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CN-121796667-B - Antibacterial suture line for surgical suture and preparation method thereof

CN121796667BCN 121796667 BCN121796667 BCN 121796667BCN-121796667-B

Abstract

The invention belongs to the technical field of medical materials, and relates to an antibacterial suture line for surgical suturing and a preparation method thereof. The preparation method comprises the steps of dissolving 2-amino-5-acetylpyridine in hydrobromic acid glacial acetic acid solution, adding acetic acid solution containing bromine for reaction to obtain an intermediate 1, adding tetrahydrofuran into the intermediate 1, adding triethylamine and acetic anhydride for reaction to obtain an intermediate 2, adding thiourea into absolute ethyl alcohol for reaction to obtain an intermediate 3, adding p-nitrobenzaldehyde into absolute methyl alcohol into the intermediate 3, adding glacial acetic acid for reaction to obtain an intermediate 4, adding phosphorus oxychloride into N, N-dimethylformamide, adding the intermediate 4 for reaction to obtain an intermediate 5, dissolving the intermediate 5 in a mixed solvent, adding cystamine for reaction to obtain an antibacterial agent, soaking a medical silk suture in dimethyl sulfoxide dissolved with the antibacterial agent, and carrying out ultrasonic treatment, soaking, rinsing and drying to obtain the medical silk suture. The antibacterial suture line has the advantages of multi-mechanism synergistic enhanced antibacterial performance, environment response type active release mechanism and excellent interface affinity.

Inventors

  • ZHU DONGZHEN
  • DING DAWEI
  • Xu Chengchi
  • LIANG FUPING
  • ZHANG TIANYANG
  • TANG WEIWEI
  • SHI JIACHAO

Assignees

  • 上海天清生物材料有限公司

Dates

Publication Date
20260508
Application Date
20260311

Claims (10)

  1. 1. The preparation method of the antibacterial suture line for surgical suture is characterized by comprising the following steps: (1) Dissolving 2-amino-5-acetylpyridine in hydrobromic acid glacial acetic acid solution, cooling the reaction solution to 0-5 ℃, adding acetic acid solution containing bromine, and then heating to 40-50 ℃ for reacting for 2-3 hours to obtain an intermediate 1; (2) Adding the intermediate 1 obtained in the step (1) into tetrahydrofuran, adding triethylamine, uniformly stirring, cooling to 0-5 ℃, adding acetic anhydride, heating to 25-30 ℃ firstly, stirring for 2-3h, and then heating to 40-45 ℃ for reflux reaction for 1-2h to obtain an intermediate 2; (3) Adding the intermediate 2 obtained in the step (2) and thiourea into absolute ethyl alcohol, uniformly stirring, and heating to 78-80 ℃ for reflux reaction for 4-6h to obtain an intermediate 3; (4) Adding the intermediate 3 obtained in the step (3) and p-nitrobenzaldehyde into absolute methanol, adding glacial acetic acid, and heating to 65-68 ℃ for reflux reaction for 6-8h to obtain an intermediate 4; (5) Adding phosphorus oxychloride into N, N-dimethylformamide at 0-5 ℃, stirring for 30-40min, then adding the intermediate 4 obtained in the step (4), firstly stirring for 1-1.5h at 0-5 ℃, then heating to 80-90 ℃ and stirring for reacting for 5-7h to obtain an intermediate 5; (6) Dissolving the intermediate 5 obtained in the step (5) in a mixed solvent, adding cystamine, stirring for 30-40min at room temperature, heating to 50-60 ℃ and stirring for reacting for 12-16h to obtain an antibacterial agent; (7) Dissolving the antibacterial agent obtained in the step (6) in dimethyl sulfoxide to obtain an antibacterial impregnating solution, impregnating the medical silk suture in the antibacterial impregnating solution, carrying out ultrasonic vibration, soaking for 12-24h at 25-30 ℃, rinsing with sterile deionized water, and carrying out vacuum drying to obtain the medical silk suture.
  2. 2. The method for producing a surgical suture according to claim 1, wherein in the step (1), the ratio of the amount of 2-amino-5-acetylpyridine, the hydrobromic acid glacial acetic acid solution and the acetic acid solution containing bromine is 1mol:500-600mL:100mL, the ratio of the amount of bromine in the acetic acid solution containing bromine to the amount of acetic acid in the acetic acid solution containing bromine is 1.0-1.1mol:100mL, and the content of hydrobromic acid in the hydrobromic acid glacial acetic acid solution is 48wt%.
  3. 3. The method for producing a bacteriostatic suture line for surgical suture according to claim 1, wherein in the step (2), the amount ratio of the intermediate 1, tetrahydrofuran, triethylamine and acetic anhydride is 1mol:600-800ml:1.2-1.5mol:1.2-1.5mol.
  4. 4. The method for preparing a bacteriostatic suture line for surgical suture according to claim 1, wherein in the step (3), the dosage ratio of the intermediate 2, thiourea and absolute ethanol is 1mol:1.1-1.2mol:800-1000mL.
  5. 5. The method for producing a surgical suture according to claim 1, wherein in the step (4), the intermediate 3, p-nitrobenzaldehyde, absolute methanol, and glacial acetic acid are used in a ratio of 1mol:1.0 to 1.1mol:600 to 800mL:5 to 10mL.
  6. 6. The method for producing a bacteriostatic suture line for surgical suture according to claim 1, wherein in the step (5), the ratio of N, N-dimethylformamide, phosphorus oxychloride to intermediate 4 is 10-12mol:3.0-4.0mol:1mol.
  7. 7. The preparation method of the antibacterial suture line for surgical suture according to claim 1, wherein in the step (6), the mixed solvent is obtained by mixing absolute ethyl alcohol and chloroform in a volume ratio of 1:1, and the dosage ratio of the intermediate 5, the mixed solvent and cystamine is 2mol:1000mL:1.0-1.1mol.
  8. 8. The method for producing a surgical suture according to claim 1, wherein in the step (7), the ratio of the antimicrobial agent to dimethylsulfoxide is 1-2 g/100 ml.
  9. 9. The method for preparing the antibacterial suture line for surgical suture according to claim 1, wherein in the step (7), the ultrasonic vibration time is 15-30min, the vacuum drying temperature is 30-35 ℃ and the time is 6-8h.
  10. 10. A bacteriostatic suture for surgical suturing, characterized by being prepared according to the preparation method of any one of claims 1 to 9.

