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Structure–activity relationships in cytotoxic AuI/AuIII complexes derived from 2-(2′-Pyridyl)benzimidazole

Maiore, Laura and Aragoni, Maria Carla and Deiana, Carlo and Cinellu, Maria Agostina and Isaia, Francesco and Lippolis, Vito and Pintus, Anna and Serratrice, Maria and Arca, Massimiliano (2014) Structure–activity relationships in cytotoxic AuI/AuIII complexes derived from 2-(2′-Pyridyl)benzimidazole. Inorganic Chemistry, Vol. 53 (8), p. 4068-4080. ISSN 0020-1669. eISSN 1520-510X. Article.

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DOI: 10.1021/ic500022a

Abstract

Gold(I) and gold(III) complexes derived from 2-(2′-pyridyl)benzimidazole (pbiH) were proven to be a promising class of in vitro antitumor agents against A2780 human ovarian cancer cells. In this paper, a comparative electrochemical, UV—vis absorption, and emission spectroscopic investigation is reported on pbiH, the two mononuclear AuIII complexes [(pbi)AuX2] (X = Cl (1), AcO (2)), the four mononuclear AuI derivatives [(pbiH)AuCl] (3), [(pbiH)Au(PPh3)]PF6 ((4+)(PF6)), [(pbi)Au(PPh3)] (5), and [(pbi)Au(TPA)] (6), the three mixed-valence AuIII/AuI complexes [(μ-pbi)Au2Cl3] (7), [(Ph3P)Au([(μ-pbi)AuX2]PF6 (X = Cl ((8+)(PF6)), AcO ((9<7+)(PF6))), and the binuclear AuI—AuI compound [([(μ-pbi)Au2(PPh3)2]PF6 ((10+)(PF6)). All complexes feature irreversible reduction processes related to the AuIII/AuI or AuI/Au0 processes and peculiar luminescent emission at about 360–370 nm in CH2Cl2, with quantum yields that are remarkably lower ((0.7–14.5) × 10–2) in comparison to that determined for the free pbiH ligand (31.5 × 10–2) in the same solvent. The spectroscopic and electrochemical properties of all complexes were interpreted on the grounds of time-dependent PBE0/DFT calculations carried out both in the gas phase and in CH2Cl2 implicitly considered within the IEF-PCM SCRF approach. The electronic structure of the complexes, and in particular the energy and composition of the Kohn—Sham LUMOs, can be related to the antiproliferative properties against the A2780 ovarian carcinoma cell line, providing sound quantitative structure–activity relationships and shedding a light on the role played by the global charge and nature of ancillary ligands in the effectiveness of Au-based antitumor drugs.

Item Type:Article
ID Code:10240
Status:Published
Refereed:Yes
Uncontrolled Keywords:Antitumor agents, pbiH ligands, A2780 ovarian cancer cells
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:American Chemical Society
ISSN:0020-1669
eISSN:1520-510X
Deposited On:29 Oct 2014 17:37

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