Nitric oxide (NO) is a biologically-active molecule with numerous physiological roles, including regulation of vasodilation, modulation of the inflammatory response, and promotion of cell proliferation and angiogenesis. These properties have led to the investigation of NO and NO-releasing materials for biomedical applications. NO-releasing materials are most frequently prepared through incorporation of NO donor moieties such as N-diazeniumdiolates or S-nitrosothiols that release NO through decomposition under physiological conditions. One class of relevant NO delivery platforms are polysaccharides such as chitin (poly-N-acetyl-D-glucosamine) and chitosan (poly-D-glucosamine). In this work, we report the synthesis and characterization of S-nitrosated NO-releasing derivatives of chitin and chitosan that were prepared by incorporation of the symmetrical dithiols 1,2-ethanedithiol, 1,3-propanedithiol, and, 1,6-hexanedithiol. These thiolated polymers were subsequently converted to S-nitrosated derivatives by reaction with tert-butyl nitrite. The NO loading of the materials and their NO release profiles under physiological conditions (pH 7.4 phosphate buffered saline, 37 °C) were evaluated, and in vitro cytotoxicity studies were performed with human dermal fibroblasts to assess the suitability of the materials for biomedical applications.

Derivatives of chitin and chitosan for biomedical applications bearing nitric oxide-releasing S-nitrosothiol substituents

249th National Meeting (2015)

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