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We report herein the dual\u2010stimuli (ROS and CA)\u2010responsive thiocarbamate\u2010based prodrug (<jats:bold>AM\u2010TCB<\/jats:bold>) for the turn\u2010on fluorogenic delivery of the naphthalimide\u2010based anticancer agent amonafide along with the gasotransmitter hydrogen sulfide (H<jats:sub>2<\/jats:sub>S). A carbamate\u2010based prodrug <jats:bold>AM\u2010CB<\/jats:bold> was also designed, capable of releasing the anticancer agent amonafide without any H<jats:sub>2<\/jats:sub>S. The prodrugs were synthesized using multi\u2010step organic synthesis. UV\u2010Vis and fluorescence spectroscopic studies revealed selective reactivity of the boronate ester group of prodrugs towards ROS (primarily H<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>) with the release of amonafide and COS\/CO<jats:sub>2<\/jats:sub> via self\u2010immolative processes. Hydrolysis of the generated COS by carbonic anhydrase (CA) produces H<jats:sub>2<\/jats:sub>S. While the prodrug <jats:bold>AM\u2010TCB<\/jats:bold> retained the anticancer activity of free amonafide in cancer cells (MDA\u2010MB\u2010231 and HeLa), unlike amonafide, it enhanced the cellular viability of the non\u2010malignant cells (HEK\u2010293). Fluorescence imaging in HeLa cells revealed the simultaneous delivery of the anticancer agent and H<jats:sub>2<\/jats:sub>S from <jats:bold>AM\u2010TCB<\/jats:bold> with turn\u2010on fluorescence. Western blot studies further revealed the cytoprotective effects of the released H<jats:sub>2<\/jats:sub>S from <jats:bold>AM\u2010TCB<\/jats:bold>. The present adjuvant strategy therefore would be helpful in future for ameliorating the anticancer drug\u2010induced side\u2010effects.<\/jats:p>","DOI":"10.1002\/chem.202302197","type":"journal-article","created":{"date-parts":[[2023,9,4]],"date-time":"2023-09-04T07:24:26Z","timestamp":1693812266000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Dual\u2010Stimuli\u2010Activatable Hybrid Prodrug for the Self\u2010Immolative Delivery of an Anticancer Agent and Hydrogen Sulfide with Turn\u2010On Fluorescence"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8905-4360","authenticated-orcid":false,"given":"Abu","family":"Sufian","sequence":"first","affiliation":[{"name":"Department of Chemistry Indian Institute of Technology Guwahati  Guwahati 781039 Assam 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