Literature DB >> 21190852

Synthesis of 'clickable' acylhomoserine lactone quorum sensing probes: unanticipated effects on mammalian cell activation.

Amanda L Garner1, Jing Yu, Anjali Kumari Struss, Colin A Lowery, Jie Zhu, Sook Kyung Kim, Junguk Park, Alexander V Mayorov, Gunnar F Kaufmann, Vladimir V Kravchenko, Kim D Janda.   

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.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 21190852      PMCID： PMC3081916          DOI： 10.1016/j.bmcl.2010.11.122

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  34 in total

Review 1.  Establishment of Pseudomonas aeruginosa infection: lessons from a versatile opportunist.

Authors:  J B Lyczak; C L Cannon; G B Pier
Journal:  Microbes Infect       Date:  2000-07       Impact factor: 2.700

Review 2.  Biochemical target isolation for novices: affinity-based strategies.

Authors:  Shin-ichi Sato; Asako Murata; Takashi Shirakawa; Motonari Uesugi
Journal:  Chem Biol       Date:  2010-06-25

Review 3.  Quorum sensing: cell-to-cell communication in bacteria.

Authors:  Christopher M Waters; Bonnie L Bassler
Journal:  Annu Rev Cell Dev Biol       Date:  2005       Impact factor: 13.827

4.  Synthesis and validation of a probe to identify quorum sensing receptors.

Authors:  Luba Dubinsky; Lucja M Jarosz; Neri Amara; Pnina Krief; Vladimir V Kravchenko; Bastiaan P Krom; Michael M Meijler
Journal:  Chem Commun (Camb)       Date:  2009-10-28       Impact factor: 6.222

5.  The involvement of cell-to-cell signals in the development of a bacterial biofilm.

Authors:  D G Davies; M R Parsek; J P Pearson; B H Iglewski; J W Costerton; E P Greenberg
Journal:  Science       Date:  1998-04-10       Impact factor: 47.728

6.  Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes.

Authors:  J P Pearson; K M Gray; L Passador; K D Tucker; A Eberhard; B H Iglewski; E P Greenberg
Journal:  Proc Natl Acad Sci U S A       Date:  1994-01-04       Impact factor: 11.205

7.  Bacterial N-acylhomoserine lactone-induced apoptosis in breast carcinoma cells correlated with down-modulation of STAT3.

Authors:  Li Li; Doreen Hooi; Siri Ram Chhabra; David Pritchard; Peter E Shaw
Journal:  Oncogene       Date:  2004-06-17       Impact factor: 9.867

8.  Covalent inhibition of bacterial quorum sensing.

Authors:  Neri Amara; Roi Mashiach; Dotan Amar; Pnina Krief; Stéphane A H Spieser; Matthew J Bottomley; Amir Aharoni; Michael M Meijler
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

9.  Environmental regulation of Pseudomonas aeruginosa PAO1 Las and Rhl quorum-sensing systems.

Authors:  Kangmin Duan; Michael G Surette
Journal:  J Bacteriol       Date:  2007-04-20       Impact factor: 3.490

10.  Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.

Authors:  Qian Wang; Timothy R Chan; Robert Hilgraf; Valery V Fokin; K Barry Sharpless; M G Finn
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419
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  8 in total

Review 1.  Chemical Reporters for Exploring Microbiology and Microbiota Mechanisms.

Authors:  Zhenrun J Zhang; Yen-Chih Wang; Xinglin Yang; Howard C Hang
Journal:  Chembiochem       Date:  2019-12-27       Impact factor: 3.164

2.  Immunomodulation and the quorum sensing molecule 3-oxo-C12-homoserine lactone: the importance of chemical scaffolding for probe development.

Authors:  Amanda L Garner; Jing Yu; Anjali K Struss; Gunnar F Kaufmann; Vladimir V Kravchenko; Kim D Janda
Journal:  Chem Commun (Camb)       Date:  2013-02-21       Impact factor: 6.222

3.  Chemical methods to interrogate bacterial quorum sensing pathways.

Authors:  Thanit Praneenararat; Andrew G Palmer; Helen E Blackwell
Journal:  Org Biomol Chem       Date:  2012-10-03       Impact factor: 3.876

4.  Stereochemical insignificance discovered in Acinetobacter baumannii quorum sensing.

Authors:  Amanda L Garner; Sook Kyung Kim; Jie Zhu; Anjali Kumari Struss; Richard Watkins; Brent D Feske; Gunnar F Kaufmann; Kim D Janda
Journal:  PLoS One       Date:  2012-05-22       Impact factor: 3.240

5.  Amide-controlled, one-pot synthesis of tri-substituted purines generates structural diversity and analogues with trypanocidal activity.

Authors:  Maria J Pineda de las Infantas y Villatoro; Juan D Unciti-Broceta; Rafael Contreras-Montoya; Jose A Garcia-Salcedo; Miguel A Gallo Mezo; Asier Unciti-Broceta; Juan J Diaz-Mochon
Journal:  Sci Rep       Date:  2015-03-16       Impact factor: 4.379

6.  Immunoediting role for major vault protein in apoptotic signaling induced by bacterial N-acyl homoserine lactones.

Authors:  Josep Rayo; Rachel Gregor; Nicholas T Jacob; Rambabu Dandela; Luba Dubinsky; Alex Yashkin; Alexander Aranovich; Manikandan Thangaraj; Orna Ernst; Eran Barash; Sergey Malitsky; Bogdan I Florea; Bastiaan P Krom; Erik A C Wiemer; Valerie A Kickhoefer; Leonard H Rome; John C Mathison; Gunnar F Kaufmann; Herman S Overkleeft; Benjamin F Cravatt; Tsaffrir Zor; Kim D Janda; Richard J Ulevitch; Vladimir V Kravchenko; Michael M Meijler
Journal:  Proc Natl Acad Sci U S A       Date:  2021-03-23       Impact factor: 12.779

7.  The Pseudomonas aeruginosa N-acylhomoserine lactone quorum sensing molecules target IQGAP1 and modulate epithelial cell migration.

Authors:  Thommie Karlsson; Maria V Turkina; Olena Yakymenko; Karl-Eric Magnusson; Elena Vikström
Journal:  PLoS Pathog       Date:  2012-10-11       Impact factor: 6.823

Review 8.  Quorum sensing communication between bacteria and human cells: signals, targets, and functions.

Authors:  Angelika Holm; Elena Vikström
Journal:  Front Plant Sci       Date:  2014-06-26       Impact factor: 5.753
  8 in total

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