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A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation.

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Title: A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation.
Authors: Liu, Shi-Rong1, Chang, Chao-Yiu1, Wu, Shu-Pao1 spwu@faculty.nctu.edu.tw
Source: Analytica Chimica Acta. Nov2014, Vol. 849, p64-69. 6p.
Subjects: Fluorescence, Homocysteine, Thiols, Chemical synthesis, Ring formation (Chemistry), Macrophages
Abstract: We synthesized a new coumarin-based probe TP, containing a disulfide moiety, to detect biothiols in cells. A fluorescence turn-on response is induced by the thiol–disulfide exchange of the probe, with subsequent intramolecular benzothiazolidine ring formation giving rise to a fluorescent product. The probe exhibits an excellent selectivity for cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The fluorescent probe also exhibits a highly sensitive fluorescence turn-on response to Cys and Hcy with detection limits of 0.8 μM for Cys and 0.5 μM for Hcy. In addition, confocal fluorescence microscopy imaging using RAW264.7 macrophages demonstrates that the probe TP could be an efficient fluorescent detector for thiols in living cells. [ABSTRACT FROM AUTHOR]
Copyright of Analytica Chimica Acta is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 98806931
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation.
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  Data: <searchLink fieldCode="AR" term="%22Liu%2C+Shi-Rong%22">Liu, Shi-Rong</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Chang%2C+Chao-Yiu%22">Chang, Chao-Yiu</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Wu%2C+Shu-Pao%22">Wu, Shu-Pao</searchLink><relatesTo>1</relatesTo><i> spwu@faculty.nctu.edu.tw</i>
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  Data: <searchLink fieldCode="JN" term="%22Analytica+Chimica+Acta%22">Analytica Chimica Acta</searchLink>. Nov2014, Vol. 849, p64-69. 6p.
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  Data: <searchLink fieldCode="DE" term="%22Fluorescence%22">Fluorescence</searchLink><br /><searchLink fieldCode="DE" term="%22Homocysteine%22">Homocysteine</searchLink><br /><searchLink fieldCode="DE" term="%22Thiols%22">Thiols</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+synthesis%22">Chemical synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Macrophages%22">Macrophages</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: We synthesized a new coumarin-based probe TP, containing a disulfide moiety, to detect biothiols in cells. A fluorescence turn-on response is induced by the thiol–disulfide exchange of the probe, with subsequent intramolecular benzothiazolidine ring formation giving rise to a fluorescent product. The probe exhibits an excellent selectivity for cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The fluorescent probe also exhibits a highly sensitive fluorescence turn-on response to Cys and Hcy with detection limits of 0.8 μM for Cys and 0.5 μM for Hcy. In addition, confocal fluorescence microscopy imaging using RAW264.7 macrophages demonstrates that the probe TP could be an efficient fluorescent detector for thiols in living cells. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Analytica Chimica Acta is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.aca.2014.08.024
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      – Code: eng
        Text: English
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        PageCount: 6
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    Subjects:
      – SubjectFull: Fluorescence
        Type: general
      – SubjectFull: Homocysteine
        Type: general
      – SubjectFull: Thiols
        Type: general
      – SubjectFull: Chemical synthesis
        Type: general
      – SubjectFull: Ring formation (Chemistry)
        Type: general
      – SubjectFull: Macrophages
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      – TitleFull: A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation.
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            – D: 07
              M: 11
              Text: Nov2014
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              Y: 2014
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