CN119034016A

CN119034016A - Drainage tube for glaucoma treatment and preparation method thereof

Info

Publication number: CN119034016A
Application number: CN202411540967.9A
Authority: CN
Inventors: 王宁利; 王克敏; 任冬妮
Original assignee: Mingche Biotechnology Suzhou Co ltd
Current assignee: Mingche Biotechnology Suzhou Co ltd
Priority date: 2024-10-31
Filing date: 2024-10-31
Publication date: 2024-11-29
Anticipated expiration: 2044-10-31
Also published as: CN119034016B

Abstract

The present invention relates to the technical field of medical devices, and in particular to a drainage tube for treating glaucoma and a preparation method thereof. The drainage tube has a tubular structure and is prepared by aldehyde-amine condensation cross-linking reaction of component A and component B; the component A is a substance containing multiple amino groups; the component B is a dialdehyde structure; and the multiple amino substances include an amino-containing polymer matrix and a uracil-based macromolecule. The drainage tube for treating glaucoma provided by the present invention is based on gelatin, and homemade uracil-based macromolecules are added to the aldehyde-amine condensation cross-linking to form; on the one hand, the cross-linking reaction of the amino group and the aldehyde group is a controllable reaction, and the product is highly designable; on the other hand, the prepared drainage tube for treating glaucoma has no small molecule residues, and has good anti-fibroblast proliferation effect and anti-cell adhesion performance, and has a good drainage and filtration effect; and the preparation raw materials are easily available substances, which have the advantages of safety and non-toxicity.

Description

Drainage tube for glaucoma treatment and preparation method thereof

Technical Field

The invention relates to the technical field of medical equipment, in particular to a drainage tube for treating glaucoma and a preparation method thereof.

Background

Glaucoma is a type of optic nerve damage disease caused by pathological ocular hypertension, and control of intraocular pressure is the primary means of treating glaucoma. Most glaucoma diseases in clinic can be treated by implantation of a drainage device, which can achieve ocular hypotensive effect and controlled treatment of glaucoma.

Glaucoma drainage tubes are tubular structures that can be implanted minimally invasively, with an outer diameter of only 100-900 μm and an inner diameter of 10-100 μm, and are generally very thin and flexible and resilient to allow aqueous humor to be drained from the eye. The existing drainage tube is mostly prepared by adopting natural polymer materials.

However, when the drainage tube prepared from the natural polymer material is implanted into the body for a long time, the drainage tube is easy to be blocked due to the proliferation of the post-operation ciliated cells, so that the drainage tube is invalid.

Disclosure of Invention

The invention aims to solve the problem that a drainage tube for treating glaucoma fails due to blockage of the drainage tube caused by hyperplasia of fiber cells in the long-term use process in the prior art, and provides the drainage tube for treating glaucoma, which is prepared by aldol amine condensation.

The technical scheme adopted for solving the technical problems is as follows:

A drainage tube for treating glaucoma, which is in a tubular structure;

The drainage tube for treating glaucoma is prepared from a component A and a component B through aldehyde-amine condensation crosslinking reaction;

the component A is a polyamino substance;

The component B is dialdehyde group structure, and

The polyamino substance comprises an amino-containing macromolecule matrix and uracil-based macromolecules;

The uracil-based macromolecule is prepared according to the following method:

S11, ring-opening reaction is carried out on an epoxy ring-opening agent containing uracil structure and epoxy containing acryloyloxy to obtain an intermediate product I;

S12, carrying out free radical polymerization reaction on a vinyl silane coupling agent, unsaturated quaternary ammonium salt and acrylamide to obtain an intermediate product II;

S13, carrying out hydrolysis-coupling reaction on the intermediate product I and the intermediate product II to obtain an intermediate product III;

s14, carrying out Michael addition reaction on the intermediate product III and the polyamino structure to obtain the uracil-based macromolecule.

Optionally, the epoxy ring-opening agent containing uracil structure is uracil containing amino or uracil containing carboxyl.

Alternatively, the amino-containing uracil is 4-aminouracil.

Optionally, the uracil containing carboxyl is orotic acid.

Optionally, the epoxy containing acryloyloxy group is selected from at least one of glycidyl methacrylate and (glycidoxy) ethyl methacrylate.

Optionally, in step S11, the amount of the epoxy ring-opening agent containing uracil structure and the amount of the epoxy containing acryloyloxy group are added according to a molar ratio of 1:1 of the epoxy ring-opening agent to the epoxy group.

Optionally, the unsaturated quaternary ammonium salt is methacryloyloxyethyl trimethyl ammonium chloride.

Optionally, in the step S12, the molar ratio of the vinyl silane coupling agent, the unsaturated quaternary ammonium salt and the acrylamide is (0.2-0.4): 0.2-0.3): 0.3-0.6.

Optionally, the amino function number of the polyamino structure in step S14 is not less than 2.

Optionally, in the polyamino substance, the mass ratio of the amino-containing polymer matrix to the uracil-based macromolecule is 100 (3-5).

Optionally, the dialdehyde group structure is a linear fatty aldehyde, and the number of carbon atoms of the linear fatty aldehyde is 4-8.

Another object of the present invention is to provide a method for preparing the drainage tube for glaucoma treatment as described above, comprising the steps of:

S1, dissolving the component A according to the formula amount, removing bubbles, adding the component A into a die, standing for 6-10h, and cooling to obtain a primary drainage tube;

s2, preparing a B component organic solution according to the formula amount;

S3, placing the primary drainage tube in the B-component organic solution according to the formula amount, and carrying out oscillation reaction to obtain a crosslinked drainage tube;

s4, performing alkaline washing and vibration dialysis on the crosslinked drainage tube, and preserving at a low temperature to obtain the drainage tube for treating glaucoma.

The beneficial effects of the invention are as follows:

The drainage tube for treating glaucoma provided by the invention takes gelatin as a main body, and self-made uracil-based macromolecules and an aldehyde structure are added to carry out aldehyde-amine condensation crosslinking to form the drainage tube, on one hand, the crosslinking reaction of amino groups and aldehyde groups is a controllable reaction, the designability of products is strong, on the other hand, the prepared drainage tube for treating glaucoma has no small molecule residues, has good anti-ciliated cell proliferation effect and anti-cell adhesion performance, has good drainage and filtration effects, and has the advantages of easily obtained raw materials, strong operability, safety, no toxicity and the like.

