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<p>Dual-responsive fluorescent probes capable of discriminatively monitoring amino acids and thiols remain challenging yet critical for deciphering pathophysiological processes. We have developed a dual-site responsive monobrominated 2-[<i>O-</i>(<i>1-ethyloxyamide</i>)] oxime-4-bromophenol (BrHS) probe, which demonstrates bidirectional fluorescence responses. Specifically, arginine (Arg) induces a 2.2-fold increase in fluorescence intensity with a detection limit of 246 pM through proton-transfer complexation. In contrast, glutathione (GSH) triggers selective fluorescence quenching with a detection limit of 372 pM via γ-glutamyl-specific hydrogen bonding (O···H–N) and nucleophilic aromatic substitution (SNAr). Real-time cellular imaging conducted in MCF-7 cells enables dynamic monitoring of GSH levels, with observations of dose-dependent fluorescence quenching. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations reveal that glutathione (GSH) exhibits a substantial thermodynamic advantage. Specifically, the Gibbs free energy change (ΔG) of GSH is − 201.75&#xa0;kJ/mol, indicating it is approximately 14.9 times more reactive than cysteine (Cys). These findings are corroborated by Mayer bond order analysis and electrostatic potential (ESP) charge distribution data. The probe exhibits a wide pH response range and rapid response times (&lt; 10&#xa0;s for Arg, &lt; 60&#xa0;s for GSH), enabling effective detection in complex real-world samples. This semi-system, akin to Salamo, presents a novel methodology for dual analyte tracking and detection with atomic-scale specificity, thereby offering transformative potential for the diagnosis of oxidative stress.</p>

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Dual-site responsive semi-salamo fluorescence probe with different binding energies for detection of arginine and glutathione

  • 期刊论文

  • 发表日期：

    2026年5月25日

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  • Wenting Guo,
  • Rui Yang,
  • Yunzhao He,
  • Dongzhen Bai,
  • Yan Ma,
  • Tongxin Ji,
  • Wenkui Dong

摘要

Dual-responsive fluorescent probes capable of discriminatively monitoring amino acids and thiols remain challenging yet critical for deciphering pathophysiological processes. We have developed a dual-site responsive monobrominated 2-[O-(1-ethyloxyamide)] oxime-4-bromophenol (BrHS) probe, which demonstrates bidirectional fluorescence responses. Specifically, arginine (Arg) induces a 2.2-fold increase in fluorescence intensity with a detection limit of 246 pM through proton-transfer complexation. In contrast, glutathione (GSH) triggers selective fluorescence quenching with a detection limit of 372 pM via γ-glutamyl-specific hydrogen bonding (O···H–N) and nucleophilic aromatic substitution (SNAr). Real-time cellular imaging conducted in MCF-7 cells enables dynamic monitoring of GSH levels, with observations of dose-dependent fluorescence quenching. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations reveal that glutathione (GSH) exhibits a substantial thermodynamic advantage. Specifically, the Gibbs free energy change (ΔG) of GSH is − 201.75 kJ/mol, indicating it is approximately 14.9 times more reactive than cysteine (Cys). These findings are corroborated by Mayer bond order analysis and electrostatic potential (ESP) charge distribution data. The probe exhibits a wide pH response range and rapid response times (< 10 s for Arg, < 60 s for GSH), enabling effective detection in complex real-world samples. This semi-system, akin to Salamo, presents a novel methodology for dual analyte tracking and detection with atomic-scale specificity, thereby offering transformative potential for the diagnosis of oxidative stress.