1-(2-Picolyl)-substituted 1,2,3-triazole as novel chelating ligand for the preparation of ruthenium complexes with potential anticancer activity

被引：80

作者：

Bratsos, Ioannis ^{[1
]}

Urankar, Damijana ^{[2
]}

Zangrando, Ennio ^{[1
]}

Genova-Kalou, Petia ^{[3
]}

Kosmrlj, Janez ^{[2
]}

Alessio, Enzo ^{[1
]}

Turel, Iztok ^{[2
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim & Farmaceut, I-34127 Trieste, Italy

[2] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana, Slovenia

[3] Natl Ctr Infect & Parasit Dis, Dept Virol, Lab Herpesvirus Infect & Cell Cultures, Sofia 1233, Bulgaria

来源：

DALTON TRANSACTIONS | 2011年 / 40卷 / 19期

关键词：

AZIDE-ALKYNE CYCLOADDITION; PRECLINICAL DEVELOPMENT; SULFOXIDE COMPLEXES; TERMINAL ALKYNES; ARENE COMPLEXES; HALF-SANDWICH; IN-VITRO; PHASE-I; AGENT; CLICK;

D O I：

10.1039/c0dt01807d

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The 1,4-disubstituted 1,2,3-triazole ligand prepared by click chemistry 1-(2-picolyl)-4-phenyl-1H-1,2,3-triazole (ppt) was investigated as novel chelating ligand for Ru(II) complexes with potential antitumor activity. The preparation and structural characterization, mainly by NMR spectroscopy in solution and by X-Ray crystallography in the solid state, of four new Ru(II) complexes is reported: two isomeric Ru-dmso compounds, trans, cis-[RuCl2(dmso-S)(2)(ppt)] (1) and cis, cis-[RuCl2(dmso-S)(2)(ppt)] (2), and two half-sandwich Ru-[9]aneS(3) coordination compounds, [Ru([9]aneS(3))(dmso-S)(ppt)][CF3SO3](2) (3) and [Ru([9]aneS(3))Cl(ppt)][CF3SO3] (4). In all compounds ppt firmly binds to ruthenium in a bidentate fashion through the pyridyl nitrogen atom and the triazole N2, thus forming a puckered six-membered ring. The chemical behavior in aqueous solution of the water-soluble complexes 3 and 4 was studied by UV-Vis and NMR spectroscopy and compared to that of the previously described organometallic analogue [Ru(eta(6)-p-cymene)Cl(ppt)][Cl] (5) in view of their potential antitumor activity. Compounds 3-5 were tested also in vitro for cytotoxic activity against two human cancer cell lines, one sensitive and one resistant to cisplatin, in comparison with cisplatin. Compound 4, the one that aquates faster, was found to be more cytotoxic than cisplatin against human lung squamose carcinoma cell line (A-549).

引用

页码：5188 / 5199

页数：12

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