Drawings

The invention will be further described with reference to the drawings and examples.

FIG. 1 is an infrared spectrum of intermediate I in example 1 of the present invention;

FIG. 2 is an infrared spectrum of intermediate II in example 1 of the present invention;

FIG. 3 is an infrared spectrum of intermediate III in example 1 of the present invention;

FIG. 4 is an infrared spectrum of uracil-based macromolecules in example 1 of the present invention.

Detailed Description

The present invention will now be described in further detail. The embodiments described below are exemplary and intended to illustrate the invention and should not be construed as limiting the invention, as all other embodiments, based on which a person of ordinary skill in the art would obtain without inventive faculty, are within the scope of the invention.

The drainage tube is implanted in the body for a long time, and besides the phenomenon that the drainage tube is blocked by the proliferation of the fibroblast after operation, cells in tissue fluid are adhered to the drainage tube, so that the filtration effect of the drainage tube is poor and the drainage tube is invalid finally. In addition, the raw materials are required to be safe, nontoxic and free of anaphylactic reaction, and the release of small molecules in the synthetic materials is required to be avoided by strict control. Currently, 2 means are generally adopted for solving the problem of small molecule release in synthetic materials, and the purpose of the method is to make small molecules large molecules. The first method is to use reactive functional small molecules to cure simultaneously in the material forming process, but the small molecules cannot react completely and remain, and unreacted small molecules are removed in the soaking and dialysis processes. The method has larger demand for the reactive small molecules and larger waste in cost. The other means is that the reactive functional small molecules are polymerized to form macromolecules, then are blended with the matrix, and finally are solidified. In this method, there are few small molecules left, but functional structures and matrix-forming chain entanglement cannot be effectively developed.

Gelatin (Gelatin), on the other hand, is a water-soluble protein obtained by partial degradation of collagen from animal skin, bone and other connective tissues, and also has a large amount of residual amino groups present. It is widely used in the medical field for its biodegradability, good biocompatibility and film forming properties. The preparation of the drainage tube by condensing and crosslinking gelatin and aldehyde groups through aldehyde amine has unique advantages, but the drainage tube also has the problems of cell proliferation and cell adhesion after operation affecting drainage efficiency.

Based on the above, in order to solve the problem that the drainage tube for glaucoma treatment in the prior art fails due to the blockage of the drainage tube by fibroblast proliferation in the long-term use process, the invention provides the drainage tube for glaucoma treatment, which is in a tubular structure, wherein the drainage tube for glaucoma treatment is prepared from an A component and a B component through aldehyde-amine condensation crosslinking reaction, the A component is specifically a polyamino-containing substance, the B component is in a dialdehyde structure, the polyamino substance comprises an amino-containing polymer matrix and a uracil-based polymer, the amino-containing polymer matrix specifically preferably comprises gelatin and at least one of chitosan and polyamino acid, and further preferably comprises 0-10wt% of an amino-containing polymer matrix, wherein 0wt% of chitosan and/or polyamino acid is not added.

The preferred uracil-based macromolecules of the present invention are prepared as follows:

s13, performing hydrolysis-coupling reaction on the intermediate product I and the intermediate product II to obtain an intermediate product III;

The preparation flow of the uracil-based macromolecule is as follows, and it should be noted that the preparation flow is only referred to as a reference, and does not limit the invention:

;

Wherein x, y and z are natural numbers greater than 1.

The uracil-based macromolecule is used as one of raw materials of a drainage tube for glaucoma treatment, and comprises uracil, silane, quaternary ammonium salt, amino and amido structures, wherein the uracil-based macromolecule comprises the uracil structure, the uracil-based macromolecule can prevent cell division, has an excellent antimetabolite effect, can reduce scar formation at a postoperative operation position and improve drainage filtration effect, the silane structure has low atomic surface energy, can reduce cell adhesion on one hand, can enable macromolecules to migrate to an interface and enrich the interface (inner wall and outer wall) to further improve the drainage filtration effect on the other hand, the silane is of a flexible chain structure and has certain flexibility, the quaternary ammonium salt structure is of a broad-spectrum antibacterial structure and has excellent broad-spectrum antibacterial property, the amino group can serve as a reaction site to react with an aldehyde-based cross-linking agent, is bonded into a system, further fixes the size of the drainage tube and improves safety reliability, the amino group and the quaternary ammonium salt have excellent hydrophilicity, the silane structure can be compensated for water repellency and the drainage filtration performance can be improved, and the sixth macromolecular structure is of structures such as polyamino, the amido and the amino group and the like, and the amino group and the like are similar to gelatin, and have a uniform transition layer with main resin in the migration process, so that defects are avoided.

Specifically, the epoxy ring-opening agent in the step S11 is preferably of an amino or carboxyl structure, namely the epoxy ring-opening agent containing uracil structure is amino-containing uracil or carboxyl-containing uracil, further preferably of 4-amino uracil, and preferably of orotic acid.

In the present invention, the epoxy group containing an acryloyloxy group in step S11 is preferably at least one selected from glycidyl methacrylate and (glycidoxy) ethyl methacrylate.

In order to achieve both the performance and the economical efficiency of the drainage tube for glaucoma treatment, the epoxy ring-opening agent containing uracil structure and the epoxy containing acryloyloxy group in step S11 are preferably added in a molar ratio of 1:1.

Specifically, step S11 may be performed as follows:

S11, adding an epoxy ring-opening agent containing uracil structure, epoxy containing acryloyloxy and hydroquinone into tetrahydrofuran in a dark place, reacting for 6-24 hours at 25-70 ℃, cooling to room temperature, adding deionized water A, oscillating, adding ethyl acetate for extraction, taking an organic phase, drying with anhydrous sodium sulfate A, filtering, taking filtrate, distilling under reduced pressure, and drying in vacuum at 40 ℃ for 12 hours to obtain an intermediate product I.

The epoxy ring-opening agent containing uracil structure, epoxy containing acryloyloxy, tetrahydrofuran, deionized water A, ethyl acetate and anhydrous sodium sulfate A are preferably added according to the dosage ratio of 0.1mol:0.1mol:200mL:300mL:600mL:5g, and the dosage of hydroquinone is 0.1wt% of the mass of the epoxy containing acryloyloxy.

