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However, developing H\n                    <jats:sub>2<\/jats:sub>\n                    S donors with both tunable release kinetics and high release efficiency for subcellular delivery has been challenging. Here, we describe a click and release reaction between pyrone\/pyranthiones and bicyclononyne (BCN). This reaction features a release of CO\n                    <jats:sub>2<\/jats:sub>\n                    \/COS with second\u2010order rate constants comparable to Strain\u2010Promoted Azide\u2010Alkyne Cycloaddition reactions (SPAACs). Interestingly, pyranthiones showed enhanced reaction rates compared to their pyrone counterparts. We investigated pyrone biorthogonality and demonstrated their utility in protein labeling applications. Moreover, we synthesized substituted pyranthiones with H\n                    <jats:sub>2<\/jats:sub>\n                    S release kinetics that can address the range of physiologically relevant H\n                    <jats:sub>2<\/jats:sub>\n                    S dynamics in cells and achieved quantitative H\n                    <jats:sub>2<\/jats:sub>\n                    S release efficiency\n                    <jats:italic>in\u2005vitro<\/jats:italic>\n                    . Finally, we explored the potential of pyranthiones as H\n                    <jats:sub>2<\/jats:sub>\n                    S\/COS donors for mitochondrial\u2010targeted H\n                    <jats:sub>2<\/jats:sub>\n                    S delivery in living cells.\n                  <\/jats:p>","DOI":"10.1002\/chem.202303465","type":"journal-article","created":{"date-parts":[[2023,11,21]],"date-time":"2023-11-21T08:43:58Z","timestamp":1700556238000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Pyranthiones\/Pyrones: \u201cClick and Release\u201d Donors for Subcellular Hydrogen Sulfide Delivery and Labeling**"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2555-0140","authenticated-orcid":false,"given":"Wei","family":"Huang","sequence":"first","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY 11790 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nipuni","family":"Gunawardhana","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY 11790 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yunlei","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY 11790 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6756-0991","authenticated-orcid":false,"given":"Jorge","family":"Escorihuela","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universitat de Val\u00e8ncia  Avda. Vicente Andr\u00e9s Estell\u00e9s s\/n, Burjassot 46100 Valencia Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9134-1200","authenticated-orcid":false,"given":"Scott T.","family":"Laughlin","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY 11790 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,12,11]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00395E"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c00124"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2022.05.018"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201800402"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2079-1"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-03880-y"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05093"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b11217"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c07922"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c00531"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja101766r"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC02574A"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305969"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202203375"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC02610F"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tibs.2014.03.003"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2017.11.019"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1080\/10715762.2020.1862827"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.coph.2019.07.001"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jare.2021.08.012"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00205"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd4433"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.niox.2014.03.163"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1115634109"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2012.04.007"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09547J"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03780"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908052"},{"key":"e_1_2_8_29_1","volume":"61","author":"Chen Y.","year":"2022","journal-title":"Angew. 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