Steric Control in Activator-Induced Nucleophilic Quencher Detachment-Based Probes: High-Contrast Imaging of Aldehyde Dehydrogenase 1A1 in Cancer Stem Cells
Bibliographic Information
- Other Title
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- Steric Control in Activator‐Induced Nucleophilic Quencher Detachment‐Based Probes: High‐Contrast Imaging of Aldehyde Dehydrogenase 1A1 in Cancer Stem Cells
Description
Turn-on fluorescence probes can visualize the enzyme activity with high contrast. We have established a new turn-on mechanism, activator-induced nucleophilic quencher detachment (AiQd), and developed AiQd-based turn-on fluorescence probes for the detection of enzymes. Herein, we demonstrate that the precise steric control efficiently quenches the fluorescence of AiQd-based turn-on probes before the enzymatic transformation. Theoretical calculation appropriately predicted the ratio of the fluorescence-quenched closed-ring form of probes. βC5S-A, which has a sterically demanding methyl group at the β-position of a fluorescence-quenching nucleophilic mercapto group, showed a low background signal. βC5S-A responded to aldehyde dehydrogenase 1A1 (ALDH1A1) with high selectivity, thereby enabling high-contrast live imaging of cancer stem cells (signal-to-noise ratio >10). The ALDH1A1-responsiveness of βC5S-A was not significantly affected by amino acids and biological thiols, such as cysteine and glutathione.
Journal
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- ChemPlusChem
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ChemPlusChem 87 (11), 2022-11
Wiley
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Details 詳細情報について
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- CRID
- 1050013010132849792
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- HANDLE
- 2433/277808
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- ISSN
- 21926506
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- Text Lang
- en
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- Article Type
- journal article
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- Data Source
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- IRDB
- Crossref
- KAKEN