{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T09:06:51Z","timestamp":1773306411062,"version":"3.50.1"},"reference-count":52,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,10,31]],"date-time":"2022-10-31T00:00:00Z","timestamp":1667174400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008982","name":"National Science Foundation","doi-asserted-by":"publisher","award":["IOS2012106"],"award-info":[{"award-number":["IOS2012106"]}],"id":[{"id":"10.13039\/501100008982","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008982","name":"National Science Foundation","doi-asserted-by":"publisher","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}],"id":[{"id":"10.13039\/501100008982","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008982","name":"National Science Foundation","doi-asserted-by":"publisher","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}],"id":[{"id":"10.13039\/501100008982","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institute of Health","doi-asserted-by":"publisher","award":["IOS2012106"],"award-info":[{"award-number":["IOS2012106"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institute of Health","doi-asserted-by":"publisher","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institute of Health","doi-asserted-by":"publisher","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["IOS2012106"],"award-info":[{"award-number":["IOS2012106"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System (KDS)","award":["IOS2012106"],"award-info":[{"award-number":["IOS2012106"]}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System (KDS)","award":["R01NS094535"],"award-info":[{"award-number":["R01NS094535"]}]},{"name":"Biomedical Research Foundation at Central Arkansas Veteran\u2019s Healthcare System (KDS)","award":["BE-0048"],"award-info":[{"award-number":["BE-0048"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>1,4-Napththoquinones (NQs) are clinically relevant therapeutics that affect cell function through production of reactive oxygen species (ROS) and formation of adducts with regulatory protein thiols. Reactive sulfur species (RSS) are chemically and biologically similar to ROS and here we examine RSS production by NQ oxidation of hydrogen sulfide (H2S) using RSS-specific fluorophores, liquid chromatography-mass spectrometry, UV-Vis absorption spectrometry, oxygen-sensitive optodes, thiosulfate-specific nanoparticles, HPLC-monobromobimane derivatization, and ion chromatographic assays. We show that NQs, catalytically oxidize H2S to per- and polysulfides (H2Sn, n = 2\u20136), thiosulfate, sulfite and sulfate in reactions that consume oxygen and are accelerated by superoxide dismutase (SOD) and inhibited by catalase. The approximate efficacy of NQs (in decreasing order) is, 1,4-NQ \u2248 juglone \u2248 plumbagin &gt; 2-methoxy-1,4-NQ \u2248 menadione &gt;&gt; phylloquinone \u2248 anthraquinone \u2248 menaquinone \u2248 lawsone. We propose that the most probable reactions are an initial two-electron oxidation of H2S to S0 and reduction of NQ to NQH2. S0 may react with H2S or elongate H2Sn in variety of reactions. Reoxidation of NQH2 likely involves a semiquinone radical (NQ\u00b7\u2212) intermediate via several mechanisms involving oxygen and comproportionation to produce NQ and superoxide. Dismutation of the latter forms hydrogen peroxide which then further oxidizes RSS to sulfoxides. These findings provide the chemical background for novel sulfur-based approaches to naphthoquinone-directed therapies.<\/jats:p>","DOI":"10.3390\/ijms232113293","type":"journal-article","created":{"date-parts":[[2022,11,1]],"date-time":"2022-11-01T06:01:28Z","timestamp":1667282488000},"page":"13293","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Naphthoquinones Oxidize H2S to Polysulfides and Thiosulfate, Implications for Therapeutic Applications"],"prefix":"10.3390","volume":"23","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":[{"role":"author","vocabulary":"crossref"}]},{"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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paul J.","family":"Derry","sequence":"additional","affiliation":[{"name":"Center for Genomics and Precision Medicine, Institute of Biosciences and Technology, Texas A&M Health Science Center, Houston, TX 77030, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yan","family":"Gao","sequence":"additional","affiliation":[{"name":"Indiana University School of Medicine\u2014South Bend, South Bend, IN 46617, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"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":[{"role":"author","vocabulary":"crossref"}]},{"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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alyssa","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":[{"role":"author","vocabulary":"crossref"}]},{"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":[{"role":"author","vocabulary":"crossref"}]},{"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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kathleen","family":"Narloch","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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cecilia L.","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":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-4130-6936","authenticated-orcid":false,"given":"Ifeyinwa","family":"Nwebube","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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Collin