Selenium-containing small molecules loaded with fluorescent groups, methods of making and using the same

Abstract

This invention provides a selenium-containing small molecule loaded with a fluorescent group, its preparation method, and its applications. This small molecule exhibits good killing effects on tumor cells, can specifically target mitochondria, and acts as a mitochondrial contrast agent. This small molecule can be used for integrated diagnosis and treatment of tumors.

Description

Technical Field

[0001] This invention belongs to the field of synthetic medicinal chemistry technology, and specifically relates to a selenium-containing small molecule loaded with a fluorescent group, a method for preparing the selenium-containing small molecule loaded with a fluorescent group, and its application in antitumor drugs. Background Technology

[0002] Selenium is an essential trace element for the human body. It participates in various physiological processes through at least 25 eukaryotic selenoproteins. Among these, organoselenium compounds have been the most extensively developed and studied. Compared to inorganic selenium compounds, organoselenium compounds exhibit lower toxicity and higher biological activity. Various organoselenium compounds have been reported. Selenium-containing heterocyclic compounds constitute a large class of selenium compounds with diverse biological properties, including anticancer, anti-inflammatory, and antiviral effects. Selenidazole is a particularly valuable agent in medicinal chemistry. Indole-derived hemicyanine dyes are renowned for their wide application in many research fields. Their unique π-conjugated structure gives them rich color and fluorescence properties in light absorption and emission, making them increasingly widely used in biomarkers.

[0003] Therefore, by combining fluorescent groups with selenium diazole functional molecules with anti-tumor activity, the dual purpose of labeling and killing tumors can be achieved, which is of great research significance for realizing the integration of diagnosis and treatment in tumor therapy. Summary of the Invention

[0004] In view of the shortcomings of the prior art described above, the purpose of this invention is to connect a fluorescent group with biomarker function and a selenium diazole pharmacophore with tumor-killing effect through ester bond, so as to realize the integration of tumor treatment and diagnosis.

[0005] This application provides a selenium-containing small molecule loaded with a fluorescent group, which is prepared by the following reaction:

[0006]

[0007] A method for preparing selenium-containing small molecules loaded with fluorescent groups includes the following steps:

[0008] (1) Synthesis of PhSe;

[0009] (2) Synthesis of miCy-OH;

[0010] (3) Synthesis of miCy-Se: A mixture of compound PhSe, miCy-OH, 4-dimethylaminopyridine and 1-ethyl-(3-dimethylaminopropyl)carbodiimide was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature; the reaction was detected by TLC, the mixture was concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography to obtain the target compound miCy-Se.

[0011] Specifically, in step (3), a mixture of 0.8-1.2 parts of compound PhSe, 0.4-0.6 parts of miCy-OH, 0.8-1.2 parts of 4-dimethylaminopyridine, and 0.8-1.2 parts of 1-ethyl-(3-dimethylaminopropyl)carbodiimide is dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature; the amounts mentioned above are measured in moles. According to the preparation method of claim 1, step (1) specifically includes: mixing 3,4-diaminobenzoic acid and selenium dioxide in an aqueous solution, adding concentrated hydrochloric acid dropwise while stirring at room temperature, filtering the product, washing with water and ethanol, and vacuum drying to obtain compound PhSe.

[0012] Specifically, in step (1), the molar ratio of 3,4-diaminobenzoic acid and selenium dioxide is 1:1 to 1-1.2.

[0013] Specifically, step (2) includes: first, adding 1,1,2-trimethyl-1H-benzo[e]indole and iodoethane to a round-bottom flask containing acetonitrile under nitrogen protection; stirring and refluxing the mixed solution at a certain temperature; removing the solvent by a rotary evaporator, and washing the crude product multiple times with petroleum ether to obtain compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium; dissolving compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium and 6-hydroxy-2-naphthal in EtOH, and then adding a small amount of piperidine; heating the mixture under reflux overnight; cooling the mixture to room temperature, removing the solvent by a rotary evaporator, and removing the solvent from the crude product by a rotary evaporator; purifying the crude product using silica gel rapid chromatography with dichloromethane / methanol as eluent to obtain yellow solid miCy-OH.

