Copper(ii) complexes based on quinoline-derived Schiff-base ligands: synthesis, characterization, HSA/DNA binding ability, and anticancer activity

Three copper(ii) complexes, [Cu(L1)(NO ) ] ( ), [Cu(L2)Cl ] ( ) and [Cu(L2)SO ] ·H O ( ), were designed and synthesized by the reaction of Cu(NO ) ·3H O, CuCl ·2H O and CuSO ·5H O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-a...

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Bibliographic Details
Published in:MedChemComm 2018-10, Vol.9 (10), p.1663-1672
Main Authors: Hu, Kun, Liu, Chensi, Li, Jingui, Liang, Fupei
Format: Article
Language:English
Subjects:
Anticancer properties
Antitumor activity
Apoptosis
Biotechnology
Calf thymus
Cell cycle
Chemical synthesis
Cisplatin
Coordination compounds
Copper
Copper chloride
Copper compounds
Crystallography
Cytotoxicity
Deoxyribonucleic acid
DNA
DNA biosynthesis
Fluorescence
G1 phase
Human serum albumin
Hydrophobicity
Imines
Ligands
Mitochondria
Molecular docking
Quinoline
Reactive oxygen species
Serum albumin
Spectroscopy
Toxicity
Tumor cell lines
Tumors
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Summary:Three copper(ii) complexes, [Cu(L1)(NO ) ] ( ), [Cu(L2)Cl ] ( ) and [Cu(L2)SO ] ·H O ( ), were designed and synthesized by the reaction of Cu(NO ) ·3H O, CuCl ·2H O and CuSO ·5H O with a quinoline-derived Schiff base ligand, L1 or L2, prepared by the condensation of quinoline-8-carbaldehyde with 4-aminobenzoic acid methyl ester or 4-aminobenzoic acid ethyl ester (benzocaine). The efficient bindings of the - complexes with human serum albumin (HSA) and calf thymus DNA (CT-DNA) were analyzed by spectroscopy and molecular docking. These complexes could significantly quench the fluorescence of HSA through the static quenching process, and hydrophobic interactions with HSA through the sub-domain IIA and IIIA cavities. The complexes bind to DNA the intercalative mode and they fit well into the curved contour of the DNA target in the minor groove region. Furthermore, the interaction abilities of the Cu(ii) complexes with HSA/DNA were greater as compared to their corresponding ligands. Interestingly, - , particularly , exhibited more cytotoxicity toward HeLa cells compared to normal HL-7702 cells and three other tumor cell lines (Hep-G2, NCI-H460, and MGC80-3). Their cytotoxicity toward the HeLa cell lines was 1.9-3.5-fold more potent than cisplatin. Further studies indicated that these complexes arrested the cell cycle in the G0/G1 phase and promoted tumor cell apoptosis a reactive oxygen species (ROS)-mediated mitochondrial pathway.
ISSN:2040-2503
2040-2511
DOI:10.1039/c8md00223a