Synthesis, characterization, cytotoxic activities, and DNA-binding studies of ternary copper(II) complexes with new coumarin derivatives

Lei Jia; Xi-Ming Xu; Jun Xu; Long-Hai Chen; Peng Jiang; Fei-Xiang Cheng; Guang-Nong Lu; Qin Wang; Jin-Cai Wu; Ning Tang

doi:10.1248/cpb.58.1003

Synthesis, characterization, cytotoxic activities, and DNA-binding studies of ternary copper(II) complexes with new coumarin derivatives

Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1003-8. doi: 10.1248/cpb.58.1003.

Authors

Lei Jia¹, Xi-Ming Xu, Jun Xu, Long-Hai Chen, Peng Jiang, Fei-Xiang Cheng, Guang-Nong Lu, Qin Wang, Jin-Cai Wu, Ning Tang

Affiliation

¹ Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P.R. China.

PMID: 20686250
DOI: 10.1248/cpb.58.1003

Abstract

In this study, two novel complexes [Cu(MCVH)phen(H(2)O)].ClO(4) (1) and [Cu(MCLH)phen(H(2)O)].ClO(4) (2) (here, MCVH(2)=(7-hydroxy-4-methyl-8-coumarinyl) valine, MCLH(2)=(7-hydroxy-4-methyl-8-coumarinyl) leucine) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), (1)H-NMR and UV-Vis measurements. The interactions of them with calf thymus DNA (ct DNA) have been investigated by absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy and viscosity measurements. Experimental results reveal an intercalative interaction with DNA for the complexes, furthermore the binding affinity of 2 is higher than that of 1 according to the calculated binding constant values. In addition, they were evaluated for their cytotoxic activities toward human prostate cancer cell (PC3), human liver cell (L02) and human myeloid leukemia cancer cell (HL-60) by acid phosphoatase assay. Both of them showed significant cytotoxic potency.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Antineoplastic Agents / toxicity
Binding Sites
Cattle
Cell Line, Tumor
Cell Proliferation / drug effects
Coumarins / chemical synthesis*
Coumarins / chemistry
Coumarins / pharmacology*
Coumarins / toxicity
DNA / chemistry*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Leucine / analogs & derivatives*
Leucine / chemical synthesis
Leucine / chemistry
Leucine / pharmacology
Leucine / toxicity
Ligands
Molecular Structure
Organometallic Compounds / chemical synthesis*
Organometallic Compounds / chemistry
Organometallic Compounds / pharmacology*
Organometallic Compounds / toxicity
Stereoisomerism
Valine / analogs & derivatives*
Valine / chemical synthesis
Valine / chemistry
Valine / pharmacology
Valine / toxicity

Substances

(Cu((7-hydroxy-4-methyl-8-coumarinyl)leucine)phen(H2O))ClO4
(Cu((7-hydroxy-4-methyl-8-coumarinyl)valine)phen(H2O))ClO4
Antineoplastic Agents
Coumarins
Ligands
Organometallic Compounds
DNA
calf thymus DNA
Leucine
Valine