Citation: Haixian Ren, Yuting Du, Xiaojing Yang, Fangjun Huo, Le Zhang, Caixia Yin. Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl[J]. Chinese Chemical Letters, ;2025, 36(2): 109867. doi: 10.1016/j.cclet.2024.109867 shu

Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl

Haixian Ren ^a ,
Yuting Du ^a ,
Xiaojing Yang ^a ,
Fangjun Huo ^c ,
Le Zhang ^d ,
Caixia Yin ^{a, b, *,}

a.
Department of Chemistry, Xinzhou Normal University, Xinzhou 034000, China
b.
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China
c.
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China
d.
Department of Chemistry, The University of Texas at Austin, Austin, TX 78712, United States

yincx@sxu.edu.cn

Received Date: 15 February 2024
Revised Date: 2 April 2024
Accepted Date: 7 April 2024
Available Online: 8 April 2024

Figures(26)

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence probes are particularly attractive due to their unique properties including environmental sensitivity, a large Stokes shift, and potential for ratiometric sensing. In general, ESIPT-based fluorophore incorporates an intramolecular hydrogen bonding interaction between a hydrogen bond donor (–OH and NH₂ are common) and a hydrogen bond acceptor (C=N and C=O). More, protection–deprotection of hydroxyl group as hydrogen bond donor could induce an off-on switch of ESIPT-based emission. Therefore, protection–deprotection of hydroxyl group has been the widely used strategy to design fluorescent probes, where the potential key issue is selecting a protective group that can specifically leave in the presence of the target analyte. In this review, we mainly summarize the specific protecting groups (sites) and deprotection mechanisms for biologically important species (including reactive sulfur species (RSS), reactive oxygen species (ROS), enzymes, etc.), and analyze the advantages and disadvantages of different protection mechanisms from some aspects including probe stability, selectivity, response rate and assay system, etc. Based on the aforementioned, we further point out the current challenges and the potential future direction for developing ESIPT-based probes.
- ESIPT,
- Protection-deprotection,
- Specificity,
- Fluorescence probe,
- Bioimaging
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