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

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.

Synthesis and Host–Guest Chemistry of Chiral Spirobifluorene-Based Macrocycles Soluble in Basic Aqueous Solution

“…Such chemistry aims at understanding the noncovalent interactions for molecular recognition, thermodynamics, and physical properties, and catalysis, or leading to the artificial functional supramolecular systems and applications, including such as sensors and biotargeted systems . In our previous work, water-soluble calixarenes-mediated various transport applications of choline and choline conjugates were developed . Various other synthetic host molecules that can work in aqueous solution have been developed so far.…”