A gemini quaternary ammonium salt type sulfur-containing polyester, and a preparation method and application thereof

Abstract

The application discloses a gemini quaternary ammonium salt type sulfur-containing polyester and a preparation method and application thereof, and relates to the technical field of polymers. The gemini quaternary ammonium salt type sulfur-containing polyester is prepared by the following steps: carrying out a substitution reaction on dimethylamino bisacrylate and a halogenated alkyl quaternary ammonium salt to obtain a gemini quaternary ammonium salt type bisacrylate; and carrying out a thiol-ene click polymerization reaction on the gemini quaternary ammonium salt type bisacrylate and an alkyl dithiol, so as to obtain the gemini quaternary ammonium salt type sulfur-containing polyester. The gemini quaternary ammonium salt type sulfur-containing polyester provided by the application has excellent inhibition and killing activities on helicobacter pylori, and has good blood compatibility and low cytotoxicity.

Description

Technical Field

[0001] This invention belongs to the field of sterilization technology, and particularly relates to a gemini quaternary ammonium salt type sulfur-containing polyester, its preparation method and application. Background Technology

[0002] Helicobacter pylori (Hp) is closely associated with a variety of gastrointestinal diseases, such as chronic gastritis, gastric ulcers, duodenal ulcers, and even gastric cancer.

[0003] Currently, antibiotics are the primary treatment for Helicobacter pylori infections. However, the widespread use of antibiotics has led to a significant increase in bacterial resistance and disrupts the balance of bacteria in the body, resulting in the simultaneous killing of beneficial bacteria. Therefore, developing quaternary ammonium salt-based antibacterial polymers that can kill Helicobacter pylori is of great significance.

[0004] However, there are few reports on quaternary ammonium salt-based antibacterial polymers that can effectively kill Helicobacter pylori in the human body, and currently, quaternary ammonium salt-based antibacterial polymers generally suffer from excessive toxicity. Therefore, it is of great significance to develop quaternary ammonium salt-based antibacterial polymers that can inhibit and kill Helicobacter pylori, counteract the side effects of long-term antibiotic use, and have good biocompatibility. Summary of the Invention

[0005] Based on the above-mentioned technical problems, the present invention provides a geminal quaternary ammonium salt type sulfur-containing polyester, its preparation method and application, which has excellent inhibitory and killing activity against Helicobacter pylori, and has good blood compatibility and low cytotoxicity.

[0006] The present invention proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: Where a is an integer from 2 to 10, b is an integer from 2 to 6, n is the degree of polymerization, which is an integer greater than 0, R1, R2, and R3 are independently hydrogen or saturated straight-chain alkyl groups of C1-C6, X is a halogen, and Y is a halogen, nitrate, tetrafluoroborate, hexafluorophosphate, or bis(trifluoromethanesulfonyl)imide ion.

[0007] Preferably, R1, R2, and R3 are methyl groups, X is Br, and Y is also Br.

[0008] Preferably, the sulfur-containing polyester has the following structural formula: or .

[0009] Preferably, the sulfur-containing polyester has the following structural formula: or .

[0010] The present invention also proposes a method for preparing the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester, comprising the following steps:

[0011] S1. A substitution reaction is carried out between dimethylaminodiacrylate and haloalkyl quaternary ammonium salt to obtain gemini quaternary ammonium salt type diacrylate.

[0012] S2. The gemini quaternary ammonium salt type diacrylate and alkyl dithiol are subjected to a mercapto-olefin click polymerization reaction to obtain the gemini quaternary ammonium salt type sulfur-containing polyester.

[0013] Preferably, in step S1, the haloalkyl quaternary ammonium salt is at least one selected from 2-bromoethyltrimethylammonium bromide, 3-bromopropyltrimethylammonium bromide, 4-bromobutyltrimethylammonium bromide, 5-bromopentyltrimethylammonium bromide, or 6-bromohexyltrimethylammonium bromide;

[0014] Preferably, the substitution reaction is carried out at a temperature of 50-70°C for a time of 18-36 hours.

[0015] Preferably, in step S2, the alkyl dithiol is at least one selected from 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, or 1,10-decanedithiol.

[0016] Preferably, the temperature of the mercapto-olefin click polymerization reaction is 40-60°C and the time is 6-24 hours.

[0017] Preferably, the reaction route of the sulfur-containing polyester is as follows: Where a is an integer from 2 to 10, b is an integer from 2 to 6, n is the degree of polymerization, which is an integer greater than 0, R1, R2, and R3 are independently hydrogen or saturated straight-chain alkyl groups of C1-C6, X is a halogen, and Y is a halogen, nitrate, tetrafluoroborate, hexafluorophosphate, or bis(trifluoromethanesulfonyl)imide ion.

