{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T03:12:43Z","timestamp":1792379563138,"version":"4.4.0"},"reference-count":37,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2025,11,19]],"date-time":"2025-11-19T00:00:00Z","timestamp":1763510400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2026,1,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Hydrogen cyanide (HCN) is an emerging gasotransmitter, joining NO, CO, and H\n                    <jats:sub>2<\/jats:sub>\n                    S in a group of important endogenous signaling and regulatory molecules. Despite this importance, synthetic HCN donors that respond to broadly tunable stimuli remain absent. Here, I report a platform approach for developing synthetic HCN donors that can be tuned to release HCN on demand in response to endogenous stimuli. The reported donors are stable in solution until activated by a specific stimulus, in this case esterases, after which they release a caged cyanohydrin that is spontaneously hydrolyzed in water to generate HCN. This approach is also compatible with responsive self\u2010immolative 1,6\u2010elimination platforms, allowing for significant modification of release rates, while providing a general, modular, and tunable platform for HCN delivery in response to specific stimuli. Moreover, the developed donors are shown to release HCN in live cells, thereby significantly advancing the available approaches for HCN delivery in complex environments.\n                  <\/jats:p>","DOI":"10.1002\/anie.202521917","type":"journal-article","created":{"date-parts":[[2025,11,19]],"date-time":"2025-11-19T08:41:38Z","timestamp":1763541698000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Harnessing Hydrogen Cyanide (HCN): Responsive Chemical Tools for Delivering an Emerging Gasotransmitter"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3604-653X","authenticated-orcid":false,"given":"Michael D.","family":"Pluth","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry Materials Science Institute Knight Campus for Accelerating Scientific Impact Institute of Molecular Biology University of Oregon  Eugene Oregon 97403 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,19]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1124\/pr.57.4.3"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031\u20106997(25)06663\u20103"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1152\/physrev.00028.2021"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr000040l"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs15272j"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr010152s"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c00823"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2017.11.014"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00683"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.redox.2025.103921"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1111\/febs.16135"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/antiox5040042"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42255\u2010025\u201001225\u2010w"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2026245118"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1104\/pp.18.01083"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26030719"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev\u2010arplant\u2010050213\u2010040027"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.0014\u20102956.2001.02641.x"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2pp05359d"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC01248A"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.5c00527"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol5010643"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00315"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03780"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC01936E"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.5c03272"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.2c01049"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c11410"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2PY00414C"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500088"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep16592"},{"key":"e_1_2_6_32_1","unstructured":"Note: Treatment of mandelonitrile with benzyl chloroformates provided the expected carbonate product. However model mandelonitrile\u2010derived carbonates were unstable toward esterase limiting biological utility."},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo300400q"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2017.09.142"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.8b00981"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c06405"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth.2019"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202521917","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T15:17:53Z","timestamp":1768058273000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202521917"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,19]]},"references-count":37,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2026,1,9]]}},"alternative-id":["10.1002\/anie.202521917"],"URL":"https:\/\/doi.org\/10.1002\/anie.202521917","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,11,19]]},"assertion":[{"value":"2025-10-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-12","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e21917"}}