CN110755618B - 一种透明质酸-铜(ii)复合纳米粒子及其制备方法 - Google Patents
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Abstract
本发明公开了一种透明质酸‑铜(II)复合纳米粒子及其制备方法，该铜(II)复合纳米粒子是通过二乙撑三胺桥联修饰的透明质酸与铜(II)盐为原料制备的。本发明的制备方法操作简单、方便、原料便宜且易得，通过透明质酸修饰的铜(II)复合纳米粒子，对癌细胞具有靶向性、生物相容性好，具有较低的毒副作用。并且，二乙撑三胺修饰的透明质酸‑铜(II)复合纳米粒子在近红外区域有良好的吸收，具有光热转换的可能。光热性质研究证实了其具有良好的光热性能。本发明制备的透明质酸‑铜(II)复合纳米粒子光热治疗，在癌症治疗领域具有广阔的应用前景。
Description
技术领域
本发明涉及铜复合纳米粒子，具体是二乙撑三胺修饰的透明质酸-铜(II)复合纳米粒子的制备方法及应用。
背景技术
含铜的光热材料作为光热治疗当下最热门的研究方向之一，当前仍有待进一步的研究。目前，含铜的光热材料主要是无机光热材料。例如：以铜为基础的半导体纳米材料、CuS、Cu3BiS3等。但是，这些无机光热材料在实验研究中往往存在着一些不足。例如：基于半导体碳材料诱发的毒性反应、生物相容性差以及长期毒性等。
透明质酸，一种天然的生物多糖，被广泛的用于生物材料的设计中。在肿瘤治疗中，透明质酸可以作为功能小分子的精准递送载体而被应用于精准肿瘤成像、治疗等方面。然而，透明质酸和二价铜离子在分子水平上的配位是很难形成的。目前，透明质酸上的羧基需要在调节pH后的溶液中才能以羧基负离子的形式和二价铜离子配位。为了丰富通明质酸-铜(II)复合纳米粒子的制备方法，我们考虑到利用酰胺反应将二乙撑三胺共价接枝在透明质酸上，而后再利用二乙撑三胺上的胺基和铜离子配位。进而得到一种新型配位驱动自组装形成的透明质酸-铜(II)复合纳米粒子。
发明内容
本发明的目的是针对现有技术的不足，选择合成了一种新型的具有优异的光热转化效率的二乙撑三胺修饰的透明质酸-铜(II)复合纳米粒子。由于二乙撑三胺桥联修饰的透明质酸其端胺具有配位活性，使其在正常环境下可以与Cu(II)发生配位作用。配位后由于配位场能级改变d电子发生d-d跃迁，加强了纳米粒子的近红外吸收，因而具有优异的光热性能。其中，生物多糖透明质酸可以降低铜配合物的细胞毒性，并提供一个良好的水分散性、及CD44受体介导的癌细胞靶向性。可作为一种有效的光热纳米材料进一步应用于癌症光热治疗。
本发明一种透明质酸-铜(II)复合纳米粒子的制备方法，以透明质酸、CuCl2、二乙撑三胺为原料，包括以下步骤：
1) 称取透明质酸溶解于二次水，稀释至浓度为0.04 mol/L，取1 mL；
2）在步骤1）中加入1-（3-二甲氨基丙基）-3-乙基碳二亚胺盐酸盐和N-羟基琥珀酰亚胺搅拌活化；
3）在步骤2）所得的活化溶液中加入二乙撑三胺进行搅拌；
4）将步骤3）所得的溶液用透析袋透析，冻干，得到透明质酸二乙撑三胺配体；
5）将CuCl2溶于的二次水中，稀释至浓度为0.03mol/L，取1 mL；
6）取步骤4）所得的配体加入到步骤5）所得的1 mL溶液中，然后用二次水稀释，稀释至浓度为0.03 mol/L，即得到透明质酸-铜(II)复合纳米粒子。
制备方法中，透明质酸（分子量8000-10000 Da）、1-（3-二甲氨基丙基）-3-乙基碳二亚胺盐酸盐、 N-羟基琥珀酰亚胺和二乙撑三胺的摩尔比为2:1:1；
配体和CuCl2的摩尔比为2:1。
制备方法步骤2）中，活化时间为2-4h；
步骤3）中，搅拌时间为23-24h；
步骤4）透析袋的分子量为3000，透析时间为45-50h。
本发明的另一个目的是提供通过上述所述的方法制备的具有光热转换效果的透明质酸-铜(II)复合纳米粒子。
研究发现，通过本发明的方法制备的透明质酸-铜(II)复合纳米粒子具有强的近红外吸收及良好的光热转换性能，这将进一步拓展其在光热治疗领域的应用。
