Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs.

Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. Research Abstract Details 

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Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. Abstract Text:

A novel coumarin-based highly water-soluble photocleavable protective group was designed and synthesized, and then this photosensitive protecting group was used to design paclitaxel prodrugs. These novel paclitaxel conjugates demonstrated excellent water solubility, over 100mgmL(-1). Thus, the use of a detergent in the formulation can be omitted completely, even at high doses. Phototaxel 11 released the parent drug, paclitaxel, quickly and efficiently by minimal tissue-damaging 365nm UV light irradiation at low power, while laser activation at 355nm led to extensive decomposition of the prodrug. The carbamate-type prodrug, phototaxel 11, was stable in the dark prior to activation, whereas carbonate-type phototaxel 9 demonstrated poor stability under aqueous conditions. For such prodrugs, tumor-tissue targeting after administration could be achieved by selective light delivery, similar to that used in photodynamic therapy. In addition, newly designed coumarin derivative 8 can be applied in organic chemistry as a photosensitive protective group and for the design of caged compounds.

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Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Bioorganic & medicinal chemistry

VOLUME: 16

Page Numbers: 5389-97

Journal Abbreviation: Bioorg. Med. Chem.

ISSN: 1464-3391

DAY: 15

MONTH: 04

YEAR: 2008

Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. Information

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LANGUAGE: eng

NlmUniqueID: 9413298

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Grant and Affiliation Information for Development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs.

AFFILIATION: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science and 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.

Country: England

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MEDLINETA: Bioorg Med Chem

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