Literature DB >> 17169556

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.

Marine Frezza1, Laurent Soulère, Damien Balestrino, Michel Gohar, Christian Deshayes, Yves Queneau, Christiane Forestier, Alain Doutheau.   

Abstract

Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD), was prepared both as a racemic mixture and in the optically active form found in naturally occurring DPD. It was shown to exhibit the same ability as DPD to induce bioluminescence in Vibrio harveyi and beta-galactosidase activity in Salmonella enterica Typhimurium, both gram-negative bacteria. Likewise, it was also shown to inhibit biofilm formation in gram-positive Bacillus cereus. The most likely hypothesis is that Ac2-DPD activity is due to the release of DPD by in situ hydrolysis of the ester groups. Importantly, by contrast with DPD, Ac2-DPD proved to be a stable compound which can be purified and stored.

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Year:  2006        PMID: 17169556     DOI: 10.1016/j.bmcl.2006.11.076

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  12 in total

1.  Engineered biological nanofactories trigger quorum sensing response in targeted bacteria.

Authors:  Rohan Fernandes; Varnika Roy; Hsuan-Chen Wu; William E Bentley
Journal:  Nat Nanotechnol       Date:  2010-01-17       Impact factor: 39.213

2.  Probing autoinducer-2 based quorum sensing: the biological consequences of molecules unable to traverse equilibrium states.

Authors:  Kyoji Tsuchikama; Colin A Lowery; Kim D Janda
Journal:  J Org Chem       Date:  2011-06-28       Impact factor: 4.354

3.  Medicinal chemistry as a conduit for the modulation of quorum sensing.

Authors:  Colin A Lowery; Nicholas T Salzameda; Daisuke Sawada; Gunnar F Kaufmann; Kim D Janda
Journal:  J Med Chem       Date:  2010-11-11       Impact factor: 7.446

4.  Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response.

Authors:  Lark J Perez; Wai-Leung Ng; Paul Marano; Karolina Brook; Bonnie L Bassler; Martin F Semmelhack
Journal:  J Med Chem       Date:  2012-11-08       Impact factor: 7.446

5.  Dissecting AI-2-mediated quorum sensing through C5-analogue synthesis and biochemical analysis.

Authors:  Karen C Collins; Kyoji Tsuchikama; Colin A Lowery; Jie Zhu; Kim D Janda
Journal:  Tetrahedron       Date:  2015-06       Impact factor: 2.457

6.  Cloning and characterizations of the Serratia marcescens metK and pfs genes involved in AI-2-dependent quorum-sensing system.

Authors:  Hu Zhu; Ya-Ling Shen; Dong-Zhi Wei; Jia-Wen Zhu
Journal:  Mol Cell Biochem       Date:  2008-05-16       Impact factor: 3.396

7.  S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit.

Authors:  Stanislaw F Wnuk; Jennifer Lalama; Craig A Garmendia; Jenay Robert; Jinge Zhu; Dehua Pei
Journal:  Bioorg Med Chem       Date:  2008-03-14       Impact factor: 3.641

8.  Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position.

Authors:  Stanislaw F Wnuk; Jenay Robert; Adam J Sobczak; Brandon P Meyers; Venkata L A Malladi; Jinge Zhu; Bhaskar Gopishetty; Dehua Pei
Journal:  Bioorg Med Chem       Date:  2009-07-26       Impact factor: 3.641

9.  Small molecule inhibitors of AI-2 signaling in bacteria: state-of-the-art and future perspectives for anti-quorum sensing agents.

Authors:  Min Guo; Sonja Gamby; Yue Zheng; Herman O Sintim
Journal:  Int J Mol Sci       Date:  2013-08-29       Impact factor: 5.923

10.  A pro-drug approach for selective modulation of AI-2-mediated bacterial cell-to-cell communication.

Authors:  Min Guo; Sonja Gamby; Shizuka Nakayama; Jacqueline Smith; Herman O Sintim
Journal:  Sensors (Basel)       Date:  2012-03-21       Impact factor: 3.576

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