CN101744771A - Method for preparing solid enrofloxacin nano particles - Google Patents
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- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229960000740 enrofloxacin Drugs 0.000 title claims abstract description 53
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 44
- 239000007787 solid Substances 0.000 title claims abstract description 32
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- 238000003760 magnetic stirring Methods 0.000 claims abstract description 17
- 229940079593 drug Drugs 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 16
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
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Abstract
一种固体恩诺沙星纳米粒的制备方法。特征是该方法为：先以蒸馏水配制成浓度为1％的冰醋酸水溶液，在磁力搅拌的条件下，再加入壳聚糖，使其溶解，得壳聚糖浓度为1.5-2.5mg/mL的壳聚糖溶液；接着将恩诺沙星原料药加入上述壳聚糖溶液中，并保持磁力搅拌10分钟使其分散均匀，后调节pH至5.0，得到恩诺沙星壳聚糖溶液；再接着将三聚磷酸钠溶于蒸馏水中，配制成浓度为1.2-1.8mg/mL的三聚磷酸钠溶液，且将其缓慢滴入磁力搅拌状态下的上述恩诺沙星壳聚糖溶液中，滴加完成后继续磁力搅拌1小时固定，得恩诺沙星壳聚糖纳米粒混悬液；最后将上述固定化的恩诺沙星壳聚糖纳米粒混悬液分装于冷冻瓶中，在-70℃下预冷冻2小时，然后在-50℃下抽真空冷冻干燥，制成固体恩诺沙星纳米粒。
A method for preparing solid enrofloxacin nanoparticles. The feature is that the method is as follows: first prepare a glacial acetic acid aqueous solution with a concentration of 1% with distilled water, and then add chitosan to dissolve it under the condition of magnetic stirring to obtain a chitosan with a concentration of 1.5-2.5 mg/mL. Chitosan solution; then add the enrofloxacin bulk drug in the above-mentioned chitosan solution, and keep magnetic stirring for 10 minutes to make it uniformly dispersed, then adjust the pH to 5.0 to obtain the enrofloxacin chitosan solution; then Dissolve sodium tripolyphosphate in distilled water to prepare a sodium tripolyphosphate solution with a concentration of 1.2-1.8mg/mL, and slowly drop it into the above-mentioned enrofloxacin-chitosan solution under magnetic stirring, drop Continue magnetic stirring for 1 hour to fix after the addition is completed, and obtain the enrofloxacin chitosan nanoparticle suspension; Pre-freeze at -70°C for 2 hours, and then vacuum freeze-dry at -50°C to prepare solid enrofloxacin nanoparticles.
Description
技术领域：Technical field:
本发明属于水产药物制剂技术领域，尤其是涉及一种固体恩诺沙星纳米粒的制备方法。The invention belongs to the technical field of aquatic pharmaceutical preparations, and in particular relates to a preparation method of solid enrofloxacin nanoparticles.
背景技术：Background technique:
恩诺沙星(Enrofloxacin，ENR)又名乙基环丙沙星，于1996年获美国FDA批准，为禽畜和水产专用第3代氟喹诺酮类抗菌药物，能通过抑制细菌DNA螺旋酶来达到抗菌效果，具有杀菌谱广、体内分布广泛、与其他药物无交叉耐药性等特点。Enrofloxacin (ENR), also known as ethyl ciprofloxacin, was approved by the US FDA in 1996. It is a third-generation fluoroquinolone antimicrobial drug dedicated to poultry, livestock and aquatic products, which can be achieved by inhibiting bacterial DNA helicase. The antibacterial effect has the characteristics of broad bactericidal spectrum, wide distribution in the body, and no cross-resistance with other drugs.
目前，在生产中恩诺沙星仍然采用以粉剂为代表的第一、二代传统剂型，普遍存在着生物利用度低、药效期短、肠胃刺激大、易产生耐药性等缺点，且抗逆性差，药物生产、运输、保存等过程中易受光、热反应产生降解，导致治疗过程中药物疗效低、剂量增大、治疗周期延长等问题，从而间接造成由药物残留等水产品安全隐患。At present, enrofloxacin still adopts the first and second-generation traditional dosage forms represented by powder in production, which generally have disadvantages such as low bioavailability, short drug effect period, large gastrointestinal irritation, and easy drug resistance. Poor stress resistance, easy to be degraded by light and heat reactions in the process of drug production, transportation, storage, etc., leading to problems such as low drug efficacy, increased dosage, and prolonged treatment cycle during the treatment process, thus indirectly causing safety hazards of aquatic products such as drug residues .
