TY  - JOUR
AU  - Arlt, Sören
AU  - Petković, Vladana
AU  - Ludwig, Gerd
AU  - Eichhorn, Thomas
AU  - Lang, Heinrich
AU  - Rüffer, Tobias
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Kaluđerović, Goran
PY  - 2021
UR  - https://www.mdpi.com/1420-3049/26/7/1860
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/4220
AB  - Neutral [Ru(η6-arene)Cl2{Ph2P(CH2)3SPh-κP}] (arene = benzene, indane, 1,2,3,4-tetrahydronaphthalene: 2a, 2c and 2d) and cationic [Ru(η6-arene)Cl(Ph2P(CH2)3SPh-κP,κS)]X complexes (arene = mesitylene, 1,4-dihydronaphthalene; X = Cl: 3b, 3e; arene = benzene, mesitylene, indane, 1,2,3,4-tetrahydronaphthalene, and 1,4-dihydronaphthalene; X = PF6: 4a–4e) complexes were prepared and characterized by elemental analysis, IR, 1H, 13C and 31P NMR spectroscopy and also by single-crystal X-ray diffraction analyses. The stability of the complexes has been investigated in DMSO. Complexes have been assessed for their cytotoxic activity against 518A2, 8505C, A253, MCF-7 and SW480 cell lines. Generally, complexes exhibited activity in the lower micromolar range; moreover, they are found to be more active than cisplatin. For the most active ruthenium(II) complex, 4b, bearing mesitylene as ligand, the mechanism of action against 8505C cisplatin resistant cell line was determined. Complex 4b induced apoptosis accompanied by caspase activation.
PB  - MDPI
T2  - Molecules
T1  - Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand
IS  - 7
VL  - 26
DO  - 10.3390/molecules26071860
SP  - 1860
ER  - 

@article{
author = "Arlt, Sören and Petković, Vladana and Ludwig, Gerd and Eichhorn, Thomas and Lang, Heinrich and Rüffer, Tobias and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Kaluđerović, Goran",
year = "2021",
abstract = "Neutral [Ru(η6-arene)Cl2{Ph2P(CH2)3SPh-κP}] (arene = benzene, indane, 1,2,3,4-tetrahydronaphthalene: 2a, 2c and 2d) and cationic [Ru(η6-arene)Cl(Ph2P(CH2)3SPh-κP,κS)]X complexes (arene = mesitylene, 1,4-dihydronaphthalene; X = Cl: 3b, 3e; arene = benzene, mesitylene, indane, 1,2,3,4-tetrahydronaphthalene, and 1,4-dihydronaphthalene; X = PF6: 4a–4e) complexes were prepared and characterized by elemental analysis, IR, 1H, 13C and 31P NMR spectroscopy and also by single-crystal X-ray diffraction analyses. The stability of the complexes has been investigated in DMSO. Complexes have been assessed for their cytotoxic activity against 518A2, 8505C, A253, MCF-7 and SW480 cell lines. Generally, complexes exhibited activity in the lower micromolar range; moreover, they are found to be more active than cisplatin. For the most active ruthenium(II) complex, 4b, bearing mesitylene as ligand, the mechanism of action against 8505C cisplatin resistant cell line was determined. Complex 4b induced apoptosis accompanied by caspase activation.",
publisher = "MDPI",
journal = "Molecules",
title = "Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand",
number = "7",
volume = "26",
doi = "10.3390/molecules26071860",
pages = "1860"
}

Arlt, S., Petković, V., Ludwig, G., Eichhorn, T., Lang, H., Rüffer, T., Mijatović, S., Maksimović-Ivanić, D.,& Kaluđerović, G.. (2021). Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand. in Molecules
MDPI., 26(7), 1860.
https://doi.org/10.3390/molecules26071860

Arlt S, Petković V, Ludwig G, Eichhorn T, Lang H, Rüffer T, Mijatović S, Maksimović-Ivanić D, Kaluđerović G. Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand. in Molecules. 2021;26(7):1860.
doi:10.3390/molecules26071860 .

Arlt, Sören, Petković, Vladana, Ludwig, Gerd, Eichhorn, Thomas, Lang, Heinrich, Rüffer, Tobias, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Kaluđerović, Goran, "Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand" in Molecules, 26, no. 7 (2021):1860,
https://doi.org/10.3390/molecules26071860 . .

