Synthesis of EDTA core dendrimers through a consecutive esterification-CuAAC process

Ramírez-Palma, María Teresa; Apolonio, Víctor M.; González, Jaime; Martínez-Barrera, Gonzalo; Corona, David; Cuevas-Yáñez, Erick

doi:10.1080/10601325.2017.1381920

Cited by 3 publications

(3 citation statements)

References 23 publications

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“…R f = 0.35 (CH 2 Cl 2 ). Tert-butyl(4-hydroxyphenetyl)carbamate (6) The intermediary (3) was obtained as colorless crystals (98% yield). R f = 0.5 (CH 2 Cl 2 ).…”

Section: Tert-butyl(4-hydroxyphenyl)carbamate (4)mentioning

confidence: 99%

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Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior

González-Méndez,

Sorroza-Martínez,

González-Sánchez

et al. 2023

IJMS

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The synthesis of a new family of ethylenediaminetetraacetic acid (EDTA) core dimers and G0 dendrimers end-capped with two and four β-cyclodextrin (βCD) moieties was performed by click-chemistry conjugation, varying the spacers attached to the core. The structure analyses were achieved in DMSO-d6 and the self-inclusion process was studied in D2O by 1H-NMR spectroscopy for all platforms. It was demonstrated that the interaction with adamantane carboxylic acid (AdCOOH) results in a guest-induced shift of the self-inclusion effect, demonstrating the full host ability of the βCD units in these new platforms without any influence of the spacer. The results of the quantitative size and water solubility measurements demonstrated the equivalence between the novel EDTA-βCD platforms and the classical PAMAM-βCD dendrimer. Finally, we determined the toxicity for all EDTA-βCD platforms in four different cell lines: two human breast cancer cells (MCF-7 and MDA-MB-231), human cervical adenocarcinoma cancer cells (HeLa), and human lung adenocarcinoma cells (SK-LU-1). The new EDTA-βCD carriers did not present any cytotoxicity in the tested cell lines, which showed that these new classes of platforms are promising candidates for drug delivery.

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“…R f = 0.35 (CH 2 Cl 2 ). Tert-butyl(4-hydroxyphenetyl)carbamate (6) The intermediary (3) was obtained as colorless crystals (98% yield). R f = 0.5 (CH 2 Cl 2 ).…”

Section: Tert-butyl(4-hydroxyphenyl)carbamate (4)mentioning

confidence: 99%

“…In this regard, ethylenediaminetetraacetic acid (EDTA) is a potential molecule that has been used as new core for the preparation of dendrimers. EDTA has tertiary amines and is tetra-directional, which offers an adequate number of branching sites [6].…”

Section: Introductionmentioning

confidence: 99%

Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior

González-Méndez,

Sorroza-Martínez,

González-Sánchez

et al. 2023

IJMS

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“…It is of interest to use of click chemistry in the synthesis of the chelating dendrimers . For example, a class of thermostable G0 and G1 dendrimers was obtained from the coupling of both propargyl and azido esters derived from EDTA via CuAAC . In another interesting example, copper granules were used in the CuAAC click‐synthesis of dendrimers based on lilac aldehyde and vanillin .…”

Section: Preparation Of Chelating Dendrimersmentioning

confidence: 99%

Synthetic Methodologies for Chelating Polymer Ligands: Recent Advances and Future Development

Джардималиева

Uflyand

2018

ChemistrySelect

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This review summarizes recent progress in synthetic methodologies of chelating polymer ligands such as linear, branched, cross‐linked, grafted polymers, polymer films, liquid crystal polymers, dendrimers, star‐shaped and hyperbranched polymers. The features of methods for producing chelating polymer ligands are considered in detail: free‐radical (co)polymerization, living/controlled radical, metathesis, grafted, chemical oxidized, microwave‐assisted and asymmetric polymerization, electropolymerization, cyclopolymerization, polycondensation, post‐polymerization modification, click chemistry methods and “green” synthesis. The main directions of the development of synthetic chemistry of chelating polymeric ligands are analyzed. The bibliography includes works published in the last five years.

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

et al. 2022

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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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Synthesis of EDTA core dendrimers through a consecutive esterification-CuAAC process

Cited by 3 publications

References 23 publications

Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior

Exploring the Influence of Spacers in EDTA–β-Cyclodextrin Dendrimers: Physicochemical Properties and In Vitro Biological Behavior

Synthetic Methodologies for Chelating Polymer Ligands: Recent Advances and Future Development

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

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