J.","family":"Pallissery","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":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7634-0114","authenticated-orcid":false,"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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Brian P.","family":"Villa","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":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas A.","family":"Kent","sequence":"additional","affiliation":[{"name":"Center for Genomics and Precision Medicine, Institute of Biosciences and Technology, Texas A&M Health Science Center, Houston, TX 77030, USA"},{"name":"Department of Chemistry, Rice University, Houston, TX 77005, USA"},{"name":"Stanley H. Appel Department of Neurology, Houston Methodist Hospital and Research Institute, 6560 Fannin Street, Houston, TX 77030, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6803-0853","authenticated-orcid":false,"given":"Gang","family":"Wu","sequence":"additional","affiliation":[{"name":"Department of Internal Medicine, University of Texas\u2014McGovern Medical School, Houston, TX 77030, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karl D.","family":"Straub","sequence":"additional","affiliation":[{"name":"Central Arkansas Veteran\u2019s Healthcare System, Little Rock, AR 72205, USA"},{"name":"Departments of Medicine and Biochemistry, University of Arkansas for Medical Sciences, Little Rock, AR 72202, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1021\/tx500089x","article-title":"Metal-independent reduction of hydrogen peroxide by semiquinones","volume":"27","author":"Santos","year":"2014","journal-title":"Chem. Res. Toxicol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1111\/cbdd.13141","article-title":"Naphthoquinones: A continuing source for discovery of therapeutic antineoplastic agents","volume":"91","author":"Qiu","year":"2018","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1159\/000500828","article-title":"Henna as a Hair Dye: A Current Fashion Trend with Ancient Roots","volume":"235","author":"Chowdhury","year":"2019","journal-title":"Dermatology"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1093\/nutrit\/nuab061","article-title":"Vitamin K-sources, physiological role, kinetics, deficiency, detection, therapeutic use, and toxicity","volume":"80","author":"Carazo","year":"2022","journal-title":"Nutr. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Ahmad, T., and Suzuki, Y.J. (2019). Juglone in Oxidative Stress and Cell Signaling. Antioxidants, 8.","DOI":"10.3390\/antiox8040091"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1080\/21691401.2017.1417865","article-title":"Current development in novel drug delivery systems of bioactive molecule plumbagin","volume":"46","author":"Rajalakshmi","year":"2018","journal-title":"Artif. Cells Nanomed. Biotechnol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"112785","DOI":"10.1016\/j.biopha.2022.112785","article-title":"Molecular biological mechanism of action in cancer therapies: Juglone and its derivatives, the future of development","volume":"148","author":"Tang","year":"2022","journal-title":"Biomed. Amp. Pharmacother."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1515\/hsz-2021-0290","article-title":"The phytochemical plumbagin reciprocally modulates osteoblasts and osteoclasts","volume":"403","author":"Yadav","year":"2022","journal-title":"Biol. Chem."},{"key":"ref_9","first-page":"1","article-title":"Anticancer Effects and Mechanisms of Action of Plumbagin: Review of Research Advances","volume":"2020","author":"Yin","year":"2020","journal-title":"BioMed Res. Int."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"105968","DOI":"10.1016\/j.phrs.2021.105968","article-title":"Redox ticklers and beyond: Naphthoquinone repository in the spotlight against inflammation and associated maladies","volume":"174","author":"Kapoor","year":"2021","journal-title":"Pharm. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"14902","DOI":"10.3390\/molecules190914902","article-title":"1,4-naphthoquinones: From oxidative damage to cellular and inter-cellular signaling","volume":"19","author":"Klotz","year":"2014","journal-title":"Molecules"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1016\/j.freeradbiomed.2010.05.009","article-title":"Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide","volume":"49","author":"Song","year":"2010","journal-title":"Free Radic. Biol. Med."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"148210","DOI":"10.1016\/j.bbabio.2020.148210","article-title":"Mitochondria-targeted 1,4-naphthoquinone (SkQN) is a powerful prooxidant and cytotoxic agent","volume":"1861","author":"Goleva","year":"2020","journal-title":"Biochim. Biophys. Acta Bioenerg."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Swiderska, A., Coney, A.M., Alzahrani, A.A., Aldossary, H.S., Batis, N., Ray, C.J., Kumar, P., and Holmes, A.P. (2021). Mitochondrial Succinate Metabolism and Reactive Oxygen Species Are Important but Not Essential for Eliciting Carotid Body and Ventilatory Responses to Hypoxia in the Rat. Antioxidants, 10.","DOI":"10.3390\/antiox10060840"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"101731","DOI":"10.1016\/j.redox.2020.101731","article-title":"Green tea polyphenolic antioxidants oxidize hydrogen sulfide to thiosulfate and polysulfides: A possible new mechanism underpinning their biological action","volume":"37","author":"Olson","year":"2020","journal-title":"Redox. Biol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.freeradbiomed.2021.01.035","article-title":"\u201cAntioxidant\u201d berries, anthocyanins, resveratrol and rosmarinic acid oxidize hydrogen sulfide to polysulfides and thiosulfate: A novel mechanism underlying their biological actions","volume":"165","author":"Olson","year":"2021","journal-title":"Free Radic. Biol. Med."