虽然，国内已有部分关于壳聚糖作为载体的相关研究，但都局限于对纳米粒混悬液的制备和评价，不能提供该剂型投入生产和应用的有效方案。Although there have been some relevant studies on chitosan as a carrier in China, they are all limited to the preparation and evaluation of nanoparticle suspensions, and cannot provide an effective solution for the production and application of this dosage form.
发明内容：Invention content:
本发明的目的是提供一种固体恩诺沙星纳米粒的制备方法，该方法可实现纳米粒子小、重分散性好、包封率及载药量较高，并能提高药物的缓释性能和药物对光、热的抗逆性。The purpose of the present invention is to provide a preparation method of solid enrofloxacin nanoparticles, which can realize small nanoparticles, good redispersibility, high encapsulation efficiency and drug loading, and can improve the sustained release performance of drugs And drug resistance to light and heat.
为了达到上述的目的本发明的固体恩诺沙星纳米粒的制备方法包括下列步骤：In order to achieve the above-mentioned purpose, the preparation method of solid enrofloxacin nanoparticles of the present invention comprises the following steps:
(1)以蒸馏水配制成浓度为1％的冰醋酸水溶液，在磁力搅拌的条件下，再加入壳聚糖，使其溶解，得壳聚糖浓度为1.5-2.5mg/mL的壳聚糖溶液；(1) It is 1% glacial acetic acid aqueous solution that concentration is mixed with distilled water, under the condition of magnetic stirring, add chitosan again, make it dissolve, obtain the chitosan solution that chitosan concentration is 1.5-2.5mg/mL ;
(2)将恩诺沙星原料药加入上述壳聚糖溶液中，并保持磁力搅拌10分钟使其分散均匀，后调节pH至5.0，得到恩诺沙星壳聚糖溶液；(2) Add the enrofloxacin bulk drug in the above-mentioned chitosan solution, and keep magnetic stirring for 10 minutes to make it uniformly dispersed, then adjust the pH to 5.0 to obtain the enrofloxacin-chitosan solution;
(3)将三聚磷酸钠溶于蒸馏水中，配制成浓度为1.2-1.8mg/mL的三聚磷酸钠溶液，且将其缓慢滴入磁力搅拌状态下的上述恩诺沙星壳聚糖溶液中，滴加完成后继续磁力搅拌1小时固定，得恩诺沙星壳聚糖纳米粒混悬液；(3) Dissolve sodium tripolyphosphate in distilled water to prepare a sodium tripolyphosphate solution with a concentration of 1.2-1.8mg/mL, and slowly drop it into the above-mentioned enrofloxacin-chitosan solution under magnetic stirring , after the completion of the dropwise addition, continue magnetic stirring for 1 hour to fix, and obtain the enrofloxacin-chitosan nanoparticle suspension;
(4)将上述固定化的恩诺沙星壳聚糖纳米粒混悬液分装于冷冻瓶中，在-70℃下预冷冻2小时，然后在-50℃下抽真空冷冻干燥，最后制成固体恩诺沙星纳米粒。(4) The above-mentioned immobilized enrofloxacin chitosan nanoparticle suspension was divided into frozen bottles, pre-frozen at -70°C for 2 hours, then vacuum freeze-dried at -50°C, and finally prepared into solid enrofloxacin nanoparticles.
所述的pH值的调节以1.0mol/L的NaOH溶液调节。所述的壳聚糖、恩诺沙星与三聚磷酸钠的质量比为10∶2∶1-8∶4∶3。所述的磁力搅拌的搅拌速度为800rpm。所述的固体恩诺沙星纳米粒的包封率为50-70％，载药量为8-12wt％。The adjustment of the pH value is adjusted with 1.0 mol/L NaOH solution. The mass ratio of chitosan, enrofloxacin and sodium tripolyphosphate is 10:2:1-8:4:3. The stirring speed of the magnetic stirring is 800rpm. The encapsulation efficiency of the solid enrofloxacin nanoparticles is 50-70%, and the drug loading is 8-12wt%.
