Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging★

doi:10.6023/A25050200

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (10): 1252-1266.DOI: 10.6023/A25050200 Previous Articles Next Articles

Review

用于神经递质检测与生物成像的有机小分子荧光探针^★

孟倩^a, 张琪伟^a^,^b^,^*()

^a 华东师范大学化学与分子工程学院上海市绿色化学与化工过程绿色化重点实验室上海 200241
^b 华东师范大学医学磁共振与分子影像技术研究院上海 200241

投稿日期:2025-05-31 发布日期:2025-08-12
通讯作者: 张琪伟

作者简介:

孟倩, 2024年毕业于阜阳师范大学, 获硕士学位. 现为华东师范大学博士研究生, 导师为张琪伟教授. 主要从事有机发光材料的设计合成及其分析与成像应用研究.

张琪伟, 华东师范大学化学与分子工程学院教授、博士生导师, 国家自然科学基金优秀青年科学基金获得者. 2005~2014年在华东理工大学获得学士与博士学位, 师从田禾院士. 2014~2018年, 先后在荷兰奈梅亨大学(Radboud University, 合作导师Roeland J.M. Nolte院士)和美国圣母大学(University of Notre Dame, 合作导师Bradley D. Smith教授)从事博士后研究. 2018年回国入职华东师范大学, 主要从事有机光功能材料、荧光传感与生物成像和光学诊疗等领域的研究.

^★ “中国青年化学家”专辑.

基金资助:
国家自然科学基金(22322405); 国家自然科学基金(22274055); 上海市基础研究特区计划(TQ20240206)

Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging^★

Qian Meng^a, Qiwei Zhang^a^,^b^,^*()

^a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241
^b Institute of Magnetic Resonance and Molecular Imaging in Medicine, East China Normal University, Shanghai 200241

Received:2025-05-31 Published:2025-08-12
Contact: Qiwei Zhang
About author:
^★ For the VSI “Rising Stars in Chemistry”.
Supported by:
National Natural Science Foundation of China(22322405); National Natural Science Foundation of China(22274055); Shanghai Pilot Program for Basic Research(TQ20240206)

Neurotransmitters are essential mediators of neuronal communication, governing neural circuit plasticity and maintaining cerebral functional homeostasis. They can be classified into major categories including monoamines, amino acids, acetylcholine, neuropeptides, purines, gaseous neurotransmitters, etc. Deciphering the dynamic fluctuations in neurotransmitter concentrations and distributions is paramount for elucidating fundamental neurophysiological processes and unraveling the mechanisms underpinning neuropathological conditions, such as Alzheimer's disease, Parkinson's disease, depression, etc. Fluorescence imaging technique employs specific probes that transduce the biochemical event of neurotransmitter recognition into a quantifiable optical signal, enabling non-invasive, highly specific visualization with high spatiotemporal resolution in live systems, representing an exceptionally promising class of tools for neurotransmitter detection. Owing to the compact size, excellent structural stability, high biocompatibility, tunable photophysical properties, and designable recognition mechanisms, organic small-molecule fluorescent probes act as ideal candidates for sensitive and selective neurochemical imaging. This review examines the advancements in the development and application of organic fluorescent probes for neurotransmitter detection, focusing on molecular designs, recognition principles (covalent or non-covalent interactions), signal transduction mechanisms (e.g., photoinduced electron transfer, intramolecular charge transfer, fluorescence resonance energy transfer), analytical performance, and their imaging capabilities in live cells, tissues, and in vivo models. A dedicated section provides a critical analysis of the prevailing limitations hindering broader application of current organic small-molecule fluorescent probes, such as challenges with reversibility, slow response times, photobleaching, limited multiplexing capability, insufficient blood-brain barrier penetration, and depth limitations in in vivo imaging. Building upon this assessment, we offer forward-looking perspectives on the future trajectory of fluorescent probe development. Key focus areas include engineering probes with enhanced binding kinetics and reversibility for real-time monitoring, superior photostability for longitudinal studies, capabilities for multiplexed analysis, ideal excitation/emission properties for deeper tissue penetration, and improved pharmacokinetic properties for efficient BBB crossing. This review aims to provide strategic design insights and a developmental roadmap for the next generation of high-performance neurochemical probes, thereby advancing fundamental neuroscience research and clinical diagnostic technologies.

