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The interactions of piperonyl butoxide and analogues with the metabolic enzymes FE4 and CYP6CY3 of the green peach aphid Myzus persicae (Hemiptera: Aphididae)
Author(s) -
Panini Michela,
Tozzi Francesco,
Bass Chris,
Zimmer Christoph T,
Field Linda,
Borzatta Valerio,
Mazzoni Emanuele,
Moores Graham
Publication year - 2017
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4314
Subject(s) - piperonyl butoxide , myzus persicae , chemistry , stereochemistry , enzyme , esterase , biochemistry , side chain , moiety , in silico , biology , organic chemistry , toxicity , gene , botany , aphid , polymer
Abstract BACKGROUND Piperonyl butoxide ( PBO ) is a well‐known insecticide synergist capable of interacting with phase 1 metabolic enzymes, specifically esterases and cytochrome P450s. In this study, structure–activity relationship analyses were used to characterise the interaction of around 30 analogues of PBO with the esterase FE4 and the P450 CYP6CY3 from insecticide‐resistant Myzus persicae (Sulzer), in order to predict the synthesis of more potent inhibitors. RESULTS Enzyme inhibition studies were performed against esterase and oxidase activities and, together with in silico modelling, key activity determinants of the analogues were identified and optimised. Novel analogues were then designed and synthesised, some of which showed greater inhibition against both enzymatic systems: specifically, dihydrobenzofuran moieties containing an alkynyl side chain and a butyl side chain against FE4 , and benzodioxole derivatives with a propyl/butyl side chain and an alkynyl ether moiety for CYP6CY3 . CONCLUSIONS In vitro assays identified potential candidate synergists with high inhibitory potency. The in vivo confirmation of such results will allow consideration for a possible use in agriculture. © 2016 Society of Chemical Industry