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

European Journal of Medicinal Chemistry
Qingyong LiTianyu Liu

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 =...Continue Reading

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Citations

Jun 17, 2016·Clinical Proteomics·Gajanan SatheAditi Chatterjee
Oct 4, 2016·Journal of Asian Natural Products Research·Qu-Tong ZhengXing Zheng
Feb 20, 2016·European Journal of Medicinal Chemistry·Guo-Yun LiuShang-Jing Guo
Mar 13, 2017·Bioorganic & Medicinal Chemistry Letters·Zhi Sen WangFei Hu Chen
Sep 4, 2019·European Journal of Medicinal Chemistry·Sawsan A NoureddinKhalid O Al-Footy
Sep 27, 2019·European Journal of Medicinal Chemistry·Poh Yen KhorKok Wai Lam
Jul 20, 2018·ACS Omega·Joshua Almond-ThynneAnthony G M Barrett

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