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Peptide ligands stabilized by small molecules.

Shiyu Chen1, Davide Bertoldo, Alessandro Angelini

  • 1Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, 1015 Lausanne (Switzerland).

Angewandte Chemie (International Ed. in English)
|January 24, 2014
PubMed
Summary
This summary is machine-generated.

We engineered bicyclic peptides to improve therapeutic development. By incorporating hydrophilic structures, these peptides achieve enhanced stability and high binding affinity, overcoming limitations of traditional antibody therapeutics.

Keywords:
antibody mimicbicyclic peptidemacrocyclic ligandspeptidesphage display

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Drug Development

Background:

  • Bicyclic peptides are promising therapeutic ligands due to their small size and potential for chemical synthesis.
  • Current bicyclic peptides lack inherent structure in solution, leading to suboptimal binding affinity compared to antibodies.
  • Directed evolution using phage display is a key technique for identifying novel peptide sequences.

Purpose of the Study:

  • To develop stabilized bicyclic peptides with enhanced binding affinity for therapeutic applications.
  • To investigate the role of hydrophilic chemical structures in stabilizing peptide conformation.
  • To understand how small molecules influence peptide folding and binding during selection.

Main Methods:

  • Phage display for library screening and selection of bicyclic peptides.
  • Incorporation of hydrophilic chemical structures at the center of bicyclic peptides.
  • X-ray crystallography to determine the structural basis of peptide-small molecule interactions.

Main Results:

  • Developed bicyclic peptides with stabilized conformations through intramolecular interactions.
  • Demonstrated that peptide sequences are influenced by the small molecules used in screening.
  • X-ray analysis confirmed that small molecules form hydrogen bonds, stabilizing peptide-protein complexes.
  • Achieved high binding affinity due to these stabilizing noncovalent interactions.

Conclusions:

  • Engineered bicyclic peptides exhibit enhanced stability and high binding affinity, making them attractive therapeutic candidates.
  • Hydrophilic structures and interactions with small molecules are crucial for stabilizing bicyclic peptide conformation.
  • These findings advance the development of small, potent peptide-based therapeutics.