CN102070791B - Polyvinyl alcohol crosslinked thiolated hyaluronic acid/polyvinyl alcohol film and preparation method and application thereof - Google Patents

Polyvinyl alcohol crosslinked thiolated hyaluronic acid/polyvinyl alcohol film and preparation method and application thereof Download PDF

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CN102070791B
CN102070791B CN2010105999536A CN201010599953A CN102070791B CN 102070791 B CN102070791 B CN 102070791B CN 2010105999536 A CN2010105999536 A CN 2010105999536A CN 201010599953 A CN201010599953 A CN 201010599953A CN 102070791 B CN102070791 B CN 102070791B
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hyaluronic acid
polyvinyl alcohol
thiolated
film
crosslinked
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CN102070791A (en
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丁洁英
印春华
唐翠
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复旦大学
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Abstract

The invention belongs to the technical field of the macromolecular material and particularly discloses a polyvinyl alcohol crosslinked thiolated hyaluronic acid/polyvinyl alcohol film and a preparation method and application thereof. The preparation method comprises the following steps: using biodegradable thiolated hyaluronic acid and polyvinyl alcohol (PVA) as raw material to crosslink with PVAby using glutaraldehyde (GA), and performing vacuum drying at the room temperature to prepare the polyvinyl alcohol crosslinked thiolated hyaluronic acid/polyvinyl alcohol film. The film is used as the back lining layer of the drug carrier to control the one-way release of the drug. The invention expands the application range of the polymer film and provides a new back lining layer material for the drug carrier.

Description

聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜及其制备方法与应用 Crosslinked polyvinyl thiolated hyaluronic acid / polyvinyl alcohol film and its preparation method and application

技术领域 FIELD

[0001]本发明属高分子材料技术领域,具体涉及一种聚乙烯醇交联的巯基化透明质酸/ 聚乙烯醇膜及其制备方法与应用。 [0001] The present invention belongs to the technical field of polymer materials, in particular to a thiol group of polyvinyl alcohol crosslinked hyaluronic acid / polyvinyl alcohol film and a preparation method and application.

背景技术 Background technique

[0002]为提高药物在吸收部位的有效吸收,减少药物损失,可设计含有非渗透性背衬层的多层结构给药载体,达到单向释药、提高药物生物利用度的目的。 [0002] In order to improve the effective absorption of the drug in the site of absorption, reduce drug loss, administration may be designed to support a multilayered structure impermeable backing layer, to achieve a one-way release, improved bioavailability of the drug of interest. 在膜、片、水凝胶等载体中引入背衬层,形成双层或多层载体结构,已广泛应用于口服、颊黏膜、鼻黏膜、经皮等给药途径,有效提高药物的吸收。 Introducing a film, sheet, etc. hydrogel carrier backing layer to form a bilayer or multilayer support structure, it has been widely used for oral, buccal route, nasal, transdermal, effectively improve the absorption of the drug. 目前背衬层的常用材料主要为乙基纤维素等,这类材料可有效避免药物从背衬层释放,控制药物单向释放,但由于乙基纤维素难溶于水中,溶胀性较低, 与溶胀性较好的材料制备双层或多层结构载体时,因材料溶胀性相差较大,在水溶液中背衬层会出现破裂、脱落,导致药物损失。 Backing materials currently used mainly for the ethylcellulose, etc. Such materials may effectively avoid drug release from the backing layer, unidirectional controlled drug release, but the difficult to dissolve in water and ethyl cellulose, low swelling, when the swelling is better prepared bilayer or multilayer structure of the carrier material, due to large difference swellable material, the backing layer will rupture in aqueous solution, falling, leading to loss of drug.

