Cytotoxic Activity of Cerium Complexes with Coumarin Derivatives. Molecular Modeling of the Ligands

• Published in: Archiv der Pharmazie (Weinheim) Vol. 333; no. 4; pp. 93 - 98
• Main Authors: Manolov, Ilia, Kostova, Irena, Netzeva, Tatiana, Konstantinov, Spiro, Karaivanova, Margarita
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.04.2000; WILEY‐VCH Verlag GmbH; Wiley-VCH
• Subjects: 4-Hydroxycoumarins - chemistry; 4-Hydroxycoumarins - pharmacology; Antineoplastic agents; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Cell Survival - drug effects; Cerium - chemistry; Cerium - pharmacology; Cerium complexes; coumarin derivatives; Coumarins - chemistry; Coumarins - pharmacology; cytotoxic activity; General aspects; Humans; Hymecromone - chemistry; Hymecromone - pharmacology; Ligands; Magnetic Resonance Spectroscopy; Medical sciences; Models, Molecular; Organometallic Compounds - chemistry; Organometallic Compounds - pharmacology; Pharmacology. Drug treatments; quantum mechanics; Spectrophotometry, Infrared; Tumor Cells, Cultured - drug effects; Warfarin - chemistry; Warfarin - pharmacology; Antineoplastic agent; Human; Warfarin; Monocyte; Coumarine derivatives; Burkitt lymphoma; Organic ligand; Cytotoxicity; Lactone; Oxygen heterocycle; In vitro; Modeling; Infection; Cell line; Structure activity relation; Viral disease; Molecular model; Bicyclic compound; Aromatic compound; Lanthanide Complexes; Chemical synthesis; Tumor cell; Cerium Complexes
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/(SICI)1521-4184(20004)333:4<93::AID-ARDP93>3.0.CO;2-N

Cerium complexes of Umbellipherone, Mendiaxon, Warfarin, Coumachlor, and Niffcoumar have been synthesized by reaction of the ligands with cerium nitrate in a stoichiometric ratio of 1:2. The formation of the complexes has been proved on the basis of elemental analysis, conductivities, IR spectroscopy, and 1H‐NMR spectroscopy. The molecules of the ligands were optimized by means of the semiempirical quantum mechanical method PM3 to the energetically most stable conformers. All the ligands were characterized by molecular and submolecular electronic indices and the putative donor centers are proposed. It is concluded that the lactone‐ and the keto‐carbonyl groups of Warfarin, Coumachlor, and Niffcoumar are bonded to the metal ion as bidentate ligands. The other two coumarins are bonded as monodentate ligands. Conductivity measurements show the non‐electrolytic nature of the complexes. Cytotoxic screening by MTT assay was carried out. The cerium complexes were found to be more active than the inorganic salts.