A lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA, its preparation method and application

Abstract

This invention discloses a lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA, its preparation method, and its applications, belonging to the field of luminescent materials technology. The fluorescent dye MG-RhA uses Rhodamine B as a backbone, modifying the traditional Rhodamine B into a dye with aggregation-induced emission properties. The fluorescent dye provided by this invention has a novel structure and can effectively target lysosomes under acidic conditions. It can be used for wash-free staining of live cells and has a better signal-to-noise ratio than commercially available lysosome-targeting dyes. It has broad application prospects in the fields of biological staining agents, cell staining imaging, and organic semiconductor materials.

Description

Technical Field

[0001] This invention belongs to the field of luminescent materials technology, specifically relating to a lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA, its preparation method, and its application. Background Technology

[0002] Aggregation-induced emission (AIE) was first proposed by Academician Tang Benzhong in 2001. Due to the unique and highly efficient luminescence properties of AIE molecules (AIEgens) in their aggregated state, it has attracted widespread attention from peers both domestically and internationally. Currently, hundreds of research groups in dozens of countries are conducting research on AIE, achieving significant results in the development of new AIE molecules, AIE mechanisms, and the application of AIE materials in optoelectronic devices, biological probes and imaging, chemical sensing, and smart materials. AIE has become a research hotspot in luminescent materials and photophysics, and was listed as the second of the top 10 research frontiers in chemistry in the "2015 Research Frontiers" report jointly released by the Documentation and Information Center of the Chinese Academy of Sciences and Thomson Reuters. Furthermore, in 2016, Nature's NewsFeature column featured AIE materials under the title "The nanolight revolution is coming," highlighting that the discovery of AIE materials provides a solution to the problems existing in currently used quantum dots and luminescent polymer dots, representing a new generation of nanoluminescent materials.

[0003] Fluorescence bioimaging, as a powerful non-invasive imaging technique, has unique advantages in biological applications. In particular, the development and application of super-resolution microscopy have made significant progress in recent years, but it has been limited by the brightness and stability of fluorescent dyes. Compared to traditional optical imaging, super-resolution fluorescence imaging is based on a larger-scale photon statistical data set. To further improve imaging resolution and quality, researchers aim to design fluorescent dyes with higher brightness and better photostability. As a major class of fluorescent chromophores, small organic molecule fluorescent chromophore compounds have also seen significant development. Benefiting from their simple synthesis, ease of modification, and low toxicity, the development and application of small organic molecule fluorescent probes have attracted particular attention. Developing aggregation-induced emission (AIE) properties with long-wavelength emission and low phototoxicity, acid-responsive AIEgens (molecules with AIE properties) has always been a goal, but the path forward remains extremely challenging.

[0004] While rhodamine dyes are widely used in super-resolution imaging, their fluorescence brightness is typically affected by the nonradiative transition process of intramolecular torsional charge transfer (TICT) after excitation, thus their imaging potential has not been fully realized. Traditional rhodamine dyes have poor biocompatibility and complex synthetic routes; more importantly, most existing rhodamine skeletal dyes are aggregation-induced quenching (ACQ) dyes. This invention aims to modify traditional rhodamine into a dye with aggregation-induced emission (AIE) properties through rational molecular design. Summary of the Invention

[0005] To address the shortcomings of existing technologies, this invention aims to provide a lysosome-targeted acid-responsive aggregation-induced emission (AIE) fluorescent dye MG-RhA, its preparation method, and its applications.

[0006] To achieve the above objectives, the technical solution of the present invention is implemented as follows:

[0007] A lysosome-targeted acid-responsive aggregation-induced luminescent fluorescent dye, MG-RhA, has the structural formula shown in Formula I:

[0008]

[0009] This invention also provides a method for preparing the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA, comprising the following steps:

[0010] (1) Preparation of MG-B:

[0011] 4-Bromobenzaldehyde, anhydrous zinc chloride, N,N-dimethylaniline, and anhydrous ethanol were mixed in a molar ratio of 0.1:0.2:0.3 and stirred overnight at 100°C. After cooling, the mixture was concentrated to remove the remaining N,N-dimethylaniline. The mixture was then extracted with water and ethyl acrylate. The combined organic phases were dried and purified by silica gel column chromatography to obtain a white MG-Br powder. MG-Br, pinaborate, and potassium acetate were then dissolved in N,N-dimethylformamide. [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride, which was dissolved in N,N-dimethylformamide, was added as a catalyst for the Suzuki coupling reaction. The mixture was stirred at 80°C for 12 h and then cooled. The mixture was extracted with dichloromethane and water. The organic phase was collected, dried, concentrated, purified by silica gel column chromatography, and dried to obtain a white MG-B solid.

[0012] (2) Preparation of Br-Rho-COOH:

[0013] 52.8 mmol N,N-diethylaminophenol, 21.1 mmol 4-bromophthalic anhydride, 90 mL propionic acid and 0.5 mL methanesulfonic acid were mixed and refluxed. The resulting dark crude product was dissolved in dichloromethane, extracted with saturated brine, the organic phase was collected and concentrated, purified by silica gel column chromatography, and the isomers were separated by repeated silica gel chromatography with methanol / dichloromethane gradient. After drying, a dark purple Br-Rho-COOH solid was obtained.

[0014] (3) Preparation of MG-Rho-COOH:

[0015] A mixture of potassium carbonate, MG-B, and Br-Rho-COOH was added to N,N-dimethylformamide. Tetra(triphenylphosphine)palladium was added under nitrogen protection, and the mixture was refluxed. The mixture was extracted with dichloromethane, washed with saturated sodium chloride solution, and the combined organic phases were dried, concentrated, and purified by silica gel column chromatography. The first crude product was then dissolved in dichloromethane, and tetrachloro-p-benzoquinone was added. The mixture was stirred at room temperature in a one-pot manner. The resulting second crude product was purified by silica gel column chromatography to obtain a dark green MG-Rho-COOH solid.

[0016] (4) Preparation of MG-RhA:

[0017] Hydrazine hydrate and MG-Rho-COOH were dissolved separately in methanol solution and then mixed to obtain a mixture. The mixture was heated under reflux to carry out the reaction. After the reaction was completed, the mixture was cooled, extracted, and the organic phase was collected, dried, and concentrated by rotary evaporation to obtain the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the dark green fluorescent dye MG-RhA solid.

[0018] Preferably, in step (1), the molar ratio of MG-Br, pinaborate, potassium acetate and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride is 0.1:0.3:0.125:0.012.

[0019] Preferably, in step (2), the reflux temperature is 120-150℃ and the reflux time is 10-25h.

[0020] Preferably, in step (3), the molar ratio of potassium carbonate, MG-B, Br-Rho-COOH, tetra(triphenylphosphine)palladium, and tetrachloro-p-benzoquinone is (10:0.12:0.1:0.008:0.15)-(20:0.24:0.2:0.016:0.3).

[0021] Preferably, in step (3), the reflux temperature is 100-120℃ and the reflux time is 10-12h.

[0022] Preferably, in step (4), the molar ratio of hydrazine hydrate to MG-Rho-COOH is (10:1)-(20:1).

[0023] Preferably, in step (4), the reflux temperature is 50℃-70℃ and the reflux time is 3h-12h.

[0024] Preferably, in step (4), the extraction process includes: first adding saturated saline solution and 0.1M NaOH in a volume ratio of 1:1 to the mixture after the reaction, and then adding dichloromethane for extraction.

[0025] This invention also provides the application of the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA or the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA prepared by the method as a fluorescent probe in intelligent sensing, functional imaging, biological detection, and immunotherapy.

[0026] Compared with the prior art, the advantages of the present invention are as follows:

[0027] (1) The MG-RhA synthesized by this invention is a new structure and has a very broad application prospect as a novel AIE dye.

