Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione

Bakalova, Adriana; Varbanov, Hristo P.; Buyukliev, Rossen; Momekov, Georgi; Ferdinandov, Dilyan; Konstantinov, Spiro; Ivanov, D.

doi:10.1016/j.ejmech.2007.06.025

Cited by 30 publications

(22 citation statements)

References 17 publications

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“…Among the higher oxidation state complexes the tetrachloro Pt(IV) compound 3 exhibited superior activity, whereas the compound with dihydroxo axial ligands exerted only marginal activity. These findings and especially the superior activity of chloro ligands-bearing complexes are in accordance with the structure activity rules established for similar series of compounds with hydantoin ligands presented in our previous studies [4,6].…”

Section: In-vitro Toxicitysupporting

confidence: 90%

“…1. The structures are confirmed by the IR and NMR spectra of the new compounds and are in accordance with previously synthesized by us complexes [4][5][6][7].…”

Section: Chemistrysupporting

confidence: 81%

“…The elemental analysis for the new ligand 3,5-dimethyl-5-(4-pyridyl)hydantoin, its Pt(II) and Pt(IV) complexes, and the new Pt(IV) complex with 5-methyl-5-(4-pyridyl)-hydantoin were in agreement with the following formulae: C 10 (1)(2)(3)(4) are given in Fig. 1.…”

Section: Chemistrymentioning

confidence: 89%

“…The newly four synthesized and tested complexes were added to 12 previously evaluated compounds [4][5][6][7] and a set of 16 similar compounds was compiled. Free-Wilson model was derived by PLS and the contribution of each substituent was assessed quantitatively.…”

Section: Qsar Methods Qsarmentioning

confidence: 99%

“…Data from the elemental analysis, IR, NMR spectral analysis and molar conductivity demonstrated the coordination mode of the ligands with metal ions. In all complexes the ligand was coordinated monodentatelly with M 2þ and Pt 4þ via N-atom from the pyridine ring [4][5][6][7]. The present study represents the synthesis and physicochemical evaluation of four new Pt(II) and Pt(IV) complexes with 3,5-dimethyl-5-(4-pyridyl)hydantoin (L) and 5-methyl-5-(4-pyridyl)hydantoin (L 1 ).…”

Section: Introductionmentioning

confidence: 99%

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Platinum Complexes with 5‐Methyl‐5(4‐pyridyl)hydantoin and Its 3‐Methyl Derivatives: Synthesis and Cytotoxic Activity – Quantitative Structure‐Activity Relationships

Bakalova

Varbanov

Buyukliev

et al. 2010

Archiv der Pharmazie

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3,5-Dimethyl-5-(4-pyridyl)hydantoin (L) and its platinum(II) and platinum(IV) complexes with the general formula cis-[PtL(2) X(2) ] · n H(2) O and [PtL(2) Cl(4) ], where XCl, I and n = 2-4 were synthesized. A new Pt(IV) complex with 5-methyl-5-(4-pyridyl)hydantoin (L') with the formula cis-[Pt(L')(2) Cl(2) (OH)(2) ] · 5 H(2) O was also synthesized. The novel compounds were characterized by elemental analysis, IR, (1) H-, (13) C-, (195) Pt-NMR spectra and molar conductivity. The cytotoxic effects of these complexes were examined on three human tumor cell lines by MTT-dye reduction assay. These four new Pt(II) and Pt(IV) complexes and a set of another twelve Pt(II), Pt(IV), and Pd(II) complexes previously synthesized and tested were compiled and a QSAR model was derived in order to direct the further rational synthesis.

