Anion Recognition by a Bioactive Diureidodecalin Anionophore: Solid-State, Solution, and Computational Studies
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F18%3A00102479" target="_blank" >RIV/00216224:14740/18:00102479 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/chem.201800537" target="_blank" >https://doi.org/10.1002/chem.201800537</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201800537" target="_blank" >10.1002/chem.201800537</a>
Alternative languages
Result language
angličtina
Original language name
Anion Recognition by a Bioactive Diureidodecalin Anionophore: Solid-State, Solution, and Computational Studies
Original language 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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/LQ1601" target="_blank" >LQ1601: CEITEC 2020</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
1521-3765
Volume of the periodical
24
Issue of the periodical within the volume
32
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
8178-8185
UT code for WoS article
000437268400022
EID of the result in the Scopus database
2-s2.0-85048318397