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Polymer‐bound 4‐methylcoumarin/1‐heptanoyl‐5‐fluorouracil photodimers: NMR elucidation of dimer structure
Author(s) -
Sinkel Carsten,
Schwarzer Martin C.,
Frenking Gernot,
Greiner Andreas,
Agarwal Seema
Publication year - 2011
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2711
Subject(s) - chemistry , polymer , dimer , proton nmr , prodrug , chromophore , copolymer , nuclear magnetic resonance spectroscopy , combinatorial chemistry , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , photochemistry , organic chemistry , biochemistry
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. Copyright © 2011 John Wiley & Sons, Ltd.