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Therefore, organic nitro compounds capable of releasing nitrite under physiological environments have attracted considerable attention. Here, we demonstrate that simple 4\u2010nitro\u20101,8\u2010naphthalimide derivatives efficiently and almost quantitatively liberate nitrite upon reaction with biological thiols, particularly glutathione (GSH). These compounds function as NO prodrugs, enhancing NO bioavailability in mammalian cells through intracellular nitrite\u2013to\u2013NO conversion. Notably, their selectivity toward GSH and the intrinsic fluorescence of the resulting glutathione adducts enable their use as probes for monitoring intracellular GSH levels. Furthermore, cotreatment of endothelial cells with these naphthalimide derivatives and the NO probe DAF\u2010FM diacetate provides a valuable strategy to distinguish between endogenously produced NO and NO generated via synthetic nitro compound\u2013derived nitrite release. Together, these findings highlight 4\u2010nitro\u20101,8\u2010naphthalimides as a promising platform for both NO delivery and real\u2010time cellular redox sensing.\n                  <\/jats:p>","DOI":"10.1002\/chem.202502890","type":"journal-article","created":{"date-parts":[[2025,10,3]],"date-time":"2025-10-03T11:36:22Z","timestamp":1759491382000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Glutathione\u2010Triggered Nitrite Release From Organic Nitrites Enhances Nitric Oxide Bioavailability in Mammalian Cells"],"prefix":"10.1002","volume":"32","author":[{"given":"Shubham","family":"Sahu","sequence":"first","affiliation":[{"name":"Department of Inorganic and Physical Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sagar","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Inorganic and Physical Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5389-5309","authenticated-orcid":false,"given":"Govindasamy","family":"Mugesh","sequence":"additional","affiliation":[{"name":"Department of Inorganic and Physical Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,10,3]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.74.8.3203"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/288373a0"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.84.24.9265"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.HYP.16.5.477"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2022.06.010"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2016.11.125"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/sj.bjp.0704569"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)31375-9"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(17)32375-X"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.279.5359.2121"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1367-5931(00)00146-0"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1212\/WNL.0b013e318233b3e4"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd4623"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr000040l"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar100155t"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2012.03.002"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.molpharmaceut.1c00486"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c01038"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1161\/CIRCULATIONAHA.107.753897"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2466"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.redox.2012.11.005"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1093\/cvr\/cvq323"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400518y"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.vph.2017.11.003"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.1c01048"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja066011v"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.1c00282"},{"key":"e_1_2_8_28_1","volume":"61","author":"Sun J.","year":"2022","journal-title":"Angew. 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