title: Molecular modeling, synthesis, and screening of new bacterial quorumsensing antagonists.
abstract: Abstract A new series comprising 7 analogs of N-(sulfanyl ethanoyl)-L-HSL derivatives, 2 analogs of N-(fluoroalkanoyl)- L-HSL derivatives, N-(fluorosulfonyl)-L-HSL, and 2,2-dimethyl butanoyl HSL were synthesized using a solid-phase organic synthesis method. Each of the 11 synthesized compounds was analyzed using NMR and mass spectroscopies, and molecular modeling studies of the 11 ligands were performed using SYBYL packages. Thereafter, a bacterial test was designed to identify their quorum-sensing inhibition activity and antifouling efficacy. Most of the synthesized compounds were found to be effective as quorum-sensing antagonists, where antagonist screening revealed that 10 among the 11 synthesized ligands were able to antagonize the quorum sensing of A. tumefaciens.
authors.affiliation: School of Chemical & Biological Engineering, Seoul National University, Seoul, Korea.
authors.forename: Cheoljin
authors.initials: C
authors.lastname: Kim
authors.forename: Jaeeun
authors.initials: J
authors.lastname: Kim
authors.forename: Hyung-Yeon
authors.initials: HY
authors.lastname: Park
authors.forename: Robert J C
authors.initials: RJ
authors.lastname: McLean
authors.forename: Chan Kyung
authors.initials: CK
authors.lastname: Kim
authors.forename: Jongho
authors.initials: J
authors.lastname: Jeon
authors.forename: Song-Se
authors.initials: SS
authors.lastname: Yi
authors.forename: Young Gyu
authors.initials: YG
authors.lastname: Kim
authors.forename: Yoon-Sik
authors.initials: YS
authors.lastname: Lee
authors.forename: Jeyong
authors.initials: J
authors.lastname: Yoon
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects; D001681:Biological Assay; D015195:Drug Design; D008958:Models, Molecular; D011550:Pseudomonas aeruginosa / Q000187:drug effects* / Q000378:metabolism; D053038:Quorum Sensing / Q000187:drug effects*; D012231:Rhizobium / Q000187:drug effects* / Q000378:metabolism; D054852:Small Molecule Libraries / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D054852:Small Molecule Libraries; C088386:homoserine lactone; D015107:4-Butyrolactone