Investigation of acid–base behaviour of some 2-pyridylbenzimidazoles using semi-empirical methods

Kaniskan, Nevin; Öğretır, Cemi̇l

doi:10.1016/s0166-1280(02)00018-0

Cited by 11 publications

(5 citation statements)

References 5 publications

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“…The molecular structure of (36) comprised a five-coordinate copper centre with the metal bound to two chelating HTBZ and one chloride ion. Because of the contemporary presence of the benzimidazole moiety and of the carboxylic group, the ligand potential could be enhanced by the chance to act both as acid and base [127] suggesting that HTBZ and PYBZ could be either neutral or anionic chelators or that they might simply act as countercations [125,128]. Testing HTBZ, (37) In an effort to further develop this class of potential anticancer agents, Devereux et al [126] studied the synthesis and chemotherapeutic potential of a series of novel copper(II) carboxylate complexes derived from HTBZ and 2-(2-pyridyl)benzimidazole (PYBZ).…”

Section: Imidazole Benzimidazole Pyrazole and Triazole Complexesmentioning

confidence: 99%

Copper Complexes as Anticancer Agents

Marzano

Pellei²,

Tisato³

et al. 2009

ACAMC

736

395

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Metal-based antitumor drugs play a relevant role in antiblastic chemotherapy. Cisplatin is regarded as one of the most effective drugs, even if severe toxicities and drug resistance phenomena limit its clinical use. Therefore, in recent years there has been a rapid expansion in research and development of novel metal-based anticancer drugs to improve clinical effectiveness, to reduce general toxicity and to broaden the spectrum of activity. The variety of metal ion functions in biology has stimulated the development of new metallodrugs other than Pt drugs with the aim to obtain compounds acting via alternative mechanisms of action. Among non-Pt compounds, copper complexes are potentially attractive as anticancer agents. Actually, since many years a lot of researches have actively investigated copper compounds based on the assumption proposal that endogenous metals may be less toxic. It has been established that the properties of copper-coordinated compounds are largely determined by the nature of ligands and donor atoms bound to the metal ion. In this review, the most remarkable achievements in the design and development of copper(I, II) complexes as antitumor agents are discussed. Special emphasis has been focused on the identification of structure-activity relationships for the different classes of copper(I,II) complexes. This work was motivated by the observation that no comprehensive surveys of copper complexes as anticancer agents were available in the literature. Moreover, up to now, despite the enormous efforts in synthesizing different classes of copper complexes, very few data concerning the molecular basis of the mechanisms underlying their antitumor activity are available. This overview, collecting the most significant strategies adopted in the last ten years to design promising anticancer copper(I,II) compounds, would be a help to the researchers working in this field.

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Section: Imidazole Benzimidazole Pyrazole and Triazole Complexesmentioning

confidence: 99%

Copper Complexes as Anticancer Agents

Marzano

Pellei²,

Tisato³

et al. 2009

ACAMC

736

395

View full text Add to dashboard Cite

show abstract

“…Like the phenanthroline based ligands these compounds are known to chelate to metal centres although their coordination chemistry has not been as extensively explored. Furthermore, because of the presence of the benzimidazole moiety their potential as ligands is enhanced by their ability to act as both acids and bases [8] suggesting that they can be either neutral or anionic chelators or they may simply be found in complexes as cationic counterions [9]. Complexes of TBZH, whether in solution or in the solid state, tend to have the ligand bound to the metal centres (regardless of the nature of the metal ion) through the imidazolic and thiazole nitrogen atoms [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4′-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands

Devereux

Shea

Kellett

et al. 2007

Journal of Inorganic Biochemistry

183

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“…Hela and Hep-G2 were incubated for 48 h. After that, 20 μL of MTT (5 mg/mL) was added. Four hours later, the supernatant of 96-well plates was carefully blotted, and the DMSO (150 μL) was added to solve the formazan produced [38,39]. Colorimetry was performed at the wavelength of 570 nm.…”

Section: Anticancer Activitymentioning

confidence: 99%

Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

Chen

Liu

2019

Eur J Chem

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Two bis(8-quinolinolato-N,O)-platinum(II) complexes, C18H12N2O2Pt (1) and C20H16N2O2Pt (2), were synthesized and characterized by FT-IR, elementary analysis and X-ray single crystal diffraction. Complex 1 crystallizes in monoclinic, space group P21/c with a = 9.3413(7), b = 10.3893(9), c = 14.8495(12) Å, β = 100.574(7)°, V = 1416.7(2) Å3. Complex 2 crystallizes in monoclinic, space group P21/n with a = 9.5115(11), b = 15.5692(18), c = 16.720(2) Å, β = 94.544(2)°, V = 2468.3(5) Å3. Intermolecular C-H···O hydrogen bonding interactions, as well as Pt···Pt and π-π stacking interactions, help to stabilize the crystal structures. The preliminary in vitro anticancer activity of complexes 1 and 2 and the corresponding ligands (L1 and L2) were investigated using human cervical (Hela) and hepatocellular carcinoma (Hep-G2) cancer cell lines. The platinum(II) complexes can greatly inhibit the cell proliferation and show stronger cytotoxic activities against the tested cancer cell lines than both ligands.

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Investigation of acid–base behaviour of some 2-pyridylbenzimidazoles using semi-empirical methods

Cited by 11 publications

References 5 publications

Copper Complexes as Anticancer Agents

Copper Complexes as Anticancer Agents

Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4′-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands

Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

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