Comparison of insect kinin analogs with cis-peptide bond, type VI-turn motifs identifies optimal stereochemistry for interaction with a recombinant arthropod kinin receptor from the southern cattle tick Boophilus microplus

Peptides
Suparna Taneja-BageshwarR J Nachman

Abstract

The multifunctional 'insect kinins' share the evolutionarily conserved C-terminal pentapeptide motif Phe-X1-X2-Trp-Gly-NH2, where X1=His, Asn, Ser, or Tyr and X2=Ser, Pro, or Ala; and are associated with the regulation of diuresis in a variety of species of insects. We previously reported the functional expression of a southern cattle tick (Boophilus microplus) G protein-coupled receptor that is activated by insect kinins. Four different stereochemical variants of each of the 4-aminopyroglutamic acid (APy) and tetrazole moieties, mimics of a cis-peptide bond, type VI beta-turn in insect kinins were now evaluated on the expressed tick receptor using a calcium bioluminescence plate assay. This study represents the first investigation of the interaction of restricted-conformation analogs incorporating components that mimic specific conformations and/or peptide bond orientations in an expressed arthropod neuropeptide receptor. Analog Ac-RF[APy]WGa (2R,4S) was at least 10-fold more active than the other analogs, thus identifying the optimal stereochemistry for tick receptor interaction. The optimal stereochemistry for the tetrazole insect kinin analogs in the tick receptor assay was identified as (D,L). The APy is superior to the te...Continue Reading

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Citations

Feb 3, 2009·Bioorganic & Medicinal Chemistry·Jürgen Scherkenbeck, Tino Zdobinsky
Nov 6, 2008·General and Comparative Endocrinology·Suparna Taneja-BageshwarRonald J Nachman
Aug 30, 2008·General and Comparative Endocrinology·Andrew E Christie
Oct 1, 2009·Chembiochem : a European Journal of Chemical Biology·Tino ZdobinskyHeru Chen
May 22, 2009·Annals of the New York Academy of Sciences·Ronald J NachmanGeoffrey M Coast
Jun 16, 2010·Journal of Molecular Recognition : JMR·Daniel ClaytonMarie-Isabel Aguilar
Jun 27, 2012·Annals of the New York Academy of Sciences·Klaus W Beyenbach
May 13, 2009·Current Opinion in Lipidology

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