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 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.
Department of Chemistry, Federal University of Viçosa, Avenida P. H. Rolfs, CEP 36570-000, Viçosa, MG, Brazil. robsonr.teixeira@ufv.br
Róbson Ricardo
RR
Teixeira
Patrícia F
PF
Pinheiro
Luiz Cláudio de Almeida
LC
Barbosa
José Walkimar de M
JW
Carneiro
Giuseppe
G
Forlani
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015233:Models, Statistical; D010788:Photosynthesis / Q000187:drug effects*; D021281:Quantitative Structure-Activity Relationship; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism
D015107:4-Butyrolactone