Inhibition of quorum sensing in gram-negative bacteria by alkylamine-modified cyclodextrins

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• 作者：Tomohiro Morohoshi¹ ; ³ ; ^&dagger ; ; ^{morohosi@cc.utsunomiya-u.ac.jp} ; Kazuho Tokita¹ ; Satoshi Ito¹ ; ³ ; ^&dagger ; ; Yuki Saito¹ ; ³ ; Saki Maeda¹ ; Norihiro Kato² ; ³ ; Tsukasa Ikeda¹ ; ³
• 关键词：Quorum sensing ; Acylhomoserine lactone ; Cyclodextrin ; Inhibition ; Inclusion complex
• 刊名：Journal of Bioscience and Bioengineering
• 出版年：2013
• 出版时间：August, 2013
• 年：2013
• 卷：116
• 期：2
• 页码：175-179
• 全文大小：420 K

文摘

N-Acylhomoserine lactones (AHLs) are used as quorum-sensing (QS) signals by gram-negative bacteria. We have reported that the cyclic oligosaccharides known as cyclodextrins (CDs) form inclusion complexes with AHLs and disrupt QS signaling. In this study, a series of CD derivatives were designed and synthesized to improve the QS inhibitory activity over that of native CDs. The production of the red pigment prodigiosin by Serratia marcescens AS-1, which is regulated by AHL-mediated QS, was drastically decreased by adding 10?mg/ml 6-alkylacylamino-¦Â-CD with an alkyl chain ranging from C7 to C12. An improvement in the QS inhibitory activity was also observed for 6-alkylamino-¦Á- or ¦Ã-CDs and 2-alkylamino-CDs. Furthermore, 6,6¡ä-dioctylamino-¦Â-CD, which contains two octylamino groups, exhibited greater inhibitory activity than 6-monooctylamino-¦Â-CD. The synthesized CD derivatives also had strong inhibitory effects on QS by other gram-negative bacteria, including Chromobacterium violaceum and Pseudomonas aeruginosa. The synthetic alkylamine-modified CD derivatives had higher equilibrium binding constants for binding with AHL than the native CDs did, consistent with the improved QS inhibition. ¹H NMR measurements suggested that the alkyl side chains of 6-alkylacylamino-¦Â-CDs with alkyl chains up to 6 carbon atoms long could form self-inclusion complexes with the CD unit.