A coumarin-based fluorescent turn-on probe for detection of biothiols in vitro
A novel fluorescent probe (CA‐N) was designed and synthesized for detection of biothiols. CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated...
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| Veröffentlicht in: | Luminescence (Chichester, England) England), 2015-12, Vol.30 (8), p.1395-1402 |
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| container_title | Luminescence (Chichester, England) |
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| creator | Liu, Mengqiang Jiang, Qian Lu, Zhiyun Huang, Yan Tan, Yanfei Jiang, Qing |
| description | A novel fluorescent probe (CA‐N) was designed and synthesized for detection of biothiols. CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated ketones. CA‐N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA‐N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA‐N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols. Copyright © 2015 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/bio.2912 |
| format | Article |
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CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated ketones. CA‐N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA‐N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA‐N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols. Copyright © 2015 John Wiley & Sons, Ltd.</description><identifier>ISSN: 1522-7235</identifier><identifier>EISSN: 1522-7243</identifier><identifier>DOI: 10.1002/bio.2912</identifier><identifier>PMID: 25924593</identifier><language>eng</language><publisher>England: Blackwell Publishing Ltd</publisher><subject>Amino acids ; bioimaging ; Cell Line ; Cells (biology) ; Cells - chemistry ; Cells - metabolism ; coumarin ; Coumarins - chemistry ; Fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; fluorescent probe ; Humans ; In vitro testing ; Ketones ; Limit of Detection ; Luminescence ; Mathematical analysis ; Michael addition ; Michael reaction ; Spectrometry, Fluorescence - methods ; Sulfhydryl Compounds - analysis ; Sulfhydryl Compounds - metabolism</subject><ispartof>Luminescence (Chichester, England), 2015-12, Vol.30 (8), p.1395-1402</ispartof><rights>Copyright © 2015 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4902-da9c2a305b71debf912a2f18b5f358114e8da6e730123cdfafe8f2a855ff494b3</citedby><cites>FETCH-LOGICAL-c4902-da9c2a305b71debf912a2f18b5f358114e8da6e730123cdfafe8f2a855ff494b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fbio.2912$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fbio.2912$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25924593$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Mengqiang</creatorcontrib><creatorcontrib>Jiang, Qian</creatorcontrib><creatorcontrib>Lu, Zhiyun</creatorcontrib><creatorcontrib>Huang, Yan</creatorcontrib><creatorcontrib>Tan, Yanfei</creatorcontrib><creatorcontrib>Jiang, Qing</creatorcontrib><title>A coumarin-based fluorescent turn-on probe for detection of biothiols in vitro</title><title>Luminescence (Chichester, England)</title><addtitle>Luminescence</addtitle><description>A novel fluorescent probe (CA‐N) was designed and synthesized for detection of biothiols. CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated ketones. CA‐N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA‐N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA‐N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols. Copyright © 2015 John Wiley & Sons, Ltd.</description><subject>Amino acids</subject><subject>bioimaging</subject><subject>Cell Line</subject><subject>Cells (biology)</subject><subject>Cells - chemistry</subject><subject>Cells - metabolism</subject><subject>coumarin</subject><subject>Coumarins - chemistry</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>fluorescent probe</subject><subject>Humans</subject><subject>In vitro testing</subject><subject>Ketones</subject><subject>Limit of Detection</subject><subject>Luminescence</subject><subject>Mathematical analysis</subject><subject>Michael addition</subject><subject>Michael reaction</subject><subject>Spectrometry, Fluorescence - methods</subject><subject>Sulfhydryl Compounds - analysis</subject><subject>Sulfhydryl Compounds - metabolism</subject><issn>1522-7235</issn><issn>1522-7243</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctKxDAUhoMo3sEnkIAbN9VcmqZZ6uANh1FE0V1I2xOMdhpNWi9vb8RxBEFcJYSPL__5D0JblOxRQth-5fweU5QtoFUqGMsky_ni_M7FClqL8YEQUhSFWkYrTCiWC8VX0eQA136YmuC6rDIRGmzbwQeINXQ97ofQZb7DT8FXgK0PuIEe6t6lN29x-ra_d76N2HX4xfXBb6Ala9oIm7NzHd0cH12PTrPxxcnZ6GCc1bkiLGuMqpnhRFSSNlDZFN0wS8tKWC5KSnMoG1OA5IQyXjfWWCgtM6UQ1uYqr_g62v3ypmTPA8ReT12K3LamAz9ETUtCcqlUWfyPyoIoJhkjCd35hT741EAaJFFCUlrkSv4I6-BjDGD1U3CpwXdNif5ch0696M91JHR7JhyqKTRz8Lv_BGRfwKtr4f1PkT48u5gJZ7yLPbzNeRMedSG5FPp2cqIv767Oy_HlRB_zD_LCoc8</recordid><startdate>201512</startdate><enddate>201512</enddate><creator>Liu, Mengqiang</creator><creator>Jiang, Qian</creator><creator>Lu, Zhiyun</creator><creator>Huang, Yan</creator><creator>Tan, Yanfei</creator><creator>Jiang, Qing</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H95</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L.G</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201512</creationdate><title>A coumarin-based fluorescent turn-on probe for detection of biothiols in vitro</title><author>Liu, Mengqiang ; Jiang, Qian ; Lu, Zhiyun ; Huang, Yan ; Tan, Yanfei ; Jiang, Qing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4902-da9c2a305b71debf912a2f18b5f358114e8da6e730123cdfafe8f2a855ff494b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amino acids</topic><topic>bioimaging</topic><topic>Cell Line</topic><topic>Cells (biology)</topic><topic>Cells - chemistry</topic><topic>Cells - metabolism</topic><topic>coumarin</topic><topic>Coumarins - chemistry</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>fluorescent probe</topic><topic>Humans</topic><topic>In vitro testing</topic><topic>Ketones</topic><topic>Limit of Detection</topic><topic>Luminescence</topic><topic>Mathematical analysis</topic><topic>Michael addition</topic><topic>Michael reaction</topic><topic>Spectrometry, Fluorescence - methods</topic><topic>Sulfhydryl Compounds - analysis</topic><topic>Sulfhydryl Compounds - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Mengqiang</creatorcontrib><creatorcontrib>Jiang, Qian</creatorcontrib><creatorcontrib>Lu, Zhiyun</creatorcontrib><creatorcontrib>Huang, Yan</creatorcontrib><creatorcontrib>Tan, Yanfei</creatorcontrib><creatorcontrib>Jiang, Qing</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Luminescence (Chichester, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Mengqiang</au><au>Jiang, Qian</au><au>Lu, Zhiyun</au><au>Huang, Yan</au><au>Tan, Yanfei</au><au>Jiang, Qing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A coumarin-based fluorescent turn-on probe for detection of biothiols in vitro</atitle><jtitle>Luminescence (Chichester, England)</jtitle><addtitle>Luminescence</addtitle><date>2015-12</date><risdate>2015</risdate><volume>30</volume><issue>8</issue><spage>1395</spage><epage>1402</epage><pages>1395-1402</pages><issn>1522-7235</issn><eissn>1522-7243</eissn><abstract>A novel fluorescent probe (CA‐N) was designed and synthesized for detection of biothiols. CA‐N displayed a strong fluorescence in the presence of biothiols with high sensitivity, and the mechanism for detection biothiols was based on the Michael addition reaction of a thiol group to α,β‐unsaturated ketones. CA‐N showed low detection limit for cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), which were calculated as 3.16, 0.19 and 5.15 μM, respectively. At the same time, CA‐N exhibited high selectivity toward biothiols compared with other biological amino acids. In vitro cell experiments proved that CA‐N had no cytotoxicity, high cell permeability and could be employed in living cell imaging for biothiols. Copyright © 2015 John Wiley & Sons, Ltd.</abstract><cop>England</cop><pub>Blackwell Publishing Ltd</pub><pmid>25924593</pmid><doi>10.1002/bio.2912</doi><tpages>8</tpages></addata></record> |
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| subjects | Amino acids bioimaging Cell Line Cells (biology) Cells - chemistry Cells - metabolism coumarin Coumarins - chemistry Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry fluorescent probe Humans In vitro testing Ketones Limit of Detection Luminescence Mathematical analysis Michael addition Michael reaction Spectrometry, Fluorescence - methods Sulfhydryl Compounds - analysis Sulfhydryl Compounds - metabolism |
| title | A coumarin-based fluorescent turn-on probe for detection of biothiols in vitro |
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