Edaravone, a scavenger for multiple reactive oxygen species, reacts with singlet oxygen to yield 2-oxo-3-(phenylhydrazono)-butanoic acid
Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) is a synthetic antioxidant used as a drug to treat acute ischemic stroke in Japan and amyotrophic lateral sclerosis in Japan and the USA. Its pharmacological mechanism is thought to be scavenging of reactive oxygen species, which are intimately related...
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| Veröffentlicht in: | Journal of Clinical Biochemistry and Nutrition 2022, Vol.70(3), pp.240-247 |
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| creator | Amekura, Sakiko Shiozawa, Kyouhei Kiryu, Chihiro Yamamoto, Yorihiro Fujisawa, Akio |
| description | Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) is a synthetic antioxidant used as a drug to treat acute ischemic stroke in Japan and amyotrophic lateral sclerosis in Japan and the USA. Its pharmacological mechanism is thought to be scavenging of reactive oxygen species, which are intimately related with these diseases. Recently, the singlet oxygen (1O2) has attracted attention among reactive oxygen species. In this study, we investigated the reactivity of edaravone toward 1O2 and identified its reaction products. Edaravone showed a reactivity toward 1O2 greater than those of uric acid, histidine, and tryptophan, which are believed to be 1O2 scavengers in vivo. And we confirmed that 2-oxo-3-(phenylhydrazono)-butanoic acid was formed as an oxidation product. We propose a plausible mechanism for 2-oxo-3-(phenylhydrazono)-butanoic acid production by 1O2-induced edaravone oxidation. Since 2-oxo-3-(phenylhydrazono)-butanoic acid has already been identified as a radical-initiated oxidation product, free radical-induced oxidation should be seriously reconsidered. We also found that edaravone can react with not only hypochlorous anions but also 1O2 that are formed from myeloperoxidase. This result suggests that edaravone treatment can be beneficial against myeloperoxidase-related injuries such as inflammation. |
| doi_str_mv | 10.3164/jcbn.21-133 |
| format | Article |
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Its pharmacological mechanism is thought to be scavenging of reactive oxygen species, which are intimately related with these diseases. Recently, the singlet oxygen (1O2) has attracted attention among reactive oxygen species. In this study, we investigated the reactivity of edaravone toward 1O2 and identified its reaction products. Edaravone showed a reactivity toward 1O2 greater than those of uric acid, histidine, and tryptophan, which are believed to be 1O2 scavengers in vivo. And we confirmed that 2-oxo-3-(phenylhydrazono)-butanoic acid was formed as an oxidation product. We propose a plausible mechanism for 2-oxo-3-(phenylhydrazono)-butanoic acid production by 1O2-induced edaravone oxidation. Since 2-oxo-3-(phenylhydrazono)-butanoic acid has already been identified as a radical-initiated oxidation product, free radical-induced oxidation should be seriously reconsidered. We also found that edaravone can react with not only hypochlorous anions but also 1O2 that are formed from myeloperoxidase. This result suggests that edaravone treatment can be beneficial against myeloperoxidase-related injuries such as inflammation.</description><identifier>ISSN: 0912-0009</identifier><identifier>EISSN: 1880-5086</identifier><identifier>DOI: 10.3164/jcbn.21-133</identifier><identifier>PMID: 35692681</identifier><language>eng</language><publisher>Japan: SOCIETY FOR FREE RADICAL RESEARCH JAPAN</publisher><subject>Acid production ; Acids ; Amyotrophic lateral sclerosis ; Anions ; Antioxidants ; Butyric acid ; edaravone ; Free radicals ; Histidine ; Ischemia ; Original ; Oxidation ; Oxidative stress ; Oxygen ; Peroxidase ; Reaction products ; Reactive oxygen species ; Scavenging ; Singlet oxygen ; Tryptophan ; Uric acid</subject><ispartof>Journal of Clinical Biochemistry and Nutrition, 2022, Vol.70(3), pp.240-247</ispartof><rights>2022 JCBN</rights><rights>Copyright © 2022 JCBN.