Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues.
In this study, 12 asymmetric curcumin (CUR) analogues and 5 symmetric curcumin derivatives were synthesized, the antioxidant activity of these derivatives were evaluated by radicals 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay, 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) assay, ROO (TRAP) assay and O(2-) (NET) assay and anti-proliferative activities of these analogues were assessed against the human hepatoma cell line (SMMC-7721), the human breast cancer cell line (MCF-7) and the human prostate cancer cell lines (PC-3). Most of the asymmetric compounds showed stronger antioxidant activities than Vitamin C (Vc). Curcumin analogues reducing free radicals contain two reaction mechanisms: H-atom and electron transfer mechanisms. Compound 14 showed the most significant antioxidant activity compared with curcumin and other derivatives. Shorted the carbon chain of 14 can reduce the O-H bond dissociation enthalpy (BED) to improve the antioxidant activity. The antioxidant activity of 25 was similar to curcumin. All of the compounds performed better in an anti-proliferate assay than curcumin, especially compound 25, which exhibited the preferential cytotoxic activity against MCF-7 cells(25, IC50 = 9.11 μM, curcumin, IC50 = 70.2 μM). Considering these data, future studies should be performed to assess the therapeutic values of these asymmetric curcumin analogues.
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China. Electronic address: li_qingyong@126.com.
Qingyong
Q
Li
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China.
Jian
J
Chen
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China.
Shuyue
S
Luo
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China.
Jialin
J
Xu
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China.
Qiaoxian
Q
Huang
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China; Key Laboratory of Forest Plant Ecology, Northeast Forestry University, Ministry of Education, Harbin, 150040, China.
Tianyu
T
Liu
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D003474:Curcumin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D016166:Free Radical Scavengers; D003474:Curcumin
Anti-proliferate; Antioxidant; Asymmetric curcumin analogues