Anion Recognition by a Bioactive Diureidodecalin Anionophore: Solid-State, Solution, and Computational Studies

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Authors

JURČEK Ondřej VALKENIER Hennie PUTTREDDY Rakesh NOVÁK Martin SPARKES Hazel MAREK Radek RISSANEN Kari DAVIS Anthony P.

Year of publication 2018
Type Article in Periodical
Magazine / Source Chemistry - A European Journal
MU Faculty or unit

Central European Institute of Technology

Citation
Web DOI: 10.1002/chem.201800537
Doi http://dx.doi.org/10.1002/chem.201800537
Keywords anion; receptor; selectivity; recognition; x-ray diffraction; NMR; density-dunctional theory
Attached files
Description Recent work has identified a bis-(p-nitrophenyl)ureidodecalin anion carrier as a promising candidate for biomedical applications, showing good activity for chloride transport in cells yet almost no cytotoxicity. To underpin further development of this and related molecules, we report a detailed structural and binding investigation. Crystal structures of the transporter as five solvates confirm the diaxial positioning of urea groups while revealing a degree of conformational flexibility. Structures of complexes with Cl-, Br-, NO3-, SO42-, and AcO-, supported by computational studies, show how the binding site can adapt to accommodate these anions. 1H NMR binding studies reveal exceptionally high affinities for anions in DMSO, decreasing in the order SO42- > H2PO4- ~ HCO3- ~ AcO- >> HSO4- > Cl- > Br- > NO3- > I-. Analysis of the binding results suggests that selectivity is determined mainly by the hydrogen bond acceptor strength of different anions, but is also modulated by receptor geometry.
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