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

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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. Bd. 49 (2011) Heft 2 . - S. 70-75.
ISSN 1097-458X
DOI: https://doi.org/10.1002/mrc.2711

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Abstract

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.