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Olson, K.R., Gao, Y., and Straub, K.D. (2021). Oxidation of Hydrogen Sulfide by Quinones: How Polyphenols Initiate Their Cytoprotective Effects. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22020961"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.freeradbiomed.2022.02.018","article-title":"Coenzyme Q10 and related quinones oxidize H2S to polysulfides and thiosulfate","volume":"182","author":"Olson","year":"2022","journal-title":"Free Radic. Biol. Med."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Fernandes, C., Videira, A.J.C., Veloso, C.D., Benfeito, S., Soares, P., Martins, J.D., Goncalves, B., Duarte, J.F.S., Santos, A.M.S., and Oliveira, P.J. (2021). Cytotoxicity and Mitochondrial Effects of Phenolic and Quinone-Based Mitochondria-Targeted and Untargeted Antioxidants on Human Neuronal and Hepatic Cell Lines: A Comparative Analysis. Biomolecules, 11.","DOI":"10.3390\/biom11111605"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1406","DOI":"10.1021\/es60159a014","article-title":"Kinetics and mechanism of oxidation of hydrogen sulfide by hydrogen peroxide in acidic solution","volume":"13","author":"Hoffmann","year":"1977","journal-title":"Environ. Sci. Technol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.redox.2017.11.009","article-title":"Metabolism of hydrogen sulfide (H2S) and Production of Reactive Sulfur Species (RSS) by superoxide dismutase","volume":"15","author":"Olson","year":"2017","journal-title":"Redox Biol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.pharmthera.2010.01.003","article-title":"Effects of tempol and redox-cycling nitroxides in models of oxidative stress","volume":"126","author":"Wilcox","year":"2010","journal-title":"Pharmacol. Ther."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3109\/10715769609087994","article-title":"Commentary: Mannitol: Molecule magnifique or a case of radical misinterpretation?","volume":"24","author":"Gillbe","year":"1996","journal-title":"Free Radic. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1381","DOI":"10.1021\/jm00158a010","article-title":"One-electron reduction of 2- and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents","volume":"29","author":"Wilson","year":"1986","journal-title":"J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1042\/BJ20100208","article-title":"What does the commonly used DCF test for oxidative stress really show?","volume":"428","author":"Karlsson","year":"2010","journal-title":"Biochem. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1021\/es60065a008","article-title":"Kinetics of oxidation of aqueous sulfide by O2","volume":"6","author":"Chen","year":"1972","journal-title":"Environ. Sci. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1114","DOI":"10.1021\/es60135a009","article-title":"Kinetics of oxygenation of reduced sulfur species in aqueous solution","volume":"11","author":"Birkner","year":"1977","journal-title":"Environ. Sci. Technol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4093","DOI":"10.1016\/j.watres.2005.08.006","article-title":"Kinetics of the chemical oxidation of polysulfide anions in aqueous solution","volume":"39","author":"Kleinjan","year":"2005","journal-title":"Water Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1519","DOI":"10.1515\/znb-1986-1208","article-title":"On the Autoxidation of Aqueous Sodium Polysulfide","volume":"41b","author":"Steudel","year":"1986","journal-title":"Z. F\u00fcr Nat. B"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1016\/j.ces.2019.01.006","article-title":"Theoretical study on the redox reaction mechanism of quinone compounds in industrial processes","volume":"199","author":"Tarumi","year":"2019","journal-title":"Chem. Eng. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1080\/10715769800300131","article-title":"Kinetics of redox interaction between substituted 1,4-benzoquinones and ascorbate under aerobic conditions: Critical phenomena","volume":"29","author":"Roginsky","year":"1998","journal-title":"Free Radic. Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1914","DOI":"10.1002\/anie.200604525","article-title":"The sulfhydryl radical (HS(.)\/S(.-)): A contender for the isomerization of double bonds in membrane lipids","volume":"46","author":"Lykakis","year":"2007","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6633","DOI":"10.1021\/es049514e","article-title":"Equilibrium distribution of polysulfide ions in aqueous solutions at 25 degrees C: A new approach for the study of polysulfides\u2019 equilibria","volume":"38","author":"Kamyshny","year":"2004","journal-title":"Environ. Sci. Technol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1021\/acs.chemrestox.8b00158","article-title":"Interaction of Quinone-Related Electron Acceptors with Hydropersulfide Na2S2: Evidence for One-Electron Reduction Reaction","volume":"32","author":"Abiko","year":"2019","journal-title":"Chem. Res. Toxicol."