Amphiphilic ionic complexes of hyaluronic acid with organophosphonium compounds and their antimicrobial activity

International Journal of Biological Macromolecules
Ana GamarraSebastián Muñoz-Guerra

Abstract

Amphiphilic ionic complexes of hyaluronic acid and alkyltrimethylphosphonium soaps with alkyl chains containing even numbers of carbons from 12 to 22 have been produced. The complexes have a nearly stoichiometric composition, are non-water soluble, and are stable to heat up to temperatures above 200 °C. These complexes are amphiphilic and able to adopt a biphasic structure with the paraffinic and polysaccharide phases ordered arranged with a periodicity ranging between 3 and 5 nm depending on n. The paraffinic phase in complexes with n ≥ 18 was crystallized and showed melting at temperatures between 58 and 70 °C depending on the n value. The complexes decomposed upon incubation in water under physiological conditions, and undergone extensive biodegradation by the action of hyaluronidases. Biocide assays carried out in both solid and liquid media demonstrated a high antimicrobial activity of the complexes against Gram-positive S. aureus but moderate against Gram-negative E. coli and C. albicans fungi.

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