Calixarene-Mediated Liquid-Membrane Transport of Choline Conjugates

Overview

Journal European J Org Chem

Specialty Biochemistry

Date 2015 Jul 11

PMID 26161034

Citations 6

Authors

Birendra Babu Adhikari

Ayu Fujii

Michael P Schramm

Affiliations

Soon will be listed here.

Abstract

A series of supramolecular calixarenes efficiently transport distinct molecular species through a liquid membrane when attached to a receptor-complementary choline handle. Calix-[6]arene hexacarboxylic acid was highly effective at transporting different target molecules against a pH gradient. Both carboxylic- and phosphonic-acid-functionalized calix[4]arenes effect transport without requiring a pH or ion gradient. NMR binding studies, two-phase solvent extraction, and three-phase transport experiments reveal the necessary and subtle parameters to effect the transport of molecules attached to a choline "handle". On the other hand, rescorin[4]arene cavitands, which have similar guest recognition profiles, did not transport guest molecules. These developments reveal new approaches towards attempting synthetic-receptor-mediated selective small-molecule transport in vesicular and cellular systems.

Citing Articles

Synthesis, Molecular Recognition Study and Liquid Membrane-Based Applications of Highly Lipophilic Enantiopure Acridino-Crown Ethers.

Golcs A, Adam B, Horvath V, Toth T, Huszthy P Molecules. 2020; 25(11).

PMID: 32486509 PMC: 7321232. DOI: 10.3390/molecules25112571.

Characterization of an Amphiphilic Phosphonated Calixarene Carrier Loaded With Carboplatin and Paclitaxel: A Preliminary Study to Treat Colon Cancer and .

Li M, Mao L, Chen M, Li M, Wang K, Mo J Front Bioeng Biotechnol. 2019; 7:238.

PMID: 31632958 PMC: 6779836. DOI: 10.3389/fbioe.2019.00238.

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

Collins 3rd J, Fujii A, Roshandel S, To C, Schramm M Bioorg Med Chem Lett. 2017; 27(13):2953-2956.

PMID: 28512029 PMC: 5584391. DOI: 10.1016/j.bmcl.2017.05.009.

Targeted intracellular delivery of resveratrol to glioblastoma cells using apolipoprotein E-containing reconstituted HDL as a nanovehicle.

Kim S, Adhikari B, Cruz S, Schramm M, Vinson J, Narayanaswami V PLoS One. 2015; 10(8):e0135130.

PMID: 26258481 PMC: 4530947. DOI: 10.1371/journal.pone.0135130.

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

Adhikari B, Roshandel S, Fujii A, Schramm M European J Org Chem. 2015; 2015(12):2683-2690.

PMID: 26161035 PMC: 4495001. DOI: 10.1002/ejoc.201403519.

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