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Journal of Bioactive and Compatible Polymers
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Synthesis of an Amphiphilic Polysaccharide Derivative and Its Micellization for Drug Release

Hong-Wei Lu

School of Chemistry and Chemical Engineering and Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Sun Yat-Sen (Zhongshan) University, Guangzhou 510275, China

Li-Ming Zhang

School of Chemistry and Chemical Engineering and Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Sun Yat-Sen (Zhongshan) University, Guangzhou 510275, China, ceszhlm{at}mail.sysu.edu.cn

Ji-Yan Liu

School of Chemistry and Chemical Engineering and Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Sun Yat-Sen (Zhongshan) University, Guangzhou 510275, China

Ru-Fu Chen

Department of Hepatobiliary Surgery, The Second Affiliated Hospital Sun Yet-sen (Zhongshan) University, Guangzhou 510120, China

A new route for the synthesis of novel amphiphilic polysaccharides was developed, in which a synthetic biodegradable poly({varepsilon}-caprolactone) was capped with a phenylalanine group (PCL-phenylalanine). The ring-opening polymerization of {varepsilon}-caprolactone ({varepsilon}-CL) was carried out in the absence of a metal catalyst with L-phenylalanine as the initiator; this was followed by a coupling reaction with biodegradable dextran in the presence of carbonyldimidazole. The FTIR and 1H NMR analyses confirm the coupling reaction. Fluorescence, transmission electron microscopy (TEM), and dynamic light scattering (DLS) confirm that in aqueous solution the amphiphilic polysaccharides self-assemble into the nanoscale spherical micelles with good stability. The in vitro drug release behavior of the nonsteroidal indomethacin drug exhibits sustained drug release profile as described by the Higuchi model without a burst effect.

Key Words: polysaccharide derivative • dextran • poly({varepsilon}-caprolactone) • self-association • self-assembled polymeric micelles • drug delivery • controlled drug release.

Journal of Bioactive and Compatible Polymers, Vol. 23, No. 2, 154-170 (2008)
DOI: 10.1177/0883911507088272
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[Abstract] [PDF]