Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fl...
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| Veröffentlicht in: | ChemistryOpen (Weinheim) 2018-01, Vol.7 (1), p.57-60 |
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| creator | Hong, Kyeong‐Im Lee, Seong Min Jang, Woo‐Dong |
| description | We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The 1H NMR study indicated the reductive elimination of the p‐toluenesulfonyl group from Ts‐OF in the presence of antioxidants and photo‐irradiation.
Driving light: Light‐driven fluorescence enhancement is reported in the presence of antioxidant amino acids. A flavin derivative with a p‐toluenesulfonyl group is prepared as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. |
| doi_str_mv | 10.1002/open.201700144 |
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Driving light: Light‐driven fluorescence enhancement is reported in the presence of antioxidant amino acids. A flavin derivative with a p‐toluenesulfonyl group is prepared as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols.</description><identifier>ISSN: 2191-1363</identifier><identifier>EISSN: 2191-1363</identifier><identifier>DOI: 10.1002/open.201700144</identifier><identifier>PMID: 29318097</identifier><language>eng</language><publisher>Germany: John Wiley & Sons, Inc</publisher><subject>Amino acids ; Antioxidants ; biothiols ; Communication ; Communications ; flavin ; Fluorescence ; Glutathione ; Histidine ; Methionine ; photoexcitation ; reductive elimination ; Synthesis ; turn-on sensor</subject><ispartof>ChemistryOpen (Weinheim), 2018-01, Vol.7 (1), p.57-60</ispartof><rights>2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2018. This work is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5054-3b984c39cd7c368e1ee5453a13077b23ae57306725b352ce1b394952b3c2c53f3</citedby><cites>FETCH-LOGICAL-c5054-3b984c39cd7c368e1ee5453a13077b23ae57306725b352ce1b394952b3c2c53f3</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/PMC5754558/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754558/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,1416,11561,27923,27924,45573,45574,46051,46475,53790,53792</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29318097$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hong, Kyeong‐Im</creatorcontrib><creatorcontrib>Lee, Seong Min</creatorcontrib><creatorcontrib>Jang, Woo‐Dong</creatorcontrib><title>Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids</title><title>ChemistryOpen (Weinheim)</title><addtitle>ChemistryOpen</addtitle><description>We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The 1H NMR study indicated the reductive elimination of the p‐toluenesulfonyl group from Ts‐OF in the presence of antioxidants and photo‐irradiation.
Driving light: Light‐driven fluorescence enhancement is reported in the presence of antioxidant amino acids. A flavin derivative with a p‐toluenesulfonyl group is prepared as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols.</description><subject>Amino acids</subject><subject>Antioxidants</subject><subject>biothiols</subject><subject>Communication</subject><subject>Communications</subject><subject>flavin</subject><subject>Fluorescence</subject><subject>Glutathione</subject><subject>Histidine</subject><subject>Methionine</subject><subject>photoexcitation</subject><subject>reductive elimination</subject><subject>Synthesis</subject><subject>turn-on sensor</subject><issn>2191-1363</issn><issn>2191-1363</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNqFkctOGzEUhq2qFSDKlmVlqZtuEnwZj8ebSimQUikCFrBDsjyeM8RoYqf2TCi7PkKfsU9SR6HhssEbH8ufP5-jH6FDSsaUEHYUluDHjFBJCC2Kd2iPUUVHlJf8_bN6Fx2kdEfykoWiotxBu0xxWhEl99DNtDMr5__-_vPNJGjwzN3O-3w6iW4FHk-7IURIFnyPL2OoAbch4n4O-AR6sL0LHocWT3yufrnGZGyycD7giXVN-og-tKZLcPC476Pr6enV8dlodvH9x_FkNrKCiGLEa1UVlivbSMvLCiiAKAQ3lBMpa8YNCMlJKZmouWAWaM1VoQSruWVW8Jbvo68b73KoF9Csu42m08voFiY-6GCcfnnj3VzfhpUWMn8kqiz48iiI4ecAqdcLl4fuOuMhDElTVSkhSq5oRj-_Qu_CEH0eL1OKCVUQtRaON5SNIaUI7bYZSvQ6O73OTm-zyw8-PR9hi_9PKgNqA9y7Dh7e0OmLy9PzJ_k_zROnRw</recordid><startdate>201801</startdate><enddate>201801</enddate><creator>Hong, Kyeong‐Im</creator><creator>Lee, Seong Min</creator><creator>Jang, Woo‐Dong</creator><general>John Wiley & Sons, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>L6V</scope><scope>L7M</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>201801</creationdate><title>Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids</title><author>Hong, Kyeong‐Im ; Lee, Seong Min ; Jang, Woo‐Dong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5054-3b984c39cd7c368e1ee5453a13077b23ae57306725b352ce1b394952b3c2c53f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Amino acids</topic><topic>Antioxidants</topic><topic>biothiols</topic><topic>Communication</topic><topic>Communications</topic><topic>flavin</topic><topic>Fluorescence</topic><topic>Glutathione</topic><topic>Histidine</topic><topic>Methionine</topic><topic>photoexcitation</topic><topic>reductive elimination</topic><topic>Synthesis</topic><topic>turn-on sensor</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hong, Kyeong‐Im</creatorcontrib><creatorcontrib>Lee, Seong Min</creatorcontrib><creatorcontrib>Jang, Woo‐Dong</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Engineering Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Engineering Collection</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>ChemistryOpen (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hong, Kyeong‐Im</au><au>Lee, Seong Min</au><au>Jang, Woo‐Dong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids</atitle><jtitle>ChemistryOpen (Weinheim)</jtitle><addtitle>ChemistryOpen</addtitle><date>2018-01</date><risdate>2018</risdate><volume>7</volume><issue>1</issue><spage>57</spage><epage>60</epage><pages>57-60</pages><issn>2191-1363</issn><eissn>2191-1363</eissn><abstract>We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The 1H NMR study indicated the reductive elimination of the p‐toluenesulfonyl group from Ts‐OF in the presence of antioxidants and photo‐irradiation.
Driving light: Light‐driven fluorescence enhancement is reported in the presence of antioxidant amino acids. A flavin derivative with a p‐toluenesulfonyl group is prepared as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols.</abstract><cop>Germany</cop><pub>John Wiley & Sons, Inc</pub><pmid>29318097</pmid><doi>10.1002/open.201700144</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amino acids Antioxidants biothiols Communication Communications flavin Fluorescence Glutathione Histidine Methionine photoexcitation reductive elimination Synthesis turn-on sensor |
| title | Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids |
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