A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct: Design and Synthesis of Isotaxel
- 26 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 46 (18) , 3782-3784
- https://doi.org/10.1021/jm034112n
Abstract
A novel water-soluble paclitaxel prodrug, isotaxel 2, that realizes a higher water-solubility and the formation of paclitaxel through a simple pH-dependent chemical mechanism via the O−N acyl migration was synthesized and showed promising results in water-solubility and kinetics. This prodrug, a 2‘-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics.Keywords
This publication has 14 references indexed in Scilit:
- Second Generation Taxanes: from the Natural Framework to the Challenge of Drug ResistanceCurrent Medicinal Chemistry - Anti-Cancer Agents, 2003
- Pilot study of hydrolytically activated paclitaxel prodrug therapy in patients with progressive malignanciesCurrent Therapeutic Research, 2002
- Oral Delivery of TaxanesInvestigational New Drugs, 2001
- A new prodrug of paclitaxel: synthesis of ProtaxelAnti-Cancer Drugs, 2001
- Phase I clinical and pharmacokinetic study of PNU166945, a novel water-soluble polymer-conjugated prodrug of paclitaxelAnti-Cancer Drugs, 2001
- Paclitaxel Derivatives for Targeted Therapy of Cancer: Toward the Development of Smart TaxanesJournal of Medicinal Chemistry, 1999
- Synthesis and Evaluation of Water-Soluble Non-Prodrug Analogs of Docetaxel Bearing sec-Aminoethyl Group at the C-10 Position.CHEMICAL & PHARMACEUTICAL BULLETIN, 1998
- Synthesis of Water-Soluble Paclitaxel Derivatives by Enzymatic AcylationJournal of the American Chemical Society, 1997
- Rapid intravenous premedication with dexamethasone prevents hypersensitivity reactions to paclitaxelAnnals of Oncology, 1996
- Trigonal Symmetry as a Host Design Element: Novel Conformation of Dodecakis(3,5‐dimethyl‐phenylthio)coronene in its 1,4‐Dioxane ClathrateAngewandte Chemie International Edition in English, 1994