2. Academic Validation
  3. Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues

Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues

  • Eur J Med Chem. 2015 Mar 26:93:461-9. doi: 10.1016/j.ejmech.2015.02.005.
Qingyong Li 1,  Jian Chen 2,  Shuyue Luo 2,  Jialin Xu 2,  Qiaoxian Huang 2,  Tianyu Liu 2
Affiliations

Affiliations

  • 1 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: [email protected].
  • 2 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.
PMID: 25728027 DOI: 10.1016/j.ejmech.2015.02.005
Abstract

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.

Keywords

Anti-proliferate; Antioxidant; Asymmetric curcumin analogues.

Figures