Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubilization of hydrophob...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Fabio Buonsenso, Francesca Ghirga, Isabella Romeo, Gabriella Siani, Serena Pilato, Deborah Quaglio, Marco Pierini, Bruno Botta, Andrea Calcaterra
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	resorc[4]arenes supramolecular assembly solubilizing agents Glabrescione B UV-vis spectroscopy Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/fda689a27dc54e868f22449c0d38db27
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:fda689a27dc54e868f22449c0d38db27
record_format	dspace
spelling	oai:doaj.org-article:fda689a27dc54e868f22449c0d38db272021-11-11T17:14:09ZExploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates10.3390/ijms2221117851422-00671661-6596https://doaj.org/article/fda689a27dc54e868f22449c0d38db272021-10-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/21/11785https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-0067Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubilization of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone endowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized several architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phenomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV–visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.Fabio BuonsensoFrancesca GhirgaIsabella RomeoGabriella SianiSerena PilatoDeborah QuaglioMarco PieriniBruno BottaAndrea CalcaterraMDPI AGarticleresorc[4]arenessupramolecular assemblysolubilizing agentsGlabrescione BUV-vis spectroscopyBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 11785, p 11785 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	resorc[4]arenes supramolecular assembly solubilizing agents Glabrescione B UV-vis spectroscopy Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	resorc[4]arenes supramolecular assembly solubilizing agents Glabrescione B UV-vis spectroscopy Biology (General) QH301-705.5 Chemistry QD1-999 Fabio Buonsenso Francesca Ghirga Isabella Romeo Gabriella Siani Serena Pilato Deborah Quaglio Marco Pierini Bruno Botta Andrea Calcaterra Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
description	Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubilization of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone endowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized several architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phenomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV–visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.
format	article
author	Fabio Buonsenso Francesca Ghirga Isabella Romeo Gabriella Siani Serena Pilato Deborah Quaglio Marco Pierini Bruno Botta Andrea Calcaterra
author_facet	Fabio Buonsenso Francesca Ghirga Isabella Romeo Gabriella Siani Serena Pilato Deborah Quaglio Marco Pierini Bruno Botta Andrea Calcaterra
author_sort	Fabio Buonsenso
title	Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
title_short	Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
title_full	Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
title_fullStr	Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
title_full_unstemmed	Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates
title_sort	exploring the assembly of resorc[4]arenes for the construction of supramolecular nano-aggregates
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/fda689a27dc54e868f22449c0d38db27
work_keys_str_mv	AT fabiobuonsenso exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT francescaghirga exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT isabellaromeo exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT gabriellasiani exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT serenapilato exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT deborahquaglio exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT marcopierini exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT brunobotta exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates AT andreacalcaterra exploringtheassemblyofresorc4arenesfortheconstructionofsupramolecularnanoaggregates
_version_	1718432156345171968

Exploring the Assembly of Resorc[4]arenes for the Construction of Supramolecular Nano-Aggregates

Ejemplares similares