本发明的固体恩诺沙星纳米粒的制备方法具有以下特点：The preparation method of solid enrofloxacin nanoparticles of the present invention has the following characteristics:
1、本发明采用的壳聚糖是甲壳素脱乙酰化的产物，具有良好的生物降解性和生物黏附性，能延长药物在吸收部位的滞留时间，提高药物的生物利用度，在药物传递系统的研究中具有广泛的应用，此外，壳聚糖还可提高机体非特异性免疫功能，以壳聚糖作为载体材料制备纳米粒，原料来源广泛、降解性好，并且其制备过程无需添加任何有机制剂，所有辅料无毒无害，在高效低毒渔药剂型的开发和应用中具有良好的使用价值。1. The chitosan used in the present invention is the product of chitin deacetylation, has good biodegradability and bioadhesion, can prolong the residence time of the drug at the absorption site, and improve the bioavailability of the drug. In addition, chitosan can also improve the non-specific immune function of the body. Nanoparticles are prepared with chitosan as a carrier material, which has a wide range of raw materials and good degradability, and its preparation process does not need to add any organic agents , all excipients are non-toxic and harmless, and have good use value in the development and application of high-efficiency and low-toxicity fishery formulations.
2、本发明采用的三聚磷酸钠带有阴离子，可与壳聚糖正电荷氨基基团产生离子交联作用，形成聚电解质复合物。离子交联法中的凝胶化过程与体系中阴离子和阳离子浓度有关，因此纳米粒只在特定的壳聚糖和三聚磷酸钠浓度范围内形成。2. The sodium tripolyphosphate used in the present invention has anions, which can produce ionic crosslinking with chitosan positively charged amino groups to form polyelectrolyte complexes. The gelation process in the ion cross-linking method is related to the concentration of anions and cations in the system, so nanoparticles are only formed within the specific concentration range of chitosan and sodium tripolyphosphate.
3、在制备固体恩诺沙星纳米粒的过程中，优化了离子交联法制备恩诺沙星壳聚糖纳米粒混悬液的条件，并结合冷冻干燥法制备了固体恩诺沙星纳米粒，使其具有较小的粒径，纳米粒之间无团聚现象，并较高的包封率和载药量；3. In the process of preparing solid enrofloxacin nanoparticles, the conditions for preparing enrofloxacin chitosan nanoparticle suspension by ion cross-linking method were optimized, and solid enrofloxacin nanoparticle particles, so that it has a smaller particle size, no agglomeration phenomenon between nanoparticles, and higher encapsulation efficiency and drug loading;
4、与恩诺沙星粉剂相比具有良好的缓释性能，其在体外环境下1小内可减少约60％药物的释放，24小时总释放度为79.9％；4. Compared with enrofloxacin powder, it has good sustained-release performance, which can reduce the drug release by about 60% within 1 hour in an in vitro environment, and the total release rate in 24 hours is 79.9%;
5、与恩诺沙星粉剂相比具有更好的抗逆性，在4小时内热降解率和紫外降解率分别减少了38.4％和13.3％；5. Compared with enrofloxacin powder, it has better stress resistance, and the thermal degradation rate and ultraviolet degradation rate are reduced by 38.4% and 13.3% respectively within 4 hours;
6、本发明操作简便，固化方法可靠，提高生产效率，降低生产成本，为大规模生产和推广应用提供了有效的途径。6. The invention is easy to operate, reliable in curing method, improves production efficiency, reduces production cost, and provides an effective way for large-scale production and popularization and application.
附图说明：Description of drawings:
本发明由以下的实施例及其附图给出。The invention is given by the following examples and accompanying drawings.
图1是固体恩诺沙星纳米粒的透射电镜图。Figure 1 is a transmission electron microscope image of solid enrofloxacin nanoparticles.
图2是固体恩诺沙星纳米粒的体外释放特点图。Figure 2 is a graph showing the in vitro release characteristics of solid enrofloxacin nanoparticles.
