WO2011059123A1 - Composé d'héparine lié à un matériau adhésif, procédé de préparation associé, agent de revêtement de surface solide contenant ledit composé comme principe actif et procédé de revêtement de surface solide au moyen dudit agent - Google Patents

Composé d'héparine lié à un matériau adhésif, procédé de préparation associé, agent de revêtement de surface solide contenant ledit composé comme principe actif et procédé de revêtement de surface solide au moyen dudit agent Download PDF

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Publication number
WO2011059123A1
WO2011059123A1 PCT/KR2009/006612 KR2009006612W WO2011059123A1 WO 2011059123 A1 WO2011059123 A1 WO 2011059123A1 KR 2009006612 W KR2009006612 W KR 2009006612W WO 2011059123 A1 WO2011059123 A1 WO 2011059123A1
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WO
WIPO (PCT)
Prior art keywords
heparin
glucopyranosyl
deoxy
sulfamido
solid surface
Prior art date
Application number
PCT/KR2009/006612
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English (en)
Korean (ko)
Inventor
이해신
강성민
유인성
변영로
Original Assignee
주식회사 메디프렉스
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by 주식회사 메디프렉스 filed Critical 주식회사 메디프렉스
Priority to PCT/KR2009/006612 priority Critical patent/WO2011059123A1/fr
Publication of WO2011059123A1 publication Critical patent/WO2011059123A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0005—Use of materials characterised by their function or physical properties
    • A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
    • A61L33/0029—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using an intermediate layer of polymer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/10—Heparin; Derivatives thereof

