Antibacterial quaternized gellan gum based particles for controlled release of ciprofloxacin with potential dermal applications

Abstract

This paper presents the synthesis and characterization of gellan gum derivatives containing quaternary ammonium groups, with the purpose of obtaining particulate controlled release systems for ciprofloxacin. Quaternized gellan derivatives were synthesized by grafting N-(3-chloro-2-hydroxypropyl)-trimethyl ammonium chloride onto gellan primary hydroxyl groups by nucleophilic substitution, in the presence of alkali, under specific reaction conditions using various gellan/N-(3-chloro-2-hydroxypropyl)-trimethyl ammonium chloride molar ratios. Degree of quaternization was determined by 1H NMR spectroscopy and AgNO3 conductometric titration. Thermal behavior was investigated for all materials by thermogravimetric analysis. A study of the degree of quaternization and effect of the reaction conditions upon activation energy of quaternized gellan derivatives for the main degradation step by applying the Kissinger method at four heating rates is also reported. The novelty that this work brings refers to obtaining quaternized gellan and chitosan based particles with retention of quaternary ammonium moieties' antibacterial activity. In vitro transdermal release tests of ciprofloxacin from loaded particles were carried out on rat skin in isotonic phosphate buffer solution (pH=7.43). Ciprofloxacin was released up to 24h, confirming quaternized gellan–chitosan particles' potential as controlled release systems for topical dermal applications.