Issue 28, 2013

A zinc–salophen/bile-acid conjugate receptor solubilized by CTABr micelles binds phosphate in water

Abstract

Receptor 1, composed of two deoxycholic acid moieties appended to a Zn–salophen complex, was prepared, characterized and tested for anion binding by 1H NMR and UV-vis spectroscopic techniques. While in polar DMSO, 1 is able to bind phosphate (K = ∼700 M−1), the addition of water severely diminishes the association. In a 1 : 9 waterDMSO mixture, the binding constant K is only ca. 20 M−1. Notably, in an aqueous solution of CTABr micelles (CTABr 10 mM, cmc = ∼1 mM), the zinc–salophen conjugate 1, due to its two non-polar bile-acid moieties, becomes solubilized and, most importantly, it almost completely recovers its binding ability towards phosphate, displaying a remarkable affinity (K = ∼450 M−1) in water.

Graphical abstract: A zinc–salophen/bile-acid conjugate receptor solubilized by CTABr micelles binds phosphate in water

Supplementary files

Article information

Article type
Communication
Submitted
11 Apr 2013
Accepted
30 May 2013
First published
03 Jun 2013

Org. Biomol. Chem., 2013,11, 4585-4590

A zinc–salophen/bile-acid conjugate receptor solubilized by CTABr micelles binds phosphate in water

O. Jurček, M. Cametti, M. Pontini, E. Kolehmainen and K. Rissanen, Org. Biomol. Chem., 2013, 11, 4585 DOI: 10.1039/C3OB40724A

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