[0028] (2) This invention successfully developed an organic small molecule acid-responsive probe MG-RhA based on the rhodamine backbone with aggregation-induced emission (AIE) properties. It is targeted and specific, reduces the number of reaction steps and byproducts, and is easy to purify. It transforms the traditional rhodamine B into a dye with aggregation-induced emission properties. Thanks to the two quaternary ammonium salt groups of the molecule, the complete acid response of the molecule enables it to be successfully applied to ultrafast wash-free low phototoxicity imaging of live cells, which will greatly help biological research related to live cells.

[0029] (3) The fluorescent dye provided by the present invention can be used for washless staining of live cells and has a better signal-to-noise ratio than commercial lysosome-targeting dyes. Furthermore, the dye has a novel structure and can effectively target lysosomes under acidic conditions, and has broad application prospects in fields such as biological staining agents, cell staining imaging and organic semiconductor materials. Attached Figure Description

[0030] The accompanying drawings, which are incorporated in and form part of this specification, illustrate embodiments consistent with the invention and, together with the description, serve to explain the principles of the invention, wherein:

[0031] Figure 1 The hydrogen NMR spectrum of MG-RhA;

[0032] Figure 2 The carbon NMR spectrum of MG-RhA;

[0033] Figure 3 This is a high-resolution mass spectrum of MG-RhA;

[0034] Figure 4 Colocalization analysis of MG-RhA targeting lysosomes;

[0035] Figure 5 This is a fluorescence intensity diagram of the acid response of MG-RhA;

[0036] Figure 6 Here is the AIE fluorescence characteristic diagram of MG-RhA;

[0037] Figure 7 High-resolution mass spectrum of MG-Rho-COOH;

[0038] Figure 8 This is a high-resolution mass spectrum of MG-B. Detailed Implementation

[0039] The following disclosure provides many different embodiments or examples for implementing different structures of the invention. To simplify the disclosure, specific examples of components and arrangements are described below. Of course, these are merely examples and are not intended to limit the invention. Furthermore, reference numerals and / or letters may be repeated in different examples; such repetition is for simplification and clarity and does not in itself indicate a relationship between the various embodiments and / or arrangements discussed.

[0040] The technical problem to be solved by this invention is to provide a lysosome-targeted acid-responsive aggregation-induced emission (AIE) fluorescent dye MG-RhA and its preparation method. Specifically, this invention is the first to develop and synthesize a lysosome-targeted acid-responsive small organic molecule fluorescent dye, and MG-RhA is a dye with aggregation-induced emission (AIE) properties. This dye can be used for wash-free staining of live cells and has a better signal-to-noise ratio than commercially available lysosome-targeting dyes. Furthermore, the dye structure of this invention is novel and can effectively target lysosomes under acidic conditions. This method is innovative and has broad application prospects.

[0041] Example

[0042] A method for synthesizing a lysosome-targeted acid-responsive aggregation-induced emission (AIE) fluorescent dye MG-RhA, the structural formula of which is as follows:

[0043]

[0044] A method for synthesizing a lysosome-targeted acid-responsive aggregation-induced emission (AIE) fluorescent dye MG-RhA includes the following steps, as shown in Formulas II to V:

[0045]

[0046]

[0047] (1) Preparation of MG-B:

[0048] ① A mixture of 4-bromobenzaldehyde (22.1 mg, 0.1 mmol), anhydrous zinc chloride (28.1 mg, 0.2 mmol), N,N-dimethylaniline (36.2 mg, 0.3 mmol), and anhydrous ethanol (1 mL) was stirred overnight at 100 °C. After cooling to room temperature, the mixture was concentrated to remove residual N,N-dimethylaniline. The crude product was extracted with water (4 mL) and ethyl acrylate (3–5 mL). The combined organic phases were dried over anhydrous sodium sulfate, and the crude product was purified by silica gel column chromatography (PE:EA = 10:1) to give a white bromomalachite green (MG-Br) powder.

