Synthesis, biological activity, and conformational study of N-methylated allatostatin analogues inhibiting juvenile hormone biosynthesis

Journal of Agricultural and Food Chemistry
Yong XieS S Tobe

Abstract

An allatostatin (AST) neuropeptide mimic (H17) is a potential insect growth regulator, which inhibits the production of juvenile hormone (JH) by the corpora allata. To determine the effect of conformation of novel AST analogues and their ability to inhibit JH biosynthesis, eight insect AST analogues were synthesized using H17 as the lead compound by N-methylation scanning, which is a common strategy for improving the biological properties of peptides. A bioassay using JH production by corpora allata of the cockroach Diploptera punctata indicated that single N-methylation mimics (analogues 1-4) showed more activity than double N-methylation mimics (analogues 5-8). Especially, analogues 1 and 4 showed roughly equivalent activity to that of H17, with IC50 values of 5.17 × 10(-8) and 6.44 × 10(-8) M, respectively. Molecular modeling based on nuclear magnetic resonance data showed that the conformation of analogues 1 and 4 seems to be flexible, whereas analogues 2 and 3 showed a type IV β-turn. This flexible linear conformation was hypothesized to be a new important and indispensable structural element beneficial to the activity of AST mimics.

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Citations

Aug 2, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Yong XieStephen S Tobe
Oct 30, 2016·General and Comparative Endocrinology·Andrew E ChristieErica E Tassone
Apr 25, 2018·Salud pública de México·Alejandro Alvarado-DelgadoHumberto Lanz-Mendoza
Mar 24, 2018·Journal of Agricultural and Food Chemistry·Shan-Shan HuangZhen-Peng Kai

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