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Evaluation of insect CAP2b analogs with either an (E)-alkene, trans- or a (Z)-alkene, cis-Pro isostere identifies the Pro orientation for antidiuretic activity in the stink bug

Nachman, R.J. and Wang, X.J. and Etzkorn, F.A. and Kaczmarek, K. and Zabrocki, J. and Lopez, J. and Coast, Geoffrey M. (2013) Evaluation of insect CAP2b analogs with either an (E)-alkene, trans- or a (Z)-alkene, cis-Pro isostere identifies the Pro orientation for antidiuretic activity in the stink bug. Peptides 41 , pp. 101-106. ISSN 0196-9781.

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Official URL: http://dx.doi.org/10.1016/j.peptides.2012.09.026

Abstract

The CAP2b neuropeptide family plays an important role in the regulation of the processes of diuresis and/or antidiuresis in a variety of insects. While Manse-CAP2b (pELYAFPRV-NH2) and native CAP2bs elicit diuretic activity in a number of species of flies, native CAP2b sequences have been shown to elicit antidiuretic activity in the kissing bug Rhodnius prolixus and the green stink bug Acrosternum hilare, the latter being an important pest of cotton and soybean in the southern United States. Analogs of CAP2b containing either a (Z)-alkene, cis-Pro or an (E)-alkene, trans-Pro isosteric component were synthesized and evaluated in an in vitro stink bug diuretic assay, which involved measurement of fluid secretion by Malpighian tubules isolated from A. hilare. The conformationally constrained trans-Pro analog demonstrated statistically significant antidiuretic activity, whereas the cis-Pro analog failed to elicit activity. The results are consistent with the adoption of a trans orientation for the Pro in CAP2b neuropeptides during interaction with receptors associated with the antidiuretic process in the stink bug. In addition, the results are further consistent with a theory of ligand-receptor coevolution between the CAP2b and pyrokinin/PBAN neuropeptide classes, both members of the ‘-PRXamide’ superfamily. This work further identifies a scaffold with which to design mimetic CAP2b analogs as potential leads in the development of environmentally favorable pest management agents capable of disrupting CAP2b-regulated diuretic/antidiuretic functions.

Item Type: Article
Keyword(s) / Subject(s): Antidiuretic, Stink bug, Peptidomimetic, Neuropeptide, Cyclic
School or Research Centre: Birkbeck Schools and Research Centres > School of Science > Biological Sciences
Depositing User: Administrator
Date Deposited: 18 Oct 2012 11:03
Last Modified: 08 May 2013 08:03
URI: http://eprints.bbk.ac.uk/id/eprint/5304

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