Key words: fluorescent probes, neurotransmitters, organic small molecules, supermolecules, bioimaging

Cite this article

Qian Meng, Qiwei Zhang. Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging^★[J]. Acta Chimica Sinica, 2025, 83(10): 1252-1266.

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Fig. & Tab. 13

Figure 1. The neurotransmitter structures involved in the review

Figure 2. (a) Chemical structure of probes 1~3 and schematic diagram of the detection mechanism of probe 1 toward DA; schematic diagram of the mechanism of probes 4 (b), (c) 5 and (d) PBA-CA for the recognition of DA

Figure 3. (a) Schematic diagram of the detection mechanism of probe 6 toward NE, and chemical structures of probes 6~8; (b) stain mixed chromaffin cells rich in norepinephrine and adrenaline with probe 6 and PNMT antibody (cells circled in green indicate NE-enriched cells, and cells circled in red indicate EP-enriched cells)[61], Copyright 2013, American Chemical Society

Figure 4. (a) Cascade nucleophilic substitution mechanism for probe detection of norepinephrine; (b) chemical structures of probes 9~12; (c) the "hunting-shooting" strategy for probe detection of norepinephrine; (d) changes in mice brain fluorescence (ⅰ) monitored after the injection of probe 12 via the tail vein, (ⅱ) before (left) and after (right) epileptic injection of probe 12 via tail vein, (ⅲ) fluorescence intensity of the mice brains with and without epileptic seizure by anatomical experiment[68], Copyright 2023, American Chemical Society

Figure 5. (a) Schematic diagram of the ultrafast sensing mechanism of probe BPS3 for norepinephrine through dual acceleration of conformational folding and water bridging[69]; (b) schematic diagram of the detection mechanism of probe BPS3 toward NE[69]; (c) schematic of molecular conformational regulations by covalent or supramolecular approaches[69]; (d) normalized fluorescence response dynamics of aqueous solution of BPS2, BPS3, BPS4, and BPS3＋CB[7], Inset: enlarged view of the partial curve for the response of BPS3 and BPS4 toward NE[69], reproduced under a CC BY license

Figure 6. (a) Chemical structures of probe 13 and its sensing schematic diagram[70]; (b) Reaction kinetics of probe 13a in acetonitrile-water mixed solvents with different water contents[70]; (c) Calculate the relative energy of possible reaction coordinates during the nucleophilic substitution process between probes 13a~13d and NE[70]; (d) Fluorescence images of tissue sections from four brain regions, in vivo imaging, and corresponding fluorescence change histograms of probe 13a in normal mice, Parkinson's disease (PD) model mice, and PD model mice treated with N-acetylcysteine (NAC) [70]. Copyright 2023, American Chemical Society

Figure 7. (a) Chemical structure of probe 14 and optimized supramolecular probe; (b) fluorescence images of brain tissue slices from S1BF, CA1, LD, and CPU regions incubated with probe 14 after electrical stimulation[88], Copyright 2025, American Chemical Society

Figure 8. (a) Chemical structure of probe 15 and schematic diagram of the detection mechanism toward EP; (b) chemical structure of probe 16 and its detection mechanism for EP[91]; (c) quantized maps of fluorescence signals in 26 different brain regions[91], reproduced under a CC BY license

Figure 9. (a) Schematic diagram of the chemical structure of probe 17 and its detection mechanism for 5-HT; (b) Schematic diagram of the detection mechanism of probe 18 for 5-HT

Figure 10. Chemical structures of probes 19 (a) and 20 (b), and schematic diagram of the detection mechanism toward HA

Figure 11. (a) Chemical structure of hemicryptophane 1 (HC 1); (b) chemical structure of probe 21

Figure 12. (a) Schematic diagram of the detection mechanism of probe 22 for glutamate and aspartic acid and its imaging of Asp/Glu in HeLa cells[113], Copyright 2012, American Chemical Society; (b) chemical structures of probe 23 and schematic diagram of the detection mechanism toward Glu and Asp

Figure 13. (a~c) Chemical structures of probes 24~26 and schematic diagram of the detection mechanism toward Glu, Asp and pH

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用于神经递质检测与生物成像的有机小分子荧光探针^★

Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging^★

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用于神经递质检测与生物成像的有机小分子荧光探针★

Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging★

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Abstract

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Fig. & Tab. 13

References 122

Related Articles 9

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用于神经递质检测与生物成像的有机小分子荧光探针^★

Organic Small-Molecule Fluorescent Probes for Neurotransmitter Sensing and Bioimaging^★