Synthesis of new chiral heterocyclic Schiff base modulated Cu(II)/Zn(II) complexes: their comparative binding studies with CT-DNA, mononucleotides and cleavage activity

J Photochem Photobiol B. 2011 May 3;103(2):166-79. doi: 10.1016/j.jphotobiol.2011.03.001. Epub 2011 Mar 6.

Abstract

New Schiff base ligand L derived from the condensation reaction of 2-amino-3-formylchromone with (R)-2-amino-2-phenylethanol was synthesized and characterized which involves combination element of ammine functionality and naturally occurring heterocyclic chromone, 4H-benzopyran-4-one. Subsequently, their complexes 1 and 2 with Cu(NO₃)₂ and Zn(NO₃)₂, respectively were prepared. The DNA binding studies of the ligand L and complexes 1 and 2 with CT-DNA as compared to classical anticancer drug cisplatin were carried out by employing different optical methods viz, UV-vis, fluorescence, circular dichroism and viscosity measurements. Furthermore, the absorption studies, ¹H and ³¹P with mononucleotides were also monitored to examine the base specific interactions of the transition metal complexes which revealed a higher propensity of copper(II) complex 1 for 5'-GMP while for zinc(II) complex 2 towards 5'-TMP involving groove binding mechanism of the complexes towards DNA. The complex 1 exhibits a remarkable DNA cleavage activity with pBR322 DNA in presence of different activators and cleavage reaction involves various oxygen species suggesting the involvement of active oxygen species for the DNA scission.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Monophosphate / metabolism
  • Copper / chemistry*
  • Cytidine Monophosphate / metabolism
  • DNA / chemistry*
  • DNA Cleavage / drug effects*
  • Electron Spin Resonance Spectroscopy
  • Guanosine Monophosphate / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Schiff Bases / chemical synthesis*
  • Schiff Bases / chemistry
  • Spectrometry, Fluorescence
  • Thymidine Monophosphate / metabolism
  • Zinc / chemistry*

Substances

  • Schiff Bases
  • Thymidine Monophosphate
  • Adenosine Monophosphate
  • Copper
  • Guanosine Monophosphate
  • DNA
  • calf thymus DNA
  • Cytidine Monophosphate
  • Zinc