Bike peptides: a ride through the membrane

Several natural peptides have a biaryl or biaryl ether motif in their biologically active structures. A model bicyclic pentapeptide containing a biaryl bridge has been synthesized by solid‐phase peptide synthesis combining on‐resin Suzuki and Miyaura cross‐coupling reactions. Its biological properti...

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Bibliographic Details
Published in:Journal of peptide science 2017-04, Vol.23 (4), p.294-302
Main Authors: García‐Pindado, Júlia, Royo, Soledad, Teixidó, Meritxell, Giralt, Ernest
Format: Article
Language:English
Subjects:
Biological Products - blood
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - toxicity
biostability
borylation
Cell Survival - drug effects
Dose-Response Relationship, Drug
head‐to‐tail cyclization
HeLa Cells
Humans
Molecular Conformation
Natural products
Oligopeptides - blood
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - toxicity
Organic synthesis
PAMPA
Peptide synthesis
Peptides
Productes naturals
Solid-Phase Synthesis Techniques
solid‐phase peptide synthesis
stapled peptides
Structure-Activity Relationship
Suzuki cross‐coupling
Síntesi de pèptids
Síntesi orgànica
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Summary:Several natural peptides have a biaryl or biaryl ether motif in their biologically active structures. A model bicyclic pentapeptide containing a biaryl bridge has been synthesized by solid‐phase peptide synthesis combining on‐resin Suzuki and Miyaura cross‐coupling reactions. Its biological properties in terms of permeability, stability and cytotoxicity have been studied, demonstrating the positive contribution of the biaryl bridge, excellent membrane penetration and serum stability Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd. A bike peptide displaying a biaryl bridge has been synthesized by SPPS using on‐resin Suzuki and Miyaura reactions. This peptide has demonstrated to be a privileged structure that crosses the BBB by passive diffusion and has an excellent protease resistance.
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.2993