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林产化学与工业 ›› 2018, Vol. 38 ›› Issue (2): 59-66.doi: 10.3969/j.issn.0253-2417.2018.02.008

• 研究报告 • 上一篇    下一篇

松香基叔胺盐的自组装、复配及载药性能研究

林海霞, 杨明生, 田超, 韩春蕊   

  1. 北京林业大学 材料科学与技术学院;林业生物质材料与能源教育部工程 研究中心;林木生物质化学北京市重点实验室, 北京 100083
  • 收稿日期:2017-09-12 出版日期:2018-04-25 发布日期:2018-04-28
  • 通讯作者: 韩春蕊,副教授,硕士生导师,研究领域为松香资源高值化化学改性利用;E-mail:hanchunrui@bjfu.edu.cn。 E-mail:hanchunrui@bjfu.edu.cn
  • 作者简介:林海霞(1991-),女,山东烟台人,硕士生,主要从事松香资源高值化化学改性利用研究
  • 基金资助:
    国家重点研发计划项目(2016YFD0600803);中央高校基本科研业务费专项资金资助(2017JC01);国家自然科学基金资助项目(30901139)

Self-assembly,Mixed System and Drug-loading Research of Rosin-based Tertiary Amine Salt

LIN Haixia, YANG Mingsheng, TIAN Chao, HAN Chunrui   

  1. College of Materials Science and Technology, Beijing Forestry University;MOE Engineering Research Center of Forestry Biomass Materials and Bioenergy;Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing 100083, China
  • Received:2017-09-12 Online:2018-04-25 Published:2018-04-28

摘要: 以松香为原料,经D-A加成、酰氯化、酯化和成盐反应合成含3个亲水基团的马来松香基叔胺盐表面活性剂(RETAS)。RETAS的临界胶束浓度(CCMC)为0.73 mmol/L(0.50 g/L),对应的表面张力为38.58 mN/m,乳化能力为292 s。将RETAS与天然无患子皂苷进行复配,通过测定不同比例复配体系的表面张力、乳化性能和泡沫性能探究其复配效果,得到最佳协同复配比例,并通过透射电镜(TEM)等测试研究RETAS和复配体系的自组装行为和胶束形态,对胶束形成机理进行推测。结果表明:复配体系在RETAS与无患子皂苷的质量比为5:5时协同作用最强,乳化能力提高;此时复配体系的CCMC为0.40 g/L,对应的表面张力为37.57 mN/m,乳化能力为373 s。对RETAS进行人结肠腺癌细胞(Caco-2)细胞毒性研究,发现其毒性低于松香原料,低浓度下无毒或低毒。将RETAS及其复配体系应用于抗癌药物盐酸阿霉素(DOX)的载药性能研究,发现在pH值7.4和5.0时,RETAS对DOX的释放率分别为67%和接近100%,质量比为5:5时复配体系药物释放率分别为68%和接近90%,表明RETAS和复配产物均可作为DOX的靶向载体;复配对靶向载药性能未有改善,但缓释效果得到明显改善,在模拟肿瘤条件(pH值5.0)下,复配体系中DOX在24 h后仍在缓慢释放,缓释效果明显。

关键词: 马来松香, 无患子皂苷, 自组装, 靶向载药, 缓释

Abstract: A novel maleic rosin-based ester tertiary amine salt surfactant (RETAS) with three hydrophilic groups was synthesized through D-A addition reaction, acyl chlorination, esterification reaction and salt forming reaction with rosin acid as raw material. The critical micelle concentration (CCMC) of RETAS was 0.73 mmol/L (0.50 g/L), and the corresponding surface tension at CMC (γCMC) was 38.58 mN/m. The RETAS was mixed with natural soapnut saponin. The best compound proportion of mixed system was obtained by determining the surface tension, emulsification property and foam property to study the synergistic effect. And the self-assembly behavior and micelle morphology of the composite system was characterized by transmission electron microscopy (TEM) and the micelle formation mechanism was speculated in detail. The results showed that the γCMC and CCMC of mixtures were 37.57 mN/m and 0.40 g/L when the optimum mass ratio of RETAS/soapnut saponin was 5:5. The emulsifying properties of RETAS and saponin were only 292 s and 310 s respectively, but the emulsifying properties increased to 373 s in the optimum mass ratio. Finally, the cytotoxicity of RETAS on human colon adenocarcinoma cells (Caco-2) was investigated and it was found that it had non-toxic or low toxicity and was applied to study the drug loading properties of anticancer drug doxorubicin (DOX). The release rates of DOX on RETAS were 67% and close to 100% in pH value 7.4 and 5.0, respectively. While the release rates of DOX on the mixture were 68% and close to 90% in pH value 7.4 and 5.0. The results showed that both RETAS and mixed product could be used as the target carrier of DOX. Under simulated tumor conditions, DOX was still slowly released after 24 hours in pH=5.0.

Key words: maleic rosin, soapnut saponin, self-assemble, targeted drug delivery, sustained-release

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