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Section: In-vitro Toxicitysupporting

confidence: 90%

“…1. The structures are confirmed by the IR and NMR spectra of the new compounds and are in accordance with previously synthesized by us complexes [4][5][6][7].…”

Section: Chemistrysupporting

confidence: 81%

Section: Chemistrymentioning

confidence: 89%

Section: Qsar Methods Qsarmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Platinum Complexes with 5‐Methyl‐5(4‐pyridyl)hydantoin and Its 3‐Methyl Derivatives: Synthesis and Cytotoxic Activity – Quantitative Structure‐Activity Relationships

Bakalova

Varbanov

Buyukliev

et al. 2010

Archiv der Pharmazie

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Metal‐based antitumor, cytotoxic and antimicrobial activity: pharmacological evaluation of Knoevenagel condensate β‐diketone Schiff base thiosemicarbazone Cu(II) and Zn(II) complexes

Raman¹,

Jeyamurugan²,

Balasubramanian³

et al. 2009

Applied Organom Chemis

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Knoevenagel condensate Schiff base ligands [L = 3-cinnamalideneacetylacetone-thiosemicarbazone (CAT)/3-cinnamalideneacetylacetoneethylthiosemicarbazone (CAET)/3-cinnamalideneacetylacetonephenylthiosemicarbazone (CAPT)] and their copper/zinc complexes were synthesized. They were characterized by analytical and spectral techniques. From these data it was found that the ligands adopt square-planar geometry on metalation with Cu 2+ and Zn 2+ . To evaluate the antitumor and cytotoxic activity of the synthesized complexes in mice and human cancer cell lines, the antitumor activity of the complexes was evaluated against an Ehrlich ascites carcinoma (EAC) tumor model. The activity was assessed using survival time and short-term in vitro cytotoxic activity. Oral administration of complexes (100 mg/kg) increased the survival time. The cytotoxic activity of complexes was evaluated using human breast cancer (MDA-MB-231), colon cancer (HCT-116) and nonsmall lung cancer (NCI-H-23) cell lines. Both the complexes possessed significant antitumor and cytotoxic activity on EAC and human cancer cell lines. The in vitro antimicrobial screening effect of the investigated compounds was also tested against the various organisms by well diffusion method.

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Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

Shi

Nie

et al. 2020

Applied Organom Chemis

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A Cu(II)–coumarin complex, [CuL2(NO3)2] (2), where L = 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin (1), was synthesized with Cu(NO3)2⋅3H2O and characterized using elemental, infrared and single‐crystal X‐ray diffraction analyses. The crystal structure of 1 shows that all the pyrone, benzene and pyridine rings are completely coplanar. The crystal structure of 2 is stabilized by intermolecular C–H···O and C–H···N hydrogen bonds and C···C short contacts, which lead to the formation of a two‐dimensional network structure. Density functional theory results give support to the experimentally determined monomeric structure. The in vitro cytotoxic activities of 1 and 2 were investigated against HeLa (cervical carcinoma), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein) cells by MTT assay. The IC50 values show that both 1 and 2 have lower toxicity than doxorubicin and cisplatin in every case. Ligand 1 exhibits higher anti‐HeLa activity than doxorubicin. Complex 2 displays higher anti‐HeLa activity than coumarin but lower than that of cisplatin. Various spectroscopic approaches indicate that 1 and 2 could effectively bind with DNA through intercalation mode.

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Synthesis, characterization and biological activity of Pt(II) and Pt(IV) complexes with 5-methyl-5(4-pyridyl)-2,4-imidazolidenedione

Cited by 30 publications

References 17 publications

Platinum Complexes with 5‐Methyl‐5(4‐pyridyl)hydantoin and Its 3‐Methyl Derivatives: Synthesis and Cytotoxic Activity – Quantitative Structure‐Activity Relationships

Platinum Complexes with 5‐Methyl‐5(4‐pyridyl)hydantoin and Its 3‐Methyl Derivatives: Synthesis and Cytotoxic Activity – Quantitative Structure‐Activity Relationships

Metal‐based antitumor, cytotoxic and antimicrobial activity: pharmacological evaluation of Knoevenagel condensate β‐diketone Schiff base thiosemicarbazone Cu(II) and Zn(II) complexes

Synthesis, crystal structure, antiproliferative activity, DNA binding and density functional theory calculations of 3‐(pyridin‐2‐yl)‐8‐tert‐butylcoumarin and its copper(II) complex

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