Synthesis and biological activity of FGLamide allatostatin analogs with Phe3 residue modifications |
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Authors: | Yong Xie Meizi Wang Li Zhang Xiaoqing Wu Xinling Yang Stephen S Tobe |
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Institution: | 1. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, China;2. Department of Cell and Systems Biology, University of Toronto, Toronto, ON, Canada;3. State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd., Shenyang, China |
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Abstract: | 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 Phe3 residue in the C‐terminal conserved pentapeptide and search for novel analogs with high activity, a series of Phe3 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 IC50 of 38.5, 22.5, and 26 nM, respectively. As well, the activity of analog 2 (IC50: 89.5 nM) proved roughly equivalent to that of H17 . Based on the primary structure–activity relationships of Phe3 residue, we suggest that for analogs containing six‐membered aromatic rings, removing the methylene group of Phe3 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. |
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Keywords: | allatostatins Phe3 residue modifications biological activity juvenile hormone insect growth regulator |
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