[0049] ② MG-Br (40.8 mg, 0.1 mmol), pinaborate (80 mg, 0.3 mmol), and potassium acetate (49 mg, 0.125 mmol) were dissolved in N,N-dimethylformamide (3 mL). [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride (10 mg, 0.012 mmol, 10%), used as a catalyst for the Suzuki coupling reaction, was dissolved in N,N-dimethylformamide (1 mL) and added to the reactant mixture. The mixture was stirred at 80 °C for 12 hours. The mixture was then cooled, and dichloromethane (10 mL) was added. The mixture was extracted with 30 mL of water in a separatory funnel. The organic phase was collected, dried over anhydrous sodium sulfate, and then dried by rotary evaporation. The crude product was purified by silica gel column chromatography to remove the solvent, and then dried under vacuum to obtain the target product, malachite green borate ester (MG-B), as a white solid.

[0050] High-resolution mass spectrometry characterization of the intermediate MG-B was performed: the high-resolution mass spectra of MG-B are as follows: Figure 8 As shown, the mass spectrometry data is: HRMS(ESI)calcd.for C 29 H 38 BN2O2[M+H] + 457.30263, found:457.30215.

[0051] (2) Preparation of Br-Rho-COOH:

[0052] ① Heat a mixture of N,N-diethylaminophenol (7.2g, 52.8mmol), 4-bromophthalic anhydride (4.8g, 21.1mmol), propionic acid (90mL), and methanesulfonic acid (0.5mL) under reflux at 120℃-150℃ for 10-25h.

[0053] ② The dark-colored crude product was dissolved in dichloromethane (1000 mL) and extracted with saturated brine. The organic phase was collected and concentrated. The crude product was purified by silica gel column chromatography. The isomers were separated by three repeated silica gel chromatography steps using a methanol:dichloromethane (20:1-10:1) gradient. After removing the solvent, the intermediate Br-Rho-COOH was obtained as a dark purple solid after vacuum drying.

[0054] (3) Preparation of MG-Rho-COOH:

[0055] ① Add a mixture of potassium carbonate (10 mmol), MG-B (0.12 mmol), and Br-Rho-COOH (0.1 mmol) to N,N-dimethylformamide (3 mL). After purging with nitrogen, add tetrakis(triphenylphosphine)palladium (0.008 mmol).

[0056] ② The reaction mixture was refluxed for 12 h, extracted with dichloromethane, and washed three times with saturated sodium chloride solution. The combined organic phases were dried over anhydrous sodium sulfate. The crude product was concentrated and purified by silica gel column chromatography using ethyl acetate / hexane as the eluent (1:20-1:10).

[0057] ③The purified product was then dissolved in dichloromethane, and tetrachloro-p-benzoquinone (0.15 mmol) was added in a one-pot solution with stirring at room temperature for 30 min. The crude product was purified by silica gel column chromatography (methanol / dichloromethane = 1:10-1:5) to obtain the final target product MG-Rho-COOH as a dark green solid.

[0058] like Figure 7 The intermediate product MG-Rho-COOH was characterized by high-resolution mass spectrometry: HRMS(ESI) calcd. for C 51 H 54 N4O3 2+ [M] 2+ 385.20905, found:385.20925.

[0059] (4) Preparation of MG-RhA:

[0060] ① Dissolve 100 uL (1.89 mmol) of hydrazine hydrate in 2 mL of methanol, and then add it to 2 mL of methanol containing 100 mg (0.12 mmol) of MG-Rho-COOH.

[0061] ② The reaction mixture was refluxed at 65°C for 6 hours. After the reaction was completed, it was cooled to room temperature and mixed with saturated saline solution and 0.1M NaOH at a ratio of 1:1 (v:v). DCM was then added for extraction. The organic phase was collected, dried with anhydrous sodium sulfate, and concentrated by rotary evaporation to obtain the crude product.

[0062] ③ The crude product was purified by silica gel column chromatography using ethyl acetate / hexane (1:20-1:10) as the eluent. The final target product, MG-RhA, was obtained as a dark green solid.

[0063] In this invention, the target compound MG-RhA was systematically characterized during the synthesis process, including 1H NMR, 1C NMR, and high-resolution mass spectrometry. This demonstrates the feasibility of the synthesis method and the correct target compound.

