Literature DB >> 16806915

Development of first photoresponsive prodrug of paclitaxel.

Mariusz Skwarczynski1, Mayo Noguchi, Shun Hirota, Youhei Sohma, Tooru Kimura, Yoshio Hayashi, Yoshiaki Kiso.   

Abstract

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.

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Year:  2006        PMID： 16806915     DOI： 10.1016/j.bmcl.2006.06.030

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  13 in total

Review 1.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

Review 2.  Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

Authors:  Richard S Givens; Marina Rubina; Jakob Wirz
Journal:  Photochem Photobiol Sci       Date:  2012-02-16       Impact factor: 3.982

3.  A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging.

Authors:  Pamela T Wong; Shengzhuang Tang; Jayme Cannon; Jhindan Mukherjee; Danielle Isham; Kristina Gam; Michael Payne; Sean A Yanik; James R Baker; Seok Ki Choi
Journal:  Chembiochem       Date:  2016-11-30       Impact factor: 3.164

4.  Core-clickable PEG-branch-azide bivalent-bottle-brush polymers by ROMP: grafting-through and clicking-to.

Authors:  Jeremiah A Johnson; Ying Y Lu; Alan O Burts; Yeon-Hee Lim; M G Finn; Jeffrey T Koberstein; Nicholas J Turro; David A Tirrell; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2010-12-13       Impact factor: 15.419

5.  Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages.

Authors:  Elena Contreras-García; Carmen Lozano; Cristina García-Iriepa; Marco Marazzi; Arthur H Winter; Carmen Torres; Diego Sampedro
Journal:  Pharmaceutics       Date:  2022-05-17       Impact factor: 6.525

6.  Far-Red Light-Activatable Prodrug of Paclitaxel for the Combined Effects of Photodynamic Therapy and Site-Specific Paclitaxel Chemotherapy.

Authors:  Pritam Thapa; Mengjie Li; Moses Bio; Pallavi Rajaputra; Gregory Nkepang; Yajing Sun; Sukyung Woo; Youngjae You
Journal:  J Med Chem       Date:  2016-03-22       Impact factor: 7.446

7.  Phototriggerable 2',7-caged paclitaxel.

Authors:  Radu A Gropeanu; Hella Baumann; Sandra Ritz; Volker Mailänder; Thomas Surrey; Aránzazu del Campo
Journal:  PLoS One       Date:  2012-09-06       Impact factor: 3.240

8.  Phototriggered protein syntheses by using (7-diethylaminocoumarin-4-yl)methoxycarbonyl-caged aminoacyl tRNAs.

Authors:  Takashi Ohtsuki; Shigeto Kanzaki; Sae Nishimura; Yoshio Kunihiro; Masahiko Sisido; Kazunori Watanabe
Journal:  Nat Commun       Date:  2016-08-17       Impact factor: 14.919

Review 9.  Prodrug Strategies for Paclitaxel.

Authors:  Ziyuan Meng; Quanxia Lv; Jun Lu; Houzong Yao; Xiaoqing Lv; Feng Jiang; Aiping Lu; Ge Zhang
Journal:  Int J Mol Sci       Date:  2016-05-23       Impact factor: 5.923

Review 10.  Radiation- and photo-induced activation of 5-fluorouracil prodrugs as a strategy for the selective treatment of solid tumors.

Authors:  Takeo Ito; Kazuhito Tanabe; Hisatsugu Yamada; Hiroshi Hatta; Sei-ichi Nishimoto
Journal:  Molecules       Date:  2008-10-01       Impact factor: 4.411
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