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Conventional electrophilic leaving groups (quinone methides and aldehydes) deplete intracellular nucleophiles (cysteine or glutathione), thereby inducing oxidative stress and disrupting redox homeostasis. Herein, a series of near-infrared (NIR) ratiometric fluorescent probes (Cy667, Cy701, and Cy777) have been rationally designed that integrate a polarity-reversing nucleophilic self-immolative linker, a specific AChE recognition unit, and an ammonium-assisted AChE-targeting moiety. The well-regulated self-immolative nucleophilic cleavage completely eliminates undesired side reactions and electrophilic byproduct interference while maintaining intracellular redox homeostasis without exhausting glutathione (GSH). The optimal probe, Cy701, exhibits exceptional selectivity (&amp;gt;100-fold over other hydrolases) and sensitivity (LOD = 4.9 mU\/mL) toward AChE, enabling a ratiometric signal log(F636\/F832) in the NIR region. Molecular docking calculations verify that Cy701 has an excellent binding affinity for AChE, which enables real-time visualization of endogenous AChE in PC12 and HepG2 cells. Notably, Cy701 displays superior blood\u2013brain barrier (BBB) permeability and favorable intracellular retention. It has been robustly implemented for in vivo NIR ratiometric imaging of AChE dynamics in acute and chronic epileptic mouse models, unambiguously discriminating pathological states from healthy conditions with a signal-to-background ratio (SBR) of 10.0 (P &amp;lt; 0.001). This work constitutes a universal design paradigm for high-fidelity, nonperturbative enzyme-activatable fluorescent probes and offers a robust scaffold for accurate AChE monitoring and in-depth neurobiological dissection of epilepsy.<\/jats:p>","DOI":"10.1021\/acs.analchem.6c04296","type":"journal-article","created":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T16:01:39Z","timestamp":1788796899000},"page":"27103-27113","source":"Crossref","is-referenced-by-count":0,"title":["Electrophile-Free,\nSelf-Immolative Linker-Enabled\nNear-Infrared Ratiometric Fluorescent Probe for High-Fidelity, Nonperturbative\nImaging of Acetylcholinesterase (AChE) Dynamics in Epileptic Mice"],"prefix":"10.1021","volume":"98","author":[{"given":"Jiangkun","family":"Tan","sequence":"first","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]},{"name":"Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences , , , ,","place":["Yantai, Shandong, China, 264003"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuerui","family":"Kong","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huijin","family":"Feng","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuxin","family":"Yin","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoling","family":"Yang","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ziyan","family":"Sun","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1499-8759","authenticated-orcid":true,"given":"Zan","family":"Li","sequence":"additional","affiliation":[{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3764-3515","authenticated-orcid":true,"given":"Lingxin","family":"Chen","sequence":"additional","affiliation":[{"name":"Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences , , , ,","place":["Yantai, Shandong, China, 264003"]},{"name":"Shaoxing University , , ,","place":["Shaoxing, China, 312000"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5210-996X","authenticated-orcid":true,"given":"Binghuan","family":"Huang","sequence":"additional","affiliation":[{"name":"Jining Medical University , , , ,","place":["Jining, Shandong, China, 272002"]},{"name":"Qufu Normal University , , , ,","place":["Qufu, Shandong, P. R. China, 273165"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,7]]},"reference":[{"issue":"12","key":"2026091511070379600_cit1","doi-asserted-by":"publisher","first-page":"103678","DOI":"10.1016\/j.autrev.2024.103678","article-title":"Neuroimmune communication of the\ncholinergic system in gut inflammation and autoimmunity","volume":"23","author":"Halder","year":"2024","journal-title":"Autoimmun. 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Anal."},{"key":"2026091511070379600_cit18","doi-asserted-by":"publisher","first-page":"4874","DOI":"10.1021\/ja0171299","article-title":"Design and\nSynthesis of Chemiluminescent Probes for the Detection of Cholinesterase\nActivity","volume":"124","author":"Sabelle","year":"2002","journal-title":"J. Am. Chem. Soc."},{"issue":"10","key":"2026091511070379600_cit19","doi-asserted-by":"publisher","first-page":"4231","DOI":"10.1016\/j.bios.2011.03.037","article-title":"Oxidative desorption\nof thiocholine assembled on core\u2013shell Fe3O4\/AuNPs magnetic\nnanocomposites for highly sensitive determination of acetylcholinesterase\nactivity: An exposure biomarker of organophosphates","volume":"26","author":"Du","year":"2011","journal-title":"Biosens. 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Mater."},{"key":"2026091511070379600_cit35","doi-asserted-by":"publisher","first-page":"117935","DOI":"10.1016\/j.bios.2025.117935","article-title":"An enhanced\nbioluminescent probe for in vivo imaging of drug-induced apoptosis\nvia acetylcholinesterase targeting","volume":"289","author":"Sun","year":"2025","journal-title":"Biosens.\nBioelectron."},{"issue":"6\u20137","key":"2026091511070379600_cit36","doi-asserted-by":"publisher","first-page":"859","DOI":"10.1002\/adsc.200303005","article-title":"Fluorogenic\nCyanohydrin Esters as\nChiral Probes for Esterase and Lipase Activity","volume":"345","author":"Leroy","year":"2003","journal-title":"Adv. Synth. Catal."},{"issue":"3","key":"2026091511070379600_cit37","doi-asserted-by":"publisher","first-page":"521","DOI":"10.1039\/C0SC00466A","article-title":"Synthesis\nand utility of fluorogenic\nacetoxymethyl ethers","volume":"2","author":"Lavis","year":"2011","journal-title":"Chem. 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Funct. Mater."},{"key":"2026091511070379600_cit42","doi-asserted-by":"publisher","first-page":"142650","DOI":"10.1016\/j.ijbiomac.2025.142650","article-title":"A dual-function hyaluronic\nacid-encapsulated\nnanoplatform enables triple GSH depletion for apoptosis-ferroptosis\nsynergistic oncotherapy","volume":"308","author":"Wang","year":"2025","journal-title":"Int. J. Biol. Macromol."},{"key":"2026091511070379600_cit43","doi-asserted-by":"publisher","first-page":"373","DOI":"10.1021\/ac048611n","article-title":"A High-Throughput,\nLow-Volume Enzyme Assay onSolid\nSupport","volume":"77","author":"Babiak","year":"2005","journal-title":"Anal. Chem."},{"issue":"27","key":"2026091511070379600_cit44","doi-asserted-by":"publisher","first-page":"9645","DOI":"10.1002\/chem.201501127","article-title":"A New Strategy for Fluorogenic Esterase\nProbes Displaying Low Levels of Non-specific Hydrolysis","volume":"21","author":"Kim","year":"2015","journal-title":"Chem. -Eur. J."},{"issue":"25","key":"2026091511070379600_cit45","doi-asserted-by":"publisher","first-page":"5014","DOI":"10.1021\/bi300477z","article-title":"Reduction of Benzoquinones\nto Hydroquinones via Spontaneous Reaction with Glutathione and Enzymatic\nReaction by S-Glutathionyl-Hydroquinone Reductases","volume":"51","author":"Lam","year":"2012","journal-title":"Biochemistry"},{"issue":"44","key":"2026091511070379600_cit46","doi-asserted-by":"publisher","first-page":"2303195","DOI":"10.1002\/adfm.202303195","article-title":"Hijacking Endogenous\nIron and GSH Via a Polyvalent Ferroptosis Agonist to Enhance Tumor\nImmunotherapy","volume":"33","author":"Li","year":"2023","journal-title":"Adv. Funct. 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