巯基化叶酸衍生物的通用合成方案。
A General Protocol for Synthesizing Thiolated Folate Derivatives.
机构信息
Institute of Hybrid Materials, National Center of International Research for Hybrid Materials Technology, National Base of International Science & Technology Cooperation, College of Materials Science and Engineering, Qingdao University, Qingdao 266071, China.
出版信息
Molecules. 2023 Jul 5;28(13):5228. doi: 10.3390/molecules28135228.
Folic acid (FA) has shown great potential in the fields of targeted drug delivery and disease diagnosis due to its highly tumor-targeting nature, biocompatibility, and low cost. However, FA is generally introduced in targeted drug delivery systems through macromolecular linkage via complex synthetic processes, resulting in lower yields and high costs. In this work, we report a general protocol for synthesizing thiolated folate derivatives. The small molecule thiolated folate (TFa) was first synthesized with a purity higher than 98.20%. First, S-S-containing diol was synthesized with a purity higher than 99.44 through a newly developed green oxidation protocol, which was carried out in water with no catalyst. Then, folic acid was modified using the diol through esterification, and TFa was finally synthesized by breaking the disulfide bond. Further, the synthesized TFa was utilized to modify silver nanoparticles. The results showed that TFa could be easily bonded to metal particles. The protocol could be extended to the synthesis of a series of thiolated derivatives of folate, such as mercaptohexyl folate, mercaptoundecyl folate, etc., which would greatly benefit the biological applications of FA.
叶酸(FA)由于其高度的肿瘤靶向性、生物相容性和低成本,在靶向药物输送和疾病诊断领域显示出巨大的潜力。然而,FA 通常通过复杂的合成过程通过大分子连接引入靶向药物输送系统,导致产率降低和成本增加。在这项工作中,我们报告了一种合成巯基叶酸衍生物的一般方案。小分子巯基叶酸(TFa)首先以高于 98.20%的纯度合成。首先,通过新开发的绿色氧化方案,在水中无催化剂合成了纯度高于 99.44 的含 S-S 的二醇。然后,通过酯化作用修饰叶酸,最后通过打断二硫键合成 TFa。此外,合成的 TFa 用于修饰银纳米粒子。结果表明 TFa 可以很容易地与金属颗粒结合。该方案可以扩展到一系列叶酸的巯基衍生物的合成,如巯基己基叶酸、巯基十一烷基叶酸等,这将极大地有益于 FA 的生物应用。