title: Parthenolide and its photochemically synthesized 1(10)Z isomer: chemical reactivity and structure-activity relationship studies in human leucocyte chemotaxis.
abstract: The present study has achieved the photochemical conversion of a germacrolide into a melampolide. The investigation on their chemical properties allowed us to evaluate the minimum interatomic distance needed for transannular bridging of C(10) ring in germacrolides and to explain the regiochemical selectivity of electrophilic cyclizations. The antiinflammatory activity of parthenolide and its semisynthetic derivatives was evaluated by in vitro chemotaxis assay with human neutrophiles. These structure-activity relationship studies have led to hypothesize a new pharmacophore and have provided useful information for computationally designed drugs.
authors.affiliation: Laboratorio di Chimica Bioorganica, Università degli Studi di Trento, Via Sommarive 14, 38050 Povo (Trento), Italy.
authors.forename: Hannes
authors.initials: H
authors.lastname: Neukirch
authors.forename: Nicole C
authors.initials: NC
authors.lastname: Kaneider
authors.forename: Christian J
authors.initials: CJ
authors.lastname: Wiedermann
authors.forename: Antonio
authors.initials: A
authors.lastname: Guerriero
authors.forename: Michele
authors.initials: M
authors.lastname: D'Ambrosio
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology*; D002384:Catalysis; D002634:Chemotaxis, Leukocyte / Q000187:drug effects*; D006801:Humans; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D010777:Photochemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D007202:Indicators and Reagents; D012717:Sesquiterpenes; C002669:parthenolide