期刊
INTERNATIONAL JOURNAL OF PHARMACEUTICS
卷 381, 期 2, 页码 97-105出版社
ELSEVIER
DOI: 10.1016/j.ijpharm.2009.03.039
关键词
Water-soluble chitosan; Carboxymethyl trimethyl chitosan; Toll-like receptor-2 agonist; Biopolymer for mucosal vaccination
资金
- Ph.D. Student Exchange Project, Regione Abruzzo, Italy
The objective of this study was to provide a new water-soluble chitosan derivative being functionalized with a Toll-like receptor-2 (TLR-2) agonist. At first, we synthesized the water-soluble TLR-2 agonist omega-amido-[N-alpha-palmitoyl-oxy-S-[2,3-bis(palmitoyl-oxy)-(2R)-propyl]-[R]-cysteinyl]-alpha-amino poly(ethylene glycol) (Pam(3)Cys-PEG-NH2), which was characterized by H-1 and C-13 NMR as well as mass spectroscopy. Secondly, Pam(3)Cys-PEG-NH2 was then successfully grafted to 6-O-carboxymethyl-N,N,N-trimethyl chitosan polymers (CM-TMC) using EDC/NHS as condensing agents. The copolymer was analysed by means of H-1 and C-13 NMR and FTIR spectroscopy. C-13 NMR spectroscopy did not deliver evidence that an amide bond was formed between CM-TMC and Pam(3)Cys-PEG-NH2. However, H-1 NMR and FTIR spectroscopy demonstrated clearly that successful grafting took place. Based upon these results, this new TLR-2 functionalized biopolymer merits further investigations as material for vaccine delivery systems. (C) 2009 Elsevier B.V. All rights reserved.
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