[0018] The present invention also proposes the application of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester or the gemini quaternary ammonium salt type sulfur-containing polyester prepared by the above method in antibacterial agents or antibacterial drugs.

[0019] Preferably, the antibacterial agent or antimicrobial drug is used to kill Helicobacter pylori.

[0020] The beneficial effects of this invention are:

[0021] The gemini quaternary ammonium salt type sulfur-containing polyester described in this invention is a gemini quaternary ammonium salt type polymer containing ester groups and thioethers. Through the double cationic groups on the side chain and the unique thioether and ester bond groups on the main chain, it can effectively kill Helicobacter pylori while also rapidly degrading it, ultimately exhibiting good blood compatibility and low cytotoxicity.

[0022] On the one hand, because the positively charged groups in the gemini quaternary ammonium salt-type sulfur-containing polyester have a high density and are located on the periphery of the molecule, they can undergo strong electrostatic adsorption with the negatively charged Helicobacter pylori cell membrane. At the same time, the thioether groups of its main chain form strong van der Waals interactions with the peptidoglycan and peptide chains of the Helicobacter pylori cell wall skeleton structure, which enables the gemini quaternary ammonium salt-type sulfur-containing polyester molecules of the present invention to be rapidly adsorbed on the surface of the bacterial cell membrane and form defects in the cell's biphospholipid layer. On the other hand, the relatively small quaternary ammonium salts in the gemini quaternary ammonium salt-type sulfur-containing polyester of the present invention can become rigid structures, thereby easily penetrating the bacterial cell wall and forming large-sized pores after penetrating the Helicobacter pylori cell wall, which kills it in a short time. Attached Figure Description

[0023] Figure 1 The 1H NMR spectrum of the geminal quaternary ammonium salt diacrylate described in Example 1;

[0024] Figure 2 The image shows the effect of the geminal quaternary ammonium salt diacrylate in killing Helicobacter pylori as described in Example 1. Detailed Implementation

[0025] The present invention will now be described in detail through specific embodiments. However, these embodiments are clearly provided for illustrative purposes and are not intended to limit the scope of the present invention.

[0026] Example 1

[0027] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester includes the following steps:

[0028] (1) 3-Dimethylamino-1,2-propanediol (1.79 g, 15 mmol) and acryloyl chloride (3.62 g, 40 mmol) were dissolved completely in dichloromethane (200 mL), and then 4-dimethylaminopyridine (0.24 g, 2 mmol) was added as a catalyst. The mixture was stirred at 30 °C for 12 h, and the residual solvent was removed by vacuum distillation. The mixture was washed with diethyl ether and dried to obtain 3-dimethylaminodiacrylate.

[0029] (2) 3-Dimethylaminodiacrylate (2.27 g, 10 mmol) and 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol) were dissolved completely in ethanol (50 mL), heated to 80 °C and stirred under reflux for 24 h. After the reaction was completed, the residual solvent was removed by vacuum distillation, and then recrystallized three times with a mixture of ethanol / acetone to obtain a white solid, which is the Gemini quaternary ammonium salt type diacrylate. 1¹H NMR (400MHz, DMSO) δ 6.27 (dd, J=12.8, 6.4Hz, 2H), 6.07–6.03 (m, 2H), 5.57 (dd, J=8.9, 6.1Hz, 2H), 5.15 (t, J=8.5Hz, 1H), 4.53–4.48 (m, 1H), 4.29–4.23 (m, 1H), 3.62–3.51 (m, 1H), 3.36–3.24 (m, 20H), 2.23–2.11 (m, 2H); see details. Figure 1 ;

[0030] (3) The above-mentioned gemini quaternary ammonium salt type diacrylate (4.87 g, 10 mmol) and 1,4-butanedithiol (1.22 g, 10 mmol) were dissolved completely in N,N-dimethylacetamide (100 mL), and then triethylamine (0.2 g, 2 mmol) was added dropwise as a catalyst. The mixture was heated to 60 °C and stirred for 12 h. After the reaction was completed, acetone was added to precipitate the product, which was then filtered, washed with ethanol, and dried to obtain the gemini quaternary ammonium salt type sulfur-containing polyester; number average molecular weight M n It is 9600 g / mol; 1 H NMR (400MHz, DMSO) δ 5.17, 4.46, 4.21, 3.61, 3.35-3.30, 3.24, 2.83, 2.59, 2.44, 2.15, 1.65, 1.32-1.26.

