, Maksimović-Ivanić D, Mijatović S, Hey-Hawkins E. Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines. in Dalton Transactions. 2017;.
doi:10.1039/C7DT02027A .

Gozzi, Marta, Schwarze, Benedikt, Sárosi, Menyhárt-Botond, Lönnecke, Peter, Drača, Dijana, Maksimović-Ivanić, Danijela, Mijatović, Sanja, Hey-Hawkins, Evamarie, "Antiproliferative activity of (η 6 -arene)ruthenacarborane sandwich complexes against HCT116 and MCF7 cell lines" in Dalton Transactions (2017),
https://doi.org/10.1039/C7DT02027A . .

TY  - JOUR
AU  - Richter, Stefan
AU  - Singh, Sushma
AU  - Drača, Dijana
AU  - Kate, Anup
AU  - Kumbhar, Anupa
AU  - Kumbhar, Avinash S.
AU  - Maksimović-Ivanić, Danijela
AU  - Mijatović, Sanja
AU  - Lönnecke, Peter
AU  - Hey-Hawkins, Evamarie
PY  - 2016
UR  - http://xlink.rsc.org/?DOI=C6DT01782G
UR  - http://www.ncbi.nlm.nih.gov/pubmed/27264161
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2847
AB  - A series of Ru(II) arene complexes of mono- and bidentate N-donor ligands with carboxyl or ester groups and chlorido ancillary ligands were synthesised and structurally characterised. The complexes have a distorted tetrahedral piano-stool geometry. The binding interaction was studied with calf thymus DNA (CT-DNA) by absorption titration, viscosity measurement, thermal melting, circular dichroism, ethidium bromide displacement assay and DNA cleavage of plasmid DNA (pBR322), investigated by gel electrophoresis. The dichlorido complexes bind covalently to DNA in the dark, similar to cisplatin, while the monochlorido complexes bind covalently on irradiation, similar to cisplatin analogues. The compounds are selectively cytotoxic against several tumour cell lines and show specific nonlinear correlation between dose and activity. This phenomenon is closely related to their potential to act preferentially as inhibitors of cell division.
T2  - Dalton Transactions
T1  - Antiproliferative activity of ruthenium(ii) arene complexes with mono- and bidentate pyridine-based ligands
IS  - 33
VL  - 45
DO  - 10.1039/c6dt01782g
SP  - 13114
EP  - 13125
ER  - 

@article{
author = "Richter, Stefan and Singh, Sushma and Drača, Dijana and Kate, Anup and Kumbhar, Anupa and Kumbhar, Avinash S. and Maksimović-Ivanić, Danijela and Mijatović, Sanja and Lönnecke, Peter and Hey-Hawkins, Evamarie",
year = "2016",
abstract = "A series of Ru(II) arene complexes of mono- and bidentate N-donor ligands with carboxyl or ester groups and chlorido ancillary ligands were synthesised and structurally characterised. The complexes have a distorted tetrahedral piano-stool geometry. The binding interaction was studied with calf thymus DNA (CT-DNA) by absorption titration, viscosity measurement, thermal melting, circular dichroism, ethidium bromide displacement assay and DNA cleavage of plasmid DNA (pBR322), investigated by gel electrophoresis. The dichlorido complexes bind covalently to DNA in the dark, similar to cisplatin, while the monochlorido complexes bind covalently on irradiation, similar to cisplatin analogues. The compounds are selectively cytotoxic against several tumour cell lines and show specific nonlinear correlation between dose and activity. This phenomenon is closely related to their potential to act preferentially as inhibitors of cell division.",
journal = "Dalton Transactions",
title = "Antiproliferative activity of ruthenium(ii) arene complexes with mono- and bidentate pyridine-based ligands",
number = "33",
volume = "45",
doi = "10.1039/c6dt01782g",
pages = "13114-13125"
}

Richter, S., Singh, S., Drača, D., Kate, A., Kumbhar, A., Kumbhar, A. S., Maksimović-Ivanić, D., Mijatović, S., Lönnecke, P.,& Hey-Hawkins, E.. (2016). Antiproliferative activity of ruthenium(ii) arene complexes with mono- and bidentate pyridine-based ligands. in Dalton Transactions, 45(33), 13114-13125.
https://doi.org/10.1039/c6dt01782g

Richter S, Singh S, Drača D, Kate A, Kumbhar A, Kumbhar AS, Maksimović-Ivanić D, Mijatović S, Lönnecke P, Hey-Hawkins E. Antiproliferative activity of ruthenium(ii) arene complexes with mono- and bidentate pyridine-based ligands. in Dalton Transactions. 2016;45(33):13114-13125.
doi:10.1039/c6dt01782g .

Richter, Stefan, Singh, Sushma, Drača, Dijana, Kate, Anup, Kumbhar, Anupa, Kumbhar, Avinash S., Maksimović-Ivanić, Danijela, Mijatović, Sanja, Lönnecke, Peter, Hey-Hawkins, Evamarie, "Antiproliferative activity of ruthenium(ii) arene complexes with mono- and bidentate pyridine-based ligands" in Dalton Transactions, 45, no. 33 (2016):13114-13125,
https://doi.org/10.1039/c6dt01782g . .