TY  - JOUR
AU  - Ludwig, Gerd
AU  - Ranđelović, Ivan
AU  - Dimić, Dušan
AU  - Komazec, Teodora
AU  - Maksimović-Ivanić, Danijela
AU  - Mijatović, Sanja
AU  - Rüffer, Tobias
AU  - Kaluđerović, Goran N.
PY  - 2024
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6642
AB  - The (pentamethylcyclopentadienyl)chloridoiridium(III) complex bearing a κP,κS-bonded Ph2PCH2CH2SPh ligand ([Ir(η5-C5Me5)Cl(Ph2P(CH2)2SPh-κP,κS)]PF6, (1)] was synthesized and characterized. Multinuclear (1H, 13C and 31P) NMR spectroscopy was employed for the determination of the structure. Moreover, SC-XRD confirmed the proposed structure belongs to the “piano stool” type. The Hirshfeld surface analysis outlined the most important intermolecular interactions in the structure. The crystallographic structure was optimized at the B3LYP-D3BJ/6-311++G(d,p)(H,C,P,S,Cl)/LanL2DZ(Ir) level of theory. The applicability of this level was verified through a comparison of experimental and theoretical bond lengths and angles, and 1H and 13C NMR chemical shifts. The Natural Bond Orbital theory was used to identify and quantify the intramolecular stabilization interactions, especially those between donor atoms and Ir(III) ions. Complex 1 was tested on antitumor activity against five human tumor cell lines: MCF-7 breast adenocarcinoma, SW480 colon adenocarcinoma, 518A2 melanoma, 8505C human thyroid carcinoma and A253 submandibular carcinoma. Complex 1 showed superior antitumor activity against cisplatin-resistant MCF-7, SW480 and 8505C cell lines. The mechanism of tumoricidal action on 8505C cells indicates the involvement of caspase-induced apoptosis, accompanied by a considerable reduction in ROS/RNS and proliferation potential of treated cells.
PB  - Basel: MDPI
T2  - Biomolecules
T1  - (Pentamethylcyclopentadienyl)chloridoiridium(III) Complex Bearing Bidentate Ph2PCH2CH2SPh-κP,κS Ligand
IS  - 4
VL  - 14
DO  - 10.3390/biom14040420
SP  - 420
ER  - 

@article{
author = "Ludwig, Gerd and Ranđelović, Ivan and Dimić, Dušan and Komazec, Teodora and Maksimović-Ivanić, Danijela and Mijatović, Sanja and Rüffer, Tobias and Kaluđerović, Goran N.",
year = "2024",
abstract = "The (pentamethylcyclopentadienyl)chloridoiridium(III) complex bearing a κP,κS-bonded Ph2PCH2CH2SPh ligand ([Ir(η5-C5Me5)Cl(Ph2P(CH2)2SPh-κP,κS)]PF6, (1)] was synthesized and characterized. Multinuclear (1H, 13C and 31P) NMR spectroscopy was employed for the determination of the structure. Moreover, SC-XRD confirmed the proposed structure belongs to the “piano stool” type. The Hirshfeld surface analysis outlined the most important intermolecular interactions in the structure. The crystallographic structure was optimized at the B3LYP-D3BJ/6-311++G(d,p)(H,C,P,S,Cl)/LanL2DZ(Ir) level of theory. The applicability of this level was verified through a comparison of experimental and theoretical bond lengths and angles, and 1H and 13C NMR chemical shifts. The Natural Bond Orbital theory was used to identify and quantify the intramolecular stabilization interactions, especially those between donor atoms and Ir(III) ions. Complex 1 was tested on antitumor activity against five human tumor cell lines: MCF-7 breast adenocarcinoma, SW480 colon adenocarcinoma, 518A2 melanoma, 8505C human thyroid carcinoma and A253 submandibular carcinoma. Complex 1 showed superior antitumor activity against cisplatin-resistant MCF-7, SW480 and 8505C cell lines. The mechanism of tumoricidal action on 8505C cells indicates the involvement of caspase-induced apoptosis, accompanied by a considerable reduction in ROS/RNS and proliferation potential of treated cells.",
publisher = "Basel: MDPI",
journal = "Biomolecules",
title = "(Pentamethylcyclopentadienyl)chloridoiridium(III) Complex Bearing Bidentate Ph2PCH2CH2SPh-κP,κS Ligand",
number = "4",
volume = "14",
doi = "10.3390/biom14040420",
pages = "420"
}

Ludwig, G., Ranđelović, I., Dimić, D., Komazec, T., Maksimović-Ivanić, D., Mijatović, S., Rüffer, T.,& Kaluđerović, G. N.. (2024). (Pentamethylcyclopentadienyl)chloridoiridium(III) Complex Bearing Bidentate Ph2PCH2CH2SPh-κP,κS Ligand. in Biomolecules
Basel: MDPI., 14(4), 420.
https://doi.org/10.3390/biom14040420

Ludwig G, Ranđelović I, Dimić D, Komazec T, Maksimović-Ivanić D, Mijatović S, Rüffer T, Kaluđerović GN. (Pentamethylcyclopentadienyl)chloridoiridium(III) Complex Bearing Bidentate Ph2PCH2CH2SPh-κP,κS Ligand. in Biomolecules. 2024;14(4):420.
doi:10.3390/biom14040420 .

Ludwig, Gerd, Ranđelović, Ivan, Dimić, Dušan, Komazec, Teodora, Maksimović-Ivanić, Danijela, Mijatović, Sanja, Rüffer, Tobias, Kaluđerović, Goran N., "(Pentamethylcyclopentadienyl)chloridoiridium(III) Complex Bearing Bidentate Ph2PCH2CH2SPh-κP,κS Ligand" in Biomolecules, 14, no. 4 (2024):420,
https://doi.org/10.3390/biom14040420 . .

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 .