新型10-羟基喜树碱前药分子的制备与性能研究
The Preparation and Investigation of a Novel 10-Hydroxycamptothecin Prodrug
DOI: 10.12677/AAC.2022.123029, PDF,    国家自然科学基金支持
作者: 蔡丽娟, 朱金丽, 汤艳峰, 孙广平*：南通大学化学化工学院，江苏 南通
关键词: 10-羟基喜树碱前药分子；GSH刺激响应；荧光；10-Hydroxycamptothecin Prodrug； GSH Stimulus Response； Fluorescence
摘要: 本文以10-羟基喜树碱(HCPT, 10-Hydroxycamptothecin)作为前药分子，通过2,4-二硝基苯磺酰氯(DNS)的取代反应，成功构筑了一种具有荧光探针性能的喜树碱前药分子(DNS-HCPT)。荧光试验表明DNS-HCPT在谷胱甘肽(GSH)的作用下，能将前药分子HCPT快速地释放出来，发射出很强的黄色荧光，可用于肿瘤组织的追踪与识别。此外，HCPT作为喜树碱衍生物中抗癌效果最好之一，DNS-HCPT释放的HCPT还能被用于癌细胞的治疗，在癌细胞的诊断与治疗中具有潜在的应用价值。
Abstract: Prodrug DNS-HCPT was successfully prepared via the substitution reaction of 10-hydroxycampto- thecin (HCPT) and 2,4-dinitrobenzenesulfonyl chloride (DNS), which could be used as a fluorescent probe. HCPT could be effectively released under glutathione (GSH) condition and realized strong yellow fluorescence emission, suggesting potential in tracking tumor tissues. Moreover, as one of the most effective anticancer camptothecin derivatives, the released HCPT could be utilized for cancer therapy, which was potential in cancer diagnosis and therapy.
文章引用：蔡丽娟, 朱金丽, 汤艳峰, 孙广平. 新型10-羟基喜树碱前药分子的制备与性能研究[J]. 分析化学进展, 2022, 12(3): 232-239. https://doi.org/10.12677/AAC.2022.123029

参考文献

[1] Ahles, T.A. and Root, J.C. (2018) Cognitive Effects of Cancer and Cancer Treatments. Annual Review of Clinical Psychology, 14, 425-451.
[Google Scholar] [CrossRef] [PubMed]
[2] Qin, S.Y., Zhang, A.Q., Cheng, S.X., et al. (2017) Drug Self-Delivery Systems for Cancer Therapy. Biomaterials, 112, 234-247.
[Google Scholar] [CrossRef] [PubMed]
[3] He, Q. and Shi, J. (2014) MSN Anti-Cancer Nanomedicines: Chemotherapy Enhancement, Overcoming of Drug Resistance, and Metastasis Inhibition. Advanced Materials, 26, 391-411.
[Google Scholar] [CrossRef] [PubMed]
[4] Hu, X.Y., Gao, L., Mosel, S., et al. (2018) From Supramolecular Vesicles to Micelles: Controllable Construction of Tumor-Targeting Nanocarriers-Based on Host-Guest Interaction between a Pillar[5]arene-Based Prodrug and a RGD- Sulfonate Guest. Small, 14, 1803952-1803962.
[Google Scholar] [CrossRef] [PubMed]
[5] Liu, X., Shao, W., Zheng, Y., et al. (2017) GSH-Responsive supramolecular Nanoparticles Constructed by β-D-Galactose- Modified Pillar[5]arene and Camptothecin Prodrug for Targeted Anticancer Drug Delivery. Chemical Communications, 53, 8596-8599.
[Google Scholar] [CrossRef] 
[6] Zhang, Y.H., Zhang, Y.M., Sheng, X., et al. (2020) Enzyme-Responsive Fluorescent Camptothecin Prodrug/Poly- saccharide Supramolecular Assembly for Targeted Cellular Imaging and in Situ Controlled Drug Release. Chemical Communications, 56, 1042-1045.
[Google Scholar] [CrossRef] 
[7] Whang, C.H., Yoo, E., Hur, S.K., et al. (2018) A Highly GSH-Sensitive SN-38 Prodrug with an “OFF-to-ON” Fluorescence Switch as a Bifunctional Anticancer Agent. Chemical Communications, 54, 9031-9034.
[Google Scholar] [CrossRef] 
[8] Sun, G., He, Z., Hao, M., et al. (2019) Bifunctional Supramolecular Prodrug Vesicles Constructed from a Camptothecin Derivative with a Water-Soluble Pillar[5]arene for Cancer Diagnosis and Therapy. Chemical Communications, 55, 10892-10895.
[Google Scholar] [CrossRef] 
[9] Zou, H., Liu, J., Li, Y., et al. (2018) Cucurbit[8]uril-Based Polymers and Polymer Materials. Small, 14, 1802234- 1802252.
[Google Scholar] [CrossRef] [PubMed]
[10] Ding, Y.F., Wei, J., Li, S., et al. (2019) Host-Guest Interactions Initiated Supramolecular Chitosan Nanogels for Selective Intracellular Drug Delivery. ACS Applied Materials & Interfaces, 11, 28665-28670.
[Google Scholar] [CrossRef] [PubMed]
[11] Feng, W., Jin, M., Yang, K., et al. (2018) Supramolecular Delivery Systems Based on Pillararenes. Chemical Communications, 54, 13626-13640.
[Google Scholar] [CrossRef] 
[12] Zhang, Y.M., Zhang, N.Y., Xiao, K., et al. (2018) Photo-Controlled Reversible Microtubule Assembly Mediated by Paclitaxel-Modified Cyclodextrin. Angewandte Chemie International Edition, 57, 8649-8653.
[Google Scholar] [CrossRef] [PubMed]
[13] Wu, D., Li, Y., Shen, J., et al. (2018) Supramolecular Chemotherapeutic Drug Constructed from Pillararene-Based Supramolecular Amphiphile. Chemical Communications, 54, 8198-8201.
[Google Scholar] [CrossRef] 
[14] Yu, G., Yu, W., Mao, Z., et al. (2015) A Pillararene-Based Ternary Drug-Delivery System with Photocontrolled Anticancer Drug Release. Small, 11, 919-925.
[Google Scholar] [CrossRef] [PubMed]
[15] Luo, C., Sun, J., Liu, D., et al. (2016) Self-Assembled Redox Dual-Responsive Prodrug-Nanosystem Formed by Single Thioether-Bridged Paclitaxel-Fatty Acid Conjugate for Cancer Chemotherapy. Nano Letters, 16, 5401-5408.
[Google Scholar] [CrossRef] [PubMