[Synthesis and characterization of N-octyl-N-arginine chitosan--a chitosan derivant with a mimetic structure of cell-penetrating peptides].
A novel chitosan derivant, N-octyl-N-arginine chitosan (OACS) with a mimetic structure of cell-penetrating peptides was synthesized by introducing hydrophilic arginine groups and hydrophobic octyl groups to the amino-group on chitosan's side chain. Structure of the obtained polymer was characterized by FT-IR and 1H NMR. The substitution degree of octyl and arginine groups was calculated through element analysis and spectrophotometric method, separately. The critical micelle concentration of OACS was 0.12 - 0.27 mgmL(-1) tested by fluorescence spectrometry. The solubility test showed OACS could easily dissolve in pH 1 - 12 solutions and self-assemble to form a micelle solution with light blue opalescence. The OACS micelles have a mean size of 158.4 - 224.6 nm, polydisperse index of 0.038 - 0.309 and a zeta potential of +19.16 - +30.80 mV determined by malvern zetasizer. AFM images confirmed free OACS micelle has a regular sphere form with a uniform particle size. MTT test confirmed that OACS was safe in 50 - 1 000 micromol-L(-1). The result of HepG2 cell experiment showed that the cell internalization of OACS micelles enhanced with increased substitution degree of arginine by 40 folds compared to chitosan. Thus, OACS micelles were a promising nano vehicle with permeation enhancement and drug carrier capability.
Department of Pharmaceutics, China Pharmaceutical University, Nanjing 210009, China.
Chun-Yan
CY
Liu
Rui-Rui
RR
Pan
Tian-Yue
TY
Jiang
Jian-Ping
JP
Zhou
Hui-Xia
HX
Lü
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry; D002470:Cell Survival; D057846:Cell-Penetrating Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D048271:Chitosan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D004337:Drug Carriers; D056945:Hep G2 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D053758:Nanoparticles; D010316:Particle Size; D011108:Polymers; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared
D001672:Biocompatible Materials; D057846:Cell-Penetrating Peptides; D004337:Drug Carriers; D008823:Micelles; C581649:N-octyl-N-Arginine chitosan; D011108:Polymers; D048271:Chitosan; D001120:Arginine