QSAR modeling of photosynthesis-inhibiting nostoclide derivatives

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 s...

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Bibliographic Details
Published in:Pest management science 2010-02, Vol.66 (2), p.196-202
Main Authors: Teixeira, Róbson Ricardo, Pinheiro, Patrícia F, Barbosa, Luiz Cláudio de Almeida, Carneiro, José Walkimar de M, Forlani, Giuseppe
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
4-Butyrolactone - pharmacology
Biological and medical sciences
chemical structure
chloroplasts
CODESSA
CODESSA software
computer software
dipole moment
Electron transfer
electron transport chain
equations
Fundamental and applied biological sciences. Psychology
Hill reaction
mathematical models
Models, Statistical
nostoclide derivatives
Photosynthesis
Photosynthesis - drug effects
photosynthetic inhibitory activity
polarity
QSAR
Quantitative Structure-Activity Relationship
quantitative structure-activity relationships
reaction inhibition
Software packages
spinach
Spinacia oleracea
Spinacia oleracea - drug effects
Spinacia oleracea - metabolism
statistical analysis
thylakoids
Toxins
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Summary: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, R² = 0.83, F = 23.8 and R² 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
ISSN:1526-498X
1526-4998
1526-4998
DOI:10.1002/ps.1855