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Polymer-bound 4-methylcoumarin/1-heptanoyl-5-fluorouracil photodimers : NMR elucidation of dimer structure

Title data

Sinkel, Carsten ; Schwarzer, Martin C. ; Frenking, Gernot ; Greiner, Andreas ; Agarwal, Seema:
Polymer-bound 4-methylcoumarin/1-heptanoyl-5-fluorouracil photodimers : NMR elucidation of dimer structure.
In: Magnetic Resonance in Chemistry. Vol. 49 (February 2011) Issue 2 . - pp. 70-75.
ISSN 0749-1581
DOI: https://doi.org/10.1002/mrc.2711

Official URL: Volltext

Project information

Project financing: Bundesministerium für Bildung und Forschung

Abstract in another language

Heterodimers based on the polymer-bound chromophore 4-methylcoumarin and the prodrug 1-heptanoyl-5-fluorouracil, synthesized by photochemical [2 + 2]-cycloaddition are promising photoresponsive drug depots. Drug release experiments are one possibility to deliver proof of a successful reversible drug immobilization, whereas NMR spectroscopy is a potent tool for further structural characterization of these polymer-bound heterodimers. In case of the random copolymer poly(methyl methacrylate-co-7-(2'-methacryloyloxyethoxy)-4-methylcoumarin) three dimers have been identified of which the syn head-to-tail was the predominant one. In contrast, only the syn head-to-head dimer was formed in reasonable yield when the 4-methylcoumarin monofunctionalized pMMA was used as the base polymer. 1D and 2D NMR spectroscopic techniques combined with some theoretical calculations helped in successfully closing one major gap concerning polymer bound 4-methylcoumarin/1-heptanoyl-5-fluorouracil heterodimers that are of potential use in photoresponsive drug delivery devices. Copyright (C) 2011 John Wiley & Sons, Ltd.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: NMR; polymer-bound coumarin; photodimers
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry II > Chair Macromolecular Chemistry II - Univ.-Prof. Dr. Andreas Greiner
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry II
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 01 Apr 2015 07:20
Last Modified: 01 Apr 2015 07:20
URI: https://eref.uni-bayreuth.de/id/eprint/9548