A method for preparing GSH-lactose@UVC-GA clusters

Abstract

The application provides a preparation method of GSH-lactose@UVC-GA clusters, and belongs to the technical field of food processing, and comprises the following steps: step S1: gallic acid aqueous solution is irradiated under a UVC light source to obtain a UVC-GA solution; step S2: glutathione and lactose are reacted to obtain a GSH-lactose derivative; and step S3: the GSH-lactose derivative obtained in step S2 and the UVC-GA solution obtained in step S1 are subjected to a self-assembly reaction in a natural eutectic solvent to obtain the GSH-lactose@UVC-GA clusters. The gallic acid is photochemically modified by short-wave ultraviolet light, so that the gallic acid is subjected to oxidation polymerization to generate UVC-GA with a stronger conjugate system and more active functional groups; meanwhile, the glutathione and lactose are subjected to glycosylation covalent modification to improve the stability and hydrophilicity of the glutathione and lactose; finally, the natural eutectic solvent is used as a self-assembly medium, and the two are driven to form ordered nanometer clusters through non-covalent forces such as hydrogen bonds, so that the synergistic delivery of the two at the molecular level is realized, and the defect that simple physical mixing is difficult to play a synergistic effect is overcome.

Description

Technical Field

[0001] This invention relates to the field of food processing technology, and in particular to a method for preparing GSH-lactose @ UVC-GA clusters. Background Technology

[0002] Gallic acid (GA) and glutathione (GSH) are both important natural functional molecules with significant biological activities in antioxidation and free radical scavenging. However, both have inherent drawbacks when used directly: GA is chemically reactive and easily oxidized and degraded under light, high temperature, or alkaline conditions, and has low bioavailability; the active thiol groups in GSH are extremely unstable in vitro and easily oxidized and inactivated, while its transmembrane permeability is poor, resulting in extremely limited efficiency of exogenous supplementation.

[0003] To overcome the above problems, existing technologies mainly employ the following two approaches: One method involves physical mixing or simple compounding, where GA and GSH are directly mixed to form a formulation. This method is simple to operate, but it cannot solve the fundamental problem of their poor stability at the molecular level. The active ingredients are easily degraded and inactivated during preparation, storage, and in vivo transport, making it difficult to achieve synergistic effects.

[0004] The second approach involves chemical covalent cross-linking or coupling modification, which involves covalently linking GA or GSH to polymeric carriers, targeting ligands, etc., through chemical means. While this approach can improve stability to some extent, it also presents several safety risks: chemical cross-linking typically involves the use of toxic organic solvents and catalysts, leaving residues that are difficult to completely remove; covalent modification may alter the structure of key functional groups in the active molecule (such as the thiol group in GSH and the ortho-phenolic hydroxyl group in GA), leading to a loss of some biological activity; and the chemical synthesis steps are cumbersome and costly, and the covalent bonds are difficult to degrade in vivo, potentially causing unpredictable safety issues such as immunogenicity.

[0005] Natural eutectic solvents (NADES) are a novel type of green solvent with advantages such as simple preparation, biodegradability, and non-toxicity. Currently, they are mainly used in the fields of extraction and separation of natural products and organic synthesis. There are no reports of using them as self-assembly mediators to guide the directional assembly of functional molecules into ordered nanoclusters.

[0006] Therefore, how to achieve efficient synergistic delivery of GA and GSH while avoiding the safety hazards of chemical cross-linking, and at the same time overcome the inherent defects of poor stability and low bioavailability of both, is a technical problem that urgently needs to be solved in this field. Summary of the Invention

[0007] The purpose of this invention is to provide a method for preparing GSH-lactose @ UVC-GA clusters, thereby solving the existing technical problems.

[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows: A method for preparing GSH-lactose@UVC-GA clusters includes the following steps: Step S1: Irradiate the gallic acid aqueous solution under a UVC light source to obtain a UVC-GA solution; Step S2: Glutathione is reacted with lactose in a solution to obtain a GSH-lactose derivative; Step S3: The GSH-lactose derivative obtained in step S2 and the UVC-GA solution obtained in step S1 are subjected to a self-assembly reaction in a natural eutectic solvent to obtain the GSH-lactose@UVC-GA cluster.

[0009] Further, in step S1, the wavelength of the UVC light source is 254 nm, and the average radiant intensity of the UVC light source is 4540 μW / cm². 2 The distance between the UVC light source and the liquid surface is set to 15cm, and the irradiation time of the UVC light source is 6 hours.

