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Bioorg Med Chem

Title:		Ascaroside activity in Caenorhabditis elegans is highly dependent on chemical structure
Author(s):		Hollister KA; Conner ES; Zhang X; Spell M; Bernard GM; Patel P; de Carvalho AC; Butcher RA; Ragains JR;
Address:		"Department of Chemistry, Louisiana State University, Baton Rouge, 70803, United States"
Journal Title:		Bioorg Med Chem
Year:		2013
Volume:		20130718
Issue:		18
Page Number:		5754 - 5769
DOI:		10.1016/j.bmc.2013.07.018
ISSN/ISBN:		1464-3391 (Electronic) 0968-0896 (Print) 0968-0896 (Linking)
Abstract:		"The nematode Caenorhabditis elegans secretes ascarosides, structurally diverse derivatives of the 3,6-dideoxysugar ascarylose, and uses them in chemical communication. At high population densities, specific ascarosides, which are together known as the dauer pheromone, trigger entry into the stress-resistant dauer larval stage. In order to study the structure-activity relationships for the ascarosides, we synthesized a panel of ascarosides and tested them for dauer-inducing activity. This panel includes a number of natural ascarosides that were detected in crude pheromone extract, but as yet have no assigned function, as well as many unnatural ascaroside derivatives. Most of these ascarosides, some of which have significant structural similarity to the natural dauer pheromone components, have very little dauer-inducing activity. Our results provide a primer to ascaroside structure-activity relationships and suggest that slight modifications to ascaroside structure dramatically influence binding to the relevant G protein-coupled receptors that control dauer formation"
Keywords:		Animals Caenorhabditis elegans/growth & development/*metabolism Glycolipids/chemical synthesis/*chemistry/pharmacology Larva/drug effects/physiology Pheromones/chemical synthesis/*chemistry/pharmacology Structure-Activity Relationship Ascarosides Caenorha;
Notes:		"MedlineHollister, Kyle A Conner, Elizabeth S Zhang, Xinxing Spell, Mark Bernard, Gary M Patel, Pratik de Carvalho, Ana Carolina G V Butcher, Rebecca A Ragains, Justin R eng UL1 RR029890/RR/NCRR NIH HHS/ 1UL 1RR029890/RR/NCRR NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't England 2013/08/08 Bioorg Med Chem. 2013 Sep 15; 21(18):5754-69. doi: 10.1016/j.bmc.2013.07.018. Epub 2013 Jul 18"