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

  • Tushar S. Basu Baul
  • Anup Paul
  • Lorenzo Pellerito
  • Michelangelo Scopelliti
  • Palwinder Singh
  • Pooja Verma
  • Andrew Duthie
  • Dick de Vos
  • Edward R. T. Tiekink
PRECLINICAL STUDIES

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 drugs Dibutyltin(IV) compounds Arylazobenzoate Spectroscopy Cell lines Docking studies 

Supplementary material

10637_2009_9360_Fig1_ESM.gif (139 kb)
Fig. S1

Unit cell contents viewed in projection down the c-axis for 1 (GIF 138 kb)

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

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Tushar S. Basu Baul
    • 1
  • Anup Paul
    • 1
  • Lorenzo Pellerito
    • 2
  • Michelangelo Scopelliti
    • 2
  • Palwinder Singh
    • 3
  • Pooja Verma
    • 3
  • Andrew Duthie
    • 4
  • Dick de Vos
    • 5
  • Edward R. T. Tiekink
    • 6
  1. 1.Department of ChemistryNorth-Eastern Hill UniversityShillongIndia
  2. 2.Dipartimento di Chimica Inorganica e Analitica“Stanislao Cannizzaro”, Università degli Studi di PalermoPalermoItaly
  3. 3.Department of ChemistryGuru Nanak Dev UniversityAmritsarIndia
  4. 4.School of Life & Environmental ScienceDeakin UniversityGeelongAustralia
  5. 5.Pharmachemie BVHaarlemThe Netherlands
  6. 6.Department of ChemistryUniversity of MalayaKuala LumpurMalaysia

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