Definitions

  • the present invention provides a heparin compound combined with an adhesive material, a method for preparing the same, a solid surface coating agent containing the same as an active ingredient, and a method for coating a solid surface using the same.
  • the inventors of the present invention have completed the present invention by studying a method for preparing a heparin compound combined with an adhesive material by an easy method, a solid surface coating agent containing the same as an active ingredient, and a method for coating a solid surface using the same.
  • An object of the present invention is to provide a heparin compound bonded to an adhesive material, a method for preparing the same, a solid surface coating agent containing the same as an active ingredient, and a method for coating a solid surface using the same.
  • the present invention is a heparin compound bonded to an adhesive material, a method for producing a heparin compound bonded to the adhesive material by reacting the adhesive material and heparin under weakly acidic conditions, containing it as an active ingredient It provides a solid surface coating agent, and a method for coating a solid surface under weak base conditions using the same.
  • heparin not only can heparin easily be attached to heparin, but also heparin can be fixed to various solid surfaces.
  • many existing blood compatible materials have coated anti-thrombotic substances on polymeric materials such as polyurethane.
  • the dopamine bound to heparin is well coated on the polyurethane surface, and thus the present invention can be usefully used for blood compatible material development.
  • Figure 1 (a) is a result of taking a solution obtained by dissolving the compound dopamine bonded to heparin in distilled water with a UV detector, (b) is a result of taking a solution in which only heparin dissolved in distilled water by a UV detector.
  • Figure 2 (a) is a result of dissolving only heparin in distilled water, poured on the surface of the gold and evaporated, followed by FT-IR, (b) is a surface of gold by dissolving a compound in which heparin is bonded to dopamine as an adhesive substance in distilled water After pour into and evaporated, the result was taken with FT-IR, and (c) is a result of coating with a dopamine-bonded compound on heparin on the surface of the gold wafer, washed with distilled water, and then taken with FT-IR.
  • Figure 3 (a) is a coating of a heparin compound in combination with a dopamine according to the present invention on gold (Au), silicon (Si), and titanium (Ti) wafer to measure the thickness of the coating, (b) is Adsorption of fibrinogen on the coated substrates was performed to measure the thickness, and (c) was measured by dropping blood on the coated substrates to coagulate, washing with water, and measuring the thickness.
  • Figure 5 (a) is a photograph of the platelet adhesion test on the bare polyurethane surface, (b) is a photograph of the same test on the surface of the polyurethane coated with the heparin compound according to the present invention. (The scale is 10 mm.)
  • FIG. 6 shows the thickness of the coated heparin compound remaining after 2 hours, 4 hours, and 6 hours after coating the heparin compound according to the present invention on an Au surface and immersing the surface in 50% ethanol solution.
  • Figure 7 is a narrow scan (Narrow scan) photographs with a photoelectron spectroscopy (XPS), (a) is a bare polyurethane surface, (b) is a polyurethane surface coated with a heparin compound according to the present invention (c) is a polyurethane surface dipped in 50% ethanol solution for two hours after coating the heparin compound according to the invention, (d) is a bare silicone rubber surface, and (e) is according to the invention A silicone rubber surface coated with a heparin compound, and (f) is a silicone rubber surface dipped in 50% ethanol solution for two hours after coating the heparin compound according to the present invention.
  • XPS photoelectron spectroscopy
  • the present invention provides a heparin compound represented by the following Chemical Formula 1 in combination with an adhesive material:
  • K is an integer from 1 to 10;
  • X is H or OH
  • M and N are each an integer from 1 to 50;
  • a and B are independently ⁇ -D-glucuronic acid (GlcA), ⁇ -L-iduronic acid (IdoA), 2-O-sulfo- ⁇ 2-O-sulfo- ⁇ -L-iduronic acid (IdoA (2S)), 2-deoxy-2-acetamino- ⁇ -D-glucopyranosyl (2-deoxy-2- acetamido- ⁇ -D-glucopyranosyl (GlcNAc)), 2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl (2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl (GlcNS)), and 2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl-6-O-sulfate (2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl-6-O-sulfate (GlcNS (6S)) ) Is
  • a and B represent hexagonal ring units constituting heparin
  • A represents an amide bond
  • B represents an amide bond
  • the range of heparin molecular weight used for the present invention has a value between the molecular weight of 3 kDa and 50 kDa.
  • heparin used in the present invention may include all kinds present in nature.
  • the heparin compound according to Chemical Formula 1 is a composite in which A and B are optionally arranged, and M / (M + N), which is a ratio of A and B, is preferably 0.02 or more.
