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

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.

• Authors: Qingyong Li, Jian Chen, Shuyue Luo, Jialin Xu, Qiaoxian Huang, Tianyu Liu
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 93 Pg. 461-9 (Mar 26 2015) ISSN: 1768-3254 [Electronic] France
• PMID: 25728027 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Chemical References

• Antineoplastic Agents
• Free Radical Scavengers
• Curcumin

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Chemistry Techniques, Synthetic
• Curcumin (analogs & derivatives, chemical synthesis, pharmacology)
• Free Radical Scavengers (chemical synthesis, chemistry, pharmacology)
• Humans
• Structure-Activity Relationship