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Bioorg Med Chem

Title:		Synthesis and biological activity of conformationally restricted gypsy moth pheromone mimics
Author(s):		Chen H; Gong Y; Gries RM; Plettner E;
Address:		"Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, B.C., Canada V5A 1S6"
Journal Title:		Bioorg Med Chem
Year:		2010
Volume:		20100306
Issue:		8
Page Number:		2920 - 2929
DOI:		10.1016/j.bmc.2010.02.061
ISSN/ISBN:		1464-3391 (Electronic) 0968-0896 (Linking)
Abstract:		"The design and synthesis of a series of conformationally constrained mimics of gypsy moth sex pheromone, (+)-disparlure (7R,8S)-2-methyl-7,8-epoxyoctadecane, are described. The core structure of the mimics is derived from 5-(2'-hydroxyethyl)cyclopent-2-en-1-ol. Substituent optimization of the analogs was accomplished through the synthesis of mini-libraries and pure individual compounds, followed by electrophysiological experiments with male gypsy moth antennae. The electroantennogram results show that the analogs elicited weak to no antennal responses themselves. There was a clear structure-activity pattern for odorant activity, with ethyl substituents being best. Further, when puffed simultaneously with the pheromone, some of the compounds gave a significant enhancement of the antennal depolarization, indicating an additive or synergistic effect. A pure pheromone stimulus following a mixed compound/pheromone stimulus was generally not affected, with two exceptions: one compound enhanced and another inhibited a subsequent stimulus. The compounds also prolonged the stimulation of the antenna, which manifested itself in widened electroantennogram peaks. We tested the hypothesis that this prolonged stimulation may be due to the stabilization of a particular conformer of the pheromone-binding protein (PBP). Compounds that caused PBP2 to adopt a similar conformation than in the presence of pheromone also caused peak widening. This was not the case with PBP1"
Keywords:		"Alkanes/*chemical synthesis/chemistry/pharmacology Animals Carrier Proteins/metabolism Electrophysiological Phenomena Male Models, Molecular Molecular Conformation Moths/*physiology Sex Attractants/*chemical synthesis/chemistry/pharmacology Stereoisomeris;"
Notes:		"MedlineChen, Hao Gong, Yongmei Gries, Regine M Plettner, Erika eng Research Support, Non-U.S. Gov't England 2010/03/30 Bioorg Med Chem. 2010 Apr 15; 18(8):2920-9. doi: 10.1016/j.bmc.2010.02.061. Epub 2010 Mar 6"