[0003] 聚乙烯醇(PVA)是一种应用广泛的水溶性高分子材料,具有良好的成膜性、乳化性、黏结性,安全无毒,无刺激性,在体内可缓慢降解。 [0003] polyvinyl alcohol (PVA) is a widely used water-soluble polymer material, having good film-forming properties, emulsification, cohesiveness, safe, non-toxic, non-irritating, slowly degraded in vivo. 作为一种常用的生物医用材料,PVA可用于制备水凝胶、膜等多种载体,机械强度较好,在给药系统及生物医学工程等领域有较广泛的应用。 Commonly used as a biomedical material, PVA can be used to prepare the hydrogel, film more carriers, good mechanical strength, there are more widely used in drug delivery systems and biomedical engineering.

[0004] 巯基化透明质酸是透明质酸羧基经巯基化合物修饰所得的高分子聚合物,不仅具有巯基化聚合物良好的黏膜黏附和原位凝胶性质,也保留了透明质酸生物相容、生物可降解、高保水等特性,可用于制备凝胶、骨架片等给药载体和组织工程支架等。 [0004] The thiolated hyaluronic acid is hyaluronic acid-modified carboxyl group, a mercapto compound resulting polymer not only has good thiolated mucoadhesive polymers and the properties of the gel in situ, but also retain the biocompatible hyaluronic acid , biodegradable, high water retention properties, can be used to prepare the gel, the carrier matrix tablets administered in other tissue engineering scaffolds and the like.

发明内容 SUMMARY

[0005] 本发明的目的是提供一种聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜。 [0005] The object of the present invention is to provide a polyvinyl alcohol crosslinked thiolated hyaluronic acid / polyvinyl alcohol film.

[0006] 本发明的另一个目的是提供一种聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜作为给药载体背衬层的应用,以克服现有技术的不足。 [0006] Another object of the present invention is to provide one kind of thiolated hyaluronic acid, crosslinked polyvinylalcohol / polyvinyl alcohol film as a drug delivery vehicle backing layer is applied to overcome the disadvantages of the prior art.

[0007] 本发明以生物可降解的巯基化透明质酸和聚乙烯醇(PVA)为材料,经戊二醛(GA) 交联聚乙烯醇,室温真空干燥,制得聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜,作为药物载体的背衬层,控制药物单向释放。 [0007] In the present invention, a biodegradable hyaluronic acid and thiolated polyvinyl alcohol (PVA) as materials, the (GA) crosslinked polyvinyl alcohol, glutaraldehyde and dried in vacuo at room temperature, to obtain crosslinked polyvinyl alcohol thiolated hyaluronic acid / polyvinyl alcohol film, the backing layer as drug carriers, unidirectional controlled drug release.

[0008] 本发明的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜可用下述方法得到:配制巯基化透明质酸和聚乙烯醇的混合溶液,加入戊二醛交联聚乙烯醇,室温真空干燥即得。 [0008] The present invention is polyvinyl alcohol crosslinked thiolated hyaluronic acid / polyvinyl alcohol film may be obtained as follows: a mixed solution prepared thiolated hyaluronic acid and polyvinyl alcohol, cross-linked polyethylene was added glutaraldehyde alcohol, and dried in vacuo at room temperature to obtain.

[0009] 所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜中,巯基化透明质酸与聚乙烯醇的质量比为1:10-1:1。 [0009] The polyvinyl crosslinked thiolated hyaluronic acid / polyvinyl alcohol film, the quality of thiolated hyaluronic acid and polyvinyl alcohol ratio of 1: 10-1: 1.

[0010] 所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜中,戊二醛用量为聚乙烯醇质量的O. 1%-1%。 [0010] The polyvinyl crosslinked thiolated hyaluronic acid / polyvinyl alcohol film, a polyvinyl alcohol in an amount of glutaraldehyde mass of O. 1% -1%.

