Calixarene-mediated liquid membrane transport of choline conjugates 3: The effect of handle variation on neurotransmitter transport

[Display omitted] Upper rim phosphonic acid functionalized calix[4]arene affects selective transport of multiple molecular payloads through a liquid membrane. The secret is in the attachment of a receptor-complementary handle to the payload. We find that the trimethylammonium ethylene group present...

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Published in:Bioorganic & medicinal chemistry letters 2017-07, Vol.27 (13), p.2953-2956
Main Authors: Collins, James L., Fujii, Ayu, Roshandel, Sahar, To, Cuong-Alexander, Schramm, Michael P.
Format: Article
Language:English
Subjects:
Biological Transport - drug effects
Calixarene
Calixarenes - chemical synthesis
Calixarenes - chemistry
Calixarenes - pharmacology
Choline - chemistry
Choline - metabolism
Dopamine
Dopamine - metabolism
Dose-Response Relationship, Drug
Membrane-transport
Molecular Structure
Neurotransmitter Agents - chemical synthesis
Neurotransmitter Agents - chemistry
Neurotransmitter Agents - pharmacology
Serotonin
Serotonin - metabolism
Structure-Activity Relationship
Supramolecular
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Summary:[Display omitted] Upper rim phosphonic acid functionalized calix[4]arene affects selective transport of multiple molecular payloads through a liquid membrane. The secret is in the attachment of a receptor-complementary handle to the payload. We find that the trimethylammonium ethylene group present in choline is one of several general handles for the transport of drug and drug-like species. Herein we compare the effect of handle variation against the transport of serotonin and dopamine. We find that several ionizable amine termini handles are sufficient for transport and identify two ideal candidates. Their performance is significantly enhanced in HEPES buffered solutions. This inquiry completes a series of 3 studies aimed at optimization of this strategy. In completion a new approach towards synthetic receptor mediated selective small molecule transport has emerged; future work in vesicular and cellular systems will follow.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.05.009