TY  - JOUR
AU  - Ludwig, Gerd
AU  - Randelovic, Ivan
AU  - Maksimović-Ivanić, Danijela
AU  - Mijatović, Sanja
AU  - Bulatović, Mirna Z.
AU  - Miljković, Đorđe
AU  - Korb, Marcus
AU  - Lang, Heinrich
AU  - Steinborn, Dirk
AU  - Kaluđerović, Goran N.
PY  - 2014
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2193
AB  - Iridium(III) complexes of the type
   {[}Ir(eta(5)-C5Me5)Cl-2\{Ph2PCH2-CH2CH2S(O)(x)Ph-kappa P\}] (x=0-2; 1-3)
   and {[}Ir(eta(5)-C5Me5)Cl\{Ph2PCH2-CH2CH2S(O)(x)Ph-kappa P,kappa
   S\}]{[}PF6] (x=0-1; 4 and 5) with 3-(diphenyl-phosphino)propyl phenyl
   sulfide, sulfoxide, and sulfone ligands Ph2PCH2CH2CH2S(O)(x)Ph were
   designed, synthesized, and characterized fully, including X-ray
   diffraction analyses for complexes 3 and 4. In vitro studies against
   human thyroid carcinoma (8505C), submandibular carcinoma (A253), breast
   adenocarcinoma (MCF-7), colon adenocarcinoma (SW480), and melano-ma
   (518A2) cell lines provided evidence for the high biological potential
   of the neutral and cationic iridium(III) complexes. Neutral iridium(III)
   complex 5 proved to be the most active, with IC50 values up to about 0.1
   mu m, representing activities of up to one order of magnitude higher
   than cisplatin. Using 8505C cells, apoptosis was shown to be the main
   mechanism through which complex 5 exerts its tumoricidal action. The
   described iridium(III) complexes represent potential leads in the search
   for novel metal-based anticancer agents.
T2  - Chemmedchem
T1  - Anticancer Potential of
 (Pentamethylcyclopentadienyl)chloridoiridium(III) Complexes Bearing
 kappa P and kappa P,kappa S-Coordinated Ph2PCH2CH2CH2S(O)(x)Ph (x=0-2)
 Ligands
IS  - 7
VL  - 9
DO  - 10.1002/cmdc.201300479
SP  - 1586
EP  - 1593
ER  - 

@article{
author = "Ludwig, Gerd and Randelovic, Ivan and Maksimović-Ivanić, Danijela and Mijatović, Sanja and Bulatović, Mirna Z. and Miljković, Đorđe and Korb, Marcus and Lang, Heinrich and Steinborn, Dirk and Kaluđerović, Goran N.",
year = "2014",
abstract = "Iridium(III) complexes of the type
   {[}Ir(eta(5)-C5Me5)Cl-2\{Ph2PCH2-CH2CH2S(O)(x)Ph-kappa P\}] (x=0-2; 1-3)
   and {[}Ir(eta(5)-C5Me5)Cl\{Ph2PCH2-CH2CH2S(O)(x)Ph-kappa P,kappa
   S\}]{[}PF6] (x=0-1; 4 and 5) with 3-(diphenyl-phosphino)propyl phenyl
   sulfide, sulfoxide, and sulfone ligands Ph2PCH2CH2CH2S(O)(x)Ph were
   designed, synthesized, and characterized fully, including X-ray
   diffraction analyses for complexes 3 and 4. In vitro studies against
   human thyroid carcinoma (8505C), submandibular carcinoma (A253), breast
   adenocarcinoma (MCF-7), colon adenocarcinoma (SW480), and melano-ma
   (518A2) cell lines provided evidence for the high biological potential
   of the neutral and cationic iridium(III) complexes. Neutral iridium(III)
   complex 5 proved to be the most active, with IC50 values up to about 0.1
   mu m, representing activities of up to one order of magnitude higher
   than cisplatin. Using 8505C cells, apoptosis was shown to be the main
   mechanism through which complex 5 exerts its tumoricidal action. The
   described iridium(III) complexes represent potential leads in the search
   for novel metal-based anticancer agents.",
journal = "Chemmedchem",
title = "Anticancer Potential of
 (Pentamethylcyclopentadienyl)chloridoiridium(III) Complexes Bearing
 kappa P and kappa P,kappa S-Coordinated Ph2PCH2CH2CH2S(O)(x)Ph (x=0-2)
 Ligands",
number = "7",
volume = "9",
doi = "10.1002/cmdc.201300479",
pages = "1586-1593"
}