图3是固体恩诺沙星纳米粒的热降解率图。Figure 3 is a thermal degradation rate graph of solid enrofloxacin nanoparticles.
图4是固体恩诺沙星纳米粒的紫外降解率图。Figure 4 is a graph of the UV degradation rate of solid enrofloxacin nanoparticles.
具体实施方式：Detailed ways:
以下将对本发明的一种固体恩诺沙星纳米粒的制备方法作进一步的详细描述。A method for preparing solid enrofloxacin nanoparticles of the present invention will be further described in detail below.
实施例Example
1、称取40mg的壳聚糖，加入蒸馏水定溶至20mL，加入0.2mL冰醋酸使其溶解，配制成浓度为2mg/mL的壳聚糖溶液，上述在搅拌速度为800rpm的磁力搅拌的条件下进行；1. Weigh 40 mg of chitosan, add distilled water to dissolve it to 20 mL, add 0.2 mL of glacial acetic acid to dissolve it, and prepare a chitosan solution with a concentration of 2 mg/mL. The above-mentioned conditions of magnetic stirring at a stirring speed of 800 rpm under;
2、称取12mg的恩诺沙星原料药，加入上述所述的壳聚糖溶液中溶解，以800rpm速度持续磁力搅拌10分钟使溶液中各组分分散均匀，以1.0mol/L的NaOH溶液调节pH至5.0，得恩诺沙星壳聚糖溶液；2. Weigh 12 mg of enrofloxacin bulk drug, add it to the above-mentioned chitosan solution to dissolve, continue magnetic stirring at a speed of 800 rpm for 10 minutes to disperse the components in the solution evenly, and use 1.0mol/L NaOH solution Adjust the pH to 5.0, get enrofloxacin chitosan solution;
3、称取三聚磷酸钠10mg，溶于8mL蒸馏水，配制成浓度为1.25mg/mL的三聚磷酸钠溶液；3. Weigh 10 mg of sodium tripolyphosphate, dissolve it in 8 mL of distilled water, and prepare a sodium tripolyphosphate solution with a concentration of 1.25 mg/mL;
4、将8mL三聚磷酸钠溶液缓慢滴入上述恩诺沙星壳聚糖溶液中，其间以800rpm速度持续磁力搅拌，使烧杯中液体略带白色乳光，在滴加完成后再以800rpm速度继续磁力搅拌1小时加以固定，得恩诺沙星壳聚糖纳米粒混悬液；4. Slowly drop 8mL sodium tripolyphosphate solution into the above-mentioned enrofloxacin chitosan solution, and continuously magnetically stir at a speed of 800rpm to make the liquid in the beaker slightly opalescent. Continue magnetic stirring for 1 hour to fix, and obtain enrofloxacin chitosan nanoparticle suspension;
5、将上述固定化的恩诺沙星壳聚糖纳米粒混悬液分装于冷冻瓶中，在-70℃下预冷冻2小时，然后在-50℃下抽真空冷冻干燥，制成固体恩诺沙星纳米粒，所述的固体恩诺沙星纳米粒且呈表面疏松多孔的白色固体粒状，所述的固体恩诺沙星纳米粒的包封率为50-70％，载药量为8-12wt％。5. Divide the above-mentioned immobilized enrofloxacin-chitosan nanoparticle suspension into freezing bottles, pre-freeze at -70°C for 2 hours, and then vacuum freeze-dry at -50°C to make a solid Enrofloxacin nanoparticles, the solid enrofloxacin nanoparticles are in the form of loose and porous white solid particles on the surface, the encapsulation efficiency of the solid enrofloxacin nanoparticles is 50-70%, and the drug loading It is 8-12wt%.
对本发明所制成的固体恩诺沙星纳米粒，用透射电镜(TEM)、紫外分光光度计(UV)等仪器进行测定其表征、释放特点和热、光稳定性，结果表明如下：The solid enrofloxacin nanoparticles made by the present invention are measured with transmission electron microscope (TEM), ultraviolet spectrophotometer (UV) and other instruments to measure its characterization, release characteristics and heat, photostability, the results show as follows:
所制备的固体恩诺沙星纳米粒为球星或类球型颗粒，分散均匀，无团聚现象，平均粒径在237.4nm左右，见附图1。The prepared solid enrofloxacin nanoparticles are spherical or spherical particles, uniformly dispersed, without agglomeration phenomenon, and the average particle diameter is about 237.4nm, see Figure 1.
