Construction of a Novel Near-Infrared Dual-Mode Probe Based on Quinoline for HSO3- and Its Imaging Applications

doi:10.6023/A26040114

Abstract

SO₂is an important gaseous signaling molecule in living organisms, and its abnormal concentration is closely associated with various physiological and pathological processes, including respiratory and central nervous system diseases. SO₂ exists mainly as HSO₃⁻ in aqueous solution, making the development of highly specific and high-contrast detection methods for HSO₃⁻ crucial for studying the physiological functions of SO₂and the early diagnosis of related diseases. In this study, a quinoline-based near-infrared fluorescent probe, QS-EC, with an A-π-A structure was designed and synthesized. The probe initially exists in a fluorescent "dark state." Upon specific 1,4-nucleophilic addition with HSO₃⁻, its structure transforms into a D-π-A configuration, restoring the intramolecular charge transfer (ICT) effect and resulting in a dual-mode response of solution color deepening and fluorescence turn-on. The optical performance of QS-EC was systematically evaluated using UV-Vis and fluorescence spectroscopy. Spectroscopic results showed that the QS-EC responded to HSO₃⁻ within 3 s, with a detection limit of 14.69 nmol/L, and remains stable within a pH range of 6~13. Competitive experiments demonstrated that QS-EC exhibits high selectivity for HSO₃⁻ without interference from other anions or biothiols. It is worth emphasizing that QS-EC enables efficient detection of HSO₃⁻, which not only simplifies the detection process but also significantly enhances the probe's practicality and biocompatibility. Furthermore, MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetra- zolium bromide) assays were used to evaluate its biocompatibility, revealing that cell viability remained above 80% after incubation with 0~20 μmol/L of QS-EC for 24 h, confirming its low cytotoxicity. For cellular imaging, QS-EC successfully enabled dynamic monitoring of both exogenous and endogenous HSO₃⁻ in live cells. Further in vivo imaging experiments in zebrafish model showed a high signal-to-noise ratio red fluorescence turn-on signal, with fluorescence intensity increasing as the HSO₃⁻ concentration rose. This indicates that QS-EC is capable of visually tracking HSO₃⁻ distribution in complex living environments. Through systematic evaluation from molecular design and spectral performance to cellular and in vivo applications, this study fully demonstrates the potential of QS-EC for early diagnosis research in SO₂-related diseases.

Key words: sulfur dioxide, fluorescent probe, dual-mode, intramolecular charge transfer, cellular imaging

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Mingyu Tian, Lingying Meng, Keli Zhong, Lijun Tang, Fengling Song. Construction of a Novel Near-Infrared Dual-Mode Probe Based on Quinoline for HSO₃^- and Its Imaging Applications[J]. Acta Chimica Sinica, 2026, 84(9): 1435-1441.

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Fig. & Tab. 7

Figure 1. Synthetic route of QS-EC

Figure 2. (a) UV-Vis absorption spectra of different concentrations of HSO3⁻ (0~40 μmol/L) added to the aqueous solution of QS-EC; (b) fluorescence spectra of different concentrations of HSO3⁻ (0~40 μmol/L) added to the aqueous solution of QS-EC; and (c) linearity of fluorescence intensity at 660 nm versus HSO₃⁻ concentration

Figure 3. (a) UV-Vis absorption spectra of QS-EC reacting with different analytes; (b) fluorescence selectivity experiments of QS-EC reacting with different analytes and competition experiments of QS-EC adding HSO3⁻ in the presence of different analytes

Figure 4. (a) Effect of pH on fluorescence intensity of the QS-EC reaction system with HSO3⁻; (b) Video screenshots of the solution color change of QS-EC upon addition of HSO3⁻; (c) Photostability curve

Figure 5. The sensing mechanism of QS-EC to HSO3⁻

Figure 6. (a) Cell viability of MCF-7 cells after co-incubation with different concentrations of QS-EC (1, 5, 10, 15, 20 μmol/L). (b) Fluorescence images of exogenous HSO3⁻ (5, 10, 30 μmol/L) in MCF-7 cells. (c) Fluorescence imaging of endogenous HSO3⁻ in MCF-7 cells

Figure 7. Fluorescence imaging (a) and fluorescence intensity (b) of zebrafish pretreated with QS-EC (10 μmol/L) and co-incubated with different concentrations of HSO3⁻ (0, 10, 30, 50 μmol/L)

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新型喹啉基近红外HSO₃^-双模式探针的构建及生物成像

Construction of a Novel Near-Infrared Dual-Mode Probe Based on Quinoline for HSO₃^- and Its Imaging Applications

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新型喹啉基近红外HSO3-双模式探针的构建及生物成像