Investigating the Influence of Steric Hindrance on Selective Anion Transport.
anion transport
lipid bilayer
thioureas
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
02 Apr 2019
02 Apr 2019
Historique:
received:
21
03
2019
revised:
01
04
2019
accepted:
01
04
2019
entrez:
17
4
2019
pubmed:
17
4
2019
medline:
3
8
2019
Statut:
epublish
Résumé
A series of symmetrical and unsymmetrical alkyl tren based tris-thiourea anion transporters were synthesised and their anion binding and transport properties studied. Overall, increasing the steric bulk of the substituents resulted in improved chloride binding and transport abilities. Including a macrocycle in the scaffold enhanced the selectivity of chloride transport in the presence of fatty acids, by reducing the undesired H⁺ flux facilitated by fatty acid flip-flop. This study demonstrates the benefit of including enforced steric hindrance and encapsulation in the design of more selective anion receptors.
Identifiants
pubmed: 30986928
pii: molecules24071278
doi: 10.3390/molecules24071278
pmc: PMC6480120
pii:
doi:
Substances chimiques
Anions
0
Chlorides
0
Lipid Bilayers
0
Thiourea
GYV9AM2QAG
Types de publication
Journal Article
Langues
eng
Subventions
Organisme : Australian Research Council
ID : DP180100612
Organisme : Engineering and Physical Sciences Research Council
ID : EP/J009687/1
Références
Biochem Pharmacol. 2004 Oct 1;68(7):1345-52
pubmed: 15345324
J Cyst Fibros. 2002 Mar;1(1):13-29
pubmed: 15463806
J Biol Chem. 2005 Jan 28;280(4):2653-8
pubmed: 15550367
Nature. 2005 Feb 24;433(7028):876-80
pubmed: 15729345
Nature. 2006 Mar 23;440(7083):477-83
pubmed: 16554808
Biochem J. 1913 Oct;7(5):471-80
pubmed: 16742267
Nat Chem. 2010 Jul;2(7):533-8
pubmed: 20571570
Biochim Biophys Acta. 1990 May 7;1031(2):225-46
pubmed: 2160275
Nat Commun. 2012 Jun 19;3:905
pubmed: 22713747
J Cell Mol Med. 2014 Jun;18(6):1124-33
pubmed: 24725767
Nat Chem. 2014 Oct;6(10):885-92
pubmed: 25242483
Nat Chem. 2016 Jan;8(1):24-32
pubmed: 26673261
J Am Chem Soc. 2016 Jul 6;138(26):8301-8
pubmed: 27299473
J Am Chem Soc. 2016 Dec 21;138(50):16515-16522
pubmed: 27998094
J Am Chem Soc. 2016 Dec 21;138(50):16508-16514
pubmed: 27998096
Chem Soc Rev. 2017 May 9;46(9):2497-2519
pubmed: 28379234
Nat Chem. 2017 Jul;9(7):667-675
pubmed: 28644464
Sci Rep. 2017 Aug 24;7(1):9397
pubmed: 28839192
Sci Rep. 2018 Feb 8;8(1):2608
pubmed: 29422673
Chemistry. 2018 Jul 20;24(41):10475-10487
pubmed: 29786913
J Am Chem Soc. 2019 Jan 16;141(2):810-814
pubmed: 30618243
Br J Pharmacol. 2019 Mar 1;:null
pubmed: 30825185
Annu Rev Biochem. 1976;45:501-30
pubmed: 786156