[0064] The proton spectrum of MG-RhA is as follows Figure 2 As shown, the proton spectrum data are: 1 H NMR (400MHz, DMSO) δ (ppm) 8.03 (d, J = 8.0 Hz, 1H), 7.94 ( d, J = 9.6 Hz, 1H), 7.62 ( d,J=8.0Hz,1H),7.43(d,J=7.9Hz,1H),7.36(d,J=9.0Hz,2H),7.10(d,J=9.5H z,3H),7.01(d,J=8.4Hz,2H),6.63(d,J=8.6Hz,2H),6.42–6.34(m,7H),4.33( d,J=24.9Hz,2H),3.30(s,12H),2.84(d,J=6.8Hz,8H),1.08(d,J=6.6Hz,12H).

[0065] The carbon spectrum of MG-RhA is as follows Figure 3 As shown, the carbon spectrum data are: 13 C NMR(100MHz,MeOD-d4)δ(ppm)176.6,166.5,157.2,153.8,152.2,144.4,140.5,139.7,139.0,135.4,131.7,130.4, 127.5,127.1,126.9,124.4,120.8,113.5,108.2,66.6,48.2,48.0,47.8,47.6,47.4,47.2,47.0,44.0,39.6,11.5.

[0066] High-resolution mass spectrometry of MG-RhA, such as Figure 4 As shown, the mass spectrometry data is: HRMS(ESI)calcd.for C 51 H 55 N6O2 + [M] + 783.43810, found: 783.43848.

[0067] Performance testing:

[0068] (1) Lysosomal targeting:

[0069] After incubating HeLa cells with the dye MG-RhA of this invention and the commercially available dye Lyso tracker, laser scanning confocal microscopy (CLSM) was performed. The lysosomal structure was clearly visible in the red fluorescent region of MG-RhA (see...). Figure 4 The results indicate that MG-RhA is localized to lysosomes in living cells. A Pearson correlation coefficient (Rr; from +1 to 1) as high as 0.905 indicates the degree of linear dependence between the two variables, used to quantify the overlap of staining regions between MG-RhA and commercially available dyes. This experiment demonstrates the lysosomal targeting of the dye MG-RhA developed in this invention.

[0070] (2) Acid responsiveness: Photoemission (PL) spectra of MG-RhA in buffer solutions with different pH values ​​were detected, and the results are as follows: Figure 5 As shown, from Figure 5 As can be seen, the fluorescence intensity of MG-RhA increases with the increase of solution acidity, proving its acid-responsive characteristics.

[0071] (3) Fluorescence properties: The AIE characteristics of MG-RhA in water / tetrahydrofuran mixtures with different ratios were studied. See [link to relevant documentation]. Figure 6 As can be seen, the fluorescence intensity of MG-RhA increases with the gradual increase of tetrahydrofuran concentration in the water / tetrahydrofuran mixture from 0% to 90%. Figure 6 It can be observed that the strongest fluorescence intensity of MG-RhA is achieved when the proportion of tetrahydrofuran is 90%. This experiment demonstrates the fluorescence properties of the dye MG-RhA developed in this invention.

[0072] Other embodiments of the invention will readily occur to those skilled in the art upon consideration of the specification and practice of the invention herein. This invention is intended to cover any variations, uses, or adaptations of the invention that follow the general principles of the invention and include common knowledge or customary techniques in the art. The specification and examples are to be considered exemplary only, and the true scope and spirit of the invention are indicated by the claims.

[0073] It should be understood that the present invention is not limited to the precise structure described above and shown in the accompanying drawings, and various modifications and changes can be made without departing from its scope. The scope of the invention is limited only by the appended claims.

Claims

1. A lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA, characterized in that, The structural formula of the fluorescent dye is shown in Formula I: Formula I.

