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Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
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Development of a Cyclic, Cell Penetrating Peptide Compatible with In Vitro Selection Strategies.

Nicolas A Abrigo1,2, Kara K Dods1,2, Chelsea A Makovsky1,2

  • 1Chemistry, Virginia Commonwealth University, 1001 W Main Street, Richmond, 23284 Virginia, United States.

ACS Chemical Biology
|March 15, 2023
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Summary

Researchers developed novel cyclic cell-penetrating peptides (CPPs) by shifting hydrophobicity to the linker. These CPPs demonstrate efficient cellular uptake and cytosolic delivery, enabling targeted delivery of therapeutic payloads.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Drug Delivery

Background:

  • Peptide therapeutics face limitations due to poor cell permeability.
  • Arginine-rich macrocyclic peptides show promise for cellular entry.
  • Developing cell-penetrating peptides (CPPs) is crucial for intracellular drug delivery.

Purpose of the Study:

  • To develop a new strategy for creating cyclic CPPs with enhanced cellular uptake.
  • To investigate the impact of linker hydrophobicity and alkylation points on CPP efficiency.
  • To create CPPs compatible with peptide ligand discovery technologies.

Main Methods:

  • Designed cyclic peptides with hydrophobic linkers.
  • Screened linkers to optimize cellular uptake.
  • Assessed cellular uptake and cytosolic delivery of developed CPPs.
  • Tested CPPs for cargo delivery (peptide 8.6, cytotoxic peptide).

Main Results:

  • Hydrophobicity and linker alkylation sites significantly influence CPP uptake.
  • The novel peptide 4i matches or exceeds benchmark CPPs (R9, CPP12) in cellular and cytosolic delivery.
  • Peptide 4i successfully delivered cargo peptides into the cytosol.
  • A bicyclic variant of 4i demonstrated superior cytosolic entry.

Conclusions:

  • The developed strategy enables the creation of potent cyclic CPPs.
  • These CPPs are effective for delivering diverse payloads intracellularly.
  • Side-chain cyclization allows compatibility with phage and mRNA display for ligand discovery.
  • This approach facilitates the discovery of cell-permeable peptides for challenging intracellular targets.