Tris-ureas as transmembrane anion transporters.

Martina Olivari,Lucy K Mapp,Louise E Karagiannidis,Simon J Coles,Philip A Gale,Claudia Caltagirone,Peter N Horton,Riccardo Montis,Stuart N Berry

doi:10.1039/c6dt02046a

Abstract

Nine tris-urea receptors (L(1)-L(9)) have been synthesised and shown to coordinate to a range of anionic guests both by (1)H NMR titration techniques and single crystal X-ray structural analysis. The compounds have been shown to be capable of mediating the exchange of chloride and nitrate and also chloride and bicarbonate across POPC or POPC : cholesterol 7 : 3 vesicle bilayer membranes at low transporter loadings. An interesting dependency of anion transport on the nature of the cation is evidence to suggest that a M(+)/Cl(-) cotransport process may also contribute to the release of chloride from the vesicles.

Highlights

Transmembrane transport of anions across lipid bilayers is an important biological process that is normally regulated by complex membrane spanning proteins
The synthesis of receptor L3 has previously been reported by Wu.[25]
L1–L9 were synthesized via different reaction steps

Summary

Introduction

Transmembrane transport of anions across lipid bilayers is an important biological process that is normally regulated by complex membrane spanning proteins. E-mail: philip.gale@soton.ac.uk † Electronic supplementary information (ESI) available: Additional information as noted in the text including synthetic details for the preparation of L1–L9, fittings of 1H-NMR titrations, crystallographic tables, transport studies.

Results

Conclusion