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

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

22 Scopus citations

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 (US)
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
State	Published - Mar 26 2015
Externally published	Yes

Keywords

Biofilm inhibition
Pseudomonas aeruginosa
Pyrone
Quorum sensing

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2015.05.054

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

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",

year = "2015",

month = mar,

day = "26",

doi = "10.1016/j.bmcl.2015.05.054",

language = "English (US)",

volume = "25",

pages = "2913--2917",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

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}

TY - JOUR

T1 - Design, synthesis and biological evaluation of 4-(alkyloxy)-6-methyl-2H-pyran-2-one derivatives as quorum sensing inhibitors

AU - Park, Suzie

AU - Kim, Han Shin

AU - Ok, Kiwon

AU - Kim, Yunhye

AU - Park, Hee Deung

AU - Byun, Youngjoo

PY - 2015/3/26

Y1 - 2015/3/26

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.

KW - Biofilm inhibition

KW - Pseudomonas aeruginosa

KW - Pyrone

KW - Quorum sensing

UR - https://www.scopus.com/pages/publications/84930924160

UR - https://www.scopus.com/pages/publications/84930924160#tab=citedBy

U2 - 10.1016/j.bmcl.2015.05.054

DO - 10.1016/j.bmcl.2015.05.054

M3 - Article

C2 - 26048802

AN - SCOPUS:84930924160

SN - 0960-894X

VL - 25

SP - 2913

EP - 2917

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 15

ER -

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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