Cu(II), Ni(II) complexes derived from chiral Schiff-base ligands: Synthesis, characterization, cytotoxicity, protein and DNA-binding properties.
A series of novel copper (II) and nickel (II) complexes derived from chiral Schiff-base ligands [(R)/(S)-H2L(1)=(R)/(S)-2-[(1-Hydroxymethyl-propylimino)-methyl]-5-methoxy-phenol and (R)/(S)-H2L(2)=(R)/(S)-2-[(1-Hydroxymethyl-2-phenyl-ethylimino)-methyl]-5-methoxy-phenol], were synthesized and characterized by elemental analyses, (1)H NMR spectra, FT-IR spectrum. The crystal structures of complexes 1-5 were determined through single crystal X-ray diffraction (SXRD). The structures showed the ligands coordinated to the Cu/Ni (II) ion in a neutral manner via ONO donor atoms, and oxygen atoms of solvent molecules occupy the axial positions in Ni (II) complexes 3 and 4. The complexes interactions with BSA and CT-DNA were investigated by various spectroscopic methods (UV-Visible, circular dichroism spectrum, fluorescence spectroscopic and synchronous fluorescence spectra). Interactions of chiral copper (II) complexes are stronger than nickel (II) complexes. Further, the cytotoxicities of the complexes 1-6 towards three kinds of cancerous cell lines, were human lung adenocarcinoma (A549), human cervical carcinoma cell (HeLa) and human breast cancer cell (MCF-7) respectively, were evaluated by MTT assay. All complexes exhibited good cytotoxic activity. Furthermore, Cu (II) complex 5 derived from (R)-Schiff-base ligand was found to be more effective towards HeLa cancerous cell. The results showed that chirality and metal ion have important influence on their anticancer activities and interactions with DNA/BSA.
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China.
Zhen
Z
Li
College of Pharmacy, Liaocheng University, Liaocheng, Shandong 252059, China.
Hui
H
Yan
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China.
Guoliang
G
Chang
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China.
Min
M
Hong
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China.
Jianmin
J
Dou
Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059, China. Electronic address: niumeiju@163.com.
Meiju
M
Niu
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000378:metabolism*; D006367:HeLa Cells; D006801:Humans; D042541:Intracellular Space / Q000187:drug effects / Q000378:metabolism; D008024:Ligands; D062105:Molecular Docking Simulation; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D011487:Protein Conformation; D017382:Reactive Oxygen Species / Q000378:metabolism; D012545:Schiff Bases / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D008024:Ligands; D009942:Organometallic Compounds; D017382:Reactive Oxygen Species; D012545:Schiff Bases; D012710:Serum Albumin, Bovine; D003300:Copper; D009532:Nickel; D004247:DNA
BSA/DNA–binding; Chiral Schiff-base; Cytotoxicity; Metal complex