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Makarov, S.V., Horvath, A.K., and Makarova, A.S. (2019). Reactivity of Small Oxoacids of Sulfur. Molecules, 24.","DOI":"10.3390\/molecules24152768"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"21496","DOI":"10.1016\/S0021-9258(18)54666-4","article-title":"Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes","volume":"266","author":"Ollinger","year":"1991","journal-title":"J. Biol. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5221","DOI":"10.1021\/jp9907544","article-title":"Reduction potential of the sulfhydryl radical: Pulse radiolysis andlLaser flash photolysis studies of the formation and reactions of \u00b7SH and HSSH\u2014in aqueous solutions","volume":"103","author":"Das","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"22090","DOI":"10.1073\/pnas.0904082106","article-title":"Using a functional enzyme model to understand the chemistry behind hydrogen sulfide induced hibernation","volume":"106","author":"Collman","year":"2009","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1073\/pnas.71.2.253","article-title":"Redox potentials of certain vitamins K: Implications for a role in sulfite reduction by obligately anaerobic bacteria","volume":"71","author":"Wagner","year":"1974","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1080\/10715760000300251","article-title":"Autoxidation of naphthohydroquinones: Effects of pH, naphthoquinones and superoxide dismutase","volume":"32","author":"Munday","year":"2000","journal-title":"Free Radic. Res."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/S0009-2797(99)00099-X","article-title":"Kinetics of redox interaction between substituted quinones and ascorbate under aerobic conditions","volume":"121","author":"Roginsky","year":"1999","journal-title":"Chem. Biol. Interact."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1016\/j.freeradbiomed.2010.04.011","article-title":"Electrode potentials of partially reduced oxygen species, from dioxygen to water","volume":"49","author":"Koppenol","year":"2010","journal-title":"Free Radic. Biol. Med."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/0009-2797(90)90108-Y","article-title":"Effect of superoxide dismutase on the autoxidation of substituted hydro- and semi-naphthoquinones","volume":"73","author":"Ollinger","year":"1990","journal-title":"Chem. Biol. Interact."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1125","DOI":"10.1089\/ars.2020.8132","article-title":"Are Reactive Sulfur Species the New Reactive Oxygen Species?","volume":"33","author":"Olson","year":"2020","journal-title":"Antioxid. Redox Signal."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/j.redox.2018.07.016","article-title":"A selective and sensitive method for quantification of endogenous polysulfide production in biological samples","volume":"18","author":"Bibli","year":"2018","journal-title":"Redox Biol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.freeradbiomed.2019.02.011","article-title":"Effects of inhibiting antioxidant pathways on cellular hydrogen sulfide and polysulfide metabolism","volume":"135","author":"Olson","year":"2019","journal-title":"Free Radic. Biol. Med."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Olson, K.R., Gao, Y., Arif, F., Patel, S., Yuan, X., Mannam, V., Howard, S., Batinic-Haberle, I., Fukuto, J., and Minnion, M. (2019). Manganese Porphyrin-Based SOD Mimetics Produce Polysulfides from Hydrogen Sulfide. Antioxidants, 8.","DOI":"10.3390\/antiox8120639"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1152","DOI":"10.1021\/acssensors.7b00257","article-title":"High-Performance Colorimetric Detection of Thiosulfate by Using Silver Nanoparticles for Smartphone-Based Analysis","volume":"2","author":"Dong","year":"2017","journal-title":"ACS Sens."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"11981","DOI":"10.1021\/acs.analchem.9b02875","article-title":"Sensitive Method for Reliable Quantification of Sulfane Sulfur in Biological Samples","volume":"91","author":"Ran","year":"2019","journal-title":"Anal. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3000","DOI":"10.1248\/cpb.40.3000","article-title":"High performance liquid chromatographic determination of bound sulfide and sulfite and thiosulfate at their low levels in human serum by pre-column fluorescence derivatization with monobromobimane","volume":"40","author":"Togawa","year":"1992","journal-title":"Chem. Pharm. Bull."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1089\/ars.2020.8073","article-title":"High-Precision Sulfur Metabolomics Innovated by a New Specific Probe for Trapping Reactive Sulfur Species","volume":"34","author":"Kasamatsu","year":"2021","journal-title":"Antioxid. Redox Signal."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1980","DOI":"10.1039\/C8CC00187A","article-title":"Goodbye to S(2-) in aqueous solution","volume":"54","author":"May","year":"2018","journal-title":"Chem. Commun."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/21\/13293\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:07:07Z","timestamp":1760144827000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/21\/13293"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,10,31]]},"references-count":52,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2022,11]]}},"alternative-id":["ijms232113293"],"URL":"https:\/\/doi.org\/10.3390\/ijms232113293","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,10,31]]}}}