In the step, the amino ring-opening agent and the carboxyl ring-opening agent, namely the uracil containing amino and the uracil containing carboxyl can carry out ring-opening reaction with epoxy groups, but the reaction conditions are slightly different, the amino ring-opening agent is generally used at room temperature, a catalyst can be added or not, and the carboxyl ring-opening agent generally needs to be added with the catalyst (preferably tetrabutylammonium bromide is used as the catalyst) and needs a certain temperature. The other raw material of the reaction is epoxy containing acryloyloxy, and when an amino ring-opening agent is used, the amino group and the epoxy group can simultaneously carry out ring-opening reaction and Michael addition reaction of the amino group and the acryloyloxy, but the activity of the ring-opening reaction of the epoxy is higher, and under the same condition, the amino group and the epoxy can carry out ring-opening reaction preferentially.

The vinyl silane coupling agent in the step S12 is preferably at least one selected from KH151, KH171 and KH172, and is preferably KH171, the unsaturated quaternary ammonium salt is preferably methacryloxyethyl trimethyl ammonium chloride, and the molar ratio of the vinyl silane coupling agent, the unsaturated quaternary ammonium salt and the acrylamide in the step S12 is preferably (0.2-0.4): 0.2-0.3): 0.3-0.6.

Specifically, this step S12 may be performed as follows:

S12, adding a vinyl silane coupling agent, unsaturated quaternary ammonium salt, acrylamide and an initiator Azodiisobutyronitrile (AIBN) into N, N-dimethylformamide, heating to 80-90 ℃, stirring for 6-10h, and carrying out reduced pressure distillation and vacuum drying at 60 ℃ for 6h after the reaction is finished to obtain an intermediate product II.

The invention aims to properly reduce the molecular weight of a target product, and a target product with lower molecular weight is favorable for improving the interface enrichment efficiency of the target product, and meanwhile, the problem of small molecular residues is avoided. In the invention, the molecular weight of the target product is preferably 10000-20000, and the molecular weight distribution PDI is 2.0-2.5.

Step S13 in the present invention may be performed as follows:

S13, adding the intermediate product I and the intermediate product II into an ethanol water solution, adding acetic acid to adjust the pH value to 4.5-5.5, stirring for 2-4 hours at room temperature, and then carrying out reduced pressure distillation and vacuum drying at 60 ℃ for 8 hours to obtain an intermediate product III.

Wherein the dosage ratio of the intermediate product I to the ethanol aqueous solution is 0.1mol:500mL, the dosage ratio of the intermediate product I to the intermediate product II is added according to the mol ratio of hydroxyl to the vinyl silane coupling agent of 1:1, and the ethanol content in the ethanol aqueous solution is 95wt%.

The amino group number of the polyamino structure in the step S14 is preferably more than or equal to 2, the amino group number of the intermediate product III is at least 1 more than the acryloyloxy group number, so that the intermediate product III and the target product still have reactivity, the polyamino structure can be a diamine structure, a triamine structure or a tetramine structure, specifically, the diamine structure is preferably at least one selected from isophorone diamine, p-phenylenediamine, o-phenylenediamine, m-phenylenediamine, cyclohexane diamine, ethylenediamine, propylene diamine, tetramethylene diamine, pentylene diamine, hexamethylenediamine and 1, 12-diaminododecane, the diamine structure is preferably isophorone diamine, the triamine structure is preferably at least one selected from 1,2, 3-propanetriamine, melamine, 1,3, 5-triphenylamine, and the tetramine structure is preferably quaternary pentylamine.

Step S14 in the present invention may be performed as follows:

S14, adding the polyamino structure into N, N-dimethylformamide A, adding an intermediate product III into N, N-dimethylformamide B, placing in a constant pressure dropping funnel, slowly dropping at room temperature, stirring, continuing stirring for 2-4h after dropping, filtering, distilling under reduced pressure, and vacuum drying at 40 ℃ for 8h to obtain a target product, namely uracil-based macromolecules.

Preferably, in this step, the ratio of the amount of polyamino structure to N, N-dimethylformamide A, N to the amount of N-dimethylformamide B is 0.1 mol/300 mL/100 mL, and the ratio of the amount of intermediate III to the amount of polyamino structure is added in a molar ratio of acryloyloxy to polyamino structure of 1:1.

The uracil-based macromolecule prepared by the invention firstly reduces the residual risk of small molecules by a structure with a certain molecular weight, and then further solves the residual problem of the small molecules by molecular structure design and aldehyde-amine condensation reaction.

In order to achieve compatibility and drainage and filtration effects of the drainage tube for treating glaucoma, the mass ratio of the amino-containing polymer matrix to the uracil-based macromolecule in the polyamino substance is preferably 100 (3-5).

In order to achieve the mechanical properties and comfort of the drainage tube for treating glaucoma, the dialdehyde group structure is preferably linear fatty aldehyde, and the carbon number of the linear fatty aldehyde is preferably 4-8. If the number of carbon atoms is less than 4, the crosslinking reaction is insufficient or the crosslinking density is high, the brittleness of the material is high, and if the number of carbon atoms is more than 8, the crosslinking density is low and the toughness of the material is poor. In addition, the aromatic aldehyde, alicyclic aldehyde and multi-branched dialdehyde have larger steric hindrance, so that the diffusion efficiency is influenced, and the production efficiency is influenced.

In particular, the preferred dialdehyde-based structure of the present invention comprises glutaraldehyde, and may further comprise at least one of succinaldehyde, adipaldehyde, pimelic aldehyde, suberaldehyde, 2-methylpentanediol.

In summary, the invention aims to develop a drainage tube with anti-cell proliferation, anti-cell adhesion and no small molecule residue aiming at the defects of the existing drainage tube for treating glaucoma. The method is realized by designing an anti-cell proliferation structure with a certain molecular weight, taking uracil as a main raw material, having excellent anti-cell proliferation effect, and combining the low atomic surface energy of silicon element, the antibacterial effect of quaternary ammonium salt and the water-solubility characteristic of acrylamide to prepare the functional monomer with anti-cell proliferation, migration, antibacterial and water-solubility macromolecules. The theoretical basis of the realization is that the ring-opening reaction of carboxyl/amino and epoxy, the free radical polymerization of carbon-carbon double bond, the coupling reaction of hydroxyl and silane and the Michael addition reaction of acryloyloxy and amino. The uracil-based macromolecule prepared through the reaction is added into a component mainly containing gelatin, and the characteristic of low-temperature solidification of the gelatin is utilized, and the cross-linking and shaping are carried out on the solidified uracil-based macromolecule and the component mainly containing aldehyde groups to obtain the drainage tube for treating glaucoma. On one hand, the drainage tube solves the problems of cell proliferation and cell adhesion, has no small molecule residue, and has strong designability of aldehyde-amine condensation reaction represented by gelatin and glutaraldehyde, thereby having practical operation significance.

