title: Synthesis of fluorescent derivatives of wortmannin and demethoxyviridin as probes for phosphatidylinositol 3-kinase.
abstract: Fluorescent analogs were synthesized of the potent PI 3-kinase inhibitors, wortmannin and demethoxyviridin. The esterification of 11-deacetylwortmannin, 17-hydroxywortmannin, and demethoxyviridin with the fluorescent carboxylic acids NBD-sarcosine and 7-dimethylaminocoumarin-4-acetic acid generated six novel fluorescent esters. Potent inhibition of PI 3-kinase-alpha was observed for the derivatives of 11-desacetylwortmannin and demethoxyviridin.
authors.affiliation: Department of Chemistry, State University of New York-ESF, Syracuse, NY 13210, USA. jlginer@syr.edu
authors.forename: José-Luis
authors.initials: JL
authors.lastname: Giner
authors.forename: Karen A
authors.initials: KA
authors.lastname: Kehbein
authors.forename: James A
authors.initials: JA
authors.lastname: Cook
authors.forename: Michele C
authors.initials: MC
authors.lastname: Smith
authors.forename: Chris J
authors.initials: CJ
authors.lastname: Vlahos
authors.forename: John A
authors.initials: JA
authors.lastname: Badwey
mesh_terms: D000730:Androstadienes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000736:Androstenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D015336:Molecular Probe Techniques; D000081082:Phosphoinositide-3 Kinase Inhibitors; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000077191:Wortmannin
chemical_list: D000730:Androstadienes; D000736:Androstenes; D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D000081082:Phosphoinositide-3 Kinase Inhibitors; C070594:demethoxyviridin; D000077191:Wortmannin