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Copper-free click conjugation of methotrexate to a PAMAM dendrimer platform

Baohua Huang, Ankur Desai, Hong Zong, Shengzhuang Tang, Pascale Leroueil, and James R Baker

Tetrahedron Lett 52(13):4 (2011) PMID 21383864

The synthesis of a generation 5 (G5) poly(amidoamine) (PAMAM) dendrimer platform having cyclooctyne ligands that were subsequently be used for a copper-free Huisgen 1,3-dipolar cycloaddition (click reaction) with azido modified methotrexate is described. The G5 PAMAM dendrimer was first partially (70%) acetylated and then coupled with 20 cyclooctyne ligands through amide bonds. The remaining primary amine groups on the dendrimer surface were neutralized by acetylation. The platform was then 'clicked' with different numbers (5, 10, and 17) of @c-azido functionalized methotrexate. The copper-free click reactions were stoichiometric with excellent yields.

Copyright © 2011 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.tetlet.2010.12.025
Version: za2963e q8za5 q8zb5 q8zcb q8zd9 q8ze4 q8zfd q8zga
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