Parthenolide and its photochemically synthesized 1(10)Z isomer: chemical reactivity and structure-activity relationship studies in human leucocyte chemotaxis.
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.
Neukirch
Hannes
H
Laboratorio di Chimica Bioorganica, Università degli Studi di Trento, Via Sommarive 14, 38050 Povo (Trento), Italy.
Kaneider
Nicole C
NC
Wiedermann
Christian J
CJ
Guerriero
Antonio
A
D'Ambrosio
Michele
M
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007202:Indicators and Reagents; D012717:Sesquiterpenes; C002669:parthenolide