Structure-activity relationships for the anti-HIV activity of flavonoids.
Quantitative structure-activity relationship (QSAR) models are useful in providing a biochemical understanding of the biological activity of natural and synthetic chemicals based solely on molecular structure. One- to three-parameter multiregression equations were generated for three different groups of flavonoids to model experimental flavonoid-induced cytotoxicity and inhibition of human immunodeficiency virus I replication in lymphocyte-infected cells, using quantum chemical and geometrical parameters derived from optimized molecular structures. Both biological properties were basically dependent on electronic parameters describing charge distribution on the two fused rings of the flavonoid molecule. Atomic charges in C3 and the carbonyl carbon as well as the dipolar moment were important electronic descriptors to define the studied biological properties of flavonoids.
Olivero-Verbel
Jesús
J
Environmental and Computational Chemistry Group, Department of Chemistry, University of Cartagena, Cartagena, Colombia, South America. jesusolivero@yahoo.com
Pacheco-Londoño
Leonardo
L
D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology*; D016000:Cluster Analysis; D003198:Computer Simulation; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests / Q000706:statistics & numerical data; D008956:Models, Chemical; D021281:Quantitative Structure-Activity Relationship
D019380:Anti-HIV Agents; D005419:Flavonoids