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Updated: Jun 12, 2025
09:54
Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Published on: August 20, 2018
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Regulating H2S release from self-assembled peptide H2S-donor conjugates using cysteine derivatives.
Zhao Li1,2, Marius Thomas3, Christian M Berač3
1Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA. jbmatson@vt.edu.
Organic & Biomolecular Chemistry
|September 18, 2024
Summary
Researchers developed novel peptide-based nanostructures for delivering hydrogen sulfide (H2S), a molecule with therapeutic potential. The H2S release rate was precisely controlled by the charge of triggering thiols, offering a new drug delivery strategy.
Area of Science:
- Biomaterials Science
- Drug Delivery Systems
- Chemical Biology
Background:
- Self-assembled peptides are versatile platforms for drug delivery.
- Hydrogen sulfide (H2S), an endogenous gasotransmitter, has significant therapeutic potential but requires innovative delivery methods.
- Peptide/protein H2S donor conjugates (PHDCs) offer a versatile approach for H2S delivery.
Purpose of the Study:
- To design, synthesize, and characterize a novel PHDC for controlled H2S delivery.
- To investigate the self-assembly behavior of the PHDC into nanostructures.
- To explore the influence of thiol charge state on H2S release kinetics from the nanostructures.
Main Methods:
- Synthesis of a PHDC comprising an S-aroylthiooxime (SATO) H2S donor, a GFFF tetrapeptide, and a tetraethylene glycol (TEG) dendron.
- Transmission electron microscopy (TEM) to observe self-assembly into spherical structures and nanofibers.
- Circular dichroism (CD) spectroscopy to analyze secondary structure changes during self-assembly and H2S release.
- Quantification of H2S release triggered by thiols with varying charge states (negative, neutral, positive).
Main Results:
- The PHDC self-assembled into spheres under static conditions and nanofibers upon gentle heating (37 °C) and stirring.
- Self-assembly into nanofibers correlated with increased β-sheet content and decreased SATO unit organization.
- H2S release kinetics were modulated by thiol charge: positively charged thiols triggered release ~50-fold faster than negatively charged thiols.
- CD spectroscopy confirmed structural changes during H2S release, mirroring release rate trends.
Conclusions:
- The developed PHDC can self-assemble into tunable nanostructures (spheres or nanofibers).
- The charge state of triggering thiols is a critical factor in modulating H2S release rates.
- This study provides insights into self-assembly mechanisms and offers a strategy for controlled H2S delivery via charge-state-dependent release.
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