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Synthesis and photocleavage of a new polymerizable [2+2] hetero dimer for phototriggered drug delivery

Paper ID Volume ID Publish Year Pages File Format Full-Text
27463 44024 2011 7 PDF Available
Title
Synthesis and photocleavage of a new polymerizable [2+2] hetero dimer for phototriggered drug delivery
Abstract

7-Hydroxy-1,1-dimethylnaphtalenone is introduced as a versatile photocleavable linker system for drug attachment to polymer materials with significantly improved two-photon-absorption efficiency. The synthesis of TBDMS-protected 7-hydroxy-1,1-dimethylnaphtalenone monomer is described, which is the release group attached to the polymer moiety. The cytotoxic 5-fluoro-1-heptanoyluracil was photochemically attached via [2+2] cycloaddition to this release group. The linker–drug conjugate was photochemically polymerized into a HEMA/MMA copolymer. Photo-triggered drug release from the polymer via single-photon-absorption as well as two-photon-absorption in solution were carried out. The detachment of 5-FU from the polymer and its release from the polymer were monitored in the polymer as well as in the aqueous medium and multidose drug release was successfully demonstrated.

► Drug release by two-photon absorption. ► Improved non hydrolysing linker molecule 1,1-dimethylnaphtalenone. ► Multidose drug release.

Keywords
Phototriggered drug delivery; [2+2] cycloaddition; Cycloreversion; Single photon absorption; Two photon absorption; 1,1-Dimethylnaphtalenone; 5-fluorouracil
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Synthesis and photocleavage of a new polymerizable [2+2] hetero dimer for phototriggered drug delivery
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 219, Issues 2–3, 15 April 2011, Pages 228–234
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
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