A novel sensitive fluorescent probe with double channels for highly effective recognition of biothiols

[Display omitted] •A sensitive fluorescence probe TZ-NBD for the recognition of biothiols with dual-channel was constructed.•Dual-channel response improves the probe's anti-interference ability.•TZ-NBD showed fast response, good sensitivity, and near-infrared fluorescence signal.•TZ-NBD was suc...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2024-01, Vol.97, p.129563-129563, Article 129563
Hauptverfasser: Fei, Qiang, Shen, Keyi, Ke, Hongxiu, Wang, Erfei, Fan, Guorun, Wang, Feiyi, Ren, Jun
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container_title Bioorganic & medicinal chemistry letters
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creator Fei, Qiang
Shen, Keyi
Ke, Hongxiu
Wang, Erfei
Fan, Guorun
Wang, Feiyi
Ren, Jun
description [Display omitted] •A sensitive fluorescence probe TZ-NBD for the recognition of biothiols with dual-channel was constructed.•Dual-channel response improves the probe's anti-interference ability.•TZ-NBD showed fast response, good sensitivity, and near-infrared fluorescence signal.•TZ-NBD was successfully used for high-quality imaging of biothiols in living cancer cells and zebrafish. Biothiols play a crucial role in maintaining redox balance in organisms, and anomalous levels of biothiols in human organs can lead to various sicknesses and biological disorders. This work developed a novel sensitive fluorescent probe TZ-NBD with double channels for highly efficient recognition of biothiols. TZ-NBD adopts 4-Chloro-7-nitrobenzofurazan (NBD-Cl) as the recognition moiety with simultaneous fluorescence output. By incorporating NBD-Cl with the other fluorophore, benzothiazole dihydrocyclopentachromene derivative (TZ-OH), the dual-channel sensitive fluorescence probe TZ-NBD was built. The existence of Cys/ Hcy could significantly trigger both the green and red fluorescent emissions, which were derived from fluorophores amine-substituted NBD and TZ-OH, respectively. While exposing to GSH, only the red-channel fluorescence signal could be detected, indicating the release of TZ-OH. The phenomena was mainly attributed to the fact that sulfur-substituted NBD has nearly no fluorescence, while amine-substituted NBD shows obvious green fluorescence. In our study, TZ-NBD exhibited dual-channel sensitivity, fast response, and excellent selectivity to biothiols in vitro. Moreover, TZ-NBD was favorably utilized for recognition of biothiols in vivo. We believe that the sensitive fluorescence probe with double channels can afford an alternate approach for monitoring biothiols in organisms and would be useful for studying diseases associated with biothiols.
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Biothiols play a crucial role in maintaining redox balance in organisms, and anomalous levels of biothiols in human organs can lead to various sicknesses and biological disorders. This work developed a novel sensitive fluorescent probe TZ-NBD with double channels for highly efficient recognition of biothiols. TZ-NBD adopts 4-Chloro-7-nitrobenzofurazan (NBD-Cl) as the recognition moiety with simultaneous fluorescence output. By incorporating NBD-Cl with the other fluorophore, benzothiazole dihydrocyclopentachromene derivative (TZ-OH), the dual-channel sensitive fluorescence probe TZ-NBD was built. The existence of Cys/ Hcy could significantly trigger both the green and red fluorescent emissions, which were derived from fluorophores amine-substituted NBD and TZ-OH, respectively. While exposing to GSH, only the red-channel fluorescence signal could be detected, indicating the release of TZ-OH. The phenomena was mainly attributed to the fact that sulfur-substituted NBD has nearly no fluorescence, while amine-substituted NBD shows obvious green fluorescence. In our study, TZ-NBD exhibited dual-channel sensitivity, fast response, and excellent selectivity to biothiols in vitro. Moreover, TZ-NBD was favorably utilized for recognition of biothiols in vivo. 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Biothiols play a crucial role in maintaining redox balance in organisms, and anomalous levels of biothiols in human organs can lead to various sicknesses and biological disorders. This work developed a novel sensitive fluorescent probe TZ-NBD with double channels for highly efficient recognition of biothiols. TZ-NBD adopts 4-Chloro-7-nitrobenzofurazan (NBD-Cl) as the recognition moiety with simultaneous fluorescence output. By incorporating NBD-Cl with the other fluorophore, benzothiazole dihydrocyclopentachromene derivative (TZ-OH), the dual-channel sensitive fluorescence probe TZ-NBD was built. The existence of Cys/ Hcy could significantly trigger both the green and red fluorescent emissions, which were derived from fluorophores amine-substituted NBD and TZ-OH, respectively. While exposing to GSH, only the red-channel fluorescence signal could be detected, indicating the release of TZ-OH. The phenomena was mainly attributed to the fact that sulfur-substituted NBD has nearly no fluorescence, while amine-substituted NBD shows obvious green fluorescence. In our study, TZ-NBD exhibited dual-channel sensitivity, fast response, and excellent selectivity to biothiols in vitro. Moreover, TZ-NBD was favorably utilized for recognition of biothiols in vivo. We believe that the sensitive fluorescence probe with double channels can afford an alternate approach for monitoring biothiols in organisms and would be useful for studying diseases associated with biothiols.