N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties.

Two samples of N -(2-hydroxy)-propyl-3-trimethylammonium, O- palmitoyl chitosan (DPCat) with different average degrees of quaternization named as DPCat35 (DQ ¯ = 35%) and DPCat80 (DQ ¯ = 80%), were successfully synthesized by reacting glycidyltrimethylammonium chloride (GTMAC) with O -palmitoyl chitosan (DPCh) derivative (DS ¯ = 12%). Such amphiphilic derivatives of chitosan were fully water-soluble at 1.0 < pH < 12.0 and showed significant electrostatic stability enhancement of a self-assembly micellar nanostructure (100–320 nm) due to its positively-charged out-layer. In vitro mucoadhesive and cytotoxicity essays toward healthy fibroblast cells (Balb/C 3T3 clone A31 cell), human prostate cancer (DU145) and liver cancer (HepG2/C3A) cell lines revealed that the biological properties of DPCat derivatives were strongly dependent on DQ ¯. Additionally, DPCat35 had better interactions with the biological tissue and with mucin glycoproteins at pH 7.4 as well as exhibited potential to be used on the development of drug delivery systems for prostate and liver cancer treatment. • Permanent-charged amphiphilic chitosans with different degrees of quaternization • Fully water-soluble self-assembled micelle-like nanostructures were produced. • Quaternization increases the mucoadhesion of former hydrophobically-modified chitosan. • Cytotoxicity is highly dependent on the content of positively-charged groups. [ABSTRACT FROM AUTHOR]