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• W2004717523 abstract "BACKGROUND: Aiming at the rational design of new herbicides, the availability of the three-dimensional structure of the target enzyme greatly enhances the optimisation of lead compounds and the design of derivatives with increased activity. Among the most widely exploited herbicide targets is glutamine synthetase. Recently, the structure of a cytosolic form of the maize enzyme has been described, making it possible to verify whether steric, electronic and hydrophobic features of a compound are in agreement with inhibitor–protein interaction geometry. RESULTS: Three series of compounds (aminophosphonates, hydroxyphosphonates and aminomethylenebisphosphonates) were evaluated as possible inhibitors of maize glutamine synthetase. Aminomethylenebisphosphonate derivatives substituted in the phenyl ring retained the inhibitory potential, whereas variations in the scaffold, i.e. the replacement of the second phosphonate moiety with a hydroxyl or an amino residue, resulted in a significant loss of activity. A kinetic characterisation showed a non-competitive mechanism against glutamate and an uncompetitive mechanism against ATP. A docking analysis suggested the mode of bisphosphonate binding to the active site. CONCLUSION: Results made it possible to define the features required to maintain or enhance the biological activity of these compounds, which represent lead structures to be further exploited for the design of new substances endowed with herbicidal activity. Copyright © 2009 Society of Chemical Industry" @default.
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• W2004717523 date "2009-08-21" @default.
• W2004717523 modified "2023-09-26" @default.
• W2004717523 title "Effectiveness and mode of action of phosphonate inhibitors of plant glutamine synthetase" @default.
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• W2004717523 doi "https://doi.org/10.1002/ps.1830" @default.
• W2004717523 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19697446" @default.
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