NIR-FT Raman and FT-IR spectral studies and ab initio calculations of the anti-cancer drug combretastatin-A4

J. Binoy, Jose P. Abraham, I. Hubert Joe, V. S. Jayakumar, George Pettit, O. F. Nielsen

Research output: Contribution to journalArticle

63 Scopus citations

Abstract

Combretastatin-A4, a potential anti-cancer drug in advanced preclinical development, is extracted from the medicinal plant Combretum caffrum. NIR-FT Raman and FT-IR spectral studies were carried out and ab initio calculations were performed at the HF/6-31G(d) level to derive equilibrium geometry and vibrational wavenumbers and intensities. The vibrational analysis shows that the molecule exhibits similar geometric behavior to cis-stilbene, and has undergone steric repulsion resulting in phenyl ring twisting with respect to the ethylenic plane. The spectral behavior of the methoxy groups is influenced by the oxygen lone pair-aryl pz orbital conjugation and back-donation. Chelation of the OH group with the oxygen lone pair of the methoxy group produces separate bands for free OH and associated OH vibrations.

Original languageEnglish (US)
Pages (from-to)939-946
Number of pages8
JournalJournal of Raman Spectroscopy
Volume35
Issue number11
DOIs
StatePublished - Nov 1 2004

Keywords

  • Ab initio
  • Combretastatin-A4
  • FT-IR
  • NIR-FT Raman

ASJC Scopus subject areas

  • Materials Science(all)
  • Spectroscopy

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