[0011] 所述的透明质酸分子量为1.98 X 104-5 X IO6 Da,优选的分子量为IX IO5-L 5 X IO6 Da。 [0011] The molecular weight of hyaluronic acid was 1.98 X 104-5 X IO6 Da, preferably a molecular weight of IX IO5-L 5 X IO6 Da. 分子量过高,制备过程中溶液过于黏稠,不利于材料和交联剂均匀分散;分子量过低,溶液黏度和黏弹性较低,所得材料脆性较大 The molecular weight is too high, the manufacturing process was too thick, not conducive material and a crosslinking agent are uniformly dispersed; low molecular weight, low solution viscosity and viscoelasticity, the resultant material brittle

[0012] 所述的巯基化透明质酸为透明质酸-半胱氨酸、透明质酸-半胱胺、透明质酸-高半胱氨酸、透明质酸-半胱氨酸甲酯、透明质酸-半胱氨酸乙酯的一种或一种以上。 [0012] The thiolated hyaluronic acid is hyaluronic acid - cysteine, hyaluronic acid - cysteamine, hyaluronic acid - homocysteine, hyaluronic acid - cysteine ​​methyl ester, hyaluronic acid - one kind or more than one cysteine ​​ethyl ester.

[0013] 所述的巯基化透明质酸,相对每克巯基化透明质酸,共价连接的游离巯基含量为10-500 μ mol/g,二硫键含量为0-1000 μ mol/g。 [0013] The thiolated hyaluronic acid, thiol group, per gram of hyaluronic acid, covalently connected to a free sulfhydryl group content of 10-500 μ mol / g, and disulfide bond content 0-1000 μ mol / g.

[0014] 所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜,膜的厚度为25-500 μ m。 [0014] The polyvinyl crosslinked thiolated hyaluronic acid / polyvinyl alcohol film, a film thickness of 25-500 μ m.

[0015] 本发明的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜可作为药物载体的背衬层,载体包括片、膜、凝胶等,应用于口服、黏膜、经皮等多种给药途径。 [0015] The present invention is a polyvinyl alcohol crosslinked thiolated hyaluronic acid / polyvinyl alcohol film may be used as the backing layer of the drug carrier, the carrier comprising a sheet, film, gel, applied to oral, mucosal, transdermal, etc. multiple routes of administration.

[0016] 本发明的优点在于: [0016] The advantage of the present invention:

[0017] (I)本发明所用的巯基化透明质酸和聚乙烯醇均为可生物降解材料,生物相容性良好; [0017] (I) mercapto hyaluronic acid and polyvinyl alcohol used in the present invention are biodegradable materials, good biocompatibility;

[0018] (2)本发明的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜结构致密,可有效防止药物从背衬层释放; [0018] (2) a mercapto group of the polyvinyl crosslinked hyaluronic acid / polyvinyl alcohol film dense structure, can be effectively prevented drug release from the backing layer;

[0019] (3)本发明的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜与传统乙基纤维素膜相比,具有较好的溶胀性能,用于溶胀性较好的载体,不易破裂或分离。 [0019] (3) of the present invention is polyvinyl alcohol crosslinked thiolated hyaluronic acid / PVA film compared to conventional ethyl cellulose film having good swelling properties, preferably a swellable carrier , easy to break or separate.

附图说明 BRIEF DESCRIPTION

[0020] 图I为实施例2PVA交联的透明质酸-半胱胺/PVA膜作为背衬层的SEM图。 [0020] Figure I is a crosslinked hyaluronic acid 2PVA Example - cysteamine / PVA film as the backing layer SEM FIG.

[0021] 图2为实施例2PVA交联的透明质酸-半胱胺/PVA膜作载胰岛素多层膜的背衬层时的药物释放曲线。 [0021] Example 2 is an embodiment of the crosslinked hyaluronic acid 2PVA - when the drug cysteamine / PVA film backing layer of the multilayer film as a carrier of insulin release profile.

具体实施方式 Detailed ways

[0022] 下面通过具体实施例进一步描述本发明。 [0022] The present invention is further described by the following specific embodiments. 但它们不是对本发明的限定。 But they are not limitative of the present invention.