Another object of the present invention is to provide a method for manufacturing a drainage tube for glaucoma treatment, the method comprising the steps of:

s2, preparing a B component organic solution according to the formula amount;

S3, placing the primary drainage tube in the organic solution of the component B according to the formula amount, and carrying out oscillation reaction to obtain a crosslinked drainage tube;

Specifically, the preparation method can be carried out according to the following procedures:

s1, adding the component A into Phosphate Buffer (PBS) solution, heating to 55 ℃, stirring until the component A is completely dissolved, performing ultrasonic deaeration and bubble removal, maintaining the temperature, injecting the component A solution into a mold, standing for 2-4h, slowly cooling to 4 ℃, and taking out the molded material to obtain a primary drainage tube;

wherein the dosage ratio of the component A to the PBS solution is (20-30) g to 100mL;

s2, adding the aqueous solution of the component B into acetonitrile, adding a solid moisture desiccant, sealing and drying for 0.5h, and filtering to obtain an organic solution of the component B;

Wherein the dosage ratio of the aqueous solution of the component B, acetonitrile and the solid moisture desiccant is (10-20) mL (480-490) mL, 100g;

the concentration (w/v) of the aqueous solution of the component B is 50%;

S3, placing the primary drainage tube in the B-component organic solution, controlling the temperature to be 25 ℃, and carrying out oscillation reaction for 15-24 hours to obtain a crosslinked drainage tube;

s4, placing the crosslinked drainage tube in a dialysis solution at the temperature of between 2 and 4 hours and 37 ℃ for oscillating dialysis for 18 to 24 hours, changing the dialysis solution every 4 hours during the period, and preserving at the temperature of between 0 and 8 ℃ to obtain a final product, namely the drainage tube for treating glaucoma;

the dialysate is physiological saline or PBS solution, and physiological saline is preferable.

The preparation method of the drainage tube for treating glaucoma takes gelatin as a main body, and self-made uracil-based macromolecules and aldehyde-based structures are added to carry out aldehyde-amine condensation crosslinking to form the drainage tube, on one hand, the crosslinking reaction of amino groups and aldehyde groups is controllable, the designability of products is strong, on the other hand, the preparation method can enable uracil-based macromolecules to effectively migrate, meanwhile, chain entanglement of the macromolecule structures is not separated, good performance is formed, raw materials adopted by the preparation method are all biological materials or common raw materials, and the drainage tube has excellent biocompatibility, no small molecule residues, safety and no toxicity.

In order that the above objects, features and advantages of the invention will be readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.

In the following examples and comparative examples, gelatin was commercially available gelatin of animal origin, and the degree of deacetylation of chitosan was not less than 95%, unless otherwise specified.

Example 1

A method for preparing uracil-based macromolecules, comprising the following steps:

S11, adding orotic acid, tetrabutylammonium bromide, glycidyl methacrylate and hydroquinone into tetrahydrofuran in a dark place, reacting for 20 hours at 70 ℃, cooling to room temperature, adding deionized water A, oscillating, adding ethyl acetate for extraction, taking an organic phase, drying with anhydrous sodium sulfate A, filtering, taking filtrate, distilling under reduced pressure, and drying in vacuum at 40 ℃ for 12 hours to obtain an intermediate product I.

Wherein, the dosage ratio of the orotic acid, tetrabutylammonium bromide, glycidyl methacrylate, tetrahydrofuran, deionized water A, ethyl acetate and anhydrous sodium sulfate A is added according to the ratio of 0.1mol to 0.01mol to 0.1mol to 200mL to 300mL to 600mL to 5 g;

the hydroquinone was used in an amount of 0.1% by weight based on the mass of glycidyl methacrylate.

The infrared spectrum of the intermediate product I is shown in FIG. 1, and the infrared data is shown as follows, 3558cm ^-1, in which-OH exists; 1752cm ^-1, -c=o (carboxyl) is absent; 1735cm ^-1, -c=o (ester group) present; 1676cm ^-1 -C=O (amide) present, 1612cm ^-1 -C=C- (pyrimidine) present, 1555cm ^-1 -NH- (amide) present, 1263cm ^-1、893cm^-1、825cm^-1 -epoxy absent, 1604cm ^-1、811cm^-1 -C=C-present.

S12, adding a silane coupling agent KH171, methacryloxyethyl trimethyl ammonium chloride, acrylamide and an initiator AIBN into N, N-dimethylformamide, heating to 85 ℃, stirring for 8.5 hours, carrying out reduced pressure distillation after the reaction is finished, and carrying out vacuum drying at 60 ℃ for 6 hours to obtain an intermediate product II #)。

Wherein the dosage ratio of the silane coupling agent KH171 to the methacryloxyethyl trimethyl ammonium chloride to the acrylamide to the N, N-dimethylformamide is 0.3mol:0.25mol:0.45mol:500mL;

the initiator AIBN was used in an amount of 4.5% by weight of the total mass of the monomers.

The infrared spectrum of the intermediate product II is shown in FIG. 2, and the infrared data is shown as follows, 3324cm ^-1: -NH-exists; 1735cm ^-1, -c=o (ester group) present; 1683cm ^-1, -c=o (amide) present; 1615cm ^-1 -C=C-is absent, 1558cm ^-1 -NH- (amide) is present, 1109 cm ^-1、798cm^-1 -Si-O-is present.

S13, adding the intermediate product I and the intermediate product II into an ethanol water solution, adding acetic acid to adjust the pH value to 5.0, stirring for 2.5 hours at room temperature, distilling under reduced pressure, and drying in vacuum at 60 ℃ for 8 hours to obtain an intermediate product III.