</rights><rights>2022. This work is published under https://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Copyright © 2022 JCBN 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4023-e9403e2486581c2453c16219cbd967f6223b5d1aeffb17ba03dc631b3ff8e8af3</citedby><cites>FETCH-LOGICAL-c4023-e9403e2486581c2453c16219cbd967f6223b5d1aeffb17ba03dc631b3ff8e8af3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9130065/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9130065/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,1877,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35692681$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Amekura, Sakiko</creatorcontrib><creatorcontrib>Shiozawa, Kyouhei</creatorcontrib><creatorcontrib>Kiryu, Chihiro</creatorcontrib><creatorcontrib>Yamamoto, Yorihiro</creatorcontrib><creatorcontrib>Fujisawa, Akio</creatorcontrib><title>Edaravone, a scavenger for multiple reactive oxygen species, reacts with singlet oxygen to yield 2-oxo-3-(phenylhydrazono)-butanoic acid</title><title>Journal of Clinical Biochemistry and Nutrition</title><addtitle>J. Clin. Biochem. Nutr.</addtitle><description>Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) is a synthetic antioxidant used as a drug to treat acute ischemic stroke in Japan and amyotrophic lateral sclerosis in Japan and the USA. Its pharmacological mechanism is thought to be scavenging of reactive oxygen species, which are intimately related with these diseases. Recently, the singlet oxygen (1O2) has attracted attention among reactive oxygen species. In this study, we investigated the reactivity of edaravone toward 1O2 and identified its reaction products. Edaravone showed a reactivity toward 1O2 greater than those of uric acid, histidine, and tryptophan, which are believed to be 1O2 scavengers in vivo. And we confirmed that 2-oxo-3-(phenylhydrazono)-butanoic acid was formed as an oxidation product. We propose a plausible mechanism for 2-oxo-3-(phenylhydrazono)-butanoic acid production by 1O2-induced edaravone oxidation. Since 2-oxo-3-(phenylhydrazono)-butanoic acid has already been identified as a radical-initiated oxidation product, free radical-induced oxidation should be seriously reconsidered. We also found that edaravone can react with not only hypochlorous anions but also 1O2 that are formed from myeloperoxidase. This result suggests that edaravone treatment can be beneficial against myeloperoxidase-related injuries such as inflammation.</description><subject>Acid production</subject><subject>Acids</subject><subject>Amyotrophic lateral sclerosis</subject><subject>Anions</subject><subject>Antioxidants</subject><subject>Butyric acid</subject><subject>edaravone</subject><subject>Free radicals</subject><subject>Histidine</subject><subject>Ischemia</subject><subject>Original</subject><subject>Oxidation</subject><subject>Oxidative stress</subject><subject>Oxygen</subject><subject>Peroxidase</subject><subject>Reaction products</subject><subject>Reactive oxygen species</subject><subject>Scavenging</subject><subject>Singlet oxygen</subject><subject>Tryptophan</subject><subject>Uric acid</subject><issn>0912-0009</issn><issn>1880-5086</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkU1v1DAQhi0EotvCiTuyxKWIuvgjcZwLUlWVD6kSFzhbjjNJvMrawU62Db-An92s0q6Ay8zhffRoRi9Cbxi9FExmH7e28pecESbEM7RhSlGSUyWfow0tGSeU0vIEnaa0pTSTucxeohORy5JLxTboz01totkHDxfY4GTNHnwLETch4t3Uj27oAUcwdnR7wOF-bsHjNIB1kC7WIOE7N3Y4Od_2MD4xY8Czg77GnIT7QAQ5Hzrwc9_NdTS_gw_vSTWNxgdnsbGufoVeNKZP8Ppxn6Gfn29-XH8lt9-_fLu-uiU2o1wQKDMqgGdK5opZnuXCMslZaau6lEUjORdVXjMDTVOxojJU1FYKVommUaBMI87Qp9U7TNUOagt-jKbXQ3Q7E2cdjNP_Jt51ug17XTJBqcwXwfmjIIZfE6RR71yy0PfGQ5iS5rLISyULQRf03X_oNkzRL-8tVK4Ep0wVC_VhpWwMKUVojscwqg8N60PDmjO9NLzQb_--_8g-VboAVyuwTaNp4QiYODrbwyorFvNhrNJjZjsTNXjxAAtVu70</recordid><startdate>20220101</startdate><enddate>20220101</enddate><creator>Amekura, Sakiko</creator><creator>Shiozawa, Kyouhei</creator><creator>Kiryu, Chihiro</creator><creator>Yamamoto, Yorihiro</creator><creator>Fujisawa, Akio</creator><general>SOCIETY FOR FREE RADICAL RESEARCH JAPAN</general><general>Japan Science and Technology Agency</general><general>the Society for Free Radical Research Japan</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QP</scope><scope>7TK</scope><scope>7U9</scope><scope>C1K</scope><scope>H94</scope><scope>K9.