Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cycloligomers) with a good solubility profile can improve solubilization of hydrophobic drugs.[1,2] Herein, we explore the ability of resorc[4]arenes (BSK, R1, R2 and R3) to self-assembly in polar solutions and to act as molecular shuttles of a poorly water-soluble isoflavone endowed with anticancer activity, namely Glabrescione B (GlaB).[3] 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 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]arenebased systems can be modulated at given pH values, and thus promoting the solubility of GlaB.

FROM MACROCYCLES TO MOLECULAR SHUTTLES: EXPLORING THE SUPRAMOLECULAR ASSEMBLY OF RESORC[4]ARENES / Cianfoni, Gabriele; Buonsenso, Fabio; Botta, Bruno; Pierini, Marco. - (2021). ((Intervento presentato al convegno ESOC 2021 European Symposium of Organic Chemistry tenutosi a Louvain-la-Neuve, BE.

FROM MACROCYCLES TO MOLECULAR SHUTTLES: EXPLORING THE SUPRAMOLECULAR ASSEMBLY OF RESORC[4]ARENES

Gabriele Cianfoni
Primo
;
Fabio Buonsenso
Secondo
;
Bruno Botta
Penultimo
;
Marco Pierini
Ultimo
2021

Abstract

Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of host-guest complex by using calixarene-based macrocycles (i.e., resorcinol-derived cycloligomers) with a good solubility profile can improve solubilization of hydrophobic drugs.[1,2] Herein, we explore the ability of resorc[4]arenes (BSK, R1, R2 and R3) to self-assembly in polar solutions and to act as molecular shuttles of a poorly water-soluble isoflavone endowed with anticancer activity, namely Glabrescione B (GlaB).[3] 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 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]arenebased systems can be modulated at given pH values, and thus promoting the solubility of GlaB.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1561082
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