  • the adhesive material bound to heparin according to the present invention includes dopamine (dopamine, 3-hydroxytyramine hydrochloride) as shown in the following formula (2), and the chemical structure of dopamine, whether or not one or a plurality of X OH in the formula (1) It is very similar to maintain the physical and chemical properties of dopamine.
  • Haeshin Lee et al. (2006, 2007) studied mussels that have adhesion in water and on water, as well as on organic and inorganic surfaces, and found that the basic unit of adhesion is dopamine.
  • the solid surface coated by the coating agent containing the heparin compound of Formula 1 as an active ingredient is, for example, polytetrafluoroethylene (PTFE), polycarbonate (polycarnonate), polyurethane (polyurethane), nitrocellulose (nitrocellulose), Polymeric materials including polystyrene (PS), polyethylene (PE), polyethylene terephthalate (PET), polydimethylsiloxane (PDMS), and polyether ether ketone (PEEK), gold (Au), silver (Ag), platinum Precious metal materials including (Pt), palladium (Pd), and copper (Cu), metal materials including steel, nitinol alloy (NiTi), gallium arsenide (GaAs), and titanium (Ti), silicon oxide Metal oxide materials including (SiO 2 ), titanium oxide (TiO 2 ), aluminum oxide (Al 2 O 3 ), and niobium oxide (Nb 2 O 5 ), and nonmetals including silicon, silicone rubber, and glass It may
  • the present invention also provides a method for preparing a heparin compound in combination with an adhesive material.
  • step 2 Reacting the -COOH group-activated heparin with the adhesive material to prepare a heparin compound in which the adhesive material is bound (step 2):
  • K is an integer from 1 to 10;
  • X is H or OH
  • M and N are each an integer from 2 to 50;
  • a and B are independently ⁇ -D-glucuronic acid (GlcA), ⁇ -L-iduronic acid (IdoA), 2-O-sulfo- ⁇ 2-O-sulfo- ⁇ -L-iduronic acid (IdoA (2S)), 2-deoxy-2-acetamino- ⁇ -D-glucopyranosyl (2-deoxy-2- acetamido- ⁇ -D-glucopyranosyl (GlcNAc)), 2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl (2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl (GlcNS)), and 2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl-6-O-sulfate (2-deoxy-2-sulfamido- ⁇ -D-glucopyranosyl-6-O-sulfate (GlcNS (6S)) ) Is
  • Step 1 is a step of reacting heparin with NHS in order to activate the -COOH group of heparin, through the reaction, for example, the -COOH group of heparin, such as the following formula (3) is activated as shown in formula (4).
  • Step 2 is a step of bonding the adhesive material to heparin -COOH group activated, the adhesive material is preferably dopamine.
  • the adhesive material is preferably dopamine.
  • step 2 a heparin compound in which a substance of Formula 4 is reacted with an adhesive substance of Formula 5 is prepared by reacting with an amine group of dopamine.
  • Step 1 and step 2 is preferably carried out under weakly acidic conditions. This is because weakly acidic conditions inhibit dopamine self-polymerization.
  • the method for preparing a heparin compound combined with an adhesive material according to the present invention may further include performing dialysis and lyophilization. In order to prevent the self-polymerization of dopamine during dialysis, it is desirable to maintain weakly acidic conditions.
  • the present invention provides a solid surface coating agent containing a heparin compound in which the adhesive material represented by Formula 1 is bound as an active ingredient.
  • the present invention provides a method for coating a solid surface using the coating agent.
  • Coating of the solid surface with the solid surface coating agent containing the heparin compound according to the present invention as an active ingredient is preferably carried out under weak base conditions of pH 7.5 ⁇ 0.5. This is because weak base conditions induce polydopamine polymerization between dopamines bound to heparin.
  • Solid surfaces on which the solid surface coatings according to the invention can be coated are, for example, polytetrafluoroethylene (PTFE), polycarbonate (polycarnonate), polyurethane, nitrocellulose, polystyrene (PS), Polymeric materials, including polyethylene (PE), polyethylene terephthalate (PET), polydimethylsiloxane (PDMS), and polyether ether ketone (PEEK), gold (Au), silver (Ag), platinum (Pt), palladium (Pd), and precious metal materials including copper (Cu), steel, nitinol alloys (NiTi), gallium arsenide (GaAs), and metal materials including titanium (Ti), silicon oxide (SiO 2 ), Metal oxide materials including titanium oxide (TiO 2 ), aluminum oxide (Al 2 O 3 ), and niobium oxide (Nb 2 O 5 ), and nonmetallic materials including silicon, silicone rubber, and glass, It is not limited to this.
  • PTFE polytetra
  • heparin 400 mg of heparin, 230 mg of NHS, and 766 mg of EDC (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochlorid) as shown in Chemical Formula 3, 40 mg of MES (2-morpholinoethanesulfonic acid) buffer at pH 5.5 and 0.05 M Completely dissolved and reacted for 2 hours 30 minutes to activate the -COOH group of heparin:
  • Example 1 50 mg of the dopamine-coupled heparin compound prepared in Example 1 was dissolved in 5 ml of TRIS buffer at 10 mM and pH 8.5, and then coated with gold wafer pieces for 12 hours with stirring.