[0014] Specifically, it includes the following steps:

[0015] (1) Synthesis of PhSe: 3,4-diaminobenzoic acid (1.54 g, 10 mmol) and selenium dioxide (1.11 g, 10 mmol) were mixed in an aqueous solution, and concentrated hydrochloric acid was added dropwise and stirred at room temperature for 2 h; the product was filtered, washed with water and ethanol, and dried under vacuum to obtain compound PhSe;

[0016] (2) Synthesis of miCy-OH: First, 1,1,2-trimethyl-1H-benzo[e]indole (500 mg, 2.39 mmol) and iodoethane (745 mg, 4.78 mmol) were added to a round-bottom flask containing 10 mL of acetonitrile under nitrogen protection; the mixture was stirred and refluxed at 75 °C, and the reaction was monitored by TLC; the solvent was removed by rotary evaporator, and the crude product was washed several times with petroleum ether to obtain compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium, which did not require purification; compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium (249 mg, 1.05 mmol) and 6-hydroxy-2-naphthal (172.2 mg, 1 mmol) were dissolved in 20 mL of acetonitrile. In EtOH, a small amount of piperidine was added dropwise; the mixture was heated under reflux overnight; after cooling the mixture to room temperature, the solvent was removed by rotary evaporator, and the crude product was also removed by rotary evaporator; the crude product was purified by silica gel rapid chromatography using dichloromethane / methanol (v / v, 25:1) as eluent to give a yellow solid miCy-OH;

[0017] (3) Synthesis of miCy-Se: A mixture of compound PhSe (0.3668 g, 1.80 mmol), miCy-OH (0.1549 g, 0.90 mmol), 4-dimethylaminopyridine (0.2199 g, 1.80 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature. The reaction was detected by TLC, concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography (dichloromethane / methanol, v / v, 25:1) to obtain the target compound miCy-Se.

[0018] Application of selenium-containing small molecules loaded with fluorescent groups in antitumor drugs.

[0019] Application of selenium-containing small molecules loaded with fluorescent groups in mitochondrial morphology developing agents.

[0020] The improvements in this application bring the following advantages: Experimental results of this invention show that the small molecule has a good killing effect on tumor cells, can specifically target mitochondria, and acts as a mitochondrial contrast agent. This small molecule can be used for the integrated diagnosis and treatment of tumors. Attached Figure Description

[0021] Figure 1 This is the ESI-MS mass spectrum of miCy-Se in the embodiments of this application;

[0022] Figure 2 This is the miCy-Se embodiment of this application. 1 H NMR spectrum;

[0023] Figure 3 These are the infrared spectra of miCy-OH and miCy-Se from the embodiments of this application.

[0024] Figure 4 The spatial localization function of miCy-OH and miCy-Se and laser confocal colocalization imaging in the embodiments of this application are: (a) mitochondrial colocalization and (b) lysosomal colocalization. Detailed Implementation

[0025] The following specific examples illustrate the implementation of the present invention. Those skilled in the art can easily understand other advantages and effects of the present invention from the content disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and various details in this specification can also be modified or changed based on different viewpoints and applications without departing from the spirit of the present invention.

[0026] Example 1: Synthesis of selenium-containing small molecules loaded with fluorescent groups

[0027] PhSe Synthesis

[0028] 3,4-Diaminobenzoic acid (1.54 g, 10 mmol) and selenium dioxide (1.11 g, 10 mmol) were mixed in an aqueous solution, and concentrated hydrochloric acid was added dropwise while stirring at room temperature for 2 h. The product was filtered, washed with water and ethanol, and dried under vacuum to obtain the compound PhSe.

[0029] Synthesis of miCy-OH

[0030] First, 1,1,2-trimethyl-1H-benzo[e]indole (500 mg, 2.39 mmol) and iodoethane (745 mg, 4.78 mmol) were added to a round-bottom flask containing 10 mL of acetonitrile under nitrogen protection. The mixture was stirred and refluxed at 75 °C. The reaction was monitored by TLC. The solvent was removed by rotary evaporator, and the crude product was washed several times with petroleum ether to give compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium, which did not require purification. Compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium (249 mg, 1.05 mmol) and 6-hydroxy-2-naphthal (172.2 mg, 1 mmol) were dissolved in 20 mL of EtOH, and then a small amount of piperidine was added dropwise. The mixture was heated under reflux overnight. After cooling the mixture to room temperature, the solvent was removed by rotary evaporator, and the crude product was also removed by rotary evaporator. The crude product was purified by silica gel rapid chromatography using dichloromethane / methanol (v / v, 25:1) as eluent to give a yellow solid miCy-OH.

[0031] Synthesis of miCy-Se

[0032] A mixture of compounds PhSe (0.3668 g, 1.80 mmol), miCy-OH (0.1549 g, 0.90 mmol), 4-dimethylaminopyridine (0.2199 g, 1.80 mmol), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC) (0.3452 g, 1.80 mmol) was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature. The reaction was detected by TLC, concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography (dichloromethane / methanol, v / v, 25:1; i.e., the eluent was a mixture of dichloromethane and methanol in a volume ratio of 25:1) to obtain the target compound miCy-Se.

