Polymer-bound 4-methylcoumarin/1-heptanoyl-5-fluorouracil photodimers: NMR elucidation of dimer structure |
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Authors: | Sinkel Carsten Schwarzer Martin C Frenking Gernot Greiner Andreas Agarwal Seema |
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Affiliation: | Philipps‐Universit?t Marburg, Fachbereich Chemie, Hans‐Meerwein Strasse, D‐35032 Marburg, Germany |
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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. |
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Keywords: | NMR polymer‐bound coumarin photodimers |
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