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pH-Dependent transport of amino acids across lipid bilayers by simple monotopic anion carriers

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cris.lastimport.scopus2024-02-12T20:50:49Z
dc.abstract.enThe transport of amino acids across lipid membranes is vital for the proper functioning of every living cell. In spite of that, examples of synthetic transporters that can facilitate amino acid transport are rare. This is mainly because at physiological conditions amino acids predominantly exist as highly polar zwitterions and proper shielding of their charged termini, which is necessary for fast diffusion across lipophilic membranes, requires complex and synthetically challenging heteroditopic receptors. Here we report the first simple monotopic anion receptor, dithioamide 1, that efficiently transports a variety of natural amino acids across lipid bilayers at physiological pH. Mechanistic studies revealed that the receptor rapidly transports deprotonated amino acids, even though at pH 7.4 these forms account for less than 3% of the total amino acid concentration. We also describe a new fluorescent assay for the selective measurement of the transport of deprotonated amino acids into liposomes. The new assay allowed us to study the pH-dependence of amino acid transport and elucidate the mechanism of transport by 1, as well as to explain its exceptionally high activity. With the newly developed assay we screened also four other representative examples of monotopic anion transporters, of which two showed promising activity. Our results imply that heteroditopic receptors are not necessary for achieving high amino acid transport activities and that many of the previously reported anionophores might be active amino acid transporters. Based on these findings, we propose a new strategy for the development of artificial amino acid transporters with improved properties.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorChmielewski, Michał
dc.contributor.authorZawada, Bartłomiej
dc.contributor.authorBąk, Krzysztof M.
dc.contributor.authorMaslowska-Jarzyna, Krystyna
dc.date.accessioned2024-01-25T16:35:58Z
dc.date.available2024-01-25T16:35:58Z
dc.date.copyright2022-11-05
dc.date.issued2022
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number42
dc.description.versionFINAL_PUBLISHED
dc.description.volume13
dc.identifier.doi10.1039/D2SC04346G
dc.identifier.issn2041-6520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/115796
dc.identifier.weblinkhttp://pubs.rsc.org/en/content/articlepdf/2022/SC/D2SC04346G
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemical Science
dc.relation.pages12374-12381
dc.rightsCC-BY-NC
dc.sciencecloudnosend
dc.titlepH-Dependent transport of amino acids across lipid bilayers by simple monotopic anion carriers
dc.typeJournalArticle
dspace.entity.typePublication