[0010] Further, in step S1, the concentration of the gallic acid aqueous solution is 14 mmol / L.

[0011] Further, in step S2, the molar ratio of glutathione to lactose is 1:3.

[0012] Further, in step S2, the solvent is deionized water, and the reaction is carried out in an oil bath at a temperature of 130°C for 30 min. Further, in step S3, the natural eutectic solvent is a mixture of choline chloride and lactic acid, wherein the molar ratio of choline chloride to lactic acid is 1:1 to 1:4. Further, 20 wt.% of deionized water by total mass is added to the mixture.

[0013] Further, in step S3, the molar ratio of the GSH-lactose derivative to the UVC-GA solution is 1:1; the self-assembly reaction is carried out under conditions of pH 3.0-6.0.

[0014] Furthermore, in step S3, the self-assembly reaction temperature is 25-55°C; the self-assembly reaction time is 1-7 h.

[0015] A GSH-lactose @ UVC-GA cluster, prepared by a method thereof.

[0016] The present invention, by adopting the above-described technical solution, has the following beneficial effects: This invention utilizes short-wave ultraviolet light to photochemically modify gallic acid, causing it to undergo oxidative polymerization and generate UVC-GA with a stronger conjugated system and more active functional groups. Simultaneously, glutathione and lactose are covalently modified with glycosylation to improve their stability and hydrophilicity. Finally, using a natural eutectic solvent as a self-assembly medium, the two components are driven to form ordered nanoclusters through non-covalent forces such as hydrogen bonds, achieving synergistic delivery at the molecular level and overcoming the shortcomings of simple physical mixing in achieving synergistic effects.

[0017] In this invention, the choline chloride-lactic acid type natural eutectic solvent not only has excellent solubility, but also can actively drive the directional self-assembly of GSH-lactose derivatives with UVC-GA through its rich hydrogen bond network and ion interactions to prepare GSH-lactose@UVC-GA multifunctional clusters. These clusters are highly efficient in synthesis, have uniform particle size, and excellent stability.

[0018] This invention uses natural eutectic solvents and water as media, without using any toxic or harmful organic solvents or crosslinking agents. It avoids safety hazards such as organic solvent residues, blockage of active groups, difficulty in in vivo degradation, and immunogenicity risks caused by chemical covalent modification, and truly achieves green and safe synergistic delivery of active molecules. Attached Figure Description

[0019] Figure 1 This is the infrared spectrum of the GSH-lactose @ UVC-GA cluster of this invention; Figure 2 This is the Raman spectrum of the GSH-lactose @ UVC-GA cluster of this invention; Figure 3 This is the X-ray diffraction pattern of the GSH-lactose @ UVC-GA cluster of this invention; Figure 4 This is the X-ray photoelectron spectroscopy of the GSH-lactose @ UVC-GA cluster of this invention; Figure 5 This is the nuclear magnetic resonance spectrum of the GSH-lactose @ UVC-GA cluster of this invention; Figure 6 These are scanning electron microscope images of the GSH-lactose @ UVC-GA clusters of this invention; Figure 7 These are transmission electron microscope images of the GSH-lactose @ UVC-GA clusters of this invention; Figure 8This is a schematic diagram illustrating the stability evaluation results of the GSH-lactose @ UVC-GA cluster of this invention; Figure 9 This is a schematic diagram of the solubility test results of the GSH-lactose @ UVC-GA cluster of the present invention; Figure 10 This is a schematic diagram of the porosity results of the GSH-lactose @ UVC-GA clusters of the present invention; Figure 11 This is a schematic diagram showing the contact angle results of the GSH-lactose @ UVC-GA clusters of the present invention. Detailed Implementation

[0020] To make the objectives, technical solutions, and advantages of the present invention clearer, the present invention will be further described in detail below with reference to the accompanying drawings and preferred embodiments. However, it should be noted that many details listed in the specification are merely to provide the reader with a thorough understanding of one or more aspects of the present invention, and these aspects of the invention can be implemented even without these specific details.

[0021] A method for preparing GSH-lactose@UVC-GA clusters includes the following steps: Step S1: Irradiate the gallic acid aqueous solution under a UVC light source to obtain a UVC-GA solution; In step S1, the wavelength of the UVC light source is 254 nm, and the average radiant intensity of the UVC light source is 4540 μW / cm². 2 The distance between the UVC light source and the liquid surface is set to 15cm, and the irradiation time of the UVC light source is 6 hours. The concentration of the gallic acid aqueous solution was 14 mmol / L.

