Issue 13, 2017

Novel organotin(iv) complexes derived from 4-fluorophenyl-selenoacetic acid: synthesis, characterization and in vitro cytostatic activity evaluation

Abstract

A cluster of novel organotin(IV) complexes with the formulas [Me3Sn(O2CCH2SeC6H4F-p)]n (1), [(Me2Sn)43-O)2(O2CCH2SeC6H4F-p)4] (2), [n-Bu3Sn(O2CCH2SeC6H4F-p)]n (3) and [n-Bu2Sn(O2CCH2SeC6H4F-p)2] (4) were designed, synthesized, and characterized by elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) spectroscopy as well as single-crystal X-ray diffraction. Complexes 1 and 3 represent one-dimensional (1D) coordination polymers composed of alternate [Sn–O]2. The molecular spatial structure of 2 revealed it to be tetranuclear possessing a ladder-like structure and containing four carboxylate ligands. The 1D chain was formed by C–H⋯F interaction. Complex 4 was a monomer connected into a 1D coordination polymer through the intermolecular interaction C–H⋯O. Meanwhile, four novel corresponding organosulfurtin complexes (5–8) were also prepared. Furthermore, complexes 1–4 and 5–8 were evaluated for their in vitro cytostatic activity against human breast cancer cell lines (MDA-MB-231). The preliminary screening showed that the organotin derivatives with an n-butyl group (3, 4 and 7, 8) exhibited significantly higher cytostatic activity than those with a methyl group (1, 2 and 5, 6). Mechanically, further cytotoxic assessments of complex 4 in mediated MDA-MB-231 cells were conducted, and the results revealed that the anti-proliferative and pro-apoptotic effect of complex 4 in MDA-MB-231 cells prominently contributed to the boosted ROS, collapsed mitochondrial membrane potential and the release of cytochrome c from the outer membrane of the mitochondria, which sequently activated caspase-3, the executioner, which was responsible for complex 4's chemotherapeutic potential against MDA-MB-231 cells.

Graphical abstract: Novel organotin(iv) complexes derived from 4-fluorophenyl-selenoacetic acid: synthesis, characterization and in vitro cytostatic activity evaluation

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2017
Accepted
18 May 2017
First published
18 May 2017

New J. Chem., 2017,41, 5639-5650

Novel organotin(IV) complexes derived from 4-fluorophenyl-selenoacetic acid: synthesis, characterization and in vitro cytostatic activity evaluation

Y. Qiu, R. Zhang, S. Zhang, S. Cheng, Q. Li and C. Ma, New J. Chem., 2017, 41, 5639 DOI: 10.1039/C7NJ00500H

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