Description

Antibacterial suture line for surgical suture and preparation method thereof Technical Field The invention belongs to the technical field of medical materials, and particularly relates to an antibacterial suture line for surgical suturing and a preparation method thereof. Background Surgical sutures are special threads used for ligation hemostasis and suture hemostasis as well as tissue suturing in surgical operations or in trauma treatment, and generally fall into two general categories, absorbable threads and non-absorbable threads. At present, the high incidence of infection at the operation site is a main cause of slow wound recovery, operation failure and even life-threatening. However, the common medical surgical suture line has no antibacterial effect, and when the wound suture is infected by bacteria, the wound is easy to be festered and has even more serious consequences. Meanwhile, as the gaps of the common medical surgical suture line are easy to hide bacteria, the wound is more easily infected. Thus, studies on the antibacterial properties of suture are one of the main directions of functional medical suture. At present, antibacterial suture lines form local antibacterial barriers at suture positions by loading antibacterial agents such as silver nano particles, chitosan and the like on the surfaces of suture materials so as to reduce postoperative infection risks. However, the prior antibacterial agent still has unresolved problems in terms of antibacterial property, such as that bare silver nano particles are easily oxidized into silver oxide in the air, and meanwhile, the silver nano particles are easily fallen off, so that the antibacterial property of the suture is reduced, and degradation products of chitosan provide nutrition for bacterial reproduction, so that the antibacterial property of the suture is reduced. Therefore, further researches are still needed based on the durable antibacterial property of the suture, and the antibacterial suture for surgical suture is provided. Disclosure of Invention A first object of the present invention is to provide a bacteriostatic suture for surgical suture. The second aim of the invention is to provide a preparation method of the antibacterial suture line for surgical suture. In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: the invention provides a preparation method of an antibacterial suture line for surgical suture, which comprises the following steps: (1) Dissolving 2-amino-5-acetylpyridine in hydrobromic acid glacial acetic acid solution, cooling the reaction solution to 0-5 ℃, adding acetic acid solution containing bromine, and then heating to 40-50 ℃ for reacting for 2-3 hours to obtain an intermediate 1; (2) Adding the intermediate 1 obtained in the step (1) into tetrahydrofuran, adding triethylamine, uniformly stirring, cooling to 0-5 ℃, adding acetic anhydride, heating to 25-30 ℃ firstly, stirring for 2-3h, and then heating to 40-45 ℃ for reflux reaction for 1-2h to obtain an intermediate 2; (3) Adding the intermediate 2 obtained in the step (2) and thiourea into absolute ethyl alcohol, uniformly stirring, and heating to 78-80 ℃ for reflux reaction for 4-6h to obtain an intermediate 3; (4) Adding the intermediate 3 obtained in the step (3) and p-nitrobenzaldehyde into absolute methanol, adding glacial acetic acid, and heating to 65-68 ℃ for reflux reaction for 6-8h to obtain an intermediate 4; (5) Adding phosphorus oxychloride into N, N-dimethylformamide at 0-5 ℃, stirring for 30-40min, then adding the intermediate 4 obtained in the step (4), firstly stirring for 1-1.5h at 0-5 ℃, then heating to 80-90 ℃ and stirring for reacting for 5-7h to obtain an intermediate 5; (6) Dissolving the intermediate 5 obtained in the step (5) in a mixed solvent, adding cystamine, stirring for 30-40min at room temperature, heating to 50-60 ℃ and stirring for reacting for 12-16h to obtain an antibacterial agent; (7) Dissolving the antibacterial agent obtained in the step (6) in dimethyl sulfoxide to obtain an antibacterial impregnating solution, impregnating the medical silk suture in the antibacterial impregnating solution, carrying out ultrasonic vibration, soaking for 12-24h at 25-30 ℃, rinsing with sterile deionized water, and carrying out vacuum drying to obtain the medical silk suture. The invention synthesizes a novel sulfur-containing hybrid antibacterial agent with symmetrical double 1, 8-naphthyridine cores. Firstly, 2-amino-5-acetylpyridine is used as a starting material, thiazole groups with high electron cloud density are constructed through alpha-position bromination and thiourea condensation, then p-nitrobenzaldehyde is introduced to form a nitrobenzene Schiff base structure with potential redox activity, and then a Vilsmeier-Haack reaction is utilized for in-situ cyclization to generate a1, 8-naphthyridine skeleton containing chlorine and aldehyde groups, so that a multi-heterocycle high conj