Synthesis and Characterization of Sugar-Bearing Chitosan Derivatives as a Scaffold for Nitric Oxide Release

Abstract:

These new synthesized diazeniumdiolates obtained from D-gluconic acid-bearing chitosan derivatives (SBC) with different molecular weight (280 kDa and 880 KDa) and D-gluconic acid-bearing O-carboxymethyl chitosan derivatives (880 KDa) (SBCS) were used as the NO donor species. Compared with SBC with much higher molecular weight (880 KDa), the SBC with the lower molecular weight (280 kDa) exhibited a high storage capacity for NO (up to 408 nmol NO/mg), greatly increasing the “payload” of released NO with the molecular weight of SBC decreasing. The NO release durations (0.326 h) observed for secondary amine on the SBC with the lower molecular weight (280 kDa) were slightly higher than that of SBC diazeniumliolates with the higher molecular weight (880 kDa), which was only 0.294h. The release duration of SBCS-NO adducts (0.381h) was obviously longer than that of SBC-NO adducts, when they have the same molecular weight (880 kDa).

• Periodical: Advanced Materials Research (Volumes 160-162)
• Pages: 1083-1089
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.160-162.1083
• Online since: November 2010
• Authors: Yan Sun, Yong Liu
• Keywords: Chitosan (CS), D-Gluconic Acid, Nitric Oxide (NO), O-Carboxymethyl Chitosan, Release in Vitro

References

[1] F. C. Fang: J. Clin. Invest. Vol. 99 (1997), p.28185.

[2] A. Ghaffari, C. C. Miller, B. McMullin and A. Ghahary: Nitric Oxide Vol. 14(2006), p.21.

[3] R. Raulli, G. McElhaney-Feser, J. A. Hrabie and R. L. Cihlar: Recent. Res. Dev. Microbiol. Vol. 6(2002), p.177.

[4] O. W. Griffith and D. J. Stuehr: Annu. Rev. Physiol. Vol. 57(1995), p.707.

[5] J. A. Hrabie and L. K. Keefer: Chem. Rev. Vol. 102(2002), p.1135.

[6] R. S. Drago and B. R. Karstetter: J. Am. Chem. Soc. Vol. 83(1961), p.1819.

[7] K. M. Davies, D. A. Wink, J. E. Saavedra and L. K. Keefer: J. Am. Chem. Soc. Vol. 123 (2001), p.5473.

[8] A. J. Wan, Y. Sun and H. L. Li: Int. J. Bio. Macro. Vol. 43(2008), p.415.

[9] J. H. Park, Y. W. Cho, H. Chung, I. C. Kwon and S. Y. Jeong: Biomacromolecules Vol. 4 (2003), p.1087.

[10] X. G. Chen and H. J. Park: Carbohyd. Polym. Vol. 53(2003), p.355.

[11] L. K. Keefer: Chemtech. Vol. 28 (1998), p.30.

[12] J. H. Yu, Y. M. Du and H. Zheng: J. Wuhan. Univ. (Nat Sci Ed. ) Vol. 45 (1999), p.440.

[13] A. S. Dutton, J. M. Fukuto and K. N. Houk: Inorg. Chem. Vol. 43(3) (2004), p.1039.