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Eur J Med Chem. 2014 Mar 3;74:671-82. doi: 10.1016/j.ejmech.2013.10.061. Epub 2013 Nov 1.

Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents.

Author information

1
Chemical Biology Research Center at School of Pharmaceutical Sciences, Wenzhou Medical University, 1210 University Town, Wenzhou, Zhejiang 325035, China; Wenzhou Undersun Biotechnology Co., Ltd., Wenzhou, Zhejiang, China.
2
Chemical Biology Research Center at School of Pharmaceutical Sciences, Wenzhou Medical University, 1210 University Town, Wenzhou, Zhejiang 325035, China.
3
School of Environmental and Biological Engineering, Nanjing University of Science and Technology, No. 200 Xiaolingwei Road, Xuanwu District, Nanjing, Jiangsu 210094, China.
4
Department of Pediatrics, The Second Affiliated Hospital, Wenzhou Medical University, Wenzhou, Zhejiang 325035, China.
5
Chemical Biology Research Center at School of Pharmaceutical Sciences, Wenzhou Medical University, 1210 University Town, Wenzhou, Zhejiang 325035, China. Electronic address: zhj@wzmc.net.
6
Chemical Biology Research Center at School of Pharmaceutical Sciences, Wenzhou Medical University, 1210 University Town, Wenzhou, Zhejiang 325035, China. Electronic address: cuiliang1234@163.com.

Abstract

Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-α and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents.

KEYWORDS:

Anti-inflammation; Curcumin; IL-6; Mono-carbonyl analogs; QSAR; TNF-α

PMID:
24321865
DOI:
10.1016/j.ejmech.2013.10.061
[Indexed for MEDLINE]

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