[0022] Step S2: Glutathione is reacted with lactose in a solution to obtain a GSH-lactose derivative; In step S2, the molar ratio of glutathione to lactose is 1:3; In step S2, the solvent is deionized water, and the reaction is carried out in an oil bath at a temperature of 130°C for 30 min.

[0023] Step S3: The GSH-lactose derivative obtained in step S2 and the UVC-GA solution obtained in step S1 are subjected to a self-assembly reaction in a natural eutectic solvent to obtain the GSH-lactose@UVC-GA cluster. In step S3, the natural eutectic solvent is a mixture of choline chloride and lactic acid, wherein the molar ratio of choline chloride to lactic acid is 1:1 to 1:4. Add 20 wt.% of deionized water to the mixture; The molar ratio of the GSH-lactose derivative to the UVC-GA solution is 1:1; the self-assembly reaction is carried out under conditions of pH 3.0-6.0. In step S3, the self-assembly reaction temperature is 25-55°C; the self-assembly reaction time is 1-7 h.

[0024] A GSH-lactose @ UVC-GA cluster, prepared by a method thereof.

[0025] Example 1 A method for preparing GSH-lactose@UVC-GA clusters includes the following steps: Step S1: Measure 2 mL of 14 mmol / L gallic acid aqueous solution into a quartz culture dish and irradiate it for 6 h under a UVC light source with a wavelength of 254 nm and an average radiation intensity of 4540 μW / cm². The distance between the light source and the liquid surface is kept constant at 15 cm. Shake the dish every 30 min during irradiation to ensure uniform irradiation. Step S2: Glutathione (307.3 mg, 1 mmol) and lactose (1081.01 mg, 3 mmol) were dissolved in 2 mL of deionized water. The mixture was sonicated for 10 min and then reacted in an oil bath at a stable temperature of 130°C for 30 min. The reaction solution was centrifuged at 12000 r / min for 15 min, the supernatant was discarded, and the mixture was washed three times to obtain a pale yellow GSH-lactose derivative. The synthesized GSH-lactose derivative was centrifuged at 12000 rpm for 15 min, the supernatant was discarded, and the mixture was washed three times.

[0026] Step S3: Mix choline chloride and lactic acid in a 1:1 molar ratio and stir at a constant temperature of 60°C until a homogeneous and transparent solution is formed. Then add deionized water equivalent to 20 wt.% of the total mass of choline chloride and lactic acid to obtain a natural eutectic solvent with a choline chloride-lactic acid mass fraction of 83.33 wt%.

[0027] Step S4: Weigh 1 mmol (calculated as glutathione) of GSH-lactose derivative, dissolve it in 5.0 mL of the above-mentioned natural eutectic solvent, mix thoroughly, and then add an equimolar amount of UVC-GA. Adjust the pH to 4.5 by adding an appropriate amount of citrate buffer or phosphate buffer, and stir the reaction at 35℃ for 3 h to finally obtain the GSH-lactose@UVC-GA cluster.

[0028] Example 2 A method for preparing GSH-lactose@UVC-GA clusters includes the following steps: Step S1: Measure 2 mL of 14 mmol / L gallic acid aqueous solution into a quartz culture dish and irradiate it for 6 h under a UVC light source with a wavelength of 254 nm and an average radiation intensity of 4540 μW / cm². The distance between the light source and the liquid surface is kept constant at 15 cm. Shake the dish every 30 min during irradiation to ensure uniform irradiation. Step S2: Glutathione (307.3 mg, 1 mmol) and lactose (1081.01 mg, 3 mmol) were dissolved in 2 mL of deionized water. The mixture was sonicated for 10 min and then reacted in an oil bath at a stable temperature of 130°C for 30 min. The reaction solution was centrifuged at 12000 r / min for 15 min, the supernatant was discarded, and the mixture was washed three times to obtain a pale yellow GSH-lactose derivative. The synthesized GSH-lactose derivative was centrifuged at 12000 rpm for 15 min, the supernatant was discarded, and the mixture was washed three times.

[0029] Step S3: Mix choline chloride and lactic acid in a 1:2 molar ratio and stir at a constant temperature of 60°C until a homogeneous and transparent solution is formed. Then add deionized water equivalent to 20 wt.% of the total mass of choline chloride and lactic acid to obtain a natural eutectic solvent with a choline chloride-lactic acid mass fraction of 83.33 wt%.

