@inbook{fd000feb6de24fb882f013d37b1a0c13,
title = "Pyrone and pyranthione scaffolds for click-to-release and biological gas delivery",
abstract = "Click-to-release chemistry provides methods to control molecular activation in biological systems using bioorthogonal reactions. Here, we discuss several classical click-to-release reactions, including Staudinger-Bertozzi-based cleavage systems, 1,3-dipolar cycloaddition-based cleavable systems, and tetrazine-triggered inverse-electron-demand Diels-Alder (IEDDA) cleavage systems. We describe in detail pyrone and pyranthione scaffolds that undergo IEDDA reactions with endo-bicyclo[6.1.0]nonyne (endo-BCN), resulting in the release of carbon dioxide or carbonyl sulfide, with the latter converted to hydrogen sulfide by carbonic anhydrase. We discuss approaches to evaluate the kinetics and bioorthogonality of a pyrone compound library. Finally, we discuss protein labeling, quantitative analysis of hydrogen sulfide release, and mitochondrial hydrogen sulfide imaging in live HeLa cells.",
keywords = "Bioorthogonal chemistry, Click-to-release, Gasotransmitters, Hydrogen sulfide, Inverse-electron-demand Diels-Alder (IEDDA), Pyranthiones, Pyrones",
author = "Kangqiao Wen and Evans Kusi and Scott Laughlin",
note = "Publisher Copyright: {\textcopyright} 2026",
year = "2026",
month = jan,
doi = "10.1016/bs.mie.2026.05.006",
language = "English",
isbn = "9780443432248",
series = "Methods in Enzymology",
publisher = "Academic Press Inc.",
pages = "427--461",
editor = "Urbach, \{Adam R.\}",
booktitle = "Bioorthogonal Labeling",
}