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Synthesis and biological activity of FGLamide allatostatin analogs with Phe 3 residue modifications
Author(s) -
Xie Yong,
Wang Meizi,
Zhang Li,
Wu Xiaoqing,
Yang Xinling,
Tobe Stephen S.
Publication year - 2016
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2906
Subject(s) - residue (chemistry) , chemistry , stereochemistry , biochemistry
A FGLamide allatostatin neuropeptide mimic ( H17 ) is a potential insect growth regulator which inhibits the production of juvenile hormone by the corpora allata. To find more evidence to reveal the structure–activity relationships of the Phe 3 residue in the C ‐terminal conserved pentapeptide and search for novel analogs with high activity, a series of Phe 3 residue‐modified analogs were designed and synthesized using H17 as the lead compound. Bioassay using juvenile hormone (JH) production by corpora allata of the cockroach Diploptera punctata indicated that analogs 4 , 11 , and 13 showed strong ability to inhibit JH production in vitro , with IC 50 of 38.5, 22.5, and 26 nM, respectively. As well, the activity of analog 2 (IC 50 : 89.5 nM) proved roughly equivalent to that of H17 . Based on the primary structure–activity relationships of Phe 3 residue, we suggest that for analogs containing six‐membered aromatic rings, removing the methylene group of Phe 3 or an o ‐halogen or p ‐halogen‐substituted benzene ring could increase the ability to inhibit biosynthesis of JH. This study will be useful for the design of new allatostatin analogs for insect management. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.