Synthesis of an O-alkynyl-chitosan and its chemoselective conjugation with a PEG-like amino-azide through click chemistry

• Tipo: Artigo em Revista Científica Internacional
• Data: 2012

Autores

Jose Ricardo Oliveira (Autor) Outra; Cristina C L Martins (Autor) Outra; Luis Mafra (Autor) Outra; Paula Comes (Autor) FCUP

Revista

Título: Carbohydrate Polymers

Vol. 87

Páginas: 240-249

ISSN: 0144-8617

Editora: Elsevier

Indexação

ISI Web of Knowledge - 86 Citações

Scopus - 89 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-002-DZK

DOI: 10.1016/j.carbpol.2011.07.043

Abstract (EN): N-Phthaloyl-chitosan O-prop-2-ynyl carbamate was prepared as a biopolymer amenable to undergo chemoselective conjugation by azide-alkyne coupling, while allowing upturn of chitosan's amines after dephthaloylation. N-phthaloylchitosan was prepared according to previously described methods and, due to its low solubility in current organic media, subsequent modifications were run in heterogeneous conditions. Activation of hydroxyls with carbonyl-1,1 '-diimidazole and coupling to propargylamine yielded N-phthaloyl-chitosan O-prop-2-ynyl carbamate, then coupled to a model PEG-like azide by azide-alkyne coupling, giving the expected triazolyl conjugate. N-Dephthaloylation allowed recovery of the free amines, responsible for chitosan's bioadhesion and tissue-regeneration properties. The structures of all polymers were confirmed by Fourier-transformed infra-red (FT-IR) and X-ray photoelectron (XPS) spectroscopies, as well as by solid-state nuclear magnetic resonance (SSNMR). All chitosan derivatives were poorly soluble in both aqueous and organic media, which makes them suitable for topical applications or for removal of toxic substances from either the gastric intestinal tract or environmental sources.

Idioma: Inglês

Tipo (Avaliação Docente): Científica