本发明还提供所述的透明质酸-铜(II)复合纳米粒子在光热诊疗治疗的应用。
本发明的优点是：
1）制备透明质酸-铜(II)复合纳米粒子的原料便宜、易得；
2）操作简单，方便，制备条件简易；
3）制备的透明质酸-铜(II)复合纳米粒子有良好的近红外吸收，特别是还具有良好的光热转换性能。
附图说明
图1为实施例1透明质酸-铜(II)复合纳米粒子高分辨透射电镜下观测到的形貌分布图。
图2为实施例1透明质酸-铜(II)复合纳米粒子光热升温实验对比图；
其中，图a是透明质酸-铜(II)复合纳米粒子在650 nm近红外光照射下光热升温图；图b是参比水在650 nm近红外光照射下光热升温图。
具体实施方式
下面结合实施例和附图对本发明内容作进一步的详细说明，但不 不是以本发明的限定。
实施例
制备透明质酸-铜(II)复合纳米粒子，包括如下步骤：
1）称取透明质酸（HA） 1.613 g（4 mmol），移至烧杯中，后加入100 mL二次水并搅拌使其充分溶解，取1 mL；
2）在步骤1）中加入1-（3-二甲氨基丙基）-3-乙基碳二亚胺盐酸盐（EDC） 0.38 g（2mmol）和N-羟基琥珀酰亚胺（NHS） 0.23 g（2 mmol）搅拌活化3小时；
3）在步骤2）所得的活化溶液中加入二乙撑三胺0.4 g（2 mmol）搅拌24小时；
4）将步骤3）所得的溶液用分子量为3000 Da的透析袋进行透析48 h后冻干，得到透明质酸二乙撑三胺配体；
5）配制CuCl2离子母液，取CuCl2 26.5 mg使其溶于5 mL二次水中，用移液枪移取1mL；
6）按配体与铜离子溶液摩尔比2:1制作样品，然后加二次水稀释至浓度为0.03mol/L，得到透明质酸-铜(II)复合纳米粒子。
应用实施例
实验方法如下：
将上述制备所得的透明质酸-铜(II)复合纳米粒子配置成水溶液。参照图1，在透射电镜观察下，所制备的透明质酸-铜(II)配合物具有纳米粒子的形貌，说明纳米粒子已经成功形成。参照图2，在紫外-可见-近红外光谱吸收图中可以看出，在600 nm-700 nm处有吸收，说明它具有光热转换的潜力。进一步，光热性质研究证实了其具有良好的光热性能，用650 nm 激光(1.2 W cm-2)照射，用红外热成像仪记录溶液的温度随光照时间的变化。随着光照时间的增加，透明质酸-铜(II)复合纳米粒子溶液的温度显著升高，并在10 min内温度从27℃升高到56 ℃。此实验证明透明质酸-铜(II)复合纳米粒子具有良好的光热效果。证实了本发明的透明质酸-铜(II)复合纳米粒子满足光热治疗的需求。
Claims (1)
1.一种透明质酸-铜(II)复合纳米粒子的制备方法，其特征在于：以透明质酸、CuCl2、二乙撑三胺为原料，制备方法包括以下步骤：
1) 称取透明质酸溶解于二次水，稀释至浓度为0.04 mol/L，取1 mL；
2）在步骤1）中加入1-（3-二甲氨基丙基）-3-乙基碳二亚胺盐酸盐和N-羟基琥珀酰亚胺搅拌活化；
3）在步骤2）所得的活化溶液中加入二乙撑三胺进行搅拌；
4）将步骤3）所得的溶液用透析袋透析，冻干，得到透明质酸二乙撑三胺配体；
5）将CuCl2溶于的二次水中，稀释至浓度为0.03 mol/L，取1 mL；
6）取步骤4）所得的配体加入到步骤5）所取得的1 mL溶液中，然后用二次水稀释，稀释至浓度为0.03 mol/L，即得到透明质酸-铜(II)复合纳米粒子；
制备方法中，透明质酸、1-（3-二甲氨基丙基）-3-乙基碳二亚胺盐酸盐、 N-羟基琥珀酰亚胺和二乙撑三胺的摩尔比为2:1:1:1；
二乙撑三胺修饰的透明质酸配体和CuCl2的摩尔比为2:1；
步骤2）中，活化时间为2-4h；
步骤3）中，搅拌时间为23-25h；
步骤4）透析袋的分子量为3000Da，透析时间为45-50h。
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| WO2012138379A2 (en) * | 2010-10-19 | 2012-10-11 | Board Of Regents, The University Of Texas System | Multifunctional chelator-free radioactive nanoparticles for imaging and therapy |