</description><subject>Amines</subject><subject>Bioimaging</subject><subject>Biothiols</subject><subject>Cysteine</subject><subject>Dual-channel sensitive</subject><subject>Fluorescent Dyes</subject><subject>Fluorescent probe</subject><subject>Glutathione</subject><subject>Homocysteine</subject><subject>Humans</subject><subject>Spectrometry, Fluorescence</subject><subject>Ultrasensitivity</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kD1PHDEQhq0oCC7AH0gRuUyzl_Ha6-xKNAiRDwkpDUh0lu0dsz75bLB3L-Lfx8cBZQprmud9x_MQ8pnBmgGT3zZrs7Vh3ULL16wdOsk_kBUTUjRcQPeRrGCQ0PSDuD8hn0rZADABQhyTE94D9JzLFXGXNKYdBlowFj_7HVIXlpSxWIwzfczJIP3r54mOaTEBqZ10jBgKdSnTyT9M4Zmic2hfshlteoi1J0WaHDU-zZNPoZyRI6dDwfPXeUruflzfXv1qbv78_H11edNY3sm5QRC8hcEiWDl0LSKA1qi7jnXCmhHHQQgNo-GS9V193wdnR9SmN63TFeen5Ouht378acEyq62vl4SgI6alqLba4LJuERVtD6jNqZSMTj1mv9X5WTFQe79qo_Z-1d6vOvitoS-v_YvZ4vgeeRNagYsDUBXhzmNWxXqMFkdf3cxqTP5__f8AGYuOUg</recordid><startdate>20240101</startdate><enddate>20240101</enddate><creator>Fei, Qiang</creator><creator>Shen, Keyi</creator><creator>Ke, Hongxiu</creator><creator>Wang, Erfei</creator><creator>Fan, Guorun</creator><creator>Wang, Feiyi</creator><creator>Ren, Jun</creator><general>Elsevier Ltd</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><orcidid>https://orcid.org/0000-0002-9825-0790</orcidid><orcidid>https://orcid.org/0000-0003-2936-5276</orcidid></search><sort><creationdate>20240101</creationdate><title>A novel sensitive fluorescent probe with double channels for highly effective recognition of biothiols</title><author>Fei, Qiang ; Shen, Keyi ; Ke, Hongxiu ; Wang, Erfei ; Fan, Guorun ; Wang, Feiyi ; Ren, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-e043209ce0c6952ee00aaea55154cbded944a0db3618561879fcdeab8b2fa2ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amines</topic><topic>Bioimaging</topic><topic>Biothiols</topic><topic>Cysteine</topic><topic>Dual-channel sensitive</topic><topic>Fluorescent Dyes</topic><topic>Fluorescent probe</topic><topic>Glutathione</topic><topic>Homocysteine</topic><topic>Humans</topic><topic>Spectrometry, Fluorescence</topic><topic>Ultrasensitivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fei, Qiang</creatorcontrib><creatorcontrib>Shen, Keyi</creatorcontrib><creatorcontrib>Ke, Hongxiu</creatorcontrib><creatorcontrib>Wang, Erfei</creatorcontrib><creatorcontrib>Fan, Guorun</creatorcontrib><creatorcontrib>Wang, Feiyi</creatorcontrib><creatorcontrib>Ren, Jun</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>Bioorganic &amp; medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fei, Qiang</au><au>Shen, Keyi</au><au>Ke, Hongxiu</au><au>Wang, Erfei</au><au>Fan, Guorun</au><au>Wang, Feiyi</au><au>Ren, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel sensitive fluorescent probe with double channels for highly effective recognition of biothiols</atitle><jtitle>Bioorganic &amp; medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2024-01-01</date><risdate>2024</risdate><volume>97</volume><spage>129563</spage><epage>129563</epage><pages>129563-129563</pages><artnum>129563</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted] •A sensitive fluorescence probe TZ-NBD for the recognition of biothiols with dual-channel was constructed.•Dual-channel response improves the probe's anti-interference ability.•TZ-NBD showed fast response, good sensitivity, and near-infrared fluorescence signal.•TZ-NBD was successfully used for high-quality imaging of biothiols in living cancer cells and zebrafish. 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The phenomena was mainly attributed to the fact that sulfur-substituted NBD has nearly no fluorescence, while amine-substituted NBD shows obvious green fluorescence. In our study, TZ-NBD exhibited dual-channel sensitivity, fast response, and excellent selectivity to biothiols in vitro. Moreover, TZ-NBD was favorably utilized for recognition of biothiols in vivo. We believe that the sensitive fluorescence probe with double channels can afford an alternate approach for monitoring biothiols in organisms and would be useful for studying diseases associated with biothiols.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>38008336</pmid><doi>10.1016/j.bmcl.2023.129563</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-9825-0790</orcidid><orcidid>https://orcid.org/0000-0003-2936-5276</orcidid></addata></record>
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subjects Amines
Bioimaging
Biothiols
Cysteine
Dual-channel sensitive
Fluorescent Dyes
Fluorescent probe
Glutathione
Homocysteine
Humans
Spectrometry, Fluorescence
Ultrasensitivity
title A novel sensitive fluorescent probe with double channels for highly effective recognition of biothiols
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