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An iminocoumarin based covalent-assembly red-emitting fluorescent probe for detection of β-galactosidase activity in ovarian cancer cells.

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Title: An iminocoumarin based covalent-assembly red-emitting fluorescent probe for detection of β-galactosidase activity in ovarian cancer cells.
Authors: Ku, Ya-Chu1,2 (AUTHOR), Lin, Pin-Han1,3 (AUTHOR), Huang, Chung-Yu3 (AUTHOR), Lee, Chia-Wei3 (AUTHOR), Yu, Chien-Hung1,2 (AUTHOR), Chen, Shih-Cheng1 (AUTHOR) z10903032@ncku.edu.tw, Liu, Wei-Min1,3 (AUTHOR) 133797@mail.fju.edu.tw
Source: Dyes & Pigments. Feb2023, Vol. 210, pN.PAG-N.PAG. 1p.
Subjects: Intramolecular proton transfer reactions, Ovarian cancer, Fluorescent probes, Stokes shift, Detection limit, Cancer cells
Abstract: Upregulation of β-Galactosidase (β-Gal) has been generally found in primary ovarian cancer cells, making the intra-cellular β-Gal as a valuable biomarker for related tumors. In this study, we synthesized an iminocoumarin based covalent-assembly probe, Gal–IC–2, which has been designed to be activated by β-Gal and then rapidly afford to a fluorescent chromophore via a covalent-assembly mechanism with red emission for specific and sensitive detection of β-Gal activity. Gal–IC–2 showed significant fluorescence enhancement and a large Stokes shift in the presence of recombinant β-Gal, and the detection limit of this probe was 1.97 × 10−2 UmL−1. Notably, Gal–IC–2 also exhibits great stability in a broad pH range and is capable of detecting the reactivity of β-Gal in ovarian cancer cells. This is the first report, to the best of our knowledge, describing a covalent-assembly red-emitting probe for the detection and imaging of β-Gal both in vitro and in ovarian cancer cells. The first example of red-emitting covalent-assembly fluorescent probe for β-galactosidase was designed and synthesized. This probe can detect the activity of β-galactosidase both in vitro and in ovarian cancer cells with fast and high fluorescent response. [Display omitted] • A self-covalent-assembly probe for detecting β-Gal is first reported here. • Gal–IC–2 is a red-emitting probe exhibiting great stability in a broad pH range. • In the presence of β-Gal, Gal–IC–2 shows significant fluorescence enhancement. • Gal–IC–2 can be applied to monitor endogenous β-Gal activity. [ABSTRACT FROM AUTHOR]
Copyright of Dyes & Pigments 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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DbLabel: Engineering Source
An: 161120960
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: An iminocoumarin based covalent-assembly red-emitting fluorescent probe for detection of β-galactosidase activity in ovarian cancer cells.
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  Data: <searchLink fieldCode="AR" term="%22Ku%2C+Ya-Chu%22">Ku, Ya-Chu</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Lin%2C+Pin-Han%22">Lin, Pin-Han</searchLink><relatesTo>1,3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Huang%2C+Chung-Yu%22">Huang, Chung-Yu</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Lee%2C+Chia-Wei%22">Lee, Chia-Wei</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yu%2C+Chien-Hung%22">Yu, Chien-Hung</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Chen%2C+Shih-Cheng%22">Chen, Shih-Cheng</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> z10903032@ncku.edu.tw</i><br /><searchLink fieldCode="AR" term="%22Liu%2C+Wei-Min%22">Liu, Wei-Min</searchLink><relatesTo>1,3</relatesTo> (AUTHOR)<i> 133797@mail.fju.edu.tw</i>
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  Data: <searchLink fieldCode="JN" term="%22Dyes+%26+Pigments%22">Dyes & Pigments</searchLink>. Feb2023, Vol. 210, pN.PAG-N.PAG. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Intramolecular+proton+transfer+reactions%22">Intramolecular proton transfer reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Ovarian+cancer%22">Ovarian cancer</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorescent+probes%22">Fluorescent probes</searchLink><br /><searchLink fieldCode="DE" term="%22Stokes+shift%22">Stokes shift</searchLink><br /><searchLink fieldCode="DE" term="%22Detection+limit%22">Detection limit</searchLink><br /><searchLink fieldCode="DE" term="%22Cancer+cells%22">Cancer cells</searchLink>
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  Label: Abstract
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  Data: Upregulation of β-Galactosidase (β-Gal) has been generally found in primary ovarian cancer cells, making the intra-cellular β-Gal as a valuable biomarker for related tumors. In this study, we synthesized an iminocoumarin based covalent-assembly probe, Gal–IC–2, which has been designed to be activated by β-Gal and then rapidly afford to a fluorescent chromophore via a covalent-assembly mechanism with red emission for specific and sensitive detection of β-Gal activity. Gal–IC–2 showed significant fluorescence enhancement and a large Stokes shift in the presence of recombinant β-Gal, and the detection limit of this probe was 1.97 × 10−2 UmL−1. Notably, Gal–IC–2 also exhibits great stability in a broad pH range and is capable of detecting the reactivity of β-Gal in ovarian cancer cells. This is the first report, to the best of our knowledge, describing a covalent-assembly red-emitting probe for the detection and imaging of β-Gal both in vitro and in ovarian cancer cells. The first example of red-emitting covalent-assembly fluorescent probe for β-galactosidase was designed and synthesized. This probe can detect the activity of β-galactosidase both in vitro and in ovarian cancer cells with fast and high fluorescent response. [Display omitted] • A self-covalent-assembly probe for detecting β-Gal is first reported here. • Gal–IC–2 is a red-emitting probe exhibiting great stability in a broad pH range. • In the presence of β-Gal, Gal–IC–2 shows significant fluorescence enhancement. • Gal–IC–2 can be applied to monitor endogenous β-Gal activity. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Dyes & Pigments 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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RecordInfo BibRecord:
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    Identifiers:
      – Type: doi
        Value: 10.1016/j.dyepig.2022.111004
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      – Code: eng
        Text: English
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        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Intramolecular proton transfer reactions
        Type: general
      – SubjectFull: Ovarian cancer
        Type: general
      – SubjectFull: Fluorescent probes
        Type: general
      – SubjectFull: Stokes shift
        Type: general
      – SubjectFull: Detection limit
        Type: general
      – SubjectFull: Cancer cells
        Type: general
    Titles:
      – TitleFull: An iminocoumarin based covalent-assembly red-emitting fluorescent probe for detection of β-galactosidase activity in ovarian cancer cells.
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            NameFull: Ku, Ya-Chu
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            NameFull: Lin, Pin-Han
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            NameFull: Huang, Chung-Yu
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            NameFull: Lee, Chia-Wei
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            NameFull: Yu, Chien-Hung
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            – D: 15
              M: 02
              Text: Feb2023
              Type: published
              Y: 2023
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              Value: 01437208
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              Value: 210
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