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QSAR modeling of photosynthesis‐inhibiting nostoclide derivatives
Author(s) -
Teixeira Róbson Ricardo,
Pinheiro Patrícia F,
Barbosa Luiz Cláudio de Almeida,
Carneiro José Walkimar de M,
Forlani Giuseppe
Publication year - 2010
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.1855
Subject(s) - quantitative structure–activity relationship , photosynthesis , chemistry , polarity (international relations) , solvation , molecular descriptor , thylakoid , ferricyanide , biological system , computational chemistry , chloroplast , stereochemistry , molecule , biology , biochemistry , organic chemistry , gene , cell
BACKGROUND: A statistical model, built using the CODESSA software package, was developed to describe the relationship between the structure of nostoclide derivatives and their ability to interfere with the electron transport chain in the Hill reaction. RESULTS: A QSAR treatment was carried out on a series of compounds designed using the naturally occurring toxin nostoclides to correlate molecular descriptors with their in vitro biological activity (the ability to interfere with light‐driven reduction of ferricyanide by isolated spinach chloroplast thylakoid membranes). The treatment using the CODESSA software package resulted in a three‐parameter model with n = 19, R 2 = 0.83, F = 23.8 and R 2 cv = 0.72. In the proposed model, the Image of Onsager Kirkwood solvation energy, which gives a measure of the polarity of a given compound, is the most important descriptor. The model was internally validated. CONCLUSIONS: The results obtained in this study indicate that polarity, as expressed by the dipole moment, is the most relevant molecular property determining efficiency of photosynthetic inhibitory activity. Copyright © 2009 Society of Chemical Industry