[0033] Example 2: Synthesis of selenium-containing small molecules loaded with fluorescent groups

[0034] PhSe Synthesis

[0035] 3,4-Diaminobenzoic acid (1.54 g, 10 mmol) and selenium dioxide (1.221 g, 11 mmol) were mixed in an aqueous solution, and concentrated hydrochloric acid was added dropwise while stirring at room temperature for 2.5 h. The product was filtered, washed with water and ethanol, and dried under vacuum to obtain the compound PhSe.

[0036] Synthesis of miCy-OH

[0037] First, 1,1,2-trimethyl-1H-benzo[e]indole (500 mg, 2.39 mmol) and iodoethane (745 mg, 4.78 mmol) were added to a round-bottom flask containing 10 mL of acetonitrile under nitrogen protection. The mixture was stirred and refluxed at 75 °C. The reaction was monitored by TLC. The solvent was removed by rotary evaporator, and the crude product was washed several times with petroleum ether to give compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium, which did not require purification. Compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium (249 mg, 1.05 mmol) and 6-hydroxy-2-naphthal (172.2 mg, 1 mmol) were dissolved in 20 mL of EtOH, and then a small amount of piperidine was added dropwise. The mixture was heated under reflux overnight. After cooling the mixture to room temperature, the solvent was removed by rotary evaporator, and the crude product was also removed by rotary evaporator. The crude product was purified by silica gel rapid chromatography using dichloromethane / methanol (v / v, 25:1) as eluent to give a yellow solid miCy-OH.

[0038] Synthesis of miCy-Se

[0039] A mixture of compounds PhSe (0.2934 g, 1.44 mmol), miCy-OH (0.1859 g, 1.08 mmol), 4-dimethylaminopyridine (0.1759 g, 1.44 mmol), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC) (0.2760 g, 1.44 mmol) was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature. The reaction was detected by TLC, concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography (dichloromethane / methanol, v / v, 25:1; i.e., the eluent was a mixture of dichloromethane and methanol in a volume ratio of 25:1) to obtain the target compound miCy-Se.

[0040] Example 3: Synthesis of selenium-containing small molecules loaded with fluorescent groups

[0041] PhSe Synthesis

[0042] 3,4-Diaminobenzoic acid (1.54 g, 10 mmol) and selenium dioxide (1.332 g, 12 mmol) were mixed in an aqueous solution, and concentrated hydrochloric acid was added dropwise while stirring at room temperature for 3 h. The product was filtered, washed with water and ethanol, and dried under vacuum to obtain the compound PhSe.

[0043] Synthesis of miCy-OH

[0044] First, 1,1,2-trimethyl-1H-benzo[e]indole (500 mg, 2.39 mmol) and iodoethane (745 mg, 4.78 mmol) were added to a round-bottom flask containing 10 mL of acetonitrile under nitrogen protection. The mixture was stirred and refluxed at 75 °C. The reaction was monitored by TLC. The solvent was removed by rotary evaporator, and the crude product was washed several times with petroleum ether to give compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium, which did not require purification. Compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium (249 mg, 1.05 mmol) and 6-hydroxy-2-naphthal (172.2 mg, 1 mmol) were dissolved in 20 mL of EtOH, and then a small amount of piperidine was added dropwise. The mixture was heated under reflux overnight. After cooling the mixture to room temperature, the solvent was removed by rotary evaporator, and the crude product was also removed by rotary evaporator. The crude product was purified by silica gel rapid chromatography using dichloromethane / methanol (v / v, 25:1) as eluent to give a yellow solid miCy-OH.

[0045] Synthesis of miCy-Se

[0046] A mixture of compounds PhSe (0.4402 g, 2.16 mmol), miCy-OH (0.1239 g, 0.72 mmol), 4-dimethylaminopyridine (0.2639 g, 2.16 mmol), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide (EDC) (0.4141 g, 2.16 mmol) was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature. The reaction was detected by TLC, concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography (dichloromethane / methanol, v / v, 25:1; i.e., the eluent was a mixture of dichloromethane and methanol in a volume ratio of 25:1) to obtain the target compound miCy-Se.

[0047] Experiment 4: Characterization of selenium-containing small molecules loaded with fluorescent groups

[0048] (1) Mass spectrometry

[0049] A small amount of sample (miCy-Se) was dissolved in methanol for HPLC, filtered through a 0.22 μM filter, and mass spectrometry data of the complex solution were collected using positive ion mode. Figure 1 .ESI-HRMS(m / z):602.1341[C 35 H 28 [N3O2Se]+, 302.1336 was found. The results indicate the successful synthesis of this compound.

