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Applied and Environmental Microbiology, October 2007, p. 6339-6344, Vol. 73, No. 20
0099-2240/07/$08.00+0     doi:10.1128/AEM.00593-07
Copyright © 2007, American Society for Microbiology. All Rights Reserved.

Inhibition of Quorum Sensing in Serratia marcescens AS-1 by Synthetic Analogs of N-Acylhomoserine Lactone{triangledown}

Tomohiro Morohoshi,1* Toshitaka Shiono,1 Kiyomi Takidouchi,1 Masashi Kato,1 Norihiro Kato,1 Junichi Kato,2 and Tsukasa Ikeda1

Department of Applied Chemistry, Utsunomiya University, Utsunomiya, Tochigi 321-8585, Japan,1 Department of Molecular Biotechnology, Graduate School of Advanced Sciences of Matter, Hiroshima University, Higashi-Hiroshima, Hiroshima 739-8530, Japan2

Received 14 March 2007/ Accepted 27 July 2007

Quorum sensing is a regulatory system for controlling gene expression in response to increasing cell density. N-Acylhomoserine lactone (AHL) is produced by gram-negative bacteria, which use it as a quorum-sensing signal molecule. Serratia marcescens is a gram-negative opportunistic pathogen which is responsible for an increasing number of serious nosocomial infections. S. marcescens AS-1 produces N-hexanoyl homoserine lactone (C6-HSL) and N-(3-oxohexanoyl) homoserine lactone and regulates prodigiosin production, swarming motility, and biofilm formation by AHL-mediated quorum sensing. We synthesized a series of N-acyl cyclopentylamides with acyl chain lengths ranging from 4 to 12 and estimated their inhibitory effects on prodigiosin production in AS-1. One of these molecules, N-nonanoyl-cyclopentylamide (C9-CPA), had a strong inhibitory effect on prodigiosin production. C9-CPA also inhibited the swarming motility and biofilm formation of AS-1. A competition assay revealed that C9-CPA was able to inhibit quorum sensing at four times the concentration of exogenous C6-HSL and was more effective than the previously reported halogenated furanone. Our results demonstrated that C9-CPA was an effective quorum-sensing inhibitor for S. marcescens AS-1.

* Corresponding author. Mailing address: Department of Applied Chemistry, Utsunomiya University, 7-1-2 Yoto, Utsunomiya 321-8585, Japan. Phone: 81-28-689-6176. Fax: 81-28-689-6176. E-mail: morohosi{at}cc.utsunomiya-u.ac.jp

{triangledown} Published ahead of print on 3 August 2007.

Applied and Environmental Microbiology, October 2007, p. 6339-6344, Vol. 73, No. 20
0099-2240/07/$08.00+0     doi:10.1128/AEM.00593-07
Copyright © 2007, American Society for Microbiology. All Rights Reserved.





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