2. The method of preparing lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA according to claim 1, characterized in that, Includes the following steps: (1) Preparation of MG-B: 4-Bromobenzaldehyde, anhydrous zinc chloride, N,N-dimethylaniline, and anhydrous ethanol were mixed in a molar ratio of 0.1:0.2:0.3 and stirred overnight at 100°C. After cooling, the mixture was concentrated to remove the remaining N,N-dimethylaniline. The mixture was then extracted with water and ethyl acrylate. The combined organic phases were dried and purified by silica gel column chromatography to obtain a white MG-Br powder. The MG-Br, pinaborate, and potassium acetate were then dissolved in N,N-dimethylformamide. [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride, which was dissolved in N,N-dimethylformamide, was added as a catalyst for the Suzuki coupling reaction. The mixture was stirred at 80°C for 12 hours and then cooled. The mixture was extracted with dichloromethane and water. The organic phase was collected, dried, concentrated, purified by silica gel column chromatography, and dried to obtain a white MG-B solid. (2) Preparation of Br-Rho-COOH: 52.8 mmol N,N-diethylaminophenol, 21.1 mmol 4-bromophthalic anhydride, 90 mL propionic acid and 0.5 mL methanesulfonic acid were mixed and refluxed. The resulting dark crude product was dissolved in dichloromethane, extracted with saturated brine, the organic phase was collected and concentrated, purified by silica gel column chromatography, and the isomers were separated by repeated silica gel chromatography with methanol / dichloromethane gradient. After drying, a dark purple Br-Rho-COOH solid was obtained. (3) Preparation of MG-Rho-COOH: A mixture of potassium carbonate, MG-B, and Br-Rho-COOH was added to N,N-dimethylformamide. Tetra(triphenylphosphine)palladium was added under nitrogen protection, and the mixture was refluxed. The mixture was extracted with dichloromethane, washed with saturated sodium chloride solution, and the combined organic phases were dried, concentrated, and purified by silica gel column chromatography. The first crude product was then dissolved in dichloromethane, and tetrachloro-p-benzoquinone was added. The mixture was stirred at room temperature in a one-pot manner. The resulting second crude product was purified by silica gel column chromatography to obtain a dark green MG-Rho-COOH solid. (4) Preparation of MG-RhA: Hydrazine hydrate and MG-Rho-COOH were dissolved in methanol solution and then mixed to obtain a mixture. The mixture was heated under reflux to carry out the reaction. After the reaction was completed, the mixture was cooled, extracted, and the organic phase was collected. The organic phase was then dried and concentrated by rotary evaporation to obtain a crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the dark green fluorescent dye MG-RhA solid.

3. The method of preparing lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA according to claim 2, characterized in that, In step (1), the molar ratio of MG-Br, pinaborate, potassium acetate and [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride is 0.1:0.3:0.125:0.

012.

4. The method of preparing lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA according to claim 2, characterized in that, In step (2), the reflux temperature is 120-150℃ and the reflux time is 10-25 h.

5. The method of claim 2, wherein the preparation of the lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA is characterized in that, In step (3), the molar ratio of potassium carbonate, MG-B, Br-Rho-COOH, tetra(triphenylphosphine)palladium, and tetrachloro-p-benzoquinone is (10:0.12:0.1:0.008:0.15)-(20:0.24:0.2:0.016:0.3).

6. The method of preparing lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA according to claim 2, characterized in that, In step (3), the reflux temperature is 100-120℃ and the reflux time is 10-12h.

7. The method for preparing the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA according to claim 2, characterized in that, In step (4), the molar ratio of the hydrazine hydrate to the MG-Rho-COOH is (10:1)-(20:1).

8. The method of claim 2, wherein the preparation of the lysosome-targeted acid- responsive aggregation-induced emission luminous fluorescent dye MG-RhA is characterized by, In step (4), the reflux temperature is 50℃-70℃ and the reflux time is 3h-12h.

9. The method of preparing lysosome-targeted acid-responsive aggregation-induced emission luminous fluorescent dye MG-RhA according to claim 2, characterized in that, In step (4), the extraction process includes: first adding saturated saline solution and 0.1 M NaOH in a volume ratio of 1:1 to the mixture after the reaction is completed, and then adding dichloromethane for extraction.

10. The application of the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA according to claim 1 or the lysosome-targeted acid-responsive aggregation-induced emission fluorescent dye MG-RhA prepared by the preparation method according to any one of claims 2 to 8 as a fluorescent probe in intelligent sensing, functional imaging, and biological detection; the application is not for the purpose of disease diagnosis or treatment.

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