syntheses of sulfo-glycodendrimers using click chemistry and their biological evaluation合成sulfo-glycodendrimers使用点击化学和生物学评价.pdf

Molecules 2012, 17, 11877-11896; doi:10.3390/molecules171011877 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation Yoshiko Miura 1,2,*, Shunsuke Onogi 2 and Tomohiro Fukuda 2,3 1 Department of Chemical Engineering, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan 2 School of Materials Science, Japan Advanced Institute of Science and Technology, 1-1 Asahidai, Nomi, Ishikawa 923-1292, Japan 3 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; E-Mail: miuray@chem-eng.kyushu-u.ac.jp; Tel.: +81-92-802-2749; Fax: +81-92-802-2769. 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