Synthesis and characterization of phosphorylcholine-substituted chitosans soluble in physiological pH conditions

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dc.contributor.authorTiera, Marcio J.
dc.contributor.authorQiu, Xing-Ping
dc.contributor.authorBechaouch, Sofiane
dc.contributor.authorShi, Qin
dc.contributor.authorFernandes, Julio C.
dc.contributor.authorWinnik, Francoise M.
dc.contributor.institutionUniv Montreal
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionFac Sci Monastir
dc.date.accessioned2014-05-20T15:28:45Z
dc.date.available2014-05-20T15:28:45Z
dc.date.issued2006-11-13
dc.description.abstractA polymer analogous synthesis involving the reductive amination of phosphorylcholine (PC)-glyceraldehyde with primary amines of deacetylated chitosan (M-w approximate to 57000 g mol(-1)) was used to prepare phosphorylcholine-substituted chitosans (PC-CH) with a degree of substitution (DS) ranging from similar to 11 to similar to 53 mol% PC-substituted glucosamine residues. The PC-CH derivatives were characterized by H-1 NMR spectroscopy, FTIR spectroscopy, and multiangle laser light scattering gel permeation chromatography (MALLS-GPC). The pKa of the PC-substituted amine groups (pKa approximate to 7.20) was determined by H-1 NMR titration. The PC-CH samples (1.0 g L-1) were shown to be nontoxic using an MTT assay performed with human KB cells. Aqueous solutions of PC-CH samples (4.0 g L-(1)) of DS g 22 mol% PC-substituted glucosamine residues remained clear, independently of pH (4.0 < pH < 11.0). The remarkable water solubility and nontoxicity displayed by the new PC-CH samples open up new opportunities in the design of chitosan-based biomaterials and nanoparticles.en
dc.description.affiliationUniv Montreal, Fac Pharm, Montreal, PQ H3C 3J7, Canada
dc.description.affiliationUniv Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
dc.description.affiliationUNESP, Dept Quim & Ciências Ambientais, Sao Jose do Rio Preto, Brazil
dc.description.affiliationFac Sci Monastir, Lab Polymeres Biopolymeres Mat Organ, Monastir, Tunisia
dc.description.affiliationUniv Montreal, Orthoped Res Lab, Hop Sacre Coeur, Montreal, PQ H4J 1C5, Canada
dc.description.affiliationUnespUNESP, Dept Quim & Ciências Ambientais, Sao Jose do Rio Preto, Brazil
dc.format.extent3151-3156
dc.identifierhttp://dx.doi.org/10.1021/bm060381u
dc.identifier.citationBiomacromolecules. Washington: Amer Chemical Soc, v. 7, n. 11, p. 3151-3156, 2006.
dc.identifier.doi10.1021/bm060381u
dc.identifier.issn1525-7797
dc.identifier.urihttp://hdl.handle.net/11449/38506
dc.identifier.wosWOS:000241941600032
dc.language.isoeng
dc.publisherAmer Chemical Soc
dc.relation.ispartofBiomacromolecules
dc.relation.ispartofjcr5.738
dc.relation.ispartofsjr1,950
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.titleSynthesis and characterization of phosphorylcholine-substituted chitosans soluble in physiological pH conditionsen
dc.typeArtigo
dcterms.licensehttp://pubs.acs.org/paragonplus/copyright/jpa_form_a.pdf
dcterms.rightsHolderAmer Chemical Soc
unesp.author.orcid0000-0002-5472-1482[1]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Biociências Letras e Ciências Exatas, São José do Rio Pretopt

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