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

作者：Jurcek Ondrej; Valkenier Hennie; Puttreddy Rakesh; Novak Martin; Sparkes Hazel A; Marek Radek^*; Rissanen Kari^*; Davis Anthony P^*

来源：Chemistry - A European Journal, 2018, 24(32): 8178-8185.

DOI：10.1002/chem.201800537

• anions
• host-guest interactions
• hydrogen bonds
• receptors
• solid-state structures

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 compounds, a detailed structural and binding investigation is reported. 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. (HNMR)-H-1 binding studies revealed exceptionally high affinities for anions in DMSO, decreasing in the order SO42->H2PO4-approximate to HCO3-approximate to AcO->> HSO4->Cl->Br->NO3->I-. Analysis of the binding results suggests that selectivity is determined mainly by the H-bond acceptor strength of different anions, but is also modulated by receptor geometry.

• 出版日期2018-6-7