Multispectral studies of DNA binding, antioxidant and cytotoxic activities of a new pyranochromene derivative

Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15:145:353-359. doi: 10.1016/j.saa.2015.03.026. Epub 2015 Mar 9.

Abstract

The binding properties of a new pyranochromene derivative, 2-amino-4-(3-hydroxyphenyl)-5-oxo-4H, 5H-pyrano-[3, 2-c] chromene-3-carbonitrile (3-HC) with calf thymus DNA (ctDNA) have been investigated by UV-vis absorption, circular dichroism, fluorescence spectroscopy and viscosity measurement. These results indicated that 3-HC can interact with DNA through non-intercalative mode and the intrinsic binding constant (Kb) for 3-HC with DNA was estimated to be 3.6 × 10(3)M(-1). The antioxidant activity experiments show that 3-HC also exhibit good antioxidant activity in DPPH free radical scavenging and ferric reducing ability methods. Moreover, 3-HC exhibited cytotoxic activity against K562, human chronic myelogenous leukemia cells, with IC50 value of 146 μM and the cells responded to the treatment with mostly through apoptosis.

Keywords: Antioxidant potential; Cytotoxicity; Outside DNA binding; Pyranochromene.

MeSH terms

  • Antioxidants / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / toxicity*
  • Cell Death / drug effects
  • Cell Proliferation / drug effects
  • Cell Shape / drug effects
  • Cell Survival / drug effects
  • Circular Dichroism
  • DNA / metabolism*
  • DNA Fragmentation / drug effects
  • Electrons
  • Humans
  • K562 Cells
  • Methylene Blue / metabolism
  • Quercetin / pharmacology
  • Spectrometry, Fluorescence
  • Viscosity

Substances

  • Antioxidants
  • Benzopyrans
  • DNA
  • calf thymus DNA
  • Quercetin
  • Methylene Blue