[0030] Step S4: Weigh 1 mmol (calculated as glutathione) of GSH-lactose derivative, dissolve it in 5.0 mL of the above-mentioned natural eutectic solvent, mix thoroughly, and then add an equimolar amount of UVC-GA. Adjust the pH to 5.0 by adding an appropriate amount of citrate buffer or phosphate buffer, and stir the reaction at 40℃ for 4 h to finally obtain the GSH-lactose@UVC-GA cluster.

[0031] Example 3 A method for preparing GSH-lactose@UVC-GA clusters includes the following steps: Step S1: Measure 2 mL of 14 mmol / L gallic acid aqueous solution into a quartz culture dish and irradiate it for 6 h under a UVC light source with a wavelength of 254 nm and an average radiation intensity of 4540 μW / cm². The distance between the light source and the liquid surface is kept constant at 15 cm. Shake the dish every 30 min during irradiation to ensure uniform irradiation. Step S2: Glutathione (307.3 mg, 1 mmol) and lactose (1081.01 mg, 3 mmol) were dissolved in 2 mL of deionized water. The mixture was sonicated for 10 min and then reacted in an oil bath at a stable temperature of 130°C for 30 min. The reaction solution was centrifuged at 12000 r / min for 15 min, the supernatant was discarded, and the mixture was washed three times to obtain a pale yellow GSH-lactose derivative. The synthesized GSH-lactose derivative was centrifuged at 12000 rpm for 15 min, the supernatant was discarded, and the mixture was washed three times.

[0032] Step S3: Mix choline chloride and lactic acid in a 1:3 molar ratio and stir at a constant temperature of 60°C until a homogeneous and transparent solution is formed. Then add deionized water equivalent to 20 wt.% of the total mass of choline chloride and lactic acid to obtain a natural eutectic solvent with a choline chloride-lactic acid mass fraction of 83.33 wt%.

[0033] Step S4: Weigh 1 mmol (calculated as glutathione) of GSH-lactose derivative, dissolve it in 5.0 mL of the above-mentioned natural eutectic solvent, mix thoroughly, and then add an equimolar amount of UVC-GA. Adjust the pH to 5.5 by adding an appropriate amount of citrate buffer or phosphate buffer, and stir the reaction at 45℃ for 5 h to finally obtain the GSH-lactose@UVC-GA cluster.

[0034] The detection method for GSH-lactose@UVC-GA clusters in this application is as follows: Physicochemical property characterization Infrared spectroscopy analysis was performed using a Nicolet iS50 Fourier transform infrared spectrometer (Thermo Fisher Scientific, USA). 1.0 mg of sample was weighed and mixed with KBr at a mass ratio of 1:100, compressed into a slide, and the wavenumber range was 4000–400 cm⁻¹. -1 The resolution is 4 cm. -1 A total of 32 scans were performed.

[0035] Raman spectroscopy measurements were performed using a LabRAM HR Evolution confocal Raman spectrometer (Horiba Corporation, Japan), with an excitation wavelength of 532 nm, a laser power of 5 mW, and a scan wavenumber range of 50–3500 cm⁻¹. -1 .

[0036] Nuclear magnetic resonance spectroscopy measurements were performed using a Bruker Avance III HD 600 MHz nuclear magnetic resonance spectrometer (Bruker GmbH, Germany). The sample was dissolved in a mixed solvent of heavy water and deuterated dimethyl sulfoxide (9:1 by volume).

[0037] X-ray diffraction analysis was performed using a Bruker D8 Advance diffractometer (Bruker GmbH, Germany), employing CuKα radiation (λ=0.154 nm), with a scanning angle range of 2θ=5–80° and a scanning rate of 5° / min.

[0038] X-ray photoelectron spectroscopy analysis was performed using an ESCALAB 250Xi spectrometer (Thermo Fisher Scientific, USA), with Al Kα rays as the excitation source (hν = 1486.6 eV).

[0039] Morphological characterization was performed using transmission electron microscopy (TEM) and scanning electron microscopy (SEM). TEM observations were conducted using a Philips-FEI Tecnai G2 Spirit TEM (Philips-FEI, Netherlands) with an accelerating voltage set to 120 kV. Confocal laser scanning microscopy observations were performed using a TCS SP8 confocal microscope (Leica, Germany) with an excitation wavelength of 488 nm. All images were analyzed using ImageJ software.

