Design, synthesis and antibacterial activity of novel andrographolide derivatives

被引:45
作者
Wang, Zhongli
Yu, Pei [1 ]
Zhang, Gaoxiao
Xu, Lipeng
Wang, Dingyuan
Wang, Liang
Zeng, Xiangping
Wang, Yuqiang
机构
[1] Jinan Univ, Coll Pharm, Inst New Drug Res, Guangzhou 510632, Guangdong, Peoples R China
关键词
Andrographolide derivatives; Synthesis; Antibacterial; Quorum sensing; TO-CELL COMMUNICATION; PSEUDOMONAS-AERUGINOSA; QUORUM; BACTERIA; INFLAMMATION; INHIBITION; ACTIVATION; SYNTHASES; PYOCYANIN; NETWORKS;
D O I
10.1016/j.bmc.2010.04.094
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of andrographolide derivatives were synthesized through a facile condensation reaction with different carboxylic acids. The new compounds were characterized and screened for their antibacterial activities. A number of the new compounds significantly reduced bacterial quorum sensing virulence factors production in Pseudomonas aeruginosa, essential for pathogenesis. Compound 11b showed the best activity among all the new compounds. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4269 / 4274
页数:6
相关论文
共 33 条
[1]   Modular polyketide synthases and cis double bond formation:: Establishment of activated cis-3-cyclohexylpropenoic acid as the diketide intermediate in phoslactomycin biosynthesis [J].
Alhamadsheh, Mamoun M. ;
Palaniappan, Nadaraj ;
DasChouduri, Suparna ;
Reynolds, Kevin A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1910-+
[2]   Impairment of apoptotic cell engulfment by pyocyanin, a toxic metabolite of Pseudomonas aeruginosa [J].
Bianchi, Stephen M. ;
Prince, Lynne R. ;
McPhillips, Kathleen ;
Allen, Lucy ;
Marriott, Helen M. ;
Taylor, Graham W. ;
Hellewell, Paul G. ;
Sabroe, Ian ;
Dockrell, David H. ;
Henson, Peter W. ;
Whyte, Moira K. B. .
AMERICAN JOURNAL OF RESPIRATORY AND CRITICAL CARE MEDICINE, 2008, 177 (01) :35-43
[3]  
Calabrese C, 2000, PHYTOTHER RES, V14, P333, DOI 10.1002/1099-1573(200008)14:5<333::AID-PTR584>3.0.CO
[4]  
2-D
[5]   ANDROGRAPHOLIDE .1. [J].
CHAKRAVARTI, D ;
CHAKRAVARTI, RN .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAY) :1697-1700
[6]   Activity of Andrographolide and Its Derivatives against Influenza Virus in Vivo and in Vitro [J].
Chen, Jian-Xin ;
Xue, Hui-Jun ;
Ye, Wen-Cai ;
Fang, Bing-Hu ;
Liu, Ya-Hong ;
Yuan, Shao-Hua ;
Yu, Pei ;
Wang, Yu-Qiang .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2009, 32 (08) :1385-1391
[7]   Quenching quorum-sensing-dependent bacterial infection by an N-acyl homoserine lactonase [J].
Dong, YH ;
Wang, LH ;
Xu, JL ;
Zhang, HB ;
Zhang, XF ;
Zhang, LH .
NATURE, 2001, 411 (6839) :813-817
[8]   IDENTIFICATION AND CHARACTERIZATION OF GENES FOR A 2ND ANTHRANILATE SYNTHASE IN PSEUDOMONAS-AERUGINOSA - INTERCHANGEABILITY OF THE 2 ANTHRANILATE SYNTHASES AND EVOLUTIONARY IMPLICATIONS [J].
ESSAR, DW ;
EBERLY, L ;
HADERO, A ;
CRAWFORD, IP .
JOURNAL OF BACTERIOLOGY, 1990, 172 (02) :884-900
[9]   Regulation of gene expression by cell-to-cell communication: Acyl-homoserine lactone quorum sensing [J].
Fuqua, C ;
Parsek, MR ;
Greenberg, EP .
ANNUAL REVIEW OF GENETICS, 2001, 35 :439-468
[10]   The QscR quorum-sensing regulon of Pseudomonas aeruginosa:: an orphan claims its identity [J].
Fuqua, C .
JOURNAL OF BACTERIOLOGY, 2006, 188 (09) :3169-3171