Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors

Suzie Park; Han Shin Kim; Kiwon Ok; Yunhye Kim; Hee Deung Park; Youngjoo Byun

doi:10.1016/j.bmcl.2015.05.054

Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors

Suzie Park, Han Shin Kim, Kiwon Ok, Yunhye Kim, Hee Deung Park, Youngjoo Byun

School of Civil, Environmental and Architectural Engineering

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

Novel pyrone-derived quorum sensing (QS) ligands to inhibit the binding of OdDHL to the LasR of Pseudomonas aeruginosa were designed, synthesized and evaluated. Among the analogs, the most potent compound 8 exhibited strong in vitro inhibitory activities against biofilm formation and down-regulated OdDHL/LasR-associated genes by 35-67%. The binding mode of 8 in silico was highly similar to that of the crystal ligand OdDHL in the active site of LasR.

Original language	English
Pages (from-to)	2913-2917
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2015.05.054
Publication status	Published - 2015 Jun 11

Keywords

Biofilm inhibition
Pseudomonas aeruginosa
Pyrone
Quorum sensing

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors. / Park, Suzie; Kim, Han Shin; Ok, Kiwon; Kim, Yunhye; Park, Hee Deung; Byun, Youngjoo.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 15, 11.06.2015, p. 2913-2917.

Research output: Contribution to journal › Article › peer-review

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abstract = "Novel pyrone-derived quorum sensing (QS) ligands to inhibit the binding of OdDHL to the LasR of Pseudomonas aeruginosa were designed, synthesized and evaluated. Among the analogs, the most potent compound 8 exhibited strong in vitro inhibitory activities against biofilm formation and down-regulated OdDHL/LasR-associated genes by 35-67%. The binding mode of 8 in silico was highly similar to that of the crystal ligand OdDHL in the active site of LasR.",

keywords = "Biofilm inhibition, Pseudomonas aeruginosa, Pyrone, Quorum sensing",

author = "Suzie Park and Kim, {Han Shin} and Kiwon Ok and Yunhye Kim and Park, {Hee Deung} and Youngjoo Byun",

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AU - Ok, Kiwon

AU - Kim, Yunhye

AU - Park, Hee Deung

AU - Byun, Youngjoo

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N2 - Novel pyrone-derived quorum sensing (QS) ligands to inhibit the binding of OdDHL to the LasR of Pseudomonas aeruginosa were designed, synthesized and evaluated. Among the analogs, the most potent compound 8 exhibited strong in vitro inhibitory activities against biofilm formation and down-regulated OdDHL/LasR-associated genes by 35-67%. The binding mode of 8 in silico was highly similar to that of the crystal ligand OdDHL in the active site of LasR.

AB - Novel pyrone-derived quorum sensing (QS) ligands to inhibit the binding of OdDHL to the LasR of Pseudomonas aeruginosa were designed, synthesized and evaluated. Among the analogs, the most potent compound 8 exhibited strong in vitro inhibitory activities against biofilm formation and down-regulated OdDHL/LasR-associated genes by 35-67%. The binding mode of 8 in silico was highly similar to that of the crystal ligand OdDHL in the active site of LasR.

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KW - Pyrone

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Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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