所制备的固体恩诺沙星纳米粒具有一定的缓释作用，见附图2。The prepared solid enrofloxacin nanoparticles have a certain sustained-release effect, as shown in Figure 2.
相比恩诺沙星粉剂，固体恩诺沙星纳米粒具有更好的热稳定性，见附图3。Compared with enrofloxacin powder, solid enrofloxacin nanoparticles have better thermal stability, see Figure 3.
相比恩诺沙星粉剂，固体恩诺沙星纳米粒具有更好的光稳定性，见附图4。Compared with enrofloxacin powder, solid enrofloxacin nanoparticles have better photostability, see Figure 4.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102166376A (en) * | 2011-04-19 | 2011-08-31 | 重庆医科大学 | Ophthalmic medicine-carried amnion and preparation method thereof |
| CN103169665A (en) * | 2012-11-23 | 2013-06-26 | 杭州师范大学 | Oxaliplatin chitosan nanoparticle and application thereof |
| CN103536558A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Cefoperazone sodium composition freeze-dried powder for injection |
| CN103536564A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Cefonicid sodium composition powder for injection |
| CN103536556A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Pefloxacin mesylate composition freeze-dried powder for injection |
| CN103536555A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Ceftriaxone sodium composition freeze-dried powder for injection |
| CN103550176A (en) * | 2013-10-15 | 2014-02-05 | 海南卫康制药(潜山)有限公司 | Fosfomycin sodium composition lyophilized powder for injection |
| CN103585116A (en) * | 2013-10-15 | 2014-02-19 | 海南卫康制药(潜山)有限公司 | Levofloxacin composition freeze-dried powder for injection |
| CN109172802A (en) * | 2018-09-21 | 2019-01-11 | 岭南师范学院 | A kind of Tilapia mossambica fish gill antibacterial peptide chitosan nanoparticle and its preparation method and application |
| CN110141558A (en) * | 2019-05-29 | 2019-08-20 | 四川农业大学 | A kind of preparation method of mabrofloxacin nanoparticles |
| CN111249251A (en) * | 2018-12-03 | 2020-06-09 | 华中农业大学 | Enrofloxacin chitosan nanoparticles |
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2008
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102166376A (en) * | 2011-04-19 | 2011-08-31 | 重庆医科大学 | Ophthalmic medicine-carried amnion and preparation method thereof |
| CN102166376B (en) * | 2011-04-19 | 2013-12-11 | 重庆医科大学 | Ophthalmic medicine-carried amnion and preparation method thereof |
| CN103169665A (en) * | 2012-11-23 | 2013-06-26 | 杭州师范大学 | Oxaliplatin chitosan nanoparticle and application thereof |
| CN103536558A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Cefoperazone sodium composition freeze-dried powder for injection |
| CN103536564A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Cefonicid sodium composition powder for injection |
| CN103536556A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Pefloxacin mesylate composition freeze-dried powder for injection |
| CN103536555A (en) * | 2013-10-15 | 2014-01-29 | 海南卫康制药(潜山)有限公司 | Ceftriaxone sodium composition freeze-dried powder for injection |
| CN103550176A (en) * | 2013-10-15 | 2014-02-05 | 海南卫康制药(潜山)有限公司 | Fosfomycin sodium composition lyophilized powder for injection |
| CN103585116A (en) * | 2013-10-15 | 2014-02-19 | 海南卫康制药(潜山)有限公司 | Levofloxacin composition freeze-dried powder for injection |
| CN109172802A (en) * | 2018-09-21 | 2019-01-11 | 岭南师范学院 | A kind of Tilapia mossambica fish gill antibacterial peptide chitosan nanoparticle and its preparation method and application |
| CN111249251A (en) * | 2018-12-03 | 2020-06-09 | 华中农业大学 | Enrofloxacin chitosan nanoparticles |
| CN110141558A (en) * | 2019-05-29 | 2019-08-20 | 四川农业大学 | A kind of preparation method of mabrofloxacin nanoparticles |
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