Synthesis of ‘clickable’ acylhomoserine lactone quorum sensing probes: Unanticipated effects on mammalian cell activation

Bioorganic & Medicinal Chemistry Letters
2011.0

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.

Knowledge Graph

Similar Paper

Synthesis of ‘clickable’ acylhomoserine lactone quorum sensing probes: Unanticipated effects on mammalian cell activation
Bioorganic & Medicinal Chemistry Letters 2011.0
Microwave Synthesis and Evaluation of Phenacylhomoserine Lactones as Anticancer Compounds that Minimally Activate Quorum Sensing Pathways in Pseudomonas aeruginosa
Journal of Medicinal Chemistry 2009.0
Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages
Bioorganic & Medicinal Chemistry Letters 2006.0
3-Aminooxazolidinone AHL analogs as hydrolytically-stable quorum sensingagonists in Gram-negative bacteria
MedChemComm 2015.0
Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone
Journal of Medicinal Chemistry 2011.0
Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing
Bioorganic &amp; Medicinal Chemistry 2011.0
New synthetic analogues of N-acyl homoserine lactones as agonists or antagonists of transcriptional regulators involved in bacterial quorum sensing
Bioorganic &amp; Medicinal Chemistry Letters 2002.0
Evaluation of a focused library of N-aryl l-homoserine lactones reveals a new set of potent quorum sensing modulators
Bioorganic &amp; Medicinal Chemistry Letters 2008.0
(Z)-N-(4-Decenoyl)homoserine lactone, a new quorum-sensing molecule, produced by endobacteria associated with Mortierella alpina A-178
Tetrahedron Letters 2012.0
Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule N-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone as Immune Modulators
Journal of Medicinal Chemistry 2003.0