title: Synthesis of 'clickable' acylhomoserine lactone quorum sensing probes: unanticipated effects on mammalian cell activation.
abstract: Alkynyl- and azido-tagged 3-oxo-C(12)-acylhomoserine lactone probes have been synthesized to examine their potential utility as probes for discovering the mammalian protein target of the Pseudomonas aeruginosa autoinducer, 3-oxo-C(12)-acylhomoserine lactone. Although such substitutions are commonly believed to be quite conservative, from these studies, we have uncovered a drastic difference in activity between the alkynyl- and azido-modified compounds, and provide an example where such structural modification has proved to be much less than conservative.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: Amanda L
authors.initials: AL
authors.lastname: Garner
authors.forename: Jing
authors.initials: J
authors.lastname: Yu
authors.forename: Anjali Kumari
authors.initials: AK
authors.lastname: Struss
authors.forename: Colin A
authors.initials: CA
authors.lastname: Lowery
authors.forename: Jie
authors.initials: J
authors.lastname: Zhu
authors.forename: Sook Kyung
authors.initials: SK
authors.lastname: Kim
authors.forename: Junguk
authors.initials: J
authors.lastname: Park
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Mayorov
authors.forename: Gunnar F
authors.initials: GF
authors.lastname: Kaufmann
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Kravchenko
authors.forename: Kim D
authors.initials: KD
authors.lastname: Janda
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000494:pharmacology; D000818:Animals; D002477:Cells / Q000187:drug effects*; D057930:Click Chemistry; D006714:Homoserine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011549:Pseudomonas / Q000737:chemistry / Q000378:metabolism*; D053038:Quorum Sensing
chemical_list: D007783:Lactones; C506098:azidohomoalanine; D006714:Homoserine; D000409:Alanine