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Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs

In this work, two dendritic molecules containing an ethylenediaminetetraacetic acid (EDTA) core decorated with two and four β-cyclodextrin (βCD) units were synthesized and fully characterized. Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) click chemistry under microwave irradiation was used...

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Autores principales: González-Méndez, Israel, Loera-Loera, Esteban, Sorroza-Martínez, Kendra, Vonlanthen, Mireille, Cuétara-Guadarrama, Fabián, Bernad-Bernad, María Josefa, Rivera, Ernesto, Gracia-Mora, Jesús
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9697223/
https://www.ncbi.nlm.nih.gov/pubmed/36365180
http://dx.doi.org/10.3390/pharmaceutics14112363
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author González-Méndez, Israel
Loera-Loera, Esteban
Sorroza-Martínez, Kendra
Vonlanthen, Mireille
Cuétara-Guadarrama, Fabián
Bernad-Bernad, María Josefa
Rivera, Ernesto
Gracia-Mora, Jesús
author_facet González-Méndez, Israel
Loera-Loera, Esteban
Sorroza-Martínez, Kendra
Vonlanthen, Mireille
Cuétara-Guadarrama, Fabián
Bernad-Bernad, María Josefa
Rivera, Ernesto
Gracia-Mora, Jesús
author_sort González-Méndez, Israel
collection PubMed
description In this work, two dendritic molecules containing an ethylenediaminetetraacetic acid (EDTA) core decorated with two and four β-cyclodextrin (βCD) units were synthesized and fully characterized. Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) click chemistry under microwave irradiation was used to obtain the target compounds with yields up to 99%. The classical ethylenediamine (EDA) core present in PAMAM dendrimers was replaced by an EDTA core, obtaining platforms that increase the water solubility at least 80 times compared with native βCD. The synthetic methodology presented here represents a convenient alternative for the rapid and efficient construction of PAMAM analogs. These molecules are envisaged for future applications as drug carriers.
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spelling pubmed-96972232022-11-26 Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs González-Méndez, Israel Loera-Loera, Esteban Sorroza-Martínez, Kendra Vonlanthen, Mireille Cuétara-Guadarrama, Fabián Bernad-Bernad, María Josefa Rivera, Ernesto Gracia-Mora, Jesús Pharmaceutics Article In this work, two dendritic molecules containing an ethylenediaminetetraacetic acid (EDTA) core decorated with two and four β-cyclodextrin (βCD) units were synthesized and fully characterized. Copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) click chemistry under microwave irradiation was used to obtain the target compounds with yields up to 99%. The classical ethylenediamine (EDA) core present in PAMAM dendrimers was replaced by an EDTA core, obtaining platforms that increase the water solubility at least 80 times compared with native βCD. The synthetic methodology presented here represents a convenient alternative for the rapid and efficient construction of PAMAM analogs. These molecules are envisaged for future applications as drug carriers. MDPI 2022-11-02 /pmc/articles/PMC9697223/ /pubmed/36365180 http://dx.doi.org/10.3390/pharmaceutics14112363 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
González-Méndez, Israel
Loera-Loera, Esteban
Sorroza-Martínez, Kendra
Vonlanthen, Mireille
Cuétara-Guadarrama, Fabián
Bernad-Bernad, María Josefa
Rivera, Ernesto
Gracia-Mora, Jesús
Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title_full Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title_fullStr Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title_full_unstemmed Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title_short Synthesis of β-Cyclodextrin-Decorated Dendritic Compounds Based on EDTA Core: A New Class of PAMAM Dendrimer Analogs
title_sort synthesis of β-cyclodextrin-decorated dendritic compounds based on edta core: a new class of pamam dendrimer analogs
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9697223/
https://www.ncbi.nlm.nih.gov/pubmed/36365180
http://dx.doi.org/10.3390/pharmaceutics14112363
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