Semi-synthesis of an O-glycosylated docetaxel analogue.
A 7beta-O-glycosylated docetaxel analogue was semi-synthesized from 9-dihydro-13-acetylbaccatin III, the most abundant taxane isolated from the needles of Taxus canadensis. It was shown to be more bioactive than paclitaxel according to the tubulin assay. It had a reduced potency in the MCF7 cell line cytotoxicity assay compared to paclitaxel, but it demonstrated better activity against the drug resistant cell line MCF7-ADR. In addition, the presence of one sugar moiety on C-7 doubled the water solubility versus that of paclitaxel.
Nikolakakis
Anastasia
A
Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Québec, Canada H7V 1B7.
Haidara
Khadidja
K
Sauriol
Françoise
F
Mamer
Orval
O
Zamir
Lolita O
LO
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D001923:Brain Chemistry / Q000187:drug effects; D001943:Breast Neoplasms / Q000188:drug therapy; D002417:Cattle; D000077143:Docetaxel; D004317:Doxorubicin / Q000494:pharmacology; D019008:Drug Resistance, Neoplasm; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006031:Glycosylation; D006801:Humans; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology*; D043823:Taxoids; D014404:Tubulin / Q000096:biosynthesis; D014407:Tumor Cells, Cultured
D000903:Antibiotics, Antineoplastic; D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D043823:Taxoids; D014404:Tubulin; D000077143:Docetaxel; D004317:Doxorubicin; D017239:Paclitaxel