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Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation
Department of Chemical Engineering, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi, Ishikawa 923-1292, Japan
Department of Applied Chemistry and Chemical Engineering, Toyama National College of Technology, Hongo-campus, 13 Hongo-Machi, Toyama, Toyama 939-8630, Japan
* Author to whom correspondence should be addressed.
Received: 23 July 2012; in revised form: 5 September 2012 / Accepted: 18 September 2012 / Published: 9 October 2012
Abstract: A series of novel glycol-clusters containing sulfonated N-acetyl-D-glucosamine (GlcNAc) have been synthesized using click chemistry. Three dendrimers with aromatic dendrons were synthesized using chlorination, azidation and click chemistries. The resulting dendrimers were modified with azide-terminated sulfonated GlcNAc using click chemistry. The sulfonated dendrimers showed affinity for proteins, including the lectin wheat germ agglutinin and amyloid beta peptide (1-42). The dendrimers of G1 and G2 in particular showed the largest affinity for the proteins. The addition of the sulfonated GlcNAc dendrimers of G1 and G2 exhibited an inhibition effect on the aggregation of the amyloid beta peptide, reduced the b-sheet conformation, and led to a reduction in the level of nanofiber formation.
Keywords: glycopolymer; dendrimer; click chemistry; amyloidosis
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MDPI and ACS Style
Miura, Y.; Onogi, S.; Fukuda, T. Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation. Molecules 2012, 17, 11877-11896.
Miura Y, Onogi S, Fukuda T. Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation. Molecules. 2012; 17(10):11877-11896.
Miura, Yoshiko; Onogi, Shunsuke; Fukuda, Tomohiro. 2012. "Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation." Molecules 17, no. 10: 11877-11896.