| CN103030140A (zh) * | 2012-12-21 | 2013-04-10 | 郑州大学 | 透明质酸修饰的氧化石墨烯及其药物组合物的制备方法与应用 |
| CN104784691A (zh) * | 2015-04-29 | 2015-07-22 | 天津医科大学 | 一种生物相容性良好的CuS光热治疗纳米材料的制备方法 |
| WO2017164822A1 (en) * | 2016-03-24 | 2017-09-28 | Nanyang Technological University | Core-shell plasmonic nanogapped nanostructured material |
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| CN101081827A (zh) * | 2006-05-29 | 2007-12-05 | 天津瑞发化工科技发展有限公司 | 一种具有同时处理多种重金属离子的螯合剂 |
| CN103446589B (zh) * | 2012-06-01 | 2015-05-27 | 首都医科大学 | 四氢-β-咔啉-3-甲酰-二乙烯三胺-β-环糊精络铜,其制备,抗血栓作用和应用 |
| CN105233283B (zh) * | 2015-11-11 | 2021-06-11 | 广西康健奥鑫生物医药科技有限公司 | 一种光动力治疗深部肿瘤靶向纳米光敏剂及其制备方法 |
-
2019
- 2019-12-08 CN CN201911246146.3A patent/CN110755618B/zh active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012138379A2 (en) * | 2010-10-19 | 2012-10-11 | Board Of Regents, The University Of Texas System | Multifunctional chelator-free radioactive nanoparticles for imaging and therapy |
| CN103030140A (zh) * | 2012-12-21 | 2013-04-10 | 郑州大学 | 透明质酸修饰的氧化石墨烯及其药物组合物的制备方法与应用 |
| CN104784691A (zh) * | 2015-04-29 | 2015-07-22 | 天津医科大学 | 一种生物相容性良好的CuS光热治疗纳米材料的制备方法 |
| WO2017164822A1 (en) * | 2016-03-24 | 2017-09-28 | Nanyang Technological University | Core-shell plasmonic nanogapped nanostructured material |
Non-Patent Citations (2)
| Title |
|---|
| Cupreous Complex-Loaded Chitosan Nanoparticles for Photothermal Therapy and Chemotherapy of Oral Epithelial Carcinoma;Min Lin, et al.;《ACS Appl. Mater. Interfaces》;20150904;第7卷;第20801-20812页 * |
| 透明质酸修饰的氧化石墨烯在光热联合化疗中的应用;王亚婷;《中国学位论文全文数据库》;20150925;摘要、正文部分第6-35页 * |
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