The dosage ratio of the intermediate product I to the ethanol water solution is 0.1mol:0.1mol:500mL;

the ratio of the amount of the intermediate product I to the amount of the intermediate product II is added according to the molar ratio of hydroxyl to the vinyl silane coupling agent of 1:1.

The ethanol content of the ethanol aqueous solution was 95wt%.

The infrared spectrum of intermediate III is shown in FIG. 3, and the infrared data is as follows: 3558cm ^-1 -OH is absent; 3324cm ^-1: -NH-present, 1735cm ^-1: -c=o (ester group) present, 1681cm ^-1: -c=o (amide) present, 1612cm ^-1: -c=c-present, 1557cm ^-1: -NH- (amide) present, 1604cm ^-1、811cm^-1: -c=c-present, 1109 cm ^-1、798cm^-1: -Si-O-present.

S14, adding isophorone diamine into N, N-dimethylformamide A, adding an intermediate product III into N, N-dimethylformamide B, placing in a constant pressure dropping funnel, slowly dropping at room temperature, stirring, continuing stirring for 3 hours after dropping, filtering, distilling under reduced pressure, and vacuum drying at 40 ℃ for 8 hours to obtain a target product, namely uracil-based macromolecules.

Isophorone diamine, N-dimethylformamide A, N, N-dimethylformamide B in an amount ratio of 0.1mol:300mL:100mL;

the ratio of intermediate III to polyamino structure is added in a molar ratio of acryloyloxy to polyamino structure of 1:1.

The infrared spectrum of the target product is shown in FIG. 4, and the infrared data of the target product are 3331cm ^-1 for-NH-presence, 1735cm ^-1 for-C=O (ester group) presence, 1681cm ^-1 for-C=O (amide) presence, 1612cm ^-1 for-C=C- (pyrimidine) presence, 1557cm ^-1 for-NH- (amide) presence, 1604cm ^-1、811cm^-1 for-C=C-absence, and 1109 cm ^-1、798cm^-1 for-Si-O-presence.

A drainage tube for treating glaucoma, which is in a tubular structure;

wherein the A component is a polyamino-containing substance;

the component B is dialdehyde group structure, and

The polyamino substance consists of an amino-containing polymer matrix and the self-made uracil-based polymer according to the mass ratio of 100g to 4.0 g.

The macromolecule matrix containing amino is gelatin;

the dialdehyde group structure is glutaraldehyde.

The preparation method of the drainage tube for treating glaucoma comprises the following steps:

S1, adding the component A into a PBS solution, heating to 55 ℃, stirring until the component A is completely dissolved, carrying out ultrasonic deaeration and bubble removal, maintaining the temperature, injecting the component A solution into a mold, standing for 3 hours, slowly cooling to 4 ℃, and taking out a molded material to obtain a primary drainage tube;

the dosage ratio of the component A to PBS is 25g to 100mL;

The dosage ratio of the aqueous solution of the component B, acetonitrile and the solid moisture desiccant is 20mL:480mL:100g;

the concentration (w/v) of the aqueous solution of the component B is 50%;

s3, placing the primary drainage tube in the B-component organic solution, controlling the temperature to be 25 ℃, and carrying out oscillation reaction for 20 hours to obtain a crosslinked drainage tube;

S4, placing the crosslinked drainage tube in a dialysis solution at the temperature of alkali liquor for 4 hours and 37 ℃ for oscillating dialysis for 22 hours, changing the dialysis solution every 4 hours during the period, and preserving at the temperature of 4 ℃ to obtain a final product, namely the drainage tube for treating glaucoma;

The dialysate is normal saline.

Example 2

S11, adding orotic acid, tetrabutylammonium bromide, glycidyl methacrylate and hydroquinone into tetrahydrofuran in a dark place, reacting for 24 hours at 65 ℃, cooling to room temperature, adding deionized water A, oscillating, adding ethyl acetate for extraction, taking an organic phase, drying with anhydrous sodium sulfate A, filtering, taking filtrate, distilling under reduced pressure, and drying in vacuum at 40 ℃ for 12 hours to obtain an intermediate product I.

Orotic acid, tetrabutylammonium bromide, glycidyl methacrylate, tetrahydrofuran, deionized water A, ethyl acetate and anhydrous sodium sulfate A are added according to the dosage ratio of 0.1mol:0.01mol:0.1mol:200mL:300mL:600mL:5 g;

S12, adding a silane coupling agent KH171, methacryloxyethyl trimethyl ammonium chloride, acrylamide and an initiator AIBN into N, N-dimethylformamide, heating to 90 ℃, stirring for 6 hours, carrying out reduced pressure distillation after the reaction is finished, and carrying out vacuum drying at 60 ℃ for 6 hours to obtain an intermediate product II #)。

The dosage ratio of the silane coupling agent KH171, the methacryloxyethyl trimethyl ammonium chloride, the acrylamide and the N, N-dimethylformamide is 0.3mol:0.25mol:0.45mol:500mL;

the initiator AIBN was used in an amount of 4.0% by weight of the total mass of the monomers.

S13, adding the intermediate product I and the intermediate product II into an ethanol water solution, adding acetic acid to adjust the pH value to 4.5, stirring for 2 hours at room temperature, distilling under reduced pressure, and drying in vacuum at 60 ℃ for 8 hours to obtain an intermediate product III.

The dosage ratio of the intermediate product I to the ethanol water solution is 0.1mol:500mL;

The ethanol aqueous solution has an ethanol content of 95wt%.

S14, adding isophorone diamine into N, N-dimethylformamide A, adding an intermediate product II into N, N-dimethylformamide B, placing in a constant pressure dropping funnel, slowly dropping at room temperature, stirring, continuing stirring for 4 hours after dropping, filtering, distilling under reduced pressure, and vacuum drying at 40 ℃ for 8 hours to obtain a target product, namely uracil-based macromolecules.

A drainage tube for treating glaucoma, which is in a tubular structure;

The component A is a polyamino substance;

the component B is dialdehyde group structure, and

The polyamino substance consists of an amino-containing polymer matrix and the self-made uracil-based polymer according to the mass ratio of 100g to 3.0 g.

