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

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.