title: Structure-activity relationships of seco-prezizaane and picrotoxane/picrodendrane terpenoids by Quasar receptor-surface modeling.
abstract: The seco-prezizaane-type sesquiterpenes pseudoanisatin and parviflorolide from Illicium are noncompetitive antagonists at housefly (Musca domestica) gamma-aminobutyric acid (GABA) receptors. They show selectivity toward the insect receptor and thus represent new leads toward selective insecticides. Based on the binding data for 13 seco-prezizaane terpenoids and 17 picrotoxane and picrodendrane-type terpenoids to housefly and rat GABA receptors, a QSAR study was conducted by quasi-atomistic receptor-surface modeling (Quasar). The resulting models provide insight into the structural basis of selectivity and properties of the binding sites at GABA receptor-coupled chloride channels of insects and mammals.
authors.affiliation: Institut für Pharmazeutische Biologie der Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany. schmidtt@uni-duesseldorf.de
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Schmidt
authors.forename: Marion
authors.initials: M
authors.lastname: Gurrath
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Ozoe
mesh_terms: D000818:Animals; D001665:Binding Sites; D001667:Binding, Competitive; D018118:Chloride Channels / Q000187:drug effects / Q000502:physiology; D018756:GABA Antagonists / Q000737:chemistry* / Q000494:pharmacology*; D006793:Houseflies; D008958:Models, Molecular; D008968:Molecular Conformation; D051381:Rats; D018079:Receptors, GABA / Q000187:drug effects / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013499:Surface Properties / Q000187:drug effects; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D018118:Chloride Channels; D018756:GABA Antagonists; D018079:Receptors, GABA; D013729:Terpenes