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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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Published on: August 1, 2018

Disulfide-constrained peptide scaffolds enable a robust peptide-therapeutic discovery platform.

Lijuan Zhou¹, Fei Cai¹, Yanjie Li²

¹Departments of Biological Chemistry, Genentech, Inc., South San Francisco, California, United States of America.

|March 28, 2024

Summary

Disulfide-constrained peptides (DCPs) offer a stable, drug-like scaffold for therapeutic development. This study presents a robust platform using DCPs and phage display to discover and optimize peptide therapeutics, demonstrating successful HtrA1 protease inhibitors and high-affinity Notch2 ligands.

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Area of Science:

Biochemistry
Molecular Biology
Drug Discovery

Background:

Peptides are promising therapeutic agents but often lack stability.
Disulfide-constrained peptides (DCPs) offer enhanced chemical and physical stability.
DCPs provide drug-like scaffolds amenable to engineering.

Purpose of the Study:

To establish a robust platform for discovering peptide therapeutics using DCP scaffolds.
To evaluate the platform's effectiveness for functional hit discovery.
To demonstrate hit-to-lead progression for therapeutic candidates.

Main Methods:

Construction of diverse phage display libraries using seven different DCP scaffolds (2 x 10^11 diversity).
Selection and synthesis of peptides from DCP libraries.
Affinity maturation strategies applied to identified binders.

Main Results:

A high hit rate for functional discovery, comparable to synthetic antibody libraries.
Generation of functional HtrA1 protease inhibitors.
Optimization of weak Notch2 binders from micromolar to nanomolar affinity.

Conclusions:

The developed platform is effective for discovering and optimizing peptide therapeutics.
DCPs serve as valuable scaffolds for creating stable and potent peptide drugs.
The platform facilitates a viable hit-to-lead progression for drug development.