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

^*Corresponding author for this work

Environmental Biotechnology

Korea University

Research output: Contribution to journal › Journal article › peer-review

47 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
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 - 2015.06.11

Keywords

Biofilm inhibition
Pseudomonas aeruginosa
Pyrone
Quorum sensing

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10.1016/j.bmcl.2015.05.054

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@article{5ae2c7fa872b411682883ab76ab66fd6,

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 = jun,

day = "11",

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

language = "English",

volume = "25",

pages = "2913--2917",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

number = "15",

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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 - 2015/6/11

Y1 - 2015/6/11

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

U2 - 10.1016/j.bmcl.2015.05.054

DO - 10.1016/j.bmcl.2015.05.054

M3 - Journal 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

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