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Synthesis of Amino Terminal Clicked Dendrimers. Approaches to the Application as a Biomarker

Authors :
Francisco Najera
Juan Antonio Guadix
José M. Pérez-Pomares
Ezequiel Perez-Inestrosa
Yolanda Vida
Noemi Molina
Source :
The Journal of Organic Chemistry. 84:10197-10208
Publication Year :
2019
Publisher :
American Chemical Society (ACS), 2019.

Abstract

Herein, we present an easy and efficient synthesis of amino terminal dendrons, combining protection/deprotection reactions with copper-catalyzed azide alkyne cycloaddition in a convergent way. This new approach affords dendrons in gram scale with excellent yields and easy purification. By choosing the appropriate azido-functionalized core, these dendrons lead to a more efficient and controlled convergent synthesis of dendrimers with different sizes and shapes and multivalence. The amino terminal dendrimers were analyzed by diffusion-ordered spectroscopy experiments. The observed dendrimer size is in excellent correlation with the expected size and shape by molecular dynamic simulations. The construction of these kinds of nanostructures, in a simple and efficient way, opens new opportunities for biomedical applications. Moreover, by choosing the appropriate core, these versatile macromolecules become an excellent fluorescent biomarker.

Details

ISSN :
15206904 and 00223263
Volume :
84
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....1dee674a7f76b0f91e1a9c15072a2e7a
Full Text :
https://doi.org/10.1021/acs.joc.9b01369