Platinum(II) complexes with steroidal esters of l-methionine and l-histidine: Synthesis, characterization and cytotoxic activity

Twelve steroidal platinum(II) complexes were synthesized by reaction of potassium tetrachloroplatinate with steroidal esters of l-methionine and l-histidine. The steroidal esters coordinated as bidentate ligands via S and N donor atoms of l-methionine and via two N donor atoms of l-histidine. Choles...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-04, Vol.16 (7), p.3704-3713
Main Authors: Kvasnica, Miroslav, Budesinsky, Milos, Swaczynova, Jana, Pouzar, Vladimir, Kohout, Ladislav
Format: Article
Language:English
Subjects:
Antineoplastic agents
Biological and medical sciences
Cell Line, Tumor
Cell Survival - drug effects
Cytotoxicity
Esters - chemical synthesis
Esters - chemistry
Esters - toxicity
General aspects
Histidine - chemistry
Humans
l-Histidine
l-Methionine
Magnetic Resonance Spectroscopy
Medical sciences
Methionine - chemistry
Molecular Structure
NMR spectroscopy
Pharmacology. Drug treatments
Platinum - chemistry
Platinum(II) complexes
Steroid
Steroids - chemistry
Structure-Activity Relationship
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Summary:Twelve steroidal platinum(II) complexes were synthesized by reaction of potassium tetrachloroplatinate with steroidal esters of l-methionine and l-histidine. The steroidal esters coordinated as bidentate ligands via S and N donor atoms of l-methionine and via two N donor atoms of l-histidine. Cholesterol, cholestanol, diosgenine, pregnenolone, dehydroepiandrosterone, testosterone, estrone, and estradiol were used as the steroidal compounds. The esters and complexes prepared were characterized by infrared, mass, and 1H NMR spectroscopy and elemental analysis. Platinum complexes were tested for in vitro cytotoxicity against several cancer cell lines: T-lymphoblastic leukemia CEM, breast carcinoma MCF-7, lung carcinoma A-549, multiple myeloma RPMI 8226, and one normal cell line human fibroblast BJ.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2008.02.003