  • Figure 1 (b) is taken only by dissolving heparin in distilled water with an ultraviolet detector. It can be seen that no peak emerges at 280 nm, the absorbing wavelength of dopamine.
  • Figure 1 (a) is taken with an ultraviolet detector dissolved in a distilled water the dopamine-bound heparin compound prepared in Example 1 of the present invention. In Figure 1 (a) it can be seen that the peak at 280 nm, the absorption wavelength of dopamine is clearly seen. Since unreacted dopamine was removed through dialysis in Example 1, it can be seen that the peak at 280 nm is the peak of dopamine bound to heparin.
  • FIG. 2 (a) shows the result taken by FT-IR after evaporation of only heparin in distilled water, poured onto a gold wafer surface.
  • Figure 2 (b) is a result obtained by FT-IR after evaporation of the dopamine-bound heparin compound prepared in Example 1 of the present invention dissolved in distilled water and poured on the surface of the gold wafer.
  • Figure 2 (b) it can be confirmed that the -CONH- peak near 1560 cm -1 , through which the binding of heparin and dopamine was well established.
  • Figure 2 (c) is a result of taking a gold wafer coated with a dopamine-bound heparin compound according to Example 2 after sufficiently washed with distilled water and FT-IR. In Figure 2 (c) it can be seen the peak -CONH- near 1560 cm -1 . Through this, it can be seen that the dopamine-coupled heparin compound according to the present invention is well adhered to the gold wafer surface.
  • the coating thicknesses were measured for the coated gold wafers, titanium wafers, and silicon wafers prepared in Examples 2, 3, and 6. An ellipsometer was used for the coating thickness measurement. According to (a) of FIG. 3, gold wafers were coated with an average of 21.026 mmW, silicon wafers with an average of 11.7 mmW, and titanium wafers with an average of 19.758 mmW.
  • the dopamine-bound heparin compound according to the present invention in order to determine whether the heparin immobilized on the surface performs the solution solution in the solution solution, under the condition of water vapor saturation, uncoated gold, silicon, and After dropping blood on the surface of gold, titanium, and silicon coated with titanium and the dopamine-conjugated heparin compound according to Examples 2, 3, and 6 of the present invention, the mixture was left for 2 hours. Thereafter, the surfaces were sufficiently washed with distilled water, and then the thickness of the blood component adsorbed on the surface was measured using an ellipsometer, which is shown in FIG.
  • the contact angle was measured to confirm that the coating of the dopamine-bound heparin compound according to the present invention on the solid surface was well performed.
  • a drop of distilled water was added dropwise to the gold wafer, the titanium wafer, the polycarbonate, the polyurethane, and the silicone rubber and the coated solid surface prepared in Examples 2 to 6 according to the present invention, and then the contact angle was checked through a contact angle meter.
  • FIG. 4 is a photograph for confirming a contact angle in each case. According to FIG.
  • the 1 cm ⁇ 1 cm heparin coated polyurethane surface prepared by Example 4 of the present invention was immersed in PBS (pH 7.4) for 24 hours. This surface was then immersed in 5 ml of platelet concentrate and maintained at 37 ° C. for 2 hours. Washed with PBS to remove weakly attached platelets. Thereafter, the surface was immediately immersed in formaldehyde for 24 hours, platelets were fixed, and the remaining formaldehyde was removed with PBS. This surface was then immersed in 50, 60, 70, 80, 90% ethanol solution for 15 minutes in order to replace water with ethanol. Finally, the surface was analyzed by SEM, which is shown in FIG. 5.
  • Heparin compound-coated gold wafers, polyurethanes, and silicone rubbers prepared according to Examples 2, 4, and 6 according to the present invention were immersed in 50% ethanol solution.
  • the gold wafer coated with the heparin compound was immersed in the ethanol solution for 2 hours, 4 hours, and 6 hours under static conditions, respectively, and the thickness thereof was measured with an ellipsometer. Indicated.
  • the polyurethane and silicone rubber coated with heparin compound were immersed in a 50% ethanol solution in a static state for 2 hours and then taken out and analyzed by XPS. At this time, as a control, the bare polyurethane and bare silicone rubber were analyzed by XPS, and the results are shown in FIG. 7.
  • heparin-coated gold surface according to the present invention can be seen that the thickness does not change significantly after 2 hours, 4 hours, 6 hours in 50% ethanol solution. This shows that heparin coated on gold is stably coated on the surface.
  • the S2p peak comes out from the surface of heparin-coated polyurethane dipped in 50% ethanol for 2 hours.
  • the heparin compound according to the present invention was stably coated on the polyurethane surface.
  • the peak of N1s did not come out from the surface of the bare silicone rubber in FIG.
  • the heparin-coated silicone rubber surface showed a N1s peak.
  • the N1s peak also appeared on the surface of heparin-coated silicone rubber dipped in 50% ethanol for 2 hours in Figure 7 (f).
  • the heparin compound according to the present invention is stably coated on the silicone rubber surface.