[0050] (2) Nuclear magnetic resonance

[0051] The compound was dissolved in deuterated dimethyl sulfoxide, and its proton NMR spectrum was analyzed using a 300 MHz NMR spectrometer. For example... Figure 2 As shown, 1 ¹H NMR (300 MHz, DMSO-d⁶) δ 8.87 (s, 1H), 8.79 (s, 2H), 8.53–8.46 (m, 2H), 8.34 (d, J = 9.0 Hz, 1H), 8.29–8.14 (m, 5H), 8.09 (dd, J = 5.5, 3.2 Hz, 2H), 7.93–7.81 (m, 2H), 7.80–7.69 (m, 2H), 4.93 (d, J = 7.2 Hz, 2H), 2.11 (s, 6H), 1.59 (t, J = 7.2 Hz, 3H), indicating that the compound miCy-Se was successfully synthesized.

[0052] (3) Infrared

[0053] Take a small amount of powder and test it with an infrared spectrometer, such as... Figure 3As shown, a strong C=O absorption peak of the ester appears at 1735-1750 cm⁻¹, and a CO absorption peak appears at 1000-1300 cm⁻¹, proving the successful synthesis of the ester bond. Experiment 5: Investigation of the in vitro antitumor activity of selenium-containing small molecules loaded with fluorescent groups.

[0054] The method for measuring the growth inhibition of miCy-Se on tumor cells (4T1, MDA-MB-231, HeLa, Siha, MCF-7 cells) and normal cells (H9C, Wi38) in Experiment 1 using the MTT assay mainly includes the following steps:

[0055] (1) Dissolve miCy-Se in DMSO (dimethyl sulfoxide), sonicate on an ultrasonic instrument for 1-2 min, and prepare a 5 mmol / L solution for later use;

[0056] (2) Different tumor cells and normal cells in the logarithmic growth phase (US Model Culture Collection) were collected at a density of 2 × 10⁻⁶. 4 Cells were seeded at 100 μL / well in 96-well plates and allowed to adhere for 24 hours. Then, 100 μL of different concentrations of the drug from step (1) were added to each well, and the plates were cultured for another 72 hours. After some cell damage was observed, 30 μL of MTT solution (5 mg / mL, PBS) was added to each well, and the plates were incubated for 3 hours. Next, the supernatant (DMEM high-glucose medium, Gibco) was removed from the 96-well plates, and 150 μL of DMSO (dimethyl sulfoxide) was added. The plates were gently shaken for 15 minutes to dissolve the purple crystals. The absorbance at 570 nm was measured using a multi-mode microplate reader, and cell viability was calculated. A graph was also plotted to determine the half-maximal inhibitory concentration (IC50). 50 Cell viability (%) = (OD) 570 Experimental group / OD 570 (Control group) × 100%.

[0057] Test results:

[0058] As shown in Table 1, miCy-Se exhibits significant inhibitory effects on most cancer cells, demonstrating strong toxicity, particularly against MDA-MB-231 cells, but exhibiting relatively low toxicity to normal cells. The drug shows high selectivity for both cancer and normal cells, and also demonstrates very high selectivity for the tested human cancer cells MDA-MB-231 and MCF-7, which exhibit differences in metastatic and invasiveness. Therefore, miCy-Se has significant research value for cancer treatment.

[0059] Table 1. MTT toxicity test results of miCy-Se on tumor cells and normal cells.

[0060]

[0061]

[0062] Experiment 6: Spatial localization and fluorescence imaging of selenium-containing small molecules loaded with fluorescent groups within cells.

[0063] Confocal conlocalization imaging was used to investigate the intracellular spatial localization and fluorescence imaging of miCy-Se. The steps are as follows:

[0064] MDA-MB-231 cells were seeded in laser confocal dishes and allowed to adhere for 24 hours. They were then incubated with mitochondrial tracking dye (mito tracker Deep Red) and lysosomal tracking dye (Lyso tracker green) for 30 minutes. After washing with PBS, they were incubated with miCy-Se for another 30 minutes. After washing with PBS, they were immediately photographed using a confocal microscope (LSM 710, Carl Zeiss, Göttingen, Germany).

[0065] Test results:

[0066] like Figure 4 In live cells, after co-treatment with commercially available specific mitochondrial deep red emission probes (MitoTracker Deep Red) and LysoTracker Green, the intensity change curves of bright red emission from miCy-OH and miCy-Se matched those of the purple fluorescence from MitoTracker Deep Red, indicating that miCy-Se has the ability to target mitochondria. Furthermore, clearly visible small tubular mitochondria were observed in images containing miCy-Se. However, the co-localization fluorescence intensity change curves of miCy-Se and the commercially available specific lysosomal green emission probe (LysoTracker GreenDND-26) showed low similarity, indicating that miCy-Se does not have the ability to target lysosomes. These results demonstrate that miCy-Se can specifically target mitochondria and can be used as a mitochondrial morphology imaging agent.

