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Permeation through phospholipid bilayers, skin-cell penetration, plasma stability, and CD spectra of α- and β-oligoproline derivatives

After a survey of the special role, which the amino acid proline plays in the chemistry of life, the cell-penetrating properties of polycationic proline-containing peptides are discussed, and the widely unknown discovery by the Giralt group (J. Am. Chem. Soc. 2002, 124, 8876) is acknowledged, accord...

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Main Authors: Kolesinska, Beata (Author) , Podwysocka, Dominika J. (Author) , Rueping, Magnus A. (Author) , Seebach, Dieter (Author) , Kamena, Faustin (Author) , Walde, Peter (Author) , Sauer, Markus (Author) , Windschiegl, Barbara (Author) , Meyer‐Ács, Mira (Author) , Vor der Brüggen, Marc (Author) , Giehring, Sebastian (Author)
Format: Article (Journal)
Language:English
Published: 22 January 2013
In: Chemistry & biodiversity
Year: 2013, Volume: 10, Issue: 1, Pages: 1-38
ISSN:1612-1880
DOI:https://doi.org/10.1002/cbdv.201200393
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/cbdv.201200393
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/cbdv.201200393
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Author Notes:by Beata Kolesinska, Dominika J. Podwysocka, Magnus A. Rueping, Dieter Seebach (Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, ETH-Zürich) and Faustin Kamena (Max-Planck-Institut für Infektionsbiologie, Berlin) and Peter Walde (Institut für Polymere, Departement Materialwissenschaft, ETH-Zürich) and Markus Sauer (Physikalisch-Chemisches Institut, Universität Heidelberg) and Barbara Windschiegl, Mira Meyer‐Ács, Marc Vor der Brüggen, and Sebastian Giehring (Nanospot GmbH, Münster)
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Summary:After a survey of the special role, which the amino acid proline plays in the chemistry of life, the cell-penetrating properties of polycationic proline-containing peptides are discussed, and the widely unknown discovery by the Giralt group (J. Am. Chem. Soc. 2002, 124, 8876) is acknowledged, according to which fluorescein-labeled tetradecaproline is slowly taken up by rat kidney cells (NRK-49F). Here, we describe details of our previously mentioned (Chem. Biodiversity 2004, 1, 1111) observation that a hexa-β3-Pro derivative penetrates fibroblast cells, and we present the results of an extensive investigation of oligo-L- and oligo-D-α-prolines, as well as of oligo-β2h- and oligo-β3h-prolines without and with fluorescence labels (1-8; Fig. 1). Permeation through protein-free phospholipid bilayers is detected with the nanoFAST biochip technology (Figs. 2-4). This methodology is applied for the first time for quantitative determination of translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that may be interpreted as arising from aggregation, and broadening of the NMR signals with time confirms this assumption.
Item Description:Gesehen am 25.03.2021
Physical Description:Online Resource
ISSN:1612-1880
DOI:https://doi.org/10.1002/cbdv.201200393

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