The macromolecule matrix containing amino is gelatin;

the dialdehyde group structure is glutaraldehyde.

s1, adding the component A into a PBS solution, heating to 55 ℃, stirring until the component A is completely dissolved, carrying out ultrasonic deaeration and bubble removal, maintaining the temperature, injecting the component A solution into a mold, standing for 4 hours, slowly cooling to 4 ℃, and taking out a molded material to obtain a primary drainage tube;

the dosage ratio of the component A to PBS is 30g to 100mL;

The dosage ratio of the aqueous solution of the component B, acetonitrile and the solid moisture desiccant is 10mL:490mL:100g;

the concentration (w/v) of the aqueous solution of the component B is 50%;

s3, placing the primary drainage tube in the B-component organic solution, controlling the temperature to be 25 ℃, and carrying out oscillation reaction for 24 hours to obtain a crosslinked drainage tube;

S4, placing the crosslinked drainage tube in a dialysis solution at the temperature of 2h and 37 ℃ for oscillation dialysis for 18h, changing the dialysis solution every 4h during the period, and preserving at the temperature of 0 ℃ to obtain a final product, namely the drainage tube for treating glaucoma;

The dialysate is normal saline.

Example 3

S12, adding a silane coupling agent KH172, methacryloxyethyl trimethyl ammonium chloride, acrylamide and an initiator AIBN into N, N-dimethylformamide, heating to 80 ℃, stirring for 10 hours, carrying out reduced pressure distillation after the reaction is finished, and carrying out vacuum drying at 60 ℃ for 6 hours to obtain an intermediate product II #)。

The dosage ratio of the silane coupling agent KH172, the methacryloxyethyl trimethyl ammonium chloride, the acrylamide and the N, N-dimethylformamide is 0.3mol:0.25mol:0.45mol:500mL;

the initiator AIBN was used in an amount of 5.0% by weight of the total mass of the monomers.

S13, adding the intermediate product I and the intermediate product II into an ethanol water solution, adding acetic acid to adjust the pH value to 5.5, stirring for 4 hours at room temperature, distilling under reduced pressure, and drying in vacuum at 60 ℃ for 8 hours to obtain the intermediate product II.

The ethanol aqueous solution has an ethanol content of 95wt%.

S14, adding isophorone diamine into N, N-dimethylformamide A, adding an intermediate product III into N, N-dimethylformamide B, placing in a constant pressure dropping funnel, slowly dropping at room temperature, stirring, continuing stirring for 2 hours after dropping, filtering, distilling under reduced pressure, and vacuum drying at 40 ℃ for 8 hours to obtain a target product, namely uracil-based macromolecules.

A drainage tube for treating glaucoma, which is in a tubular structure;

The component A is a polyamino substance;

the component B is dialdehyde group structure, and

The polyamino substance is composed of an amino-containing polymer matrix and the self-made uracil-based polymer according to the mass ratio of 100g to 5.0 g.

The macromolecule matrix containing amino is gelatin;

the dialdehyde group structure is glutaraldehyde.

S1, adding the component A into a PBS solution, heating to 55 ℃, stirring until the component A is completely dissolved, carrying out ultrasonic deaeration and bubble removal, maintaining the temperature, injecting the component A solution into a mold, standing for 2 hours, slowly cooling to 4 ℃, and taking out a molded material to obtain a primary drainage tube;

The dosage ratio of the component A to PBS is 20g to 100mL;

the concentration (w/v) of the aqueous solution of the component B is 50%;

S3, placing the primary drainage tube in the B-component organic solution, controlling the temperature to be 25 ℃, and carrying out oscillation reaction for 15 hours to obtain a crosslinked drainage tube;

S4, placing the crosslinked drainage tube in a dialysis solution at the temperature of alkali liquor for 4 hours and 37 ℃ for oscillating dialysis for 24 hours, changing the dialysis solution every 4 hours during the period, and preserving at the temperature of 8 ℃ to obtain a final product, namely the drainage tube for treating glaucoma;

The dialysate is normal saline.

Example 4

The other points are that isophorone diamine is replaced with melamine in step S14 of the preparation method of uracil-based macromolecules.

Example 5

The other points are that isophorone diamine is substituted for Cheng Jiwu tetramine in step S14 of the preparation method of uracil-based macromolecules.

Example 6

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH172, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in an amount ratio of 0.4mol:0.25mol:0.35mol:500mL.

Example 7

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH172, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in an amount ratio of 0.2mol:0.25mol:0.55mol:500mL.

Example 8

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH172, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in an amount ratio of 0.3mol:0.2mol:0.5mol:500mL.

Example 9

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH172, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in a ratio of 0.3mol to 0.4mol to 500mL.

Example 10

The other points are that in the step S11 of the preparation method of uracil-based macromolecules, orotic acid is replaced by 4-amino uracil, and the specific steps are as follows:

S11, adding 4-aminouracil, triethylamine, glycidyl methacrylate and hydroquinone into tetrahydrofuran in a dark place, reacting for 6 hours at 25 ℃, cooling to room temperature, adding deionized water A, oscillating, adding ethyl acetate for extraction, taking an organic phase, drying with anhydrous sodium sulfate A, filtering, taking filtrate, distilling under reduced pressure, and drying in vacuum at 40 ℃ for 12 hours to obtain an intermediate product I.

The dosage ratio of the 4-aminouracil, the triethylamine, the glycidyl methacrylate, the tetrahydrofuran, the deionized water A, the ethyl acetate and the anhydrous sodium sulfate A is added according to the ratio of 0.1mol to 0.01mol to 0.1mol to 200mL to 300mL to 600mL to 5 g;

Example 11

The other difference is that in the A component, the macromolecule matrix containing amino is the mixture of gelatin and chitosan, wherein the chitosan accounts for 10wt% of the macromolecule matrix.

Example 12

The other points are the same as in example 1, except that the B component is succinaldehyde.

Example 13

The other points are the same as in example 1, except that the component B is suberaldehyde.

Comparative examples 1-11 are all compared to example 1:

comparative example 1

The other differences are that in the component A, the polyamino substance consists of amino-containing polymer matrix and uracil-based macromolecules according to the mass ratio of 100g to 0g, namely, the uracil-based macromolecules are not added.

