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Boronic Acids Facilitate the Transport of Ribonucleosides Through Lipid Bilayers

Boronic Acids Facilitate the Transport of Ribonucleosides Through Lipid Bilayers

P R Westmark, B D Smith

J Pharm Sci. 1996 Mar;85(3):266-9.

PMID: 8699326

Abstract:

Boronic acids were found to facilitate the transport of various ribonucleosides in and out of liposomes (artificial cells). Most experiments were conducted with large unilamellar vesicles composed of dipalmitoylphosphatidyl choline, cholesterol, and phosphatidic acid in the ratio 20:15:2. Rates of nucleoside efflux were determined by a UV assay, whereas the influx experiments used a radiotracer method. Five boronic acids were studied: 3,5-bis(trifluoromethyl)phenylboronic acid (1), 3,5-dichlorophenylboronic acid (2), 4-tert-butylphenylboronic acid (3), 1-butylboronic acid (4), and 4-carboxyphenylboronic acid (5). The order of carrier effectiveness was found to be 1 > 3 > 2 >> 4 >> 5. Efflux and influx experiments with mixtures of nucleosides and sucrose showed virtually complete transport selectivity in favor of the nucleosides. Mechanistic studies indicate that the nucleoside transport mechanism involves transient formation of a lipophilic, trigonal boronate ester.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP123324710	4-tert-Butylphenylboronic acid	123324-71-0	Price
AP135145903	2,5-Dichlorophenylboronic acid	135145-90-3	Price
AP67492506	3,5-Dichlorophenylboronic acid	67492-50-6	Price
AP73852194	3,5-Bis(trifluoromethyl)phenylboronic acid	73852-19-4	Price

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