[0031] Example 2

[0032] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (2), 2-bromoethyltrimethylammonium bromide (2.47 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 8700 g / mol; 1 HNMR (400MHz, DMSO) δ 5.18, 4.43, 4.18, 3.68-3.60, 3.31, 2.80, 2.62, 2.45, 1.64, 1.31-1.27.

[0033] Example 3

[0034] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,5-pentanedithiol (1.36 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 9800 g / mol; 1 H NMR (400MHz, DMSO) δ 5.18, 4.45, 4.20, 3.62, 3.35, 3.30-3.22, 2.82, 2.62, 2.44, 2.16, 1.63, 1.30-1.24.

[0035] Example 4

[0036] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 3, except that in step (2), 2-bromoethyltrimethylammonium bromide (2.47 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 9000 g / mol; 1 HNMR (400MHz, DMSO) δ 5.17, 4.43, 4.22, 3.67-3.61, 3.36, 3.32, 2.83, 2.61, 2.45, 1.65, 1.31-1.24.

[0037] Example 5

[0038] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,3-propanedithiol (1.08 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 9400 g / mol; 1 H NMR (400MHz, DMSO) δ5.16, 4.45, 4.20, 3.62, 3.37, 3.33-3.28, 2.82, 2.60, 2.44, 2.16, 1.63, 1.39-1.32.

[0039] Example 6

[0040] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,2-ethylenedithiol (0.94 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 10500 g / mol; 1 H NMR (400MHz, DMSO) δ5.17, 4.46, 4.21, 3.61, 3.35, 3.30-3.24, 2.83, 2.62, 2.45, 2.17, 1.38.

[0041] Example 7

[0042] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,6-hexanedithiol (1.50 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 8600 g / mol; 1 H NMR (400MHz, DMSO) δ 5.18, 4.45, 4.20, 3.62, 3.36, 3.30-3.24, 2.85, 2.64, 2.43, 2.16, 1.62, 1.41, 1.29-1.22.

[0043] Example 8

[0044] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,8-octanedithiol (1.78 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 8300 g / mol; 1 H NMR (400MHz, DMSO) δ 5.20, 4.48, 4.22, 3.64, 3.38, 3.30-3.26, 2.86, 2.64-2.62, 2.45, 2.19, 1.64, 1.43, 1.28-1.20.

[0045] Example 9

[0046] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (3), 1,10-decanedithiol (2.06 g, 10 mmol) is used instead of 1,4-butanedithiol (1.22 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 7900 g / mol; 1 H NMR (400MHz, DMSO) δ 5.18, 4.45, 4.20, 3.61, 3.35, 3.30-3.26, 2.83, 2.61, 2.44, 2.17, 1.63, 1.42, 1.31-1.26.

[0047] Example 10

[0048] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (2), 4-bromobutyltrimethylammonium bromide (2.75 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 9800 g / mol; 1 HNMR (400MHz, DMSO) δ 5.15, 4.43, 4.18, 3.62, 3.30-3.26, 2.81, 2.62, 2.43, 1.73, 1.62, 1.31-1.27.

[0049] Example 11

[0050] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (2), 5-bromopentyltrimethylammonium bromide (2.89 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 10100 g / mol; 1 HNMR (400MHz, DMSO) δ 5.17, 4.45, 4.20, 3.60, 3.31-3.27, 2.84, 2.62, 2.45, 1.67, 1.62, 1.30-1.25.

[0051] Example 12

[0052] This embodiment proposes a gemini quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned gemini quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (2), 6-bromohexyltrimethylammonium bromide (3.03 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the resulting gemini quaternary ammonium salt type sulfur-containing polyester is... n It is 11000 g / mol; 1 H NMR (400MHz, DMSO) δ 5.16, 4.46, 4.25, 3.62, 3.30-3.26, 2.85, 2.60, 2.41, 1.73, 1.63, 1.31-1.27.

[0053] Comparative Example 1

[0054] This comparative example presents a quaternary ammonium salt type sulfur-containing compound, the structural formula of which is shown below: The preparation method of the above-mentioned quaternary ammonium salt type sulfur-containing compound is based on the published patent CN111909069B.

[0055] Comparative Example 2

[0056] This comparative example presents a quaternary ammonium salt type sulfur-containing polyester, the structural formula of which is shown below: The preparation method of the above-mentioned quaternary ammonium salt type sulfur-containing polyester is the same as in Example 1, except that in step (2), 1-bromopropane (1.23 g, 10 mmol) is used instead of 3-bromopropyltrimethylammonium bromide (2.61 g, 10 mmol); the number-average molecular weight M of the obtained quaternary ammonium salt type sulfur-containing polyester is... n It is 9500 g / mol; 1 H NMR (400MHz, DMSO) δ 5.16, 4.42, 4.17, 3.62, 3.36-3.28, 2.79, 2.62, 2.43, 1.78, 1.61, 1.31-1.27, 0.91.