Ludwig, G., Randelovic, I., Maksimović-Ivanić, D., Mijatović, S., Bulatović, M. Z., Miljković, Đ., Korb, M., Lang, H., Steinborn, D.,& Kaluđerović, G. N.. (2014). Anticancer Potential of
 (Pentamethylcyclopentadienyl)chloridoiridium(III) Complexes Bearing
 kappa P and kappa P,kappa S-Coordinated Ph2PCH2CH2CH2S(O)(x)Ph (x=0-2)
 Ligands. in Chemmedchem, 9(7), 1586-1593.
https://doi.org/10.1002/cmdc.201300479

Ludwig G, Randelovic I, Maksimović-Ivanić D, Mijatović S, Bulatović MZ, Miljković Đ, Korb M, Lang H, Steinborn D, Kaluđerović GN. Anticancer Potential of
 (Pentamethylcyclopentadienyl)chloridoiridium(III) Complexes Bearing
 kappa P and kappa P,kappa S-Coordinated Ph2PCH2CH2CH2S(O)(x)Ph (x=0-2)
 Ligands. in Chemmedchem. 2014;9(7):1586-1593.
doi:10.1002/cmdc.201300479 .

Ludwig, Gerd, Randelovic, Ivan, Maksimović-Ivanić, Danijela, Mijatović, Sanja, Bulatović, Mirna Z., Miljković, Đorđe, Korb, Marcus, Lang, Heinrich, Steinborn, Dirk, Kaluđerović, Goran N., "Anticancer Potential of
 (Pentamethylcyclopentadienyl)chloridoiridium(III) Complexes Bearing
 kappa P and kappa P,kappa S-Coordinated Ph2PCH2CH2CH2S(O)(x)Ph (x=0-2)
 Ligands" in Chemmedchem, 9, no. 7 (2014):1586-1593,
https://doi.org/10.1002/cmdc.201300479 . .

TY  - JOUR
AU  - Ludwig, Gerd
AU  - Mijatović, Sanja
AU  - Ranđelović, Ivan
AU  - Bulatović, Mirna Z.
AU  - Miljković, Đorđe
AU  - Maksimović-Ivanić, Danijela
AU  - Korb, Marcus
AU  - Lang, Heinrich
AU  - Steinborn, Dirk
AU  - Kaluđerović, Goran N.
PY  - 2013
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/948
AB  - Neutral iridium(III) complexes of the type [Ir(eta(5)-C5Me5)Cl-2{Ph2PCH2S(O)(x)Ph-kappa P}] (1-3) with diphenylphosphino-functionalized methyl phenyl sulfides, sulfoxides, and sulfones Ph2PCH2S(O)(x)Ph (x = 0, L1; 1, 12; 2, L3) and the cationic complex [Ir(eta(5)-C5Me5)Cl(Ph2PCH2SPh-kappa P,kappa S}][PF6] (4) were synthesized and fully characterized analytically and spectroscopically. Furthermore, the structure of 2 was determined by X-ray diffraction analysis. The biological potential of the neutral and cationic iridium(III) complexes was tested in vitro against the cell lines 8505C, A253, MCF-7, SW480 and 518A2. Complex [Ir(eta(5)-C5Me5)Cl-2{Ph2PCH2S(O)Ph-kappa P}] (2), with ligand L2 kappa P coordinated containing a pendent sulfinyl group, is the most active one (IC50 values of about 3 mu M), thus, with activities comparable to cisplatin. Complex 2 proved to have an even a higher antiproliferative activity than cisplatin against 8505C and SW480 cell lines, used as a model system of highly anaplastic cancers with low sensitivity to conventional chemotherapeutics such as cisplatin. Additional experiments demonstrated that apoptosis and autophagic cell death contribute to the drug's tumoricidal action. (C) 2013 Elsevier Masson SAS. All rights reserved.
T2  - European Journal of Medicinal Chemistry
T1  - Biological activity of neutral and cationic iridium(III) complexes with kappa P and kappa P,kappa S coordinated Ph2PCH2S(O)(x)Ph (x=0-2) ligands
IS  - null
VL  - 69
SP  - 33
EP  - 222
UR  - https://hdl.handle.net/21.15107/rcub_ibiss_948
ER  - 

