基于酰腙键的去氢枞酸基聚乙二醇的合成及其胶束的药物缓释性能
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广西大学化学化工学院

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O631.2

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国家自然科学基金资助项目(21064001);广西自然科学基金资助项目(2014GXNSFAA118042)


Synthesis of dehydroabietic acid-poly(ethylene glycol) based on acylhydrazone bond and drug release properties of their micelles
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    摘要:

    去氢枞酸 (DHA)依次与SOCl2、水合肼反应合成了去氢枞酸酰肼 (DHA-CONHNH2);用mPEG-OH和HO-PEG-OH分别与对醛基苯甲酸反应制备了含有端醛基的聚乙二醇;后者分别与DHA-CONHNH2进行缩合反应,合成了两种基于酰腙键的去氢枞酸基聚乙二醇(mPEG1900-hyd-DHA和PEG2000-(-hyd-DHA)2),并用透析法制备了它们的胶束和载DOX(阿霉素)的胶束。使用FT-IR、1H-NMR、DLS、TEM、UV-vis等对聚合物结构、胶束大小和形貌、CMC、DOX的释放性能等进行了表征和测试。结果表明,mPEG1900-hyd-DHA和PEG2000-(-hyd-DHA)2的胶束都呈球形,平均粒径分别为46 nm和78nm;CMC值分别为5.5 mg/L和3.4 mg/L。 mPEG1900-hyd-DHA胶束对DOX的包封率和载药量大于PEG2000-(-hyd-DHA)2胶束;PEG2000-(-hyd-DHA)2载药胶束在pH=5.0和pH=7.4下,经48 h的DOX的累积释放率分别为49.5%和20.3%。因此,合成聚合物对抗癌药物有缓释作用,具有潜在的应用前景。

    Abstract:

    Dehydroabietic hydrazide (DHA-CONHNH2) was synthesized by the successive reaction of dehydroabietic acid (DHA) with SOCl2 and hydrazine hydrate. Poly(ethylene glycol) with aldehyde end groups was prepared by the reaction of mPEG-OH and HO-PEG-OH with p-formylbenzoic acid, respectively. Two kinds of dehydroabietic acid-poly(ethylene glycol) (mPEG1900-hyd-DHA and PEG2000-(-hyd-DHA)2) based on acylhydrazone bond were synthesized by the condensation reaction of the latter with DHA-CONHNH2, respectively, and their micelles and doxorubicin(DOX)-loaded micelles were prepared by dialysis method. The polymer structure, micelle size and morphology, CMC, release behaviors of DOX were characterized and tested by FT-IR, 1H-NMR, DLS, TEM, UV-vis, etc. The results showed that the micelles of mPEG1900-hyd-DHA and PEG2000-(-hyd-DHA)2 were spherical, and their average particle sizes were 46 nm and 78nm, respectively; the CMC values were 5.5 mg/L and 3.4 mg/L, respectively; The encapsulation rate and drug loading capacity of mPEG1900-hyd-DHA micelles for DOX were greater than that of PEG2000-(-hyd-DHA)2 micelles. The cumulative release rates of DOX after 48 h were 49.5% at pH=5.0 and 20.3% at pH=7.4 for PEG2000-(-hyd-DHA)2 drug-loaded micelles, respectively. Therefore, synthetic polymers have a sustained release effect on anticancer drugs and have potential application prospects.

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  • 收稿日期:2021-11-09
  • 最后修改日期:2022-01-12
  • 录用日期:2022-03-27
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