Comparative example 2

Otherwise, the process is the same as in example 1 except that in the preparation method of uracil-based macromolecules, step S12, the silane coupling agent KH171 is replaced with an intermediate product I;

and, the step S13 is as follows:

S13, in the dark, dissolving an intermediate product II and triethylamine in N, N-dimethylformamide C in a reaction container, dissolving acryloyl chloride in N, N-dimethylformamide D in a constant pressure dropping funnel, carrying out ice bath, stirring, continuously stirring for 12 hours at a temperature of 0 ℃ after the dropping is finished, filtering, carrying out reduced pressure distillation, dissolving the concentrate in dichloromethane, adding saturated sodium bicarbonate solution for washing for 3 times, washing with deionized water for 3 times, separating liquid, taking an organic phase, drying with anhydrous sodium sulfate, filtering, carrying out reduced pressure distillation on the filtrate, and carrying out vacuum drying for 4 hours at a temperature of 80 ℃ to obtain an intermediate product III.

The dosage ratio of the intermediate product II, triethylamine, N-dimethylformamide C, acryloyl chloride, N-dimethylformamide D, methylene dichloride, saturated sodium bicarbonate solution, deionized water and anhydrous sodium sulfate is 0.1mol:0.12mol:100mL:0.1mol:50mL:500mL:200 mL:5g.

Comparative example 3

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH171, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in a ratio of 0mol:0.25mol:0.75mol:500mL, i.e., the silane coupling agent KH171 is not added.

Comparative example 4

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH171, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in a proportion of 0.3mol:0 mol:0.7mol:500mL, i.e. no methacryloyloxyethyl trimethyl ammonium chloride is added.

Comparative example 5

The procedure of example 1 is otherwise repeated, except that in step S12 of the preparation method of uracil-based macromolecules, the silane coupling agent KH171, methacryloyloxyethyl trimethyl ammonium chloride, acrylamide and N, N-dimethylformamide are used in a ratio of 0.3mol:0.25mol:0mol:500mL, i.e., acrylamide is not added.

Comparative example 6

Otherwise, the preparation method of uracil-based macromolecules is as follows in the step S12:

S12, adding a silane coupling agent KH171, methacryloxyethyl trimethyl ammonium chloride, acrylamide and an initiator AIBN into N, N-dimethylformamide, heating to 80 ℃, stirring for 12 hours, carrying out reduced pressure distillation after the reaction is finished, and carrying out vacuum drying at 60 ℃ for 6 hours to obtain an intermediate product II # )。

The dosage ratio of the silane coupling agent KH171, the methacryloxyethyl trimethyl ammonium chloride, the acrylamide and the N, N-dimethylformamide is 0.3mol:0.25mol:0.45mol:500mL, and the dosage of the initiator AIBN is 2.5 percent of the total mass of the monomers.

Comparative example 7

The other points are that the preparation method of uracil based macromolecule includes the following steps S12:

S12, adding a silane coupling agent KH171, methacryloxyethyl trimethyl ammonium chloride, acrylamide and an initiator AIBN into N, N-dimethylformamide, heating to 90 ℃, stirring for 6 hours, carrying out reduced pressure distillation after the reaction is finished, and carrying out vacuum drying at 60 ℃ for 6 hours to obtain an intermediate product II # )。

The dosage ratio of the silane coupling agent KH171, the methacryloxyethyl trimethyl ammonium chloride, the acrylamide and the N, N-dimethylformamide is 0.3mol:0.25mol:0.45mol:500mL, and the dosage of the initiator AIBN is 6.0 percent of the total mass of the monomers.

Comparative example 8

The other points are that glutaraldehyde is replaced with Cheng Yi dialdehydes in the drainage tube for glaucoma treatment, as in example 1.

Comparative example 9

The other points are that glutaraldehyde is replaced with decanedialdehyde in the drainage tube for glaucoma treatment.

Comparative example 10

The other points are that glutaraldehyde is replaced with terephthalaldehyde in the drainage tube for treating glaucoma as in example 1.

Comparative example 11

The other points are that in the drainage tube for glaucoma treatment, glutaraldehyde is replaced with 2, 5-diformylfuran.

Physical properties of drainage tubes for glaucoma treatment prepared in examples 1 to 13 and comparative examples 1 to 11 of the present invention were measured, respectively, and the results are shown in Table 1.

First, as can be seen from the data of examples 1 to 13 in Table 1, the drainage tube for glaucoma treatment provided by the present invention has excellent properties such as excellent resistance to cell proliferation, cell adhesion, etc.

Secondly, it can be observed from example 1 and comparative example 1 that the self-made uracil-based macromolecule is introduced into the drainage tube for treating glaucoma, which has excellent cell proliferation resistance and cell adhesion resistance, and simultaneously has excellent drainage efficiency, antibacterial property, mechanical strength and the like; it can be observed from examples 1 and 2 that silane in the self-made uracil-based macromolecule has excellent migration performance, so that cell proliferation resistance and adhesion performance can be improved, certain flexibility is achieved, structural design and molecular weight distribution in the uracil-based macromolecule have great influence on drainage tube performance, particularly, an uracil-containing structure has excellent cell proliferation resistance, a silane structure has excellent cell adhesion resistance and synergism, a quaternary ammonium salt structure has excellent antibacterial property, a macromolecular structure is insoluble, long-acting antibacterial effect is achieved, water solubility is assisted to improve drainage efficiency, an acrylamide structure is an excellent hydrophilic substance, drainage efficiency of a material can be effectively improved, in addition, too large molecular weight can influence migration efficiency of the macromolecule, too small molecular weight and too wide distribution can have degradation material strength, a small molecular residual risk can not form a complete transition layer, drainage efficiency can be influenced, and from examples 1 and comparative examples 8-9, the cross-linking agent has a certain chain length, the cross-linking agent has a certain molecular chain length, has a long-acting antibacterial effect, and is assisted to improve the drainage efficiency, the acrylamide structure is an excellent hydrophilic substance, and the drainage efficiency is effectively improved, and the cross-linking agent has a certain molecular chain length is too small, or a certain length is not required to be too long, and the cross-linking agent has a long-linking chain is required to be too fragile.

In conclusion, the drainage tube for treating glaucoma provided by the invention has excellent performances such as excellent cell adhesion resistance, cell proliferation resistance, drainage efficiency, antibacterial property and the like, and has great practical significance in ophthalmic treatment.