@article{
author = "Ludwig, Gerd and Mijatović, Sanja and Ranđelović, Ivan and Bulatović, Mirna Z. and Miljković, Đorđe and Maksimović-Ivanić, Danijela and Korb, Marcus and Lang, Heinrich and Steinborn, Dirk and Kaluđerović, Goran N.",
year = "2013",
abstract = "Neutral iridium(III) complexes of the type [Ir(eta(5)-C5Me5)Cl-2{Ph2PCH2S(O)(x)Ph-kappa P}] (1-3) with diphenylphosphino-functionalized methyl phenyl sulfides, sulfoxides, and sulfones Ph2PCH2S(O)(x)Ph (x = 0, L1; 1, 12; 2, L3) and the cationic complex [Ir(eta(5)-C5Me5)Cl(Ph2PCH2SPh-kappa P,kappa S}][PF6] (4) were synthesized and fully characterized analytically and spectroscopically. Furthermore, the structure of 2 was determined by X-ray diffraction analysis. The biological potential of the neutral and cationic iridium(III) complexes was tested in vitro against the cell lines 8505C, A253, MCF-7, SW480 and 518A2. Complex [Ir(eta(5)-C5Me5)Cl-2{Ph2PCH2S(O)Ph-kappa P}] (2), with ligand L2 kappa P coordinated containing a pendent sulfinyl group, is the most active one (IC50 values of about 3 mu M), thus, with activities comparable to cisplatin. Complex 2 proved to have an even a higher antiproliferative activity than cisplatin against 8505C and SW480 cell lines, used as a model system of highly anaplastic cancers with low sensitivity to conventional chemotherapeutics such as cisplatin. Additional experiments demonstrated that apoptosis and autophagic cell death contribute to the drug's tumoricidal action. (C) 2013 Elsevier Masson SAS. All rights reserved.",
journal = "European Journal of Medicinal Chemistry",
title = "Biological activity of neutral and cationic iridium(III) complexes with kappa P and kappa P,kappa S coordinated Ph2PCH2S(O)(x)Ph (x=0-2) ligands",
number = "null",
volume = "69",
pages = "33-222",
url = "https://hdl.handle.net/21.15107/rcub_ibiss_948"
}

Ludwig, G., Mijatović, S., Ranđelović, I., Bulatović, M. Z., Miljković, Đ., Maksimović-Ivanić, D., Korb, M., Lang, H., Steinborn, D.,& Kaluđerović, G. N.. (2013). Biological activity of neutral and cationic iridium(III) complexes with kappa P and kappa P,kappa S coordinated Ph2PCH2S(O)(x)Ph (x=0-2) ligands. in European Journal of Medicinal Chemistry, 69(null), 33-222.
https://hdl.handle.net/21.15107/rcub_ibiss_948

Ludwig G, Mijatović S, Ranđelović I, Bulatović MZ, Miljković Đ, Maksimović-Ivanić D, Korb M, Lang H, Steinborn D, Kaluđerović GN. Biological activity of neutral and cationic iridium(III) complexes with kappa P and kappa P,kappa S coordinated Ph2PCH2S(O)(x)Ph (x=0-2) ligands. in European Journal of Medicinal Chemistry. 2013;69(null):33-222.
https://hdl.handle.net/21.15107/rcub_ibiss_948 .

Ludwig, Gerd, Mijatović, Sanja, Ranđelović, Ivan, Bulatović, Mirna Z., Miljković, Đorđe, Maksimović-Ivanić, Danijela, Korb, Marcus, Lang, Heinrich, Steinborn, Dirk, Kaluđerović, Goran N., "Biological activity of neutral and cationic iridium(III) complexes with kappa P and kappa P,kappa S coordinated Ph2PCH2S(O)(x)Ph (x=0-2) ligands" in European Journal of Medicinal Chemistry, 69, no. null (2013):33-222,
https://hdl.handle.net/21.15107/rcub_ibiss_948 .