Development of first photoresponsive prodrug of paclitaxel.
A prodrug of paclitaxel which has a coumarin derivative conjugated to the amino acid moiety of isotaxel (O-acyl isoform of paclitaxel) has been synthesized. The prodrug was selectively converted to isotaxel by visible light irradiation (430 nm) with the cleavage of coumarin. Finally, paclitaxel was released by subsequent spontaneous O-N intramolecular acyl migration.
Skwarczynski
Mariusz
M
Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science and 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Japan.
Noguchi
Mayo
M
Hirota
Shun
S
Sohma
Youhei
Y
Kimura
Tooru
T
Hayashi
Yoshio
Y
Kiso
Yoshiaki
Y
D015394:Molecular Structure; D017239:Paclitaxel / Q000138:chemical synthesis / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry
D017319:Photosensitizing Agents; D011355:Prodrugs; D017239:Paclitaxel