The test method comprises the following steps:

(1) Cell inhibition effect test:

The effect of cell inhibition was evaluated by the response of the cells, primary fibroblasts (10 cells/well) were cultured with fire Kong Peiyang base (DMEM) containing 10% by mass of fetal bovine serum. After the fibroblast cell was precipitated, the migration test was inserted into the glaucoma drainage device so that it was completely immersed in the medium. After 5 days of culture, the status of fibroblasts was examined with live/dead staining and CCK-8, and the 5-day live/dead ratio of fibroblasts (HTFs) was calculated, the higher the activity of the fibroblasts, the more severe the scarring.

(2) Cell adhesion test:

3T3 mouse embryo bromoblasts were maintained in T-75 Falcon cell culture using sterile Dulbecco's modified French Kong Peiyang base (DMEM) containing 10% Fetal Bovine Serum (FBS) and 100 units/ml penicillin and 0.1mg/ml streptomycin by mass fraction. 6 samples (36 samples total) of each overlay were placed in 6 well tissue culture plates and irradiated under ultraviolet light for 10-15 minutes. Cells were seeded onto the cover film at a density of approximately 11000 cells/cm. Cells were then incubated 24 h at 37 ℃ with 5% carbon dioxide, and the medium was then decanted and gently rinsed once with PBS. The adherent cell number is defined as the number of viable cells per 100 x field. The percentage of control was calculated by multiplying the ratio of the percentage of viable cells on the treated substrate to the percentage of viable cells on the untreated substrate by 100. The average control adhesion per sample group was determined and statistical comparisons of the viability assays were made as described above.

(3) Monomer residue test:

Gas chromatography testing was used. The monomer residue was expressed by <1ppm and >1ppm was expressed as "OK".

(4) Mechanical strength test:

After the drainage device is folded in half, the phenomenon of whether the fracture crease exists or not is observed. The mechanical strength is expressed by marking a non-crack and non-crease as "four points", marking a non-crack and slight crease as "O" and marking a non-crack and crease as "very" and marking a crack and crease as "two points".

(5) Drainage efficiency:

Based on example 1, the drainage time of drainage tubes with the same specification is counted by each example and comparative example, and the shorter the time is, the higher the efficiency is. Wherein, drainage efficiency T ₁ is the drainage time of the drainage tube prepared in example 1, and t _n is the drainage time of the drainage tube prepared in the currently examined example or comparative example.

(6) Antibacterial activity value:

The test was performed using a film-sticking test, as described with reference to WS/T650-2019. The antibacterial activity values of the tests are all more than or equal to 1.0, the test sample can be judged to have antibacterial effect, the antibacterial activity values of the tests are all more than or equal to 2.0, the test sample can be judged to have stronger antibacterial effect, and the test strain adopts escherichia coli (8099).

With the above-described preferred embodiments according to the present invention as an illustration, the above-described descriptions can be used by persons skilled in the relevant art to make various changes and modifications without departing from the scope of the technical idea of the present invention. The technical scope of the present invention is not limited to the description, but must be determined according to the scope of claims.

Claims

1. A drainage tube for treating glaucoma, characterized in that it has a tubular structure;

The drainage tube for treating glaucoma is prepared by aldehyde-amine condensation cross-linking reaction of component A and component B;

The component A is a substance containing multiple amino groups;

The B component is a dialdehyde structure; and

The polyamino substance comprises an amino-containing polymer matrix and a uracil-based macromolecule;

The uracil-based macromolecule is prepared as follows:

S11, performing a ring-opening reaction on an epoxy ring-opening agent containing a uracil structure and an epoxy group containing an acryloxy group to obtain an intermediate product I;

S12, subjecting a vinyl silane coupling agent, an unsaturated quaternary ammonium salt, and acrylamide to a free radical polymerization reaction to obtain an intermediate product II;

S13, subjecting the intermediate product I to a hydrolysis-coupling reaction with the intermediate product II to obtain an intermediate product III;

S14, subjecting the intermediate product III and the polyamino structure to Michael addition reaction to obtain a uracil-based macromolecule.

2. The drainage tube for treating glaucoma according to claim 1, wherein the epoxy ring-opening agent containing a uracil structure is an amino-containing uracil or a carboxyl-containing uracil.

3. The drainage tube for treating glaucoma according to claim 2, wherein the amino-containing uracil is 4-aminouracil.

4. The drainage tube for treating glaucoma according to claim 2, wherein the carboxyl-containing uracil is orotic acid.

5. The drainage tube for treating glaucoma according to claim 1, wherein the epoxy containing acryloxy group is selected from at least one of glycidyl methacrylate and (glycidyloxy)ethyl methacrylate.

6. The drainage tube for treating glaucoma according to claim 1, characterized in that the epoxy ring-opening agent containing a uracil structure and the epoxy containing an acryloxy group in step S11 are added at a molar ratio of 1:1 between the epoxy ring-opening agent and the epoxy group.

7. The drainage tube for treating glaucoma according to claim 1, characterized in that the unsaturated quaternary ammonium salt is methacryloyloxyethyltrimethylammonium chloride.

8. The drainage tube for treating glaucoma according to claim 1, characterized in that the molar ratio of the vinyl silane coupling agent, the unsaturated quaternary ammonium salt, and the acrylamide in step S12 is (0.2-0.4): (0.2-0.3): (0.3-0.6).

9 . The drainage tube for treating glaucoma according to claim 1 , wherein the number of amino functional groups of the polyamino structure in step S14 is ≥ 2.

10. The drainage tube for treating glaucoma according to any one of claims 1 to 9, characterized in that in the polyamino substance, the mass ratio of the amino-containing polymer matrix to the uracil-based macromolecule is 100:(3-5).

11. The drainage tube for treating glaucoma according to any one of claims 1 to 9, characterized in that the dialdehyde structure is a straight-chain fatty aldehyde, and the number of carbon atoms of the straight-chain fatty aldehyde is 4 to 8.

12. A method for preparing a drainage tube for treating glaucoma according to any one of claims 1 to 11, characterized in that it comprises the following steps:

S1, dissolve component A according to the formula, remove bubbles, add it into the mold, let it stand for 6-10 hours, and cool it to obtain a primary drainage tube;

S2, preparing the organic solution of component B according to the formula amount;

S3, placing the primary drainage tube in the organic solution of component B according to the formula amount, and oscillating the reaction to obtain a cross-linked drainage tube;

S4, washing the cross-linked drainage tube with alkali, performing oscillation dialysis, and storing it at low temperature to obtain a drainage tube for treating glaucoma.