Synthesis, characterization, cytotoxic activities, and DNA-binding properties of the La(III) complex with Naringenin Schiff-base

Bioorg Med Chem. 2006 Mar 15;14(6):1880-8. doi: 10.1016/j.bmc.2005.10.031. Epub 2005 Nov 28.

Abstract

A new Naringenin Schiff-base ligand (H3L) and its complex, [La(H2L)2(NO3).3H2O], have been synthesized and characterized on the basis of elemental analyses, molar conductivities, mass spectra, 1H NMR, thermogravimetry/differential thermal analysis (TG-DTA), UV spectra, and IR spectra. Spectrometric titrations, ethidium bromide displacement experiments, and viscosity measurements indicate that the two compounds, especially the La(III) complex, strongly bind with calf-thymus DNA, presumably via an intercalation mechanism. The intrinsic binding constants of the La(III) complex and ligand with DNA were 1.83 x 10(7) and 9.46 x 10(5) M(-1), respectively. Comparative cytotoxic activities of the La(III) complex and ligand were also determined by MTT [3-(4,5-dimethyl-2-thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide] and SRB (sulforhodamine B) methods. The results showed that the La(III) complex had significant cytotoxic activity against the tested cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / pharmacology*
  • Apoptosis*
  • Cell Line, Tumor
  • Cells, Cultured
  • DNA / metabolism*
  • Drug Screening Assays, Antitumor
  • Flavanones / chemistry*
  • Flavanones / metabolism
  • Flavanones / pharmacology
  • Humans
  • Lanthanum / chemistry*
  • Lanthanum / metabolism
  • Lanthanum / pharmacology
  • Molecular Structure
  • Schiff Bases / chemistry*
  • Schiff Bases / metabolism
  • Schiff Bases / pharmacology

Substances

  • Antineoplastic Agents
  • Flavanones
  • Schiff Bases
  • Lanthanum
  • DNA
  • naringenin