Anionic amphiphilic calixarenes for peptide assembly and delivery.

Autor: Rodik RV; Institute of Organic Chemistry, National Academy of Science of Ukraine, 02660 Kyiv, Ukraine. Electronic address: dmso@ukr.net., Cherenok SO; Institute of Organic Chemistry, National Academy of Science of Ukraine, 02660 Kyiv, Ukraine., Postupalenko VY; Laboratoire de Bioimagerie et Pathologies, UMR 7021 CNRS, Université de Strasbourg, Faculté de Pharmacie, 74, Route du Rhin, 67401 ILLKIRCH Cedex, France., Oncul S; Laboratoire de Bioimagerie et Pathologies, UMR 7021 CNRS, Université de Strasbourg, Faculté de Pharmacie, 74, Route du Rhin, 67401 ILLKIRCH Cedex, France; İstanbul Medeniyet Üniversitesi, Istanbul, Turkey., Brusianska V; Enamine Ltd, Chervonotkatska 78, 02094 Kyiv, Ukraine., Borysko P; Enamine Ltd, Chervonotkatska 78, 02094 Kyiv, Ukraine., Kalchenko VI; Institute of Organic Chemistry, National Academy of Science of Ukraine, 02660 Kyiv, Ukraine., Mely Y; Laboratoire de Bioimagerie et Pathologies, UMR 7021 CNRS, Université de Strasbourg, Faculté de Pharmacie, 74, Route du Rhin, 67401 ILLKIRCH Cedex, France., Klymchenko AS; Laboratoire de Bioimagerie et Pathologies, UMR 7021 CNRS, Université de Strasbourg, Faculté de Pharmacie, 74, Route du Rhin, 67401 ILLKIRCH Cedex, France. Electronic address: andrey.klymchenko@unistra.fr.
Jazyk: angličtina
Zdroj: Journal of colloid and interface science [J Colloid Interface Sci] 2022 Oct 15; Vol. 624, pp. 270-278. Date of Electronic Publication: 2022 May 22.
DOI: 10.1016/j.jcis.2022.05.124
Abstrakt: Shape-persistent macrocycles enable superior control on molecular self-assembly, allowing the preparation of well-defined nanostructures with new functions. Here, we report on anionic amphiphilic calixarenes of conic shape and their self-assembly behavior in aqueous media for application in intracellular delivery of peptides. Newly synthesized calixarenes bearing four phosphonate groups and two or four long alkyl chains were found to form micelles of ∼ 10 nm diameter, in contrast to an analogue with short alkyl chains. These amphiphilic calixarenes are able to complex model (oligo-lysine) and biologically relevant (HIV-1 nucleocapsid peptide) cationic peptides into small nanoparticles (20-40 nm). By contrast, a control anionic calixarene with short alkyl chains fails to form small nanoparticles with peptides, highlighting the importance of micellar assembly of amphiphilic calixarenes for peptide complexation. Cellular studies reveal that anionic amphiphilic calixarenes exhibit low cytotoxicity and enable internalization of fluorescently labelled peptides into live cells. These findings suggest anionic amphiphilic macrocycles as promising building blocks for the preparation of peptide delivery vehicles.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2022 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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