[0040] Stability assessment To assess pH stability, 5.0 mg of lyophilized GSH-lactose@UVC-GA was first dissolved in 10.0 mL of ultrapure water to prepare a 0.5 mg / mL stock solution. Subsequently, 100 μL of this stock solution was diluted to 1.0 mL and incubated at 37°C for 30 min using phosphate citrate buffer (pH range 2.0–8.0), with residual absorbance measured at 430 nm. To assess photostability, 2.0 mL of the 0.5 mg / mL solution was exposed to 39W UVC (185 / 254 nm) irradiation at 25°C, and absorbance at 430 nm was recorded at 0, 1, 2, 4, 8, 12, and 24 h. A first-order kinetic model was used to fit the degradation process. To assess storage stability, the 0.5 mg / mL stock solution was stored at 25°C in the dark for 30 days, and particle size, polydispersity index (PDI), and zeta potential were measured on days 0, 1, 3, 7, 14, and 30.

[0041] Porosity, solubility and contact angle After vacuum degassing at 115°C for 8 h, the nitrogen adsorption / desorption isotherms were determined at 77 K using a TriStar II Plus (Micromeritics, USA) instrument. Surface area, pore size, and pore volume were calculated using the Brunauer-Emmet-Teller (BET) and Barrett-Joyner-Halenda (BJH) methods. Solubility was determined using the shake-flask method and quantitatively analyzed by UV-Vis spectrophotometry at 430 nm. The standard curve equation is A. 430 =0.038C + 0.005(R) 2 =0.998).

[0042] Contact angle was measured using a JC 2000 contact angle measuring instrument (Powereach Corporation, Shanghai, China) and the seat drop method was employed.

[0043] The substances in Examples 1-3 were tested using the method described above, and the results are as follows: 1. Physicochemical property characterization results from Figure 1 As can be seen, in the near-infrared spectrum, GSH-lactose@UVC-GA exhibits the characteristic vibrational peak of COC and is located at 1735 cm⁻¹. -1 The C=O stretching vibration peak at the location is observed, while the original SH characteristic peak in glutathione disappears.

[0044] from Figure 2 As can be seen, Raman spectroscopy indicates that GSH-lactose@UVC-GA at 1710 cm⁻¹ -1 Characteristic vibrational peaks belonging to clusters appeared at the point, and characteristic peaks related to aromatic ring C=O and ring structure also shifted; in contrast, the spectrum of physical mixtures only showed a simple superposition of characteristic peaks of each component, and no new peaks were observed or peak shifts were observed.

[0045] The phase composition analysis results are consistent with the spectral characterization. The phase characteristics of GSH-lactose@UVC-GA differ from those of single components and physical mixtures, and do not show the superposition of phase characteristics of each component.

[0046] from Figure 3 It can be seen that in the X-ray diffraction pattern, the position and intensity of the characteristic peak corresponding to the diffraction angle 2θ of GSH-lactose@UVC-GA are significantly changed, which are obviously different from the diffraction peaks of glutathione, lactose and UVC-GA, and no superposition effect of characteristic peaks of physical mixtures was observed.

[0047] from Figure 4As can be seen from X-ray photoelectron spectroscopy (XPS), in the S 2p orbital spectrum, GSH-lactose@UVC-GA exhibits characteristic peaks attributable to oxidized sulfur (binding energies of 165.1 eV and 166.4 eV), while the intensity of the reduced sulfur characteristic peak (163.9 eV) is significantly reduced, and a new C–S bond characteristic peak is observed. In the C 1s orbital spectrum, a new characteristic peak appears at 286.7 eV; simultaneously, the binding energies of both the O 1s and N 1s orbitals shift, and the N 1s peak exhibits splitting. Compared to the complex, the physical mixture only shows a simple linear superposition of the binding energies of the individual component elements, without the appearance of new characteristic peaks or binding energy shifts.

[0048] from Figure 5 It can be seen that the structural differences at the spectral level are further confirmed by nuclear magnetic resonance spectroscopy, reflecting the formation of clusters from the perspective of the hydrogen atom chemical environment. Compared with glutathione, lactose, UVC-GA and their physical mixtures, the 1H NMR chemical shift of GSH-lactose@UVC-GA shows a significant change.

[0049] from Figure 6 As can be seen, the spectrum of the physical mixture is merely a simple superposition of the chemical shifts of the individual components, without any new signal peaks. Microscopic characterization revealed the microstructural features of the GSH-lactose@UVC-GA clusters, whose morphology differs significantly from that of the individual components and the physical mixture. Scanning electron microscopy (SEM) showed that GSH-lactose@UVC-GA exhibited a distinct aggregated morphology at the 200 nm scale; in contrast, the components in the physical mixture remained in a dispersed crystalline state, without aggregation.

