Synthesis, interaction with DNA and antiproliferative activities of two novel Cu(II) complexes with Schiff base of benzimidazole.
Two novel copper(II) complexes with Schiff base of benzimidazole [Cu(L)Cl]2·CH3OH have been synthesized. HL(1) (N-(benzimidazol-2-ymethyl)-5-chlorosalicylideneimine, C15H11ClN3O) and HL(2) (N-(benzimidazol-2-ymethyl)-salicylideneimine, C15H12N3O) are ligands of complex (1) and complex (2), respectively. The complexes were characterized by elemental analysis, IR, UV-Vis, TGA and X-ray diffraction. Within the complexes, Cu(II) ions were four coordinated by two nitrogen atom of azomethine and imine, one phenolic oxygen atom from HL and one chloride atom. A distorted quadrilateral structure was formed. Complex (1) crystallized in the triclinic crystal system. Results showed that π-π stacking effect occurred due to the existence of aromatic ring from Schiff base and hydrogen bonding between methanol and adjacent atoms. The DNA binding properties of the complexes were investigated by electronic absorption spectra, fluorescence spectra and viscosity measurements. Results indicated that complexes bound to DNA via partial intercalation mode. The DNA binding constants Kb/(L mol(-1)) were 1.81×10(4) (1), 1.37×10(4) (2), 6.27×10(3) (HL(1)) and 3.14×10(3) (HL(2)) at 298 K. The title complexes could quench the emission intensities of EB-DNA system significantly. The results of agarose gel electrophoresis indicated complex (1) could cleave supercoiled DNA through the oxidative mechanism. The inhibition ratios revealed that complex (1) and HL(1) had strong antiproliferative activities against human breast cancer cells (MCF-7) lines and human colorectal cancer cells (COLO205) lines in vitro. The antiproliferative activities of complex (1) against MCF-7 lines (IC50=16.9±1.5 μmol L(-1)) and against COLO205 lines (IC50=16.5±3.4 μmol L(-1)) is much stronger than that of HL(1), which had the potential to develop anti-cancer drug.
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Zhejiang 321004, PR China; College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Wen-Ji
WJ
Song
College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Jian-Ping
JP
Cheng
College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Dong-Hua
DH
Jiang
College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Li
L
Guo
College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Meng-Fei
MF
Cai
College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China.
Hu-Bin
HB
Yang
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Zhejiang 321004, PR China; College of Chemical and Life Science, Zhejiang Normal University, Zhejiang 321004, PR China. Electronic address: sky51@zjnu.cn.
Qiu-Yue
QY
Lin
D000042:Absorption; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003300:Copper / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D006801:Humans; D008968:Molecular Conformation; D010957:Plasmids / Q000378:metabolism; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013050:Spectrometry, Fluorescence; D013818:Thermogravimetry; D014783:Viscosity / Q000187:drug effects
D001562:Benzimidazoles; D012545:Schiff Bases; D003300:Copper; D004247:DNA; C031000:benzimidazole
5-Chlorosalicylaldehyde Schiff base; Antiproliferative activity; Benzimidazole; Copper complex; DNA binding