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Calixarene‐Mediated Liquid Membrane Transport of Choline Conjugates 2: Transport of Drug‐Choline Conjugates and Neurotransmitters
Author(s) -
Adhikari Birendra Babu,
Roshandel Sahar,
Fujii Ayu,
Schramm Michael P.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403519
Subject(s) - chemistry , calixarene , conjugate , amine gas treating , membrane , choline , membrane transport , combinatorial chemistry , drug delivery , carboxylic acid , molecule , biophysics , stereochemistry , organic chemistry , biochemistry , biology , mathematical analysis , mathematics
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.