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

Bioorganic & Medicinal Chemistry Letters
James L CollinsMichael P Schramm

Abstract

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.

References

Mar 12, 1975·Helvetica Chimica Acta·K Neupert-Laves, M Dobler
Sep 28, 1990·Science·R Langer
Sep 19, 2001·Chemistry : a European Journal·A J WrightP D Beer
Jul 3, 2003·Journal of the American Chemical Society·Perla BrecciaJavier de Mendoza
Dec 19, 2006·Chemical Society Reviews·Shannon M Biros, Julius Rebek
Jan 3, 2007·Drug Discovery Today·William M Pardridge
Jul 20, 2007·Journal of the American Chemical Society·Michael P SchrammJulius Rebek
Mar 25, 2008·Journal of the American Chemical Society·Tomoki OgoshiYoshiaki Nakamoto
Jun 27, 2009·Chemical Communications : Chem Comm·Ruth Pérez-FernándezJeremy K M Sanders
May 27, 2010·Beilstein Journal of Organic Chemistry·Andreas Späth, Burkhard König
Aug 3, 2011·Chemical Communications : Chem Comm·Yeon Joo KimMichael P Schramm
Nov 13, 2012·New Journal of Chemistry = Nouveau Journal De Chimie·Katie M FeherMichael P Schramm
Apr 30, 2013·Journal of the American Chemical Society·Yoo-Jin GhangRichard J Hooley
Jan 11, 2014·Chemical Communications : Chem Comm·Birendra Babu AdhikariMichael P Schramm
May 8, 2014·Journal of Controlled Release : Official Journal of the Controlled Release Society·Jennifer R Weiser, W Mark Saltzman
Sep 10, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Birendra Babu AdhikariMichael P Schramm
May 1, 2014·European Journal of Organic Chemistry·Birendra Babu AdhikariMichael P Schramm
Jul 15, 2015·European Journal of Organic Chemistry·Birendra Babu AdhikariMichael P Schramm
Nov 20, 2015·Chemical Reviews·Yingfeng TuDaniela A Wilson
Dec 22, 2015·Current Pharmaceutical Design·David S HershAnthony J Kim
Jan 12, 2016·Supramolecular Chemistry·Birendra Babu AdhikariMichael P Schramm

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