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

✍ Scribed by Baohua Huang; Ankur Desai; Hong Zong; Shengzhuang Tang; Pascale Leroueil; James R. Baker Jr.

Book ID: 104098732
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 464 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.12.025

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✦ Synopsis

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 γ-azido functionalized methotrexate. The copper-free click reactions were stoichiometric with excellent yields.

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