Synthesis, structure and in vitro pharmacological evaluation of a novel 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (2'-methylbenzoyl) hydrazone bridged copper(II) coordination polymer

Eur J Med Chem. 2013 Jun:64:148-59. doi: 10.1016/j.ejmech.2013.03.040. Epub 2013 Apr 2.

Abstract

A novel ligand bridged copper(II) coordination polymer, [Cu(HL)(NO3)]n has been synthesized by reacting 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (2'-methylbenzoyl) hydrazone (H2L) with Cu(NO3)2·3H2O, and characterized by X-ray diffraction studies. The DNA interaction studies revealed that the compounds could interact with CT-DNA through intercalation. A gel electrophoresis assay demonstrated the ability of the complex to cleave the pBR322 plasmid DNA. The protein binding studies indicated that the complex exhibited strong binding affinities. Investigations of antioxidative properties showed that the polymeric Cu(II) complex has strong radical scavenging potencies. The cytotoxic effect of the compounds showed that the polymeric complex exhibited excellent anticancer activity against Hep G2, and A431 cells which is six to ten times better than that of well-known commercial anticancer drug, cisplatin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Cattle
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Coordination Complexes / chemistry*
  • Copper / chemistry*
  • Crystallography, X-Ray
  • DNA / chemistry
  • DNA / drug effects
  • DNA Cleavage / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Hydrazones / chemistry*
  • Ligands
  • Mice
  • Models, Molecular
  • Molecular Structure
  • NIH 3T3 Cells
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Polymers / pharmacology*
  • Quinolones / chemistry*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Antioxidants
  • Coordination Complexes
  • Hydrazones
  • Ligands
  • Organometallic Compounds
  • Polymers
  • Quinolones
  • Copper
  • DNA
  • calf thymus DNA