</scope><scope>NAPCQ</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20220101</creationdate><title>Edaravone, a scavenger for multiple reactive oxygen species, reacts with singlet oxygen to yield 2-oxo-3-(phenylhydrazono)-butanoic acid</title><author>Amekura, Sakiko ; Shiozawa, Kyouhei ; Kiryu, Chihiro ; Yamamoto, Yorihiro ; Fujisawa, Akio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4023-e9403e2486581c2453c16219cbd967f6223b5d1aeffb17ba03dc631b3ff8e8af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Acid production</topic><topic>Acids</topic><topic>Amyotrophic lateral sclerosis</topic><topic>Anions</topic><topic>Antioxidants</topic><topic>Butyric acid</topic><topic>edaravone</topic><topic>Free radicals</topic><topic>Histidine</topic><topic>Ischemia</topic><topic>Original</topic><topic>Oxidation</topic><topic>Oxidative stress</topic><topic>Oxygen</topic><topic>Peroxidase</topic><topic>Reaction products</topic><topic>Reactive oxygen species</topic><topic>Scavenging</topic><topic>Singlet oxygen</topic><topic>Tryptophan</topic><topic>Uric acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amekura, Sakiko</creatorcontrib><creatorcontrib>Shiozawa, Kyouhei</creatorcontrib><creatorcontrib>Kiryu, Chihiro</creatorcontrib><creatorcontrib>Yamamoto, Yorihiro</creatorcontrib><creatorcontrib>Fujisawa, Akio</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Nursing & Allied Health Premium</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of Clinical Biochemistry and Nutrition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amekura, Sakiko</au><au>Shiozawa, Kyouhei</au><au>Kiryu, Chihiro</au><au>Yamamoto, Yorihiro</au><au>Fujisawa, Akio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Edaravone, a scavenger for multiple reactive oxygen species, reacts with singlet oxygen to yield 2-oxo-3-(phenylhydrazono)-butanoic acid</atitle><jtitle>Journal of Clinical Biochemistry and Nutrition</jtitle><addtitle>J. Clin. Biochem. Nutr.</addtitle><date>2022-01-01</date><risdate>2022</risdate><volume>70</volume><issue>3</issue><spage>240</spage><epage>247</epage><pages>240-247</pages><artnum>21-133</artnum><issn>0912-0009</issn><eissn>1880-5086</eissn><abstract>Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) is a synthetic antioxidant used as a drug to treat acute ischemic stroke in Japan and amyotrophic lateral sclerosis in Japan and the USA. Its pharmacological mechanism is thought to be scavenging of reactive oxygen species, which are intimately related with these diseases. Recently, the singlet oxygen (1O2) has attracted attention among reactive oxygen species. In this study, we investigated the reactivity of edaravone toward 1O2 and identified its reaction products. Edaravone showed a reactivity toward 1O2 greater than those of uric acid, histidine, and tryptophan, which are believed to be 1O2 scavengers in vivo. And we confirmed that 2-oxo-3-(phenylhydrazono)-butanoic acid was formed as an oxidation product. We propose a plausible mechanism for 2-oxo-3-(phenylhydrazono)-butanoic acid production by 1O2-induced edaravone oxidation. Since 2-oxo-3-(phenylhydrazono)-butanoic acid has already been identified as a radical-initiated oxidation product, free radical-induced oxidation should be seriously reconsidered. We also found that edaravone can react with not only hypochlorous anions but also 1O2 that are formed from myeloperoxidase. This result suggests that edaravone treatment can be beneficial against myeloperoxidase-related injuries such as inflammation.</abstract><cop>Japan</cop><pub>SOCIETY FOR FREE RADICAL RESEARCH JAPAN</pub><pmid>35692681</pmid><doi>10.3164/jcbn.21-133</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Acid production Acids Amyotrophic lateral sclerosis Anions Antioxidants Butyric acid edaravone Free radicals Histidine Ischemia Original Oxidation Oxidative stress Oxygen Peroxidase Reaction products Reactive oxygen species Scavenging Singlet oxygen Tryptophan Uric acid |
| title | Edaravone, a scavenger for multiple reactive oxygen species, reacts with singlet oxygen to yield 2-oxo-3-(phenylhydrazono)-butanoic acid |
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