Preparation and Thermal Properties Characterization of Cholesterol-Modified Amphiphilic Chitosan

Abstract:

In this article, cholesterol 3-hemisuccinate (CHS) was synthesized through the functionalization of the end group of liquid crystal monomer cholesterol with succinic anhydride. Hydrophobic cholesterol modified low molecular weight chitosan (CS-CH) was synthesized by 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC)-mediated coupling reaction. Chemical structure, crystalline morphology, and thermal properties of the biological material were characterized by Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetric (DSC), and polarized light microscopy (POM). The results of POM showed that CHS was a kind of crystalline material with liquid crystal property of cholesterol. DSC showed that the melting point and the crystalline temperature of CHS were 188 °C and 145 °C respectively. DSC also showed that CS-CH was a kind of thermoplastic biological material. The max melting temperature decreased from 120 °C to 110 °C with increasing the weight ratio of EDC/CHS to chitosan.

• Periodical: Advanced Materials Research (Volume 528)
• Pages: 197-201
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.528.197
• Online since: June 2012
• Authors: Feng Hong Li, Wen Jing Zhang, San Xi Li, Yong Sun, Tao Jiang
• Keywords: Amphiphilicity, Chitosan, Cholesterol, Thermal Property, Thermoplasticity

References

[1] S. Blau, T.T. Jubeh, S.M. Haupt, et al., Drug targeting by surface cationization, Critical reviews in therapeutic drug carrier systems 17 (2000) 425-465.

DOI: 10.1615/critrevtherdrugcarriersyst.v17.i5.10

[2] M.J. Chen, J.R. Yao, Z.Z. Shao, X. Chen, Biomacromolecule-based nanoparticle drug carriers, Progress in Chemistry 23 (2011) 202-212.

[3] Q. Tian, W. Wang, X. T. He, et al., Glycyrrhetinic acid-modified nanoparticles for drug delivery: Preparation and characterization, Chinese Sci. Bull. 54 (2009) 3121-3126.

DOI: 10.1007/s11434-009-0249-5

[4] X.G. Zhang, D.Y. Teng, Z.M. Wu, et al., PEG-grafted chitosan nanoparticles as an injectable carrier for sustained protein release, J. Mater. Sci. Mater. Med. 19 (2008) 3525-3533.

DOI: 10.1007/s10856-008-3500-8

[5] K.Y. Lee, J-H. Kim, I.C. Kwon, S.Y. Jeong, Self-aggregates of deoxycholic acid-modified chitosan as a novel carrier of adriamycin, Colloid Polym. Sci. 278 (2000) 1216-1219.

DOI: 10.1007/s003960000389

[6] X.B. Yuan, H. Li, Y.B. Yuan, Preparation of cholesterol-modified chitosan self-aggregated nanoparticles for delivery of drugs to ocular surface, Carbohydrate Polymers 65 (2006) 337-345.

DOI: 10.1016/j.carbpol.2006.01.020

[7] M.M. Chen, W.Z. Yang, Y. Liu, Preparation and characteristics of self-aggregated cholesterol modified chitosan nanoparticles, Journal of Functional Materials 41 (2010) 1776-1779.

[8] Y.S. Wang, Y.M. Wang, L.R. Shan, et al., Chitosan based self-assembled nanomicelles as a novel carrier for paclitaxel, Chemical Journal of Chinese Universities 29 (2008) 1065-1069.