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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Cysteine-activated hydrogen selenide (H2Se) delivery from isoselenocyanates
Reis D Dorit1, Keyan Li1, Christopher A Steven1
1Department of Chemistry and Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, and Institute of Molecular Biology, University of Oregon, Eugene, Oregon, 97403-1253, USA. pluth@uoregon.edu.
Aryl isoselenocyanates release hydrogen selenide (H2Se) when activated by cysteine. This discovery offers new tools for studying H2Se in biological systems and live cell imaging.
Area of Science:
- Chemical Biology
- Organic Chemistry
- Biochemistry
Background:
- Hydrogen selenide (H2Se) is increasingly recognized as a crucial bioregulator.
- H2Se is a precursor to essential selenium-containing biomolecules.
- Existing tools for investigating H2Se in chemical biology are limited.
Purpose of the Study:
- To develop novel aryl isoselenocyanates (ISeC-R) as controllable H2Se donors.
- To investigate the modulation of H2Se release profiles via electronic substitution.
- To demonstrate the utility of ISeC-R in live cell imaging applications.
Main Methods:
- Synthesis of various aryl isoselenocyanates (ISeC-R).
- Cysteine-mediated activation assays to quantify H2Se release.
- Spectroscopic analysis to correlate electronic structure with release kinetics.
- Live cell imaging experiments utilizing ISeC-R for H2Se detection.
Main Results:
- Aryl isoselenocyanates effectively release H2Se upon activation by cysteine.
- Electronic substitution on the aryl ring significantly modulates the rate of H2Se release.
- Demonstrated successful application of ISeC-R for live cell imaging of H2Se.
Conclusions:
- Aryl isoselenocyanates represent a versatile platform for controlled H2Se delivery.
- This work expands the toolkit for chemical biology research involving H2Se.
- The developed compounds show promise for advancing the study of selenium
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