[0023] 实施例I [0023] Example I

[0024] 称取O. 02 g透明质酸-半胱氨酸(透明质酸分子量为IX 105),置称量瓶(25 mmX25 mm冲,加I mL水溶解,得浓度为2%的透明质酸-半胱氨酸溶液;加入O. I g PVA, 溶解后加入10 UL 5% GA,室温密封放置12 h,置真空干燥箱室温真空干燥,得PVA交联的透明质酸-半胱氨酸/PVA膜。 [0024] Weigh O. 02 g of hyaluronic acid - cysteine ​​(molecular weight of hyaluronic acid IX 105), opposing weighing bottle (25 mmX25 mm punch, plus I mL water was dissolved to give a concentration of 2% by transparent hyaluronic acid - cysteine ​​solution; added O. I g PVA, was added 10 UL 5% GA dissolved, sealed and stored at room temperature for 12 h, at room temperature in a vacuum oven and dried in vacuo to give PVA crosslinked hyaluronic acid - cysteine acid / PVA film.

[0025] 实施例2 [0025] Example 2

[0026] 称取0.01 g透明质酸-半胱胺(透明质酸分子量为5X105),置称量瓶(25 mmX25 mm)中,加I mL水溶解,得浓度为1%的透明质酸_半胱氨酸溶液;加入O. 05 g PVA,溶解后加入10 μ L 5% GA,室温密封放置12 h,置真空干燥箱室温真空干燥,得PVA交联的透明质酸-半胱胺/PVA膜。 [0026] Weigh 0.01 g of hyaluronic acid - cysteamine (hyaluronic acid molecular weight 5x105), opposing weighing bottle (25 mmX25 mm) in I mL water was added dissolved to give a concentration of 1% hyaluronic acid _ cysteine ​​solution; added O. 05 g PVA, dissolved was added 10 μ L 5% GA, sealed and stored at room temperature for 12 h, at room temperature in a vacuum oven and dried in vacuo to give a crosslinked hyaluronan PVA - cysteamine / PVA film.

[0027] 实施例3 [0027] Example 3

[0028] 称取0.01 g透明质酸-高半胱氨酸(透明质酸分子量为I. 5X106),置称量瓶(25 mmX25 mm)中,加I mL水溶解,得浓度为1%的透明质酸_高半胱氨酸溶液;加入O. 02 g PVA,溶解后加入4 μ L 5% GA,室温密封放置12 h,置真空干燥箱室温真空干燥,得PVA交联的透明质酸-高半胱氨酸/PVA膜。 [0028] Weigh 0.01 g of hyaluronic acid - homocysteine ​​(molecular weight hyaluronic I. 5X106), opposing weighing bottle (25 mmX25 mm) in I mL water was added dissolved to give a concentration of 1% _ homocysteine ​​hyaluronic acid solution; adding O. 02 g PVA, was added 4 μ L 5% GA dissolved, sealed and stored at room temperature for 12 h, at room temperature in a vacuum oven and dried in vacuo to give PVA crosslinked hyaluronan - homocysteine ​​/ PVA film.

[0029] 实施例4[0030] 称取0.05 g透明质酸-半胱氨酸甲酯(透明质酸分子量为I. 98X 104),置称量瓶(25mm X 25mm)中,加I mL水溶解,得浓度为5%的透明质酸-半胱氨酸甲酯溶液;加入 [0029] Example 4 [0030] Weigh 0.05 g of hyaluronic acid - cysteine ​​methyl ester (molecular weight of hyaluronic I. 98X 104), opposing weighing bottle (25mm X 25mm) in I mL water was added dissolved to give a concentration of 5% of hyaluronic acid - cysteine ​​methyl ester; added

O. 05 g PVA,溶解后加入I μ L 5% GA,室温密封放置12 h,置真空干燥箱室温真空干燥,得PVA交联的透明质酸-半胱氨酸甲酯/PVA膜。 O. 05 g PVA, dissolved and added I μ L 5% GA, sealed and stored at room temperature for 12 h, at room temperature in a vacuum oven and dried in vacuo to give PVA crosslinked hyaluronic acid - cysteine ​​methyl ester / PVA film.

