Investigational New Drugs

, Volume 29, Issue 2, pp 285–299

Dibutyltin(IV) complexes containing arylazobenzoate ligands: chemistry, in vitro cytotoxic effects on human tumor cell lines and mode of interaction with some enzymes

Authors

    • Department of ChemistryNorth-Eastern Hill University
  • Anup Paul
    • Department of ChemistryNorth-Eastern Hill University
  • Lorenzo Pellerito
    • Dipartimento di Chimica Inorganica e Analitica“Stanislao Cannizzaro”, Università degli Studi di Palermo
  • Michelangelo Scopelliti
    • Dipartimento di Chimica Inorganica e Analitica“Stanislao Cannizzaro”, Università degli Studi di Palermo
  • Palwinder Singh
    • Department of ChemistryGuru Nanak Dev University
  • Pooja Verma
    • Department of ChemistryGuru Nanak Dev University
  • Andrew Duthie
    • School of Life & Environmental ScienceDeakin University
  • Dick de Vos
    • Pharmachemie BV
  • Edward R. T. Tiekink
    • Department of ChemistryUniversity of Malaya
PRECLINICAL STUDIES

DOI: 10.1007/s10637-009-9360-3

Cite this article as:
Basu Baul, T.S., Paul, A., Pellerito, L. et al. Invest New Drugs (2011) 29: 285. doi:10.1007/s10637-009-9360-3

Summary

Dibutyltin(IV) complexes of composition Bu2Sn(LH)2, where LH is a carboxylate residue derived from 2-[(E)-(5-tert-butyl-2-hydroxyphenyl)diazenyl]benzoate (L1H) with water molecule (1), 4-[(E)-(5-tert-butyl-2-hydroxyphenyl)diazenyl]benzoate (L2H) (2) and 4-[(E)-(4-hydroxy-5-methylphenyl)diazenyl]benzoate (L3H) (3), were synthesized and characterized by spectroscopic (1H, 13C and 119Sn NMR, IR, 119Sn Mössbauer) techniques. A full characterization was accomplished from the crystal structure of complex 1. The molecular structures and geometries of the complexes (1a i.e. 1 without water molecule and 3) were fully optimized using the quantum mechanical method (PM6). Complexes 1 and 3 were found to exhibit stronger cytotoxic activity in vitro across a panel of human tumor cell lines viz., A498, EVSA-T, H226, IGROV, M19 MEL, MCF-7 and WIDR. Compound 3 is found to be four times superior for the A498, EVSA-T and MCF-7 cell lines than CCDP (cisplatin), and four, eight and sixteen times superior for the A498, H226 and MCF-7 cell lines, respectively, compared to ETO (etoposide). The mechanistic role of cytotoxic activity of test compounds is discussed in relation to the theoretical results of docking studies with some key enzymes such as ribonucleotide reductase, thymidylate synthase, thymidylate phosphorylase and topoisomerase II associated with the propagation of cancer.

Keywords

Anti-cancer drugsDibutyltin(IV) compoundsArylazobenzoateSpectroscopyCell linesDocking studies

Supplementary material

10637_2009_9360_Fig1_ESM.tif (384 kb)
High resolution image (TIFF 383 kb)

Copyright information

© Springer Science+Business Media, LLC 2009