Synthesis, crystal structure and anti-cancer activity of the complex chlorido-(η(2)-ethyl-ene)(quinolin-8-olato-κ(2)N,O)platinum(II) by experimental and theoretical methods

采用实验和理论方法合成、研究氯代-(η(2)-亚乙基)(喹啉-8-醇盐-κ(2)N,O)铂(II)配合物的晶体结构及其抗癌活性

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Abstract

The complex [Pt(C(9)H(6)NO)Cl(C(2)H(4))], (I), was synthesized and structurally characterized by ESI mass spectrometry, IR, NMR spectroscopy, DFT calculations and X-ray diffraction. The results showed that the deprotonated 8-hy-droxy-quinoline (C(9)H(6)NO) coordinates with the Pt(II) atom via the N and O atoms while the ethyl-ene coordinates in the η(2) manner and in the trans position compared to the coordinating N atom. The crystal packing is characterized by C-H⋯O, C-H⋯π, Cl⋯π and Pt⋯π inter-actions. Complex (I) showed high selective activity against Lu-1 and Hep-G2 cell lines with IC(50) values of 0.8 and 0.4 µM, respectively, 54 and 33-fold more active than cisplatin. In particular, complex (I) is about 10 times less toxic to normal cells (HEK-293) than cancer cells Lu-1 and Hep-G2. Furthermore, the reaction of complex (I) with guanine at the N7 position was proposed and investigated using the DFT method. The results indicated that replacement of the ethyl-ene ligand with guanine is thermodynamically more favorable than the Cl ligand and that the reaction occurs via two consecutive steps, namely the replacement of ethyl-ene with H(2)O and the water with the guanine mol-ecule.

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