Synthesis and characterization of chitosan quaternary ammonium salt and its application as drug carrier for ribavirin

Abstract

N-(2-hydroxyl) propyl-3-trimethyl ammonium chitosan chloride (HTCC) is hydro-soluble chitosan (CS) derivative, which can be obtained by the reaction between epoxypropyl trimethyl ammonium chloride (ETA) and CS. The preparation parameters for the synthesis of HTCC were optimized by orthogonal experimental design. ETA was successfully grafted into the free amino group of CS. Grafting of ETA with CS had great effect on the crystal structure of HTCC, which was confirmed by the XRD results. HTCC displayed higher capability to form nanoparticles by crosslinking with negatively charged sodium tripolyphosphate (TPP). Ribavrin- (RIV-) loaded HTCC nanoparticles were positively charged and were spherical in shape with average particle size of 200 nm. More efficient drug encapsulation efficiency and loading capacity were obtained for HTCC in comparison with CS, however, HTCC nanoparticles displayed faster release rate due to its hydro-soluble properties. The results suggest that HTCC is a promising CS derivative for the encapsulation of hydrophilic drugs in obtaining sustained release of drugs.

Functional chemical modification of a porcine acellular dermal matrix with a modified naturally derived polysaccharide crosslinker

“…2‐Hydroxypropyltrimethyl ammonium chloride chitosan (HTCC) represents a type of quaternary ammonium salt of chitosan, as a derivative of chitosan, exhibits better solubility in aqueous solution and improved antimicrobial effects than chitosan, benefiting from the introduction of a quaternary ammonium salt. Nowadays, it has been widely used in biomedicine, environmental protection, food industry, and so on . The use of HTCC for modifying pADM could introduce suitable antibacterial properties to the material, and this kind of physical blending represents a commonly used method.…”

Cyclosporine A/porous quaternized chitosan microspheres as a novel pulmonary drug delivery system

“…CsA was supplied by Minsheng Pharmaceutical Factory (Hangzhou, China). HTCC was synthesized and characterized in accordance with a previously described process [4,5]. The molecular weights of HTCC were 1360 kDa, 450 kDa, and 170 cps with DS of 88.74, 83.60, and 73.95%, respectively.…”

“…All experiments were triplicated (n ¼ 3). The fine particle fraction (FPF), respirable fraction (RF), and emitted dose (ED) were calculated as follows in Equations (3)(4)(5) Ciliotoxicity study: Ciliotoxicity studies were carried out using an in situ toad palate model. The upper palates of the toads (n ¼ 6) were exposed and treated with HTCC (10 mg), CsA (0.4 mg), MS (20 mg) and 0.5 ml of normal saline, respectively.…”

“…HTCC was obtained via the reaction between hydroxypropyl trimethyl ammonium chloride (EPTAC) and CTS [4]. HTCC has also been extensively investigated as a class of drug delivery vehicles because of its unique features, including biocompatible material, antibacterial property, good water solubility in a wide range of pH, high drug-loading capacity, and the varying release rate by modulating the degree of substitution (DS) of HTCC [5]. Moreover, HTCC is able to increase the paracellular permeability and/or absorption of peptide drugs across mucosal epithelia at neutral pH values as the positive surface charge of HTCC can bind to the negative-charged epithelial cell membranes by electrostatic interactions [6].…”

Desenvolvimento de sistemas anfifílicos baseados em derivados de quitosana para transporte e liberação sustentada de fármacos

“…Wang, H. et al (2010) (LI, S. et al, 2014). Outros exemplos da utilização de derivados de quitosana modificados com grupos quaternários de amônio para transporte e liberação de fármacos podem ser citados (FANG et al, 2015;MENNINI et al, 2014).…”