[0050] from Figure 7 As can be seen, transmission electron microscopy (TEM) images further confirm that GSH-lactose@UVC-GA exhibits a distinct cluster aggregate morphology; while glutathione and lactose both exhibit typical crystal morphology, and the physical mixture only shows a mechanical mixing state of the crystals analyzed from each group, without forming a cluster structure.

[0051] 2. Stability assessment results from Figure 8 It can be seen that the storage stability test results show that after the aqueous dispersion of the cluster material was stored at pH=7.0, 25℃ and in the dark for one month, its particle size, polydispersity index (PDI) and zeta potential did not change significantly.

[0052] 3. Results of porosity, solubility, and contact angle from Figure 9Solubility tests show that the cluster exhibits the highest solubility in dimethyl sulfoxide (DMSO), reaching 86.27 mg / mL; in N,N-dimethylformamide (DMF), it is 72.56 mg / mL; while its solubility in nonpolar solvents such as chloroform (0.12 mg / mL) and ethyl acetate (0.85 mg / mL) is extremely low. The material shows good solubility (>5 mg / mL) in water, phosphate-buffered saline (PBS), and ethanol, but is almost insoluble in chloroform.

[0053] from Figure 10 As can be seen from the nitrogen adsorption-desorption isotherms and pore size distribution, the GSH-lactose@UVC-GA cluster exhibits a typical Type IV isotherm, and an H3-type hysteresis loop appears in the relative pressure range of P / P0 = 0.4-0.8, indicating that the cluster has mesoporous structure characteristics, with pores mainly composed of slit-like pores formed by aggregates of plate-like particles. The BET specific surface area is 162.4 m² / g, the total pore volume is 0.133 cm³ / g, and the average pore size is 3.24 nm.

[0054] from Figure 11 As can be seen, the hydrophilic behavior of this cluster material was systematically evaluated using the contact angle measurement method. Tests were conducted on four substrates: the surface of the cluster material pellet, a hydrophilic glass slide, hydrophobic polytetrafluoroethylene (PTFE), and food-grade stainless steel. The measured water contact angles were 38.2°, 38.2°, 42.5°, and 39.1°, respectively. The cluster material exhibited a water contact angle of 38.2°, a contact angle of 12.6° with n-hexadecane, and a contact angle of 15.3° with soybean oil.

[0055] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A method for preparing GSH-lactose@UVC-GA clusters, characterized in that: Includes the following steps: Step S1: Irradiate the gallic acid aqueous solution under a UVC light source to obtain a UVC-GA solution; Step S2: Glutathione is reacted with lactose in a solution to obtain a GSH-lactose derivative; Step S3: The GSH-lactose derivative obtained in step S2 and the UVC-GA solution obtained in step S1 are subjected to a self-assembly reaction in a natural eutectic solvent to obtain the GSH-lactose@UVC-GA cluster.

2. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S1, the wavelength of the UVC light source is 254 nm, and the average radiant intensity of the UVC light source is 4540 μW / cm². 2 The distance between the UVC light source and the liquid surface is set to 15cm, and the irradiation time of the UVC light source is 6 hours.

3. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S1, the concentration of the gallic acid aqueous solution is 14 mmol / L.

4. The method for preparing a GSH-lactose@UVC-GA cluster according to claim 1, characterized in that: In step S2, the molar ratio of glutathione to lactose is 1:

3.

5. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S2, the solvent for the reaction is deionized water, and the reaction is carried out in an oil bath at a temperature of 130°C for 30 minutes.

6. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S3, the natural eutectic solvent is a mixture of choline chloride and lactic acid, wherein the molar ratio of choline chloride to lactic acid is 1:1 to 1:

4.

7. The method for preparing a GSH-lactose@UVC-GA cluster according to claim 6, characterized in that: The mixture is supplemented with 20 wt.% of deionized water by its total mass.

8. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S3, the molar ratio of the GSH-lactose derivative to the UVC-GA solution is 1:

1.

9. The method for preparing GSH-lactose@UVC-GA clusters according to claim 1, characterized in that: In step S3, the self-assembly reaction is carried out at a pH of 3.0-6.0; the temperature of the self-assembly reaction is 25-55°C; and the time of the self-assembly reaction is 1-7 h.

10. A GSH-lactose @ UVC-GA cluster, characterized in that, It is prepared by the method for preparing GSH-lactose @ UVC-GA clusters according to any one of claims 1-9.

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