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Issue 25, 2016

Amphiphilic calixresorcinarene associates as effective solubilizing agents for hydrophobic organic acids: construction of nano-aggregates

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Abstract

Here we represent the first example of the formation of mixed nanoscale associates, constructed from amphiphilic calixresorcinarenes and hydrophobic carboxylic acids including drugs. The amidoamino-calixresorcinarene self-associates effectively solubilize hydrophobic carboxylic acids – drugs such as naproxen, ibuprofen, ursodeoxycholic acid and aliphatic dodecanoic acid – with the formation of the mixed aggregates with the macrocycle/substrate stoichiometry from 1/1 to 1/7. The ionization of organic acids and the peripheral nitrogen atoms of the macrocycles with the subsequent inclusion of hydrophobic acids into the macrocycle self-associates is the driving force of solubilization. In some cases, this leads to the co-assembly of the macrocycle polydisperse associates into supramolecular monodisperse nanoparticles with the diameter of about 100 nm. The efficiency of drug loading into the nanoparticles is up to 45% and depends on the structure of organic acid. The dissociation of the mixed aggregates and release of organic acid are attained by decreasing pH.

Graphical abstract: Amphiphilic calixresorcinarene associates as effective solubilizing agents for hydrophobic organic acids: construction of nano-aggregates

Supplementary files

Article information


Submitted
24 Mar 2016
Accepted
19 May 2016
First published
02 Jun 2016

This article is Open Access

Soft Matter, 2016,12, 5590-5599
Article type
Paper

Amphiphilic calixresorcinarene associates as effective solubilizing agents for hydrophobic organic acids: construction of nano-aggregates

Ju. E. Morozova, V. V. Syakaev, E. Kh. Kazakova, Ya. V. Shalaeva, I. R. Nizameev, M. K. Kadirov, A. D. Voloshina, V. V. Zobov and A. I. Konovalov, Soft Matter, 2016, 12, 5590 DOI: 10.1039/C6SM00719H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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