{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:48:28Z","timestamp":1787028508478,"version":"build-2736575974"},"reference-count":35,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2023,4,19]],"date-time":"2023-04-19T00:00:00Z","timestamp":1681862400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Foundation","award":["IOS2012106 (KRO)"],"award-info":[{"award-number":["IOS2012106 (KRO)"]}]},{"name":"National Science Foundation","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"National Science Foundation","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]},{"name":"National Institute of Health","award":["IOS2012106 (KRO)"],"award-info":[{"award-number":["IOS2012106 (KRO)"]}]},{"name":"National Institute of Health","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"National Institute of Health","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]},{"name":"Welch Foundation","award":["IOS2012106 (KRO)"],"award-info":[{"award-number":["IOS2012106 (KRO)"]}]},{"name":"Welch Foundation","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"Welch Foundation","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]},{"name":"IU South Bend","award":["IOS2012106 (KRO)"],"award-info":[{"award-number":["IOS2012106 (KRO)"]}]},{"name":"IU South Bend","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"IU South Bend","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System","award":["IOS2012106 (KRO)"],"award-info":[{"award-number":["IOS2012106 (KRO)"]}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Naphthoquinone (1,4-NQ) and its derivatives (NQs, juglone, plumbagin, 2-methoxy-1,4-NQ, and menadione) have a variety of therapeutic applications, many of which are attributed to redox cycling and the production of reactive oxygen species (ROS). We previously demonstrated that NQs also oxidize hydrogen sulfide (H2S) to reactive sulfur species (RSS), potentially conveying identical benefits. Here we use RSS-specific fluorophores, mass spectroscopy, EPR and UV-Vis spectrometry, and oxygen-sensitive optodes to examine the effects of thiols and thiol-NQ adducts on H2S-NQ reactions. In the presence of glutathione (GSH) and cysteine (Cys), 1,4-NQ oxidizes H2S to both inorganic and organic hydroper-\/hydropolysulfides (R2Sn, R=H, Cys, GSH; n = 2\u20134) and organic sulfoxides (GSnOH, n = 1, 2). These reactions reduce NQs and consume oxygen via a semiquinone intermediate. NQs are also reduced as they form adducts with GSH, Cys, protein thiols, and amines. Thiol, but not amine, adducts may increase or decrease H2S oxidation in reactions that are both NQ- and thiol-specific. Amine adducts also inhibit the formation of thiol adducts. These results suggest that NQs may react with endogenous thiols, including GSH, Cys, and protein Cys, and that these adducts may affect both thiol reactions as well as RSS production from H2S.<\/jats:p>","DOI":"10.3390\/ijms24087516","type":"journal-article","created":{"date-parts":[[2023,4,20]],"date-time":"2023-04-20T03:25:11Z","timestamp":1681961111000},"page":"7516","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Redox and Nucleophilic Reactions of Naphthoquinones with Small Thiols and Their Effects on Oxidization of H2S to Inorganic and Organic Hydropolysulfides and Thiosulfate"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0178-2203","authenticated-orcid":false,"given":"Kenneth R.","family":"Olson","sequence":"first","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8628-681X","authenticated-orcid":false,"given":"Kasey J.","family":"Clear","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, Indiana University South Bend, South Bend, IN 46615, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Gao","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2493-0889","authenticated-orcid":false,"given":"Zhilin","family":"Ma","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4354-2358","authenticated-orcid":false,"given":"Nathaniel M.","family":"Cieplik","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alyssa R.","family":"Fiume","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominic J.","family":"Gaziano","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen M.","family":"Kasko","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer","family":"Luu","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ella","family":"Pfaff","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anthony","family":"Travlos","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cecilia","family":"Velander","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katherine J.","family":"Wilson","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"},{"name":"Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, 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(Camb.)"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/8\/7516\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:19:04Z","timestamp":1760123944000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/8\/7516"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4,19]]},"references-count":35,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["ijms24087516"],"URL":"https:\/\/doi.org\/10.3390\/ijms24087516","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,4,19]]}}}