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Synthesis of 'clickable' acylhomoserine lactone quorum sensing probes: unanticipated effects on mammalian cell activation.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2011 May 01; Vol. 21 (9), pp. 2702-5. Date of Electronic Publication: 2010 Dec 04. - Publication Year :
- 2011
-
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.<br /> (Copyright © 2010 Elsevier Ltd. All rights reserved.)
- Subjects :
- Alanine analogs & derivatives
Alanine pharmacology
Animals
Click Chemistry
Homoserine chemistry
Humans
Lactones chemistry
Lactones pharmacology
Molecular Structure
Pseudomonas chemistry
Cells drug effects
Homoserine chemical synthesis
Homoserine pharmacology
Lactones chemical synthesis
Pseudomonas metabolism
Quorum Sensing
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 21
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 21190852
- Full Text :
- https://doi.org/10.1016/j.bmcl.2010.11.122