Preliminary investigation of anticancer activity by determining the DNA binding and antioxidant potency of new ferrocene incorporated N,N',N″-trisubstituted phenylguanidines

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 3:117:264-9. doi: 10.1016/j.saa.2013.08.033. Epub 2013 Aug 13.

Abstract

Six new bioactive ferrocene based phenylguanidines were successively synthesized and characterized by means of various analytical techniques like elemental analysis, FT-IR, multinuclear ((1)H and (13)C) NMR, UV-Vis spectroscopy and cyclic voltammetry. The interaction of compounds with DNA was investigated by spectroscopic and cyclic voltammetric measurements. The interaction was found to be the electrostatic and the binding constants values were impressively larger. Compounds f-1, f-2, f-3 have slight larger binding constant values ranging from 0.8×10(5) to 2.4×10(5) as compared to g-1, g-2 and g-3 ranging from 7.6×10(4) to 1.1×10(5) which is most probably due to the presence of ferrocene at para position where the delocalization of electrons is maximum. Antioxidant activity was determined by UV-Vis spectrophotometer by using DPPH as a free radical. All the compounds exhibit good antioxidant activity and the results so obtained support the structure activity relationship.

Keywords: Antioxidant activity; DNA binding; Trisubstituted ferrocenyl phenylguanidines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / chemistry
  • DNA / metabolism*
  • Electrochemistry
  • Ferrous Compounds / chemistry*
  • Guanidines / chemistry
  • Guanidines / pharmacology*
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy
  • Metallocenes
  • Molecular Structure
  • Oxidation-Reduction
  • Picrates / chemistry
  • Spectrophotometry, Ultraviolet
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Biphenyl Compounds
  • Ferrous Compounds
  • Guanidines
  • Indicators and Reagents
  • Metallocenes
  • Picrates
  • phenylguanidine
  • DNA
  • 1,1-diphenyl-2-picrylhydrazyl
  • ferrocene