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

Manolov, Ilia; Kostova, Irena; Netzeva, Tatiana I.; Konstantinov, Spiro; Karaivanova, Margarita

doi:10.1002/(sici)1521-4184(20004)333:4<93::aid-ardp93>3.0.co;2-n

Cited by 56 publications

(37 citation statements)

References 7 publications

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“…The complexes have revealed good anticoagulant action. As a result from our earlier work the cytotoxic profile of some complexes of mendiaxon, warfarin, coumachlor, and niffcoumar with lanthanides against P3HR1, K-562, and THP-1 cell lines was proved [10][11][12] .…”

Section: Introductionmentioning

confidence: 89%

Synthesis, Physicochemical Characterization, and Cytotoxic Screening of New Zirconium Complexes with Coumarin Derivatives

Kostova

Manolov

Karaivanova

2001

Arch. Pharm. Pharm. Med. Chem.

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Zirconium complexes of mendiaxon, warfarin, coumachlor, and niffcoumar have been synthesized by reaction of the ligands with zirconium chloride in stoichiometric ratio 1:2. The formation of the complexes has been proved on the basis of elemental analysis, IR‐spectroscopy, 1H‐NMR spectroscopy, and thermal studies. Differential thermal analyses and thermogravimetric analyses have been applied to study the compositions of the new complexes. 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, but mendiaxon is bonded as monodentate ligand. Cytotoxic screening by MTT‐assay was carried out. Among these compounds the zirconium complex of mendiaxon showed highest cytotoxic activity against human promyelocytic leukemic HL‐60 cells. The inorganic salt was found to be active against this cell line.

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Section: Introductionmentioning

confidence: 89%

Synthesis, Physicochemical Characterization, and Cytotoxic Screening of New Zirconium Complexes with Coumarin Derivatives

Kostova

Manolov

Karaivanova

2001

Arch. Pharm. Pharm. Med. Chem.

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“…[12] The compound has been characterized and identified on the basis of elemental analysis, conductivities, and NMR-spectroscopy.…”

Section: Experimental Synthesismentioning

confidence: 99%

“…In acenocoumarol sodium salt the carbonyl vibration C 35 O 36 stretch is calculated at 1727 cm −1 and is observed at ν IR = 1713 cm −1 as a medium band, ν Raman = 1707 cm −1 as a weak band. The C 12 …”

Section: Carbonyl Vibrationmentioning

confidence: 99%

Theoretical and vibrational spectral investigation of sodium salt of acenocoumarol

Joe¹,

Kostova²,

Ravikumar³

et al. 2009

J Raman Spectroscopy

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The FT-IR and FT-Raman spectra of sodium salt of 4-hydroxy-3[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one (acenocoumarol sodium salt) in solid phase have been recorded and analyzed. The optimization geometry, intramolecular hydrogen bonding, and harmonic vibrational wavenumbers of acenocoumarol sodium salt have been investigated with the help of B3LYP density functional theory (DFT) methods. The infrared and Raman spectra were predicted theoretically from the calculated intensities. Natural bond orbital (NBO) analysis indicates the presence of C-H· · ·O hydrogen bonding in the molecule. The first static hyperpolarizability of the molecule has been computed.

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“…These researchers found that the most potent platinum-coumarin complex had functional groups attached at position six. More recently, Manalov et al (2002) investigated the in vitro cytotoxicity of a number of coumarin complexes with the late transition metal, cerium, using both Burkitt lymphoma (P3HR1) and leukemic (THP-1) cell lines. These researchers found that complexation resulted in a 40% increase in cytotoxicity, compared to the metal-free ligand.…”

Section: Introductionmentioning

confidence: 99%

Apoptotic cell death: A possible key event in mediating the in vitro anti-proliferative effect of a novel copper(II) complex, [Cu(4-Mecdoa)(phen)2] (phen=phenanthroline, 4-Mecdoa=4-methylcoumarin-6,7-dioxactetate), in human malignant cancer cells

Thati

Noble

Creaven

et al. 2007

European Journal of Pharmacology

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The central objective of the current study was to investigate the potential in vitro anti-proliferative effect of the parent ligand, 4-methylcoumarin-6,7-dioxyacyeic acid (4-MecdoaH 2 ), and its copper (II) complex, bis(phenanthroline4-methylcoumarin-6,7-dioxacetatocopper(II) ([Cu(4-Mecdoa)(phen) 2 ]) using four human model cell lines. In addition, selected mechanistic studies were carried out using the most sensitive of the four cell lines. Results obtained show that the complex could alter proliferation of both human neoplastic renal (A-498) and hepatic (HepG2) cells. Furthermore, non-neoplastic hepatic (CHANG) cells appeared to be less sensitive. However, this effect was not duplicated with nonneoplastic renal (HK-2) cells, a profile shared by cisplatin. The observed anti-proliferative effect appeared to be dose-and time-dependent, and could be attributed to the complex, rather than any of the free components i.e. the 1,10-phenanthroline or coumarin ligand, or the simple metal salt. Furthermore, the complex was shown to decrease DNA synthesis, but did not intercalate with it. Based on IC 50 values, [Cu(4-Mecdoa)(phen) 2 ] was shown to be almost 12 times more potent than cisplatin. Moreover, there was no evidence that P-glycoprotein-mediated multi-drug resistance was likely to decrease anti-proliferative activity. Cytological stains, analysis of genomic DNA, and biochemical assays [caspase-3 and -9 and cleaved poly(ADP-ribose)-polymerase protein], showed that cell death could switch between apoptosis and necrosis, and this effect appeared to be concentration-dependent. Additionally, flow cytometric analysis showed that the complex functioned through an alteration in cell cycle progression. Taken together, [Cu(4-Mecdoa)(phen) 2 ] has been shown to be a more potent anti-proliferative agent than either the ligand or cisplatin, and is capable of altering key biochemical events leading to the execution of apoptotic and/or necrotic cell death, suggesting that it is worthy of further investigation.

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

Cited by 56 publications

References 7 publications

Synthesis, Physicochemical Characterization, and Cytotoxic Screening of New Zirconium Complexes with Coumarin Derivatives

Synthesis, Physicochemical Characterization, and Cytotoxic Screening of New Zirconium Complexes with Coumarin Derivatives

Theoretical and vibrational spectral investigation of sodium salt of acenocoumarol

Apoptotic cell death: A possible key event in mediating the in vitro anti-proliferative effect of a novel copper(II) complex, [Cu(4-Mecdoa)(phen)2] (phen=phenanthroline, 4-Mecdoa=4-methylcoumarin-6,7-dioxactetate), in human malignant cancer cells

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