A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel

A Novel Approach of Water-Soluble Paclitaxel Prodrug with No Auxiliary and No Byproduct:  Design and Synthesis of Isotaxel

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‘-...

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Veröffentlicht in:Journal of medicinal chemistry 2003-08, Vol.46 (18), p.3782-3784
Hauptverfasser: Hayashi, Yoshio, Skwarczynski, Mariusz, Hamada, Yoshio, Sohma, Youhei, Kimura, Tooru, Kiso, Yoshiaki
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Biological and medical sciences
General aspects
Hydrogen-Ion Concentration
Kinetics
Medical sciences
Paclitaxel - administration & dosage
Paclitaxel - analogs & derivatives
Paclitaxel - chemical synthesis
Paclitaxel - chemistry
Pharmacology. Drug treatments
Prodrugs - chemical synthesis
Prodrugs - chemistry
Solubility
Water
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Zusammenfassung: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm034112n