[0057] Performance testing:

[0058] Culture of Helicobacter pylori: The standard strain of Helicobacter pylori SS1 was revived on Columbia solid medium plates containing 5% sterile defibrinated sheep blood and cultured at 37°C under microaerobic conditions (5% O2, 10% CO2, 85% N2). After the bacteria had grown to the full extent on the medium plate, they were scraped off and resuspended in 0.85% physiological saline using a disposable sterile spreader in a clean bench, and then inoculated onto a new Columbia solid medium containing 5% sterile defibrinated sheep blood and cultured for 48 hours.

[0059] Determination of Minimum Inhibitory Concentration (MIC): Preparation of complete liquid culture medium (BHI): Fetal bovine serum (FBS) was added to BHI to achieve a final FBS concentration of 10%. The following experimental groups were established: blank control group (BHI culture medium), growth control group (BHI culture medium + *Helicobacter pylori*), negative control group (BHI culture medium + *Helicobacter pylori* + DMSO), positive control group (BHI culture medium + *Helicobacter pylori* + antibiotics / other quaternary ammonium salts), and test polymer group (BHI culture medium + *Helicobacter pylori* + gemini quaternary ammonium salt-containing sulfur-containing polyesters). The cultured *Helicobacter pylori* were resuspended in BHI culture medium, and the bacterial concentration was adjusted to 2 × 10⁻⁶. 6 CFU / mL; Under aseptic conditions, the polyesters or compounds described in the examples and comparative examples were dissolved in dimethyl sulfoxide (DMSO) to achieve test concentrations ranging from 0 to 200 μg / mL, for a total of 10 concentration gradients; 50 μL of the above bacterial suspension and 50 μL of the above polyester or compound solution were added to each well of a 96-well plate, and the 96-well plate was incubated at 37°C under microaerobic conditions (5% O2, 10% CO2, 85% N2) with shaking at 150 rpm for 72 h. The experiment was repeated 3 times; the 96-well plate was removed, and the colony growth was photographed and recorded. The minimum drug concentration at which Helicobacter pylori growth was not observed was determined as the MIC of the test polyester or compound against Helicobacter pylori. The results are shown in Table 1.

[0060] Determination of Minimum Bacterial Combat Concentration (MBC): After the MIC determination, 50 μL of culture medium from micro-dilution wells where bacterial growth was not visible to the naked eye was inoculated onto Columbia agar plates containing 5% sterile defibrinated sheep blood. Results were observed after 72 hours of incubation. The experiment was repeated three times. The minimum drug concentration that could reduce bacterial concentration by four orders of magnitude, i.e., the minimum drug concentration that killed more than 99.99% of bacteria in the experimental group compared to the untreated control group, was defined as the MBC. Results are shown in Table 1; specific bactericidal effect diagrams are shown below. Figure 2 ;

[0061] Table 1. MIC and MBC of the polyesters or compounds described in the Examples and Comparative Examples against Helicobacter pylori.

[0062]

[0063] As shown in Table 1 above, the polyesters described in this invention can effectively inhibit the growth of Helicobacter pylori and can be used to prevent and / or treat Helicobacter pylori infection and related diseases. Furthermore, compared to other compounds, polyesters I-1, I-2, II-1, and II-2 exhibit the best inhibitory activity against Helicobacter pylori, comparable to positive control drugs, and can be used to prepare anti-Helicobacter pylori drugs or as lead compounds for the development of anti-Helicobacter pylori drugs.

[0064] Determination of MIC (pH=3) and MBC (pH=3) under acidic conditions: Bacterial culture was performed as above, except that the Columbia solid medium containing 5% sterile defibrinated sheep blood was adjusted to pH 3.0 with concentrated hydrochloric acid; the determination of MIC was performed as above, except that the complete culture medium containing 10% BHI was adjusted to pH approximately 3.0 with concentrated hydrochloric acid; the determination of MBC was performed as above, except that the Columbia solid medium containing 5% sterile defibrinated sheep blood was adjusted to pH approximately 3.0 with concentrated hydrochloric acid; the results are shown in Table 2.

[0065] Table 2. MIC and MBC of the polyesters or compounds described in the Examples and Comparative Examples against Helicobacter pylori under acidic conditions.

[0066]

[0067] As shown in Table 2 above, the polyester described in this invention still has a good effect on killing Helicobacter pylori under acidic conditions.