[0031] 实施例5 [0032] 称取O. 01 g透明质酸-半胱氨酸乙酯(透明质酸分子量为2X105),置称量瓶(25mmX25mm)中,加I mL水溶解,得浓度为2%的透明质酸-半胱氨酸乙酯溶液;加入O. I g PVA,溶解后加入4 μ L 5% GA,室温密封放置12 h,置真空干燥箱室温真空干燥,得PVA 交联的透明质酸-半胱氨酸乙酯/PVA膜。 [0031] Example 5 [0032] Weigh O. 01 g of hyaluronic acid - cysteine ​​ethyl ester (hyaluronic acid molecular weight 2x105), opposing weighing bottle (25 mmX25mm) in I mL water was added to dissolve to give concentration of 2% hyaluronic acid - cysteine ​​ethyl ester solution; adding O. I g PVA, was added 4 μ L 5% GA dissolved, sealed and stored at room temperature for 12 h, at room temperature in a vacuum oven and dried in vacuo to give PVA crosslinked hyaluronic acid - ethyl cysteine ​​/ PVA film.

[0033] 实施例6 [0033] Example 6

[0034] 实施例2所得的PVA交联的透明质酸-半胱胺/PVA膜用作载胰岛素多层膜的背衬层,纵切面进行扫描电子显微镜(SEM)观察。 PVA crosslinked hyaluronic acid [0034] 2 obtained in Example - cysteamine / PVA film is used as a carrier of insulin backing layer of the multilayer film, longitudinal section scanning electron microscope (SEM) observation. 如附图I所示,背衬层结构致密,其和载药层易于分辨,无分裂,背衬层厚度约为50 μπι。 As shown in I, the backing layer dense structure which is easily distinguishable and drug layer, without splitting, the thickness of the backing layer is about 50 μπι drawings.

[0035] 实施例7 [0035] Example 7

[0036] 实施例2所得的PVA交联的透明质酸-半胱胺/PVA膜用作载胰岛素多层膜的背衬层,用Valia-Chien扩散池考察胰岛素从膜两侧的释放。 PVA crosslinked hyaluronic acid [0036] 2 obtained in Example - cysteamine / PVA film is used as a carrier of insulin multilayer film backing layer with Valia-Chien diffusion cell release of insulin from the investigated sides of the membrane. 将载胰岛素多层膜置两个扩散池间,分别在两侧加入5 mL pH 7.4的磷酸盐缓冲液作为释放介质,37 ° C孵育,定时取样。 The insulin contained between the two opposing multi-layered film diffusion cells were added to 5 mL pH 7.4 phosphate buffer as release medium, 37 ° C incubation, the sampling timing of both sides. 胰岛素的释放由附图2可知,背衬层侧的胰岛素释放量较少,表明PVA交联的透明质酸-半胱胺/PVA膜可有效阻止胰岛素的扩散,控制药物单向释放。 Insulin release seen from Figure 2, the backing layer side is less insulin release, indicating that the hyaluronic acid crosslinked PVA - cysteamine / PVA film can effectively prevent the diffusion of insulin, unidirectional controlled drug release.