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Abstract

L'invention concerne un composé d'héparine lié à un matériau adhésif, un procédé de préparation associé, un agent de revêtement de surface solide contenant ledit composé comme principe actif et un procédé de revêtement de surface solide au moyen dudit agent. Le procédé de préparation de composé d'héparine lié à un matériau adhésif consiste à activer un groupe carboxyle d'héparine dans des conditions de faible acidité et à mettre en réaction le groupe activé avec un matériau adhésif. Ainsi, un agent de revêtement contenant le composé préparé comme principe actif peut être déposé facilement sur une surface solide, dans des conditions de faible basicité. Selon l'invention, divers types de surfaces solides peuvent être revêtues d'héparine par une adhérence facilitée à l'héparine. Les surfaces solides ainsi revêtues d'héparine peuvent être très utiles dans le domaine médical, en particulier dans l'élaboration de matériaux hémocompatibles.
PCT/KR2009/006612 2009-11-11 2009-11-11 Composé d'héparine lié à un matériau adhésif, procédé de préparation associé, agent de revêtement de surface solide contenant ledit composé comme principe actif et procédé de revêtement de surface solide au moyen dudit agent WO2011059123A1 (fr)

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PCT/KR2009/006612 WO2011059123A1 (fr) 2009-11-11 2009-11-11 Composé d'héparine lié à un matériau adhésif, procédé de préparation associé, agent de revêtement de surface solide contenant ledit composé comme principe actif et procédé de revêtement de surface solide au moyen dudit agent

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PCT/KR2009/006612 WO2011059123A1 (fr) 2009-11-11 2009-11-11 Composé d'héparine lié à un matériau adhésif, procédé de préparation associé, agent de revêtement de surface solide contenant ledit composé comme principe actif et procédé de revêtement de surface solide au moyen dudit agent

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Cited By (6)

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CN103157144A (zh) * 2011-12-15 2013-06-19 贵州金玖生物技术有限公司 一种血管支架上抗凝血涂层的制备方法
CN103736156A (zh) * 2013-10-10 2014-04-23 西北大学 一种通过聚多巴胺涂层构建功能化表界面的方法
CN109873159A (zh) * 2017-12-01 2019-06-11 现代自动车株式会社 锂二次电池以及用于锂二次电池阳极的粘合剂
CN110323415A (zh) * 2018-03-29 2019-10-11 现代自动车株式会社 锂二次电池及该锂二次电池的制造方法
CN111500217A (zh) * 2020-04-06 2020-08-07 恩平市盈嘉丰胶粘制品有限公司 一种多功能纳米材料改性压敏胶的制备方法
CN113209383A (zh) * 2021-05-17 2021-08-06 吉林大学 一种负载bmp-2基因缓释涂层的peek复合生物植入材料及其制备方法

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103157144A (zh) * 2011-12-15 2013-06-19 贵州金玖生物技术有限公司 一种血管支架上抗凝血涂层的制备方法
CN103736156A (zh) * 2013-10-10 2014-04-23 西北大学 一种通过聚多巴胺涂层构建功能化表界面的方法
CN109873159A (zh) * 2017-12-01 2019-06-11 现代自动车株式会社 锂二次电池以及用于锂二次电池阳极的粘合剂
CN109873159B (zh) * 2017-12-01 2023-03-07 现代自动车株式会社 锂二次电池以及用于锂二次电池阳极的粘合剂
CN110323415A (zh) * 2018-03-29 2019-10-11 现代自动车株式会社 锂二次电池及该锂二次电池的制造方法
CN110323415B (zh) * 2018-03-29 2023-03-10 现代自动车株式会社 锂二次电池及该锂二次电池的制造方法
CN111500217A (zh) * 2020-04-06 2020-08-07 恩平市盈嘉丰胶粘制品有限公司 一种多功能纳米材料改性压敏胶的制备方法
CN113209383A (zh) * 2021-05-17 2021-08-06 吉林大学 一种负载bmp-2基因缓释涂层的peek复合生物植入材料及其制备方法
CN113209383B (zh) * 2021-05-17 2022-01-11 吉林大学 一种负载bmp-2基因缓释涂层的peek复合生物植入材料及其制备方法

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