Literature DB >> 12930140

A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: design and synthesis of isotaxel.

Yoshio Hayashi1, Mariusz Skwarczynski, Yoshio Hamada, Youhei Sohma, Tooru Kimura, Yoshiaki Kiso.   

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.

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Year:  2003        PMID： 12930140     DOI： 10.1021/jm034112n

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  6 in total

1.  Conjugation of Paclitaxel to Hybrid Peptide Carrier and Biological Evaluation in Jurkat and A549 Cancer Cell Lines.

Authors:  Luladey Ayalew; Jessica Acuna; Selina F Urfano; Cristobal Morfin; Anthony Sablan; Myungeun Oh; Alicia Gamboa; Katarzyna Slowinska
Journal:  ACS Med Chem Lett       Date:  2017-07-27       Impact factor: 4.345

2.  2'-Behenoyl-paclitaxel conjugate containing lipid nanoparticles for the treatment of metastatic breast cancer.

Authors:  Ping Ma; S Rahima Benhabbour; Lan Feng; Russell J Mumper
Journal:  Cancer Lett       Date:  2012-08-16       Impact factor: 8.679

3.  Novel Type of Prodrug Activation through a Long-Range O,N-Acyl Transfer: A Case of Water-Soluble CREB Inhibitor.

Authors:  Bingbing X Li; Fuchun Xie; Qiuhua Fan; Kerry M Barnhart; Curtis E Moore; Arnold L Rheingold; Xiangshu Xiao
Journal:  ACS Med Chem Lett       Date:  2014-08-22       Impact factor: 4.345

Review 4.  Improved biochemical strategies for targeted delivery of taxoids.

Authors:  Thota Ganesh
Journal:  Bioorg Med Chem       Date:  2007-03-18       Impact factor: 3.641

5.  Antitumor effect of iRGD-modified liposomes containing conjugated linoleic acid-paclitaxel (CLA-PTX) on B16-F10 melanoma.

Authors:  Ruo Du; Ting Zhong; Wei-Qiang Zhang; Ping Song; Wen-Ding Song; Yang Zhao; Chao Wang; Yi-Qun Tang; Xuan Zhang; Qiang Zhang
Journal:  Int J Nanomedicine       Date:  2014-06-24

Review 6.  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
  6 in total

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