Fluorescent Sensor Based on BINOL for Recognition of Cysteine, Homocysteine, and Glutathione
A new and simple fluorescent sensor based on unmodified BINOL was developed. The fluorescence of BINOL could be turned off with high selectivity toward Cu(II) among 27 metal ions. Meanwhile, it was found that BINOL was oxidized to dibenzo[a,kl]xanthen-1-ol (A) by Cu(NO3)2. A new peak appeared at ∼48...
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Veröffentlicht in: | Journal of organic chemistry 2013-11, Vol.78 (22), p.11602-11605 |
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container_title | Journal of organic chemistry |
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creator | Peng, Ruixue Lin, Lili Wu, Xiaoxia Liu, Xiaohua Feng, Xiaoming |
description | A new and simple fluorescent sensor based on unmodified BINOL was developed. The fluorescence of BINOL could be turned off with high selectivity toward Cu(II) among 27 metal ions. Meanwhile, it was found that BINOL was oxidized to dibenzo[a,kl]xanthen-1-ol (A) by Cu(NO3)2. A new peak appeared at ∼482 nm upon addition of thiol-containing cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). Thus, a cascade recognition of Cu(II) and Cys, Hcy, and GSH are well presented. |
doi_str_mv | 10.1021/jo401932n |
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The fluorescence of BINOL could be turned off with high selectivity toward Cu(II) among 27 metal ions. Meanwhile, it was found that BINOL was oxidized to dibenzo[a,kl]xanthen-1-ol (A) by Cu(NO3)2. A new peak appeared at ∼482 nm upon addition of thiol-containing cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). Thus, a cascade recognition of Cu(II) and Cys, Hcy, and GSH are well presented.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo401932n</identifier><identifier>PMID: 24160671</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Copper - analysis ; Cysteine - analysis ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Glutathione - analysis ; Homocysteine - analysis ; Molecular Structure ; Naphthols - chemical synthesis ; Naphthols - chemistry</subject><ispartof>Journal of organic chemistry, 2013-11, Vol.78 (22), p.11602-11605</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-c939b8bb19158601004391203d5fc4f31a27bfb4c5b1a1189f11ebd735b8cec83</citedby><cites>FETCH-LOGICAL-a315t-c939b8bb19158601004391203d5fc4f31a27bfb4c5b1a1189f11ebd735b8cec83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo401932n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo401932n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24160671$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Peng, Ruixue</creatorcontrib><creatorcontrib>Lin, Lili</creatorcontrib><creatorcontrib>Wu, Xiaoxia</creatorcontrib><creatorcontrib>Liu, Xiaohua</creatorcontrib><creatorcontrib>Feng, Xiaoming</creatorcontrib><title>Fluorescent Sensor Based on BINOL for Recognition of Cysteine, Homocysteine, and Glutathione</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A new and simple fluorescent sensor based on unmodified BINOL was developed. The fluorescence of BINOL could be turned off with high selectivity toward Cu(II) among 27 metal ions. Meanwhile, it was found that BINOL was oxidized to dibenzo[a,kl]xanthen-1-ol (A) by Cu(NO3)2. A new peak appeared at ∼482 nm upon addition of thiol-containing cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). Thus, a cascade recognition of Cu(II) and Cys, Hcy, and GSH are well presented.</description><subject>Copper - analysis</subject><subject>Cysteine - analysis</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Glutathione - analysis</subject><subject>Homocysteine - analysis</subject><subject>Molecular Structure</subject><subject>Naphthols - chemical synthesis</subject><subject>Naphthols - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLAzEUhYMotlYX_gGZjaDgaG4ymU6WttgHFAs-dsKQZBKdMk1qMrPovzfS2pV3c7mH7x44B6FLwPeACTysXIaBU2KPUB8YwWnOcXaM-hgTklKS0x46C2GF4zDGTlGPZJDjfAh99DFpOud1UNq2yau2wflkJIKuEmeT0fx5uUhMlF60cp-2buuoOpOMt6HVtdV3ycytnTpcwlbJtOla0X5FUp-jEyOaoC_2e4DeJ09v41m6WE7n48dFKiiwNlWccllICRxYkWPAOKMcCKYVMyozFAQZSiMzxSQIgIIbAC2rIWWyUFoVdIBudr4b7747HdpyXcdETSOsdl0oIWPRGnNKI3q7Q5V3IXhtyo2v18JvS8Dlb5nloczIXu1tO7nW1YH8ay8C1ztAqBD_Om9jyn-MfgDm_Xok</recordid><startdate>20131115</startdate><enddate>20131115</enddate><creator>Peng, Ruixue</creator><creator>Lin, Lili</creator><creator>Wu, Xiaoxia</creator><creator>Liu, Xiaohua</creator><creator>Feng, Xiaoming</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20131115</creationdate><title>Fluorescent Sensor Based on BINOL for Recognition of Cysteine, Homocysteine, and Glutathione</title><author>Peng, Ruixue ; Lin, Lili ; Wu, Xiaoxia ; Liu, Xiaohua ; Feng, Xiaoming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-c939b8bb19158601004391203d5fc4f31a27bfb4c5b1a1189f11ebd735b8cec83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Copper - analysis</topic><topic>Cysteine - analysis</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Glutathione - analysis</topic><topic>Homocysteine - analysis</topic><topic>Molecular Structure</topic><topic>Naphthols - chemical synthesis</topic><topic>Naphthols - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peng, Ruixue</creatorcontrib><creatorcontrib>Lin, Lili</creatorcontrib><creatorcontrib>Wu, Xiaoxia</creatorcontrib><creatorcontrib>Liu, Xiaohua</creatorcontrib><creatorcontrib>Feng, Xiaoming</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peng, Ruixue</au><au>Lin, Lili</au><au>Wu, Xiaoxia</au><au>Liu, Xiaohua</au><au>Feng, Xiaoming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fluorescent Sensor Based on BINOL for Recognition of Cysteine, Homocysteine, and Glutathione</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2013-11-15</date><risdate>2013</risdate><volume>78</volume><issue>22</issue><spage>11602</spage><epage>11605</epage><pages>11602-11605</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A new and simple fluorescent sensor based on unmodified BINOL was developed. The fluorescence of BINOL could be turned off with high selectivity toward Cu(II) among 27 metal ions. Meanwhile, it was found that BINOL was oxidized to dibenzo[a,kl]xanthen-1-ol (A) by Cu(NO3)2. A new peak appeared at ∼482 nm upon addition of thiol-containing cysteine (Cys), homocysteine (Hcy), and glutathione (GSH). Thus, a cascade recognition of Cu(II) and Cys, Hcy, and GSH are well presented.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24160671</pmid><doi>10.1021/jo401932n</doi><tpages>4</tpages></addata></record> |
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subjects | Copper - analysis Cysteine - analysis Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Glutathione - analysis Homocysteine - analysis Molecular Structure Naphthols - chemical synthesis Naphthols - chemistry |
title | Fluorescent Sensor Based on BINOL for Recognition of Cysteine, Homocysteine, and Glutathione |
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