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Synthesis 2011(18): 2968-2974  
DOI: 10.1055/s-0030-1260151
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Design and Synthesis of a Multivalent Heterobifunctional CD22 Ligand as a Potential Immunomodulator

Hajjaj H. M. Abdu-Allah*a,b, Kozo Watanabec, Shusaku Daikokud, Osamu Kanied, Takeshi Tsubatac, Hiromune Andoa,e, Hideharu Ishidaa, Makoto Kiso*a,e
a Department of Applied Bio-organic Chemistry, The United Graduate School of Agricultural Sciences, Gifu University, Gifu 501-1193, Japan
Fax: +81(58)2932840; e-Mail: kiso@gifu-u.ac.jp; e-Mail: moazhajjaj@yahoo.com;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt
c Laboratory of Immunology, School of Biomedical Science, Tokyo Medical and Dental University, Japan
d Japan Science and Technology Agency (JST), ERATO, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan
e Institute for Integrated Cell-Material Sciences (iCeMS), Kyoto University, Kyoto 606-8501, Japan
Further Information

Publication History

Received 21 April 2011
Publication Date:
05 August 2011 (online)

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Abstract

We describe the design and synthesis of a trivalent CD22 ligand conjugated with a trivalent nitrophenol (ligand for decameric anti-nitrophenol immunoglobulin M). To generate such a bifunctional ligand, we designed and prepared two synthetic building blocks possessing different terminal functionalities. Coupling of these compounds afforded a trivalent azide-terminated scaffold. Ligation of the scaffold with an alkyne-terminated CD22 ligand by the use of click chemistry afforded the target trivalent cluster. We anticipate that our ligand will be valuable in a variety of applications, including targeting B cells and modulation of the humoral immune response.

Key words

bifunctional ligand - multivalent compounds - CD22 - targeting - coupling - click chemistry