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. 2015 Apr 1;2015(12):2683-2690.
doi: 10.1002/ejoc.201403519.

Calixarene-Mediated Liquid Membrane Transport of Choline Conjugates 2: Transport of Drug-Choline Conjugates and Neurotransmitters

Birendra Babu Adhikari  1 , Sahar Roshandel  1 , Ayu Fujii  1 , Michael P Schramm  1
Affiliations

Calixarene-Mediated Liquid Membrane Transport of Choline Conjugates 2: Transport of Drug-Choline Conjugates and Neurotransmitters

Birendra Babu Adhikari et al. European J Org Chem. .

Abstract

Lower rim carboxylic acid calix[n]arenes and upper rim phosphonic acid functionalized calix[4]arenes effect selective transport of distinct molecular payloads through a liquid membrane. The secret to this success lies in the attachment of a receptor-complementary handle. We find that the trimethylammonium ethylene group present in choline is a general handle for the transport of drug and drug-like species. Furthermore, neurotransmitters possessing ionizable amine termini are also transported. Some limitations to this strategy have been uncovered as payloads become increasingly lipophilic. These developments reveal new approaches to synthetic receptor-mediated selective small molecule transport in vesicular and cellular systems.

Keywords: Calixarenes; Dopamine; Drug delivery; Drug design; Medicinal chemistry; Receptors; Serotonin.

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Figures

Figure 1
Figure 1
Structure of calixarene-based receptors 1–4 and drug conjugate substrates 5–10.
Figure 2
Figure 2
Structure of calixarene ether 11 and ester 12 receptors and guests: dopamine 13, serotonin 14.
Figure 3
Figure 3
Structure of calcein 15.
Figure 4
Figure 4
U-tube dimensions.
See this image and copyright information in PMC

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