Glycosylated Cell Penetrating Peptides, GCPPs
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Title: | Glycosylated Cell Penetrating Peptides, GCPPs |
Author: | Gallego Gómez, Iván Rioboo Vidal, Alicia Reina, José J. Díaz, Bernardo Canales, Ángeles Cañada, F. Javier Guerra Varela, Jorge Sánchez Piñón, Laura Elena Montenegro García, Javier |
Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica Universidade de Santiago de Compostela. Departamento de Zooloxía, Xenética e Antropoloxía Física |
Subject: | Penetrating peptides | Peptide synthesis | Glycosylation | Cell delivery | |
Date of Issue: | 2019-01-23 |
Publisher: | Wiley |
Citation: | Gallego, I., Rioboo, A., Reina, J., Díaz, B., Canales, Á., Cañada, F., Guerra-Varela, J., Sánchez, L. and Montenegro, J. (2019), Glycosylated Cell Penetrating Peptides, GCPPs. ChemBioChem. doi:10.1002/cbic.201800720 |
Abstract: | The cell membrane regulates the exchange of molecules and information with the external environment. However, this control barrier hinders the delivery of exogenous bioactive molecules that can be applied to correct cellular malfunctions. Therefore, the traffic of macromolecules across the cell membrane represents a great challenge for the development of the next generation of therapies and diagnostic methods. Cell penetrating peptides are short peptide sequences capable of delivering a broad range of biomacromolecules across the cellular membrane. However, penetrating peptides still suffer from limitations mainly related with their lack of specificity and potential toxicity. Glycosylation has emerged as a potential promising strategy for the biological improvement of synthetic materials. In this work we have developed a new convergent strategy for the synthesis of penetrating peptides functionalized with glycan residues by an oxime bond connection. We have systematically characterized the uptake efficiency and the intracellular distribution of these glycopeptides by flow cytometry, confocal microscopy and in zebrafish animal models. The incorporation of these glycan residues into the peptide structure influenced the internalization efficiency and the cellular toxicity of the resulting glycopeptide hybrids in the different cell lines tested. The results reported here highlight the potential of the glycosylation of penetrating peptides to modulate their activity |
Description: | This is the peer reviewed version of the following article: Gallego, I. , Rioboo, A. , Reina, J. ., Díaz, B. , Canales, Á., Cañada, F. ., Guerra-Varela, J. , Sánchez, L. and Montenegro, J. (2019), Glycosylated Cell Penetrating Peptides, GCPPs. ChemBioChem. doi:10.1002/cbic.201800720, which has been published in final form at https://doi.org/10.1002/cbic.201800720. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions |
Publisher version: | https://doi.org/10.1002/cbic.201800720 |
URI: | http://hdl.handle.net/10347/18288 |
DOI: | 10.1002/cbic.201800720 |
E-ISSN: | 1439-7633 |
Rights: | © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions |
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