Claims (8)

1. 一种聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜的制备方法,其特征在于具体步骤如下:配制巯基化透明质酸和聚乙烯醇的混合溶液,加入戊二醛交联聚乙烯醇,室温真空干燥即得;其中:所用的巯基化透明质酸与聚乙烯醇的质量比为1:10-1:1 ;戊二醛用量为聚乙烯醇质量的O. 1%-1% ;所述的巯基化透明质酸的分子量为I. 98X 104-5X IO6 Da ; 所述的巯基化透明质酸为透明质酸-半胱氨酸、透明质酸-半胱胺、透明质酸-高半胱氨酸、透明质酸-半胱氨酸甲酯、透明质酸-半胱氨酸乙酯的一种或一种以上。 A crosslinked polyvinyl thiolated hyaluronic acid / polyvinyl alcohol film production method wherein the following steps: preparing a mixed solution of thiolated hyaluronic acid and polyvinyl alcohol, glutaraldehyde was added linked polyvinyl alcohol, and dried in vacuo at room temperature to obtain; wherein: mass of the polyvinyl alcohol and hyaluronic acid employed thiolated ratio of 1: 10-1: 1; mass of glutaraldehyde in an amount of O. 1% polyvinyl alcohol -1%; the thiolated hyaluronic acid molecular I. 98X 104-5X IO6 Da; the thiolated hyaluronic acid is hyaluronic acid - cysteine, hyaluronic acid - cysteamine, hyaluronic acid - homocysteine, hyaluronic acid - cysteine ​​methyl ester, hyaluronic acid - one kind or more than one cysteine ​​ethyl ester.
2.根据权利要求I所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜的制备方法, 其特征在于相对每克巯基化透明质酸,共价连接的游离巯基含量为10-500 μ mol/g, 二硫键含量为0-1000 μ mol/g。 The I according crosslinked polyvinyl thiolated hyaluronic acid / polyvinyl alcohol film production method as claimed in claim, characterized in that the free sulfhydryl group content, per gram of thiolated hyaluronic acid, covalently linked 10 -500 μ mol / g, and disulfide bond content 0-1000 μ mol / g.
3.根据权利要求I或2所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜的制备方法,其特征在于膜的厚度为25-500 I according to claim 2 or polyvinyl alcohol crosslinked thiolated hyaluronic acid / polyvinyl alcohol film production method as claimed in claim, wherein the thickness of the film is 25-500
4.如权利要求I一3之一所述方法制备的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜。 I as claimed in one of the pair 3 of crosslinked polyvinyl alcohol prepared thiolated hyaluronic acid / polyvinyl alcohol film requirements.
5.如权利要求4所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜作为药物载体背衬层的应用。 5. thiolated claim 4, wherein the polyvinyl alcohol crosslinked hyaluronic acid / polyvinyl alcohol layer applied as a drug carrier film backing.
6.根据权利要求5所述的应用,其特征在于所述的药物载体为片、膜或凝胶。 6. The use as claimed in claim 5, wherein the pharmaceutical carrier is a sheet, a film or a gel.
7.如权利要求4所述的聚乙烯醇交联的巯基化透明质酸/聚乙烯醇膜作为药物载体背衬层在给药系统中的应用。 7. thiolated claim 4, wherein the polyvinyl alcohol crosslinked hyaluronic acid / application layer in a drug delivery system as drug carriers polyvinyl alcohol film backing.
8.根据权利要求7所述的应用,其特征在于所述的给药系统的给药途径为口服、黏膜或经皮。 The use according to claim 7, characterized in that the system of the route of administration is oral, mucosal or transdermal.
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Citations (2)

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Publication number Priority date Publication date Assignee Title
CN1515232A (en) 2003-01-09 2004-07-28 成都博联医疗信息产业有限责任公司 Preparation method of medical film for dentistry
CN1961974A (en) 2005-11-09 2007-05-16 中国科学院化学研究所 Nano copolymer fibrous membrane material capable of being biodegraded and absorbed and preparation process and use thereof

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GB9902652D0 (en) * 1999-02-05 1999-03-31 Fermentech Med Ltd Process

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1515232A (en) 2003-01-09 2004-07-28 成都博联医疗信息产业有限责任公司 Preparation method of medical film for dentistry
CN1961974A (en) 2005-11-09 2007-05-16 中国科学院化学研究所 Nano copolymer fibrous membrane material capable of being biodegraded and absorbed and preparation process and use thereof

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