[0067] The above description is merely a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.

Claims

1. A selenium-containing small molecule loaded with a fluorescent group, characterized in that, It is prepared by the following reaction:

2. The method for preparing selenium-containing small molecules loaded with fluorescent groups according to claim 1, characterized in that, Includes the following steps: (1) Synthesis of PhSe; (2) Synthesis of miCy-OH; (3) Synthesis of miCy-Se: A mixture of compound PhSe, miCy-OH, 4-dimethylaminopyridine and 1-ethyl-(3-dimethylaminopropyl)carbodiimide was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature; the reaction was detected by TLC, the mixture was concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography to obtain the target compound miCy-Se.

3. The preparation method according to claim 2, characterized in that, In step (3), a mixture of 0.8-1.2 parts of compound PhSe, 0.4-0.6 parts of miCy-OH, 0.8-1.2 parts of 4-dimethylaminopyridine and 0.8-1.2 parts of 1-ethyl-(3-dimethylaminopropyl)carbodiimide is dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature; the above amounts are measured in moles.

4. The preparation method according to claim 2, characterized in that, The specific steps (1) include: mixing 3,4-diaminobenzoic acid and selenium dioxide in an aqueous solution, adding concentrated hydrochloric acid dropwise and stirring at room temperature, filtering the product, washing it with water and ethanol, and drying it under vacuum to obtain the compound PhSe.

5. The preparation method according to claim 4, characterized in that, In step (1), the molar ratio of 3,4-diaminobenzoic acid and selenium dioxide is 1:1 to 1-1.

2.

6. The preparation method according to claim 2, characterized in that, Step (2) specifically includes: First, 1,1,2-trimethyl-1H-benzo[e]indole and iodoethane are added to a round-bottom flask containing acetonitrile under nitrogen protection; the mixed solution is stirred and refluxed at a certain temperature; the solvent is removed by a rotary evaporator, and the crude product is washed multiple times with petroleum ether to obtain compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium; compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium and 6-hydroxy-2-naphthal are dissolved in EtOH, and then a small amount of piperidine is added dropwise; the mixture is heated and refluxed overnight; after the mixture is cooled to room temperature, the solvent is removed by a rotary evaporator, and the crude product is also removed by a rotary evaporator; the crude product is purified by silica gel rapid chromatography using dichloromethane / methanol as eluent to obtain yellow solid miCy-OH.

7. The preparation method according to any one of claims 2-6, characterized in that, Includes the following steps: (1) Synthesis of PhSe: 3,4-diaminobenzoic acid and selenium dioxide were mixed in an aqueous solution, and concentrated hydrochloric acid was added dropwise and stirred at room temperature for 2 hours. The product was filtered, washed with water and ethanol, and dried under vacuum to obtain the compound PhSe. (2) Synthesis of miCy-OH: First, 1,1,2-trimethyl-1H-benzo[e]indole and iodoethane were added to a round-bottom flask containing 10 mL of acetonitrile under nitrogen protection; the mixture was stirred and refluxed at 75 °C, and the reaction was monitored by TLC; the solvent was removed by rotary evaporator, and the crude product was washed several times with petroleum ether to obtain compound 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium, which did not require purification; 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium and 6-hydroxy-2-naphthal were dissolved in 20 mL of EtOH, and then a small amount of piperidine was added dropwise; the mixture was heated under reflux overnight; after cooling the mixture to room temperature, the solvent was removed by rotary evaporator, and the crude product was also removed by rotary evaporator; the crude product was purified by silica gel rapid chromatography with dichloromethane / methanol as eluent to obtain yellow solid miCy-OH; (3) Synthesis of miCy-Se: A mixture of compound PhSe, miCy-OH, 4-dimethylaminopyridine and 1-ethyl-(3-dimethylaminopropyl)carbodiimide was dissolved in anhydrous CH2Cl2 and stirred overnight at room temperature; the reaction was detected by TLC, the mixture was concentrated under reduced pressure, and the solid residue was purified by silica gel chromatography to obtain the target compound miCy-Se.

8. The use of the selenium-containing small molecule loaded with a fluorescent group as described in claim 1 in the preparation of antitumor drugs.

9. The use of the selenium-containing small molecule loaded with a fluorescent group as described in claim 1 in the preparation of a mitochondrial morphology developer.

Images