Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity

Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stabi...

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Autores principales: Numai, Sanami, Yoto, Risako, Kimura, Masataka, Simanek, Eric E., Kitano, Yoshikazu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9822332/
https://www.ncbi.nlm.nih.gov/pubmed/36615327
http://dx.doi.org/10.3390/molecules28010131
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author Numai, Sanami
Yoto, Risako
Kimura, Masataka
Simanek, Eric E.
Kitano, Yoshikazu
author_facet Numai, Sanami
Yoto, Risako
Kimura, Masataka
Simanek, Eric E.
Kitano, Yoshikazu
author_sort Numai, Sanami
collection PubMed
description Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stability, well-defined spherical structure, multivalency, potential to achieve acceptable drug loadings, and low polydispersity. In this study, the potential utility of alkyne-azide “click” cycloadditions of first-, second-, and third-generation triazine dendrimers containing three or six alkynyl groups with benzyl azide was examined using copper catalysts. “Click-and-grow” and “grow-then-click” strategies were employed. For the first- and second- generation dendrimers, the desired triazole derivatives were obtained in high yields and purified by simple reprecipitation without column chromatography; however, some difficulties were observed in the preparation of third-generation dendrimers. The desired reaction proceeded under microwave irradiation as well as with simple heating. This click chemistry can be utilized for various melamine dendrimers that are fabricated with other amine linkers.
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spelling pubmed-98223322023-01-07 Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity Numai, Sanami Yoto, Risako Kimura, Masataka Simanek, Eric E. Kitano, Yoshikazu Molecules Article Dendrimers are attractive macromolecules for a broad range of applications owing to their well-defined shapes and dimensions, highly branched and globular architectures, and opportunities for exploiting multivalency. Triazine dendrimers in particular offer advantages such as ease of synthesis, stability, well-defined spherical structure, multivalency, potential to achieve acceptable drug loadings, and low polydispersity. In this study, the potential utility of alkyne-azide “click” cycloadditions of first-, second-, and third-generation triazine dendrimers containing three or six alkynyl groups with benzyl azide was examined using copper catalysts. “Click-and-grow” and “grow-then-click” strategies were employed. For the first- and second- generation dendrimers, the desired triazole derivatives were obtained in high yields and purified by simple reprecipitation without column chromatography; however, some difficulties were observed in the preparation of third-generation dendrimers. The desired reaction proceeded under microwave irradiation as well as with simple heating. This click chemistry can be utilized for various melamine dendrimers that are fabricated with other amine linkers. MDPI 2022-12-23 /pmc/articles/PMC9822332/ /pubmed/36615327 http://dx.doi.org/10.3390/molecules28010131 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Numai, Sanami
Yoto, Risako
Kimura, Masataka
Simanek, Eric E.
Kitano, Yoshikazu
Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title_full Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title_fullStr Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title_full_unstemmed Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title_short Click Chemistry of Melamine Dendrimers: Comparison of “Click-and-Grow” and “Grow-Then-Click” Strategies Using a Divergent Route to Diversity
title_sort click chemistry of melamine dendrimers: comparison of “click-and-grow” and “grow-then-click” strategies using a divergent route to diversity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9822332/
https://www.ncbi.nlm.nih.gov/pubmed/36615327
http://dx.doi.org/10.3390/molecules28010131
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