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Synthesis of N ‐benzyl‐O‐carboxymethylchitosan and application in the solubilization enhancement of a poorly water‐soluble drug (triamcinolone)
Author(s) -
de Oliveira Rosa Tania Regina,
Debrassi Aline,
da Silva Ruth Meri Lucinda,
Bressan Camila,
de Freitas Rilton Alves,
Rodrigues Clóvis Antonio
Publication year - 2011
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.35395
Subject(s) - solubility , nuclear chemistry , chemistry , bromide , chitosan , fourier transform infrared spectroscopy , polymer , benzaldehyde , pulmonary surfactant , reductive amination , aqueous solution , polymer chemistry , organic chemistry , chemical engineering , biochemistry , engineering , catalysis
N ‐Benzyl‐ O ‐carboxymethyl chitosan (OCChB) was synthesized through a reaction of O ‐carboxymethylchitosan (OCCh) and benzaldehyde by the reductive amination method. The chemical structures and physical properties of the derivatives were confirmed by Fourier transform infrared spectroscopy and 1 H‐NMR. The cytotoxicity of the polymers was tested by MTT (3‐[4,5‐dimethylthiazol‐2‐yl]‐2,5‐diphenyltetrazolium bromide) assay at concentrations ranging from 0.01 to 1000 μg/mL. The substitution degrees of the derivatives, calculated by 1 H‐NMR, were 12 and 53% for OCChB1 and OCChB2, respectively. The results show that the derivatives were not toxic at 1000 μg/mL and could decrease the surface tension by concentration on the system surface compared with OCCh. Because of this property, OCChB was applied as a solubility enhancer for triamcinolone (TC), a poorly water‐soluble drug. The polymer solutions at 1.0 mg/mL increased the TC solubility up to 3.5 times for OCChB1 and 5.0 times for OCChB2 compared with its solubility in water. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012