[0068] Hemolytic performance test: The polyester described in the example was dissolved in PBS to obtain the test sample; 2.5 mL of fresh healthy rabbit blood was taken, centrifuged at 2000 r / min for 10 min, the supernatant was removed, and the red blood cells at the bottom were washed three times with PBS buffer solution as described above. Finally, 10 mL of PBS buffer solution was added to obtain a red blood cell suspension. The test sample was diluted with PBS buffer solution to prepare solutions of different concentration gradients. The negative control group was set with PBS buffer solution, and the positive control group was set with aqueous solution. The prepared red blood cell suspension and the above test sample were placed in 10 mL centrifuge tubes and cultured at room temperature. The OD value at 540 nm was detected by an ELISA reader to test the polyester concentration corresponding to a 10% hemolysis rate when the red blood cells were treated. The results are shown in Table 3.

[0069] Table 3 Results of hemolytic performance test

[0070]

[0071] As shown in Table 3 above, the polyester described in this invention has good blood compatibility and low cytotoxicity.

[0072] The above description is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any equivalent substitutions or modifications made by those skilled in the art within the scope of the technology disclosed in the present invention, based on the technical solution and inventive concept of the present invention, should be covered within the scope of protection of the present invention.

Claims

1. A gemini quaternary ammonium salt type sulfur-containing polyester, characterized in that, Its structural formula is shown below: Where a is an integer from 2 to 10, b is an integer from 2 to 6, n is the degree of polymerization, which is an integer greater than 0, R1, R2, and R3 are independently hydrogen or saturated straight-chain alkyl groups of C1-C6, X is a halogen, and Y is a halogen; the number average molecular weight of the sulfur-containing polyester is 7900-11000 g / mol.

2. The gemini quaternary ammonium salt type sulfur-containing polyester according to claim 1, characterized in that, R1, R2, and R3 are methyl groups, X is Br, and Y is also Br.

3. The gemini quaternary ammonium salt type sulfur-containing polyester according to claim 1 or 2, characterized in that, The structural formula of the sulfur-containing polyester is shown below: or .

4. The gemini quaternary ammonium salt type sulfur-containing polyester according to claim 1 or 2, characterized in that, The structural formula of the sulfur-containing polyester is shown below: or .

5. A method for preparing the gemini quaternary ammonium salt type sulfur-containing polyester according to any one of claims 1-4, characterized in that, Includes the following steps: S1. A substitution reaction is carried out between dimethylaminodiacrylate and haloalkyl quaternary ammonium salt to obtain gemini quaternary ammonium salt type diacrylate. S2. The gemini quaternary ammonium salt type diacrylate and alkyl dithiol are subjected to a mercapto-olefin click polymerization reaction to obtain the gemini quaternary ammonium salt type sulfur-containing polyester.

6. The method for preparing the gemini quaternary ammonium salt type sulfur-containing polyester according to claim 5, characterized in that, In step S1, the haloalkyl quaternary ammonium salt is at least one of 2-bromoethyltrimethylammonium bromide, 3-bromopropyltrimethylammonium bromide, 4-bromobutyltrimethylammonium bromide, 5-bromopentyltrimethylammonium bromide, or 6-bromohexyltrimethylammonium bromide; The substitution reaction is carried out at a temperature of 50-70°C for 18-36 hours.

7. The method for preparing the gemini quaternary ammonium salt type sulfur-containing polyester according to claim 5 or 6, characterized in that, In step S2, the alkyl dithiol is at least one of 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, or 1,10-decanedithiol. The temperature of the mercapto-olefin click polymerization reaction is 40-60℃, and the time is 6-24h.

8. The method for preparing the gemini quaternary ammonium salt type sulfur-containing polyester according to claim 5, characterized in that, The reaction route of the sulfur-containing polyester is shown below: Where a is an integer from 2 to 10, b is an integer from 2 to 6, n is the degree of polymerization, which is an integer greater than 0, R1, R2, and R3 are independently hydrogen or saturated straight-chain alkyl groups of C1-C6, X is a halogen, and Y is a halogen; the number average molecular weight of the sulfur-containing polyester is 7900-11000 g / mol.

9. The use of a gemini quaternary ammonium salt type sulfur-containing polyester according to any one of claims 1-4 or a gemini quaternary ammonium salt type sulfur-containing polyester prepared by the preparation method according to any one of claims 5-8 in the preparation of an antibacterial agent.

10. The application of the gemini quaternary ammonium salt type sulfur-containing polyester according to claim 9 in the preparation of antibacterial agents, characterized in that, The antibacterial agent is used to kill Helicobacter pylori.

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