Macrocyclic Cell Penetrating Peptides: A Study of Structure-Penetration Properties

Traboulsi, Hussein; Larkin, Heidi; Bonin, Marc-André; Volkov, Léonid; Lavoie, Christine; Marsault, Éric

doi:10.1021/acs.bioconjchem.5b00023

Cited by 66 publications

(86 citation statements)

References 54 publications

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“…Thus, arginine (Arg) represents a key residue for efficient internalization, as highlighted by the development of diverse guanidinium‐rich compounds, including synthetic oligoarginine sequences; peptoids; aminoproline‐derived peptides; oligocarbamates, oligocarbonates, or oligophosphoesters; and disulfide‐containing polymers . The efficiency and mode of cellular uptake were shown to be influenced by the content of Arg residues, and by the distance between them, which could be controlled by introducing spacers or through the cyclization of CPPs . Enhancement of the uptake was generally observed by increasing the distance between arginine residues.…”

Section: Methodsmentioning

confidence: 99%

Ribbon‐like Foldamers for Cellular Uptake and Drug Delivery

et al. 2017

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Different intracellular delivery systems of bioactive compounds have been developed, including cell-penetrating peptides. Although usually nontoxic and biocompatible, these vectors share some of the general drawbacks of peptides, notably low bioavailability and susceptibility to protease degradation, that limit their use. Herein, the conversion of short peptide sequences into poly-α-amino-γ-lactam foldamers that adopt a ribbon-like structure is investigated. This template is used to distribute critical cationic and/or hydrophobic groups on both sides of the backbone, leading to potent short, cell-permeable foldamers with a low positive-charge content. The lead compound showed dramatically improved protease resistance and was able to efficiently deliver a biologically relevant cargo inside cells. This study provided a simple strategy to convert short peptide sequences into efficient protease-resistant cell-penetrating foldamers.

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Section: Methodsmentioning

confidence: 99%

Ribbon‐like Foldamers for Cellular Uptake and Drug Delivery

et al. 2017

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“…same cell type and peptide concentration). 44, 45 Overall, this indicates that some important parameters involving peptide and cell membrane might not be accounted for, thereby leading to variability.…”

Section: Relevance Of Mammalian Membrane Oxidation In Intracellulamentioning

confidence: 99%

Membrane Oxidation in Cell Delivery and Cell Killing Applications

2017

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Cell delivery or cell killing processes often involve the crossing or disruption of cellular membranes. We review how, by modifying the composition and properties of membranes, membrane oxidation can be exploited to enhance the delivery of macromolecular cargos into live human cells. We also describe how membrane oxidation can be utilized to achieve efficient killing of bacteria by antimicrobial peptides. Finally, we present recent evidence highlighting how membrane oxidation is intimately engaged in natural biological processes such as antigen delivery in dendritic cells and in the killing of bacteria by human macrophages. Overall, the insights that have been recently gained in this area should facilitate the development of more effective delivery technologies and antimicrobial therapeutic approaches.

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“…Cells were incubated with 0.05 % Trypan Blue for 3 min prior to FACS analysis to eliminate any possible noninternalized peptide fluorescence (Figure S1) . The results showed that peptide cellular uptake was more closely correlated with hydrophobicity than with the helical contents of the peptides.…”

Section: Figurementioning

confidence: 99%

Effect of Stapling Architecture on Physiochemical Properties and Cell Permeability of Stapled α‐Helical Peptides: A Comparative Study

Tian

Jiang

et al. 2017

ChemBioChem

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Stapled peptides have emerged as a new class of targeting molecules with high binding affinity and specificity for intracellular undruggable targets. Their ability to penetrate cell membranes is exceptionally intriguing but remains elusively and controversially discussed. To understand the effect of stapling architectures on their physiochemical properties and to aid in promoting their cell permeability, we report herein a comparative study on the physiochemical properties and cell permeability of stapled α-helical peptides with different types of crosslinks. We highlight the decisive impact of the intrinsic properties of the crosslinks on cell permeability rather than the helical contents of the peptides in model amphipathic sequences targeting estrogen receptor-coactivator interaction. We envision this finding to shed further light on the chemical optimization of stapled α-helical peptides or macrocyclic cell-penetrating peptides for enhanced cell penetration.

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Macrocyclic Cell Penetrating Peptides: A Study of Structure-Penetration Properties

Cited by 66 publications

References 54 publications

Ribbon‐like Foldamers for Cellular Uptake and Drug Delivery

Ribbon‐like Foldamers for Cellular Uptake and Drug Delivery

Membrane Oxidation in Cell Delivery and Cell Killing Applications

Effect of Stapling Architecture on Physiochemical Properties and Cell Permeability of Stapled α‐Helical Peptides: A Comparative Study

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