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Related Experiment Video

Updated: Jul 9, 2026

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

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

Published on: August 1, 2018

Customized Reversible Stapling for Selective Delivery of Bioactive Peptides.

Zizhen Zeng¹, Jibao Zhu¹, Xiaoyu Deng²

¹National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Chinese Medicine, Nanchang 330006, P. R. China.

Journal of the American Chemical Society

|December 19, 2022

Summary

This study introduces reversible peptide stapling for enhanced stability and targeted delivery. The method uses macrocyclization and triggered decyclization for controlled release of therapeutic peptides.

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Area of Science:

Chemical Biology
Drug Delivery
Peptide Therapeutics

Background:

Peptide drugs offer therapeutic potential but face challenges with stability and targeted delivery.
Current methods for peptide modification often lack reversibility or precise control over release.
Developing strategies for controlled peptide activation and delivery is crucial for advancing peptide therapeutics.

Purpose of the Study:

To develop a novel, reversible peptide stapling strategy for enhanced peptide stability and targeted delivery.
To demonstrate the utility of this strategy for intracellular and extracellular peptide delivery.
To create and validate reversibly stapled antimicrobial peptides (RStAMPs) activated by specific triggers.

Main Methods:

Developed a macrocyclization strategy involving two amino groups and decyclization via dual 1,4-elimination.
Proof-of-concept: Temporarily cyclized a peptide inhibitor of lysine-specific demethylase 1 (LSD1) for improved cell membrane permeability.
Designed RStAMPs with temporarily destabilized helical conformations, activated by hydrogen peroxide (H2O2) at infection sites.

Main Results:

The reversible stapling enhanced peptide stability and cell membrane penetration, with controlled release of active peptide intracellularly under reducing conditions.
Reversibly stapled antimicrobial peptides (RStAMPs) exhibited reduced toxicity and increased protease resistance.
RStAMPs were rapidly activated by H2O2 at infection sites, restoring helical structure and potent antimicrobial activity.

Conclusions:

This macrocyclization strategy offers a versatile platform for reversible peptide modification and controlled delivery.
The developed method significantly improves peptide stability, bioavailability, and targeted activation.
This approach holds great promise for advancing peptide therapeutics in various medical applications, including antimicrobial treatments and targeted cancer therapy.