Di- and tri-organotin(IV) complexes of arylhydrazones of methylene active compounds and their antiproliferative activity

Kamran T. Mahmudov, M. Fatima C. Guedes da Silva, Maximilian N. Kopylovich, Maria Alexandra Núncio de Carvalho Ramos Fernandes, Ana Silva, Archana Mizar, Armando J. L. Pombeiro

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Abstract

Two organotin(IV) complexes, [Sn(C6H5)(3)HL1] (1) and [Sn(C2H5)(2)(1 kappa O, 2 kappa O-H3L2)(1 kappa O-2-H3L2)(mu(3)-O)](2) (2), were isolated upon interaction of Ph3SnCl and Et2SnO with 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl) benzoic acid (H2L1) and 2-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzoic acid (H4L2), respectively, in toluene solution. Complexes 1 and 2 were characterized by IR and NMR spectroscopies, elemental and single crystal X-ray diffraction analyses. While in 1 the (HL1)(-) ligand binds the metal in a chelating bidentate mode, in 2 the (H3L2)(-) anion acts not only as a chelating bidentate but also as a bridging bidentate donor. The in vitro antiproliferative activity against human colorectal carcinoma (HCT116) and human hepatocellular carcinoma (HEPG2) cells lines demonstrated that compound 1 possesses high in vitro antiproliferative activity with IC50 values of 0.0284 +/- 0.0001 mu M and 0.287 +/- 0.0001 mu M for HCT116 and HEPG2 cells, respectively. Crown Copyright (C) 2014 Published by Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)67-73
Number of pages7
JournalJournal Of Organometallic Chemistry
Volume760
DOIs
Publication statusPublished - 15 Jun 2014

Keywords

  • Organotin complexes
  • Arylhydrazones of methylene active compounds
  • X-ray analysis
  • Antiproliferative activity
  • CRYSTAL-STRUCTURES
  • COPPER(II) COMPLEXES
  • ORGANOTIN COMPOUNDS
  • ANTITUMOR-ACTIVITY
  • DIORGANOTIN(IV) DERIVATIVES
  • ANTIMICROBIAL ACTIVITY
  • CANCER-CHEMOTHERAPY
  • ANTICANCER ACTIVITY
  • CYTOTOXIC ACTIVITY
  • INDUCED APOPTOSIS

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