Chiral copper(II) complex based on natural product rosin derivative as promising antitumour agent
Bao-Li Fei, Zhi-Xiang Huang, Wu-Shuang Xu, Dong-Dong Li, Yang Lu, Wei-Lin Gao, Yue Zhao, Yu Zhang, Qing-Bo Liu
Journal of Photochemistry and Photobiology B: Biology
To evaluate the biological preference of chiral drug candidates for molecular target DNA, the synthesis and characterization of a chiral copper(II) complex (2) of a chiral ligand N,N′-(pyridin-2-ylmethylene) dehydroabietylamine (1) was carried out. The interactions of 1and 2 with salmon sperm DNA were investigated by viscosity measurements, UV, fluorescence and circular dichroism (CD) spectroscopic techniques. Absorption spectral, emission spectral and viscosity analysis reveal that 1 and 2 interacted with DNA through intercalation and 2 exhibited a higher DNA binding ability. In the absence/presence of ascorbic acid, 1 and 2 cleaved supercoiled pBR322 DNA by single-strand and 2displayed stronger DNA cleavage ability. In addition, in vitro cytotoxicity of 1 and 2against HeLa, SiHa, HepG-2 and A431 cancer cell lines study show that they exhibited effective cytotoxicity against the tested cell lines, notably, 2 showed a superior cytotoxicity than the widely used drug cisplatin under identical conditions, indicating it has the potential to act as effective anticancer drug. Flow cytometry analysis indicates 2produced death of HeLa cancer cells through an apoptotic pathway. Cell cycle analysis demonstrates that 2 mainly arrested HeLa cells at the S phase. The study represents the first step towards understanding the mode of the promising chiral rosin-derivative based copper complexes as chemotherapeutics.
Circular dichroism, Ligand binding, Biochemistry, Inorganic chemistry