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Synthesis and controlled release behaviour of dextran bioactive esters by direct reaction of dextran with the potassium salts of bioactive carboxylic acids
Author(s) -
Macias Antonio,
SánchezChaves Manuel,
Rodríguez José Luis,
Arranz Félix
Publication year - 1997
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1997.021981111
Subject(s) - chemistry , dextran , pyridine , sulfonyl , organic chemistry , polymer chemistry , potassium , carboxylic acid , alkyl
This work deals with the coupling of model bioactive carboxylic acids (1‐naphthylacetic acid, 2‐(6‐methoxy‐2‐naphthyl)propionic acid (naproxen) and nicotinic acid) to dextran by direct reaction with their potassium salts using pyridine/sulfonyl chloride as activating agent. The structure of the resulting polymeric derivatives was determined by means of 1 H and 13 C NMR spectroscopy. The influence of the pyridine concentration, the type of sulfonyl chloride and the temperature on the reaction of dextran with potassium 1‐naphthyl acetate was evaluated. The activation energy was found to be 65,7 kJ/mol. 13 C NMR spectra at 75,4 MHz of partially modified dextran with 1‐naphthyl acetate groups were studied in order to evaluate the selectivity of the reaction between dextran and potassium 1‐naphthyl acetate. Analysis of the spectra of ring carbons in the anhydroglucose units shows that the reactivity of the individual hydroxyl groups decreases in the order C2 > C4 > C3. The hydrolysis in the heterogeneous phase of some dextran polymers partially modified with 1‐naphthyl acetate groups shows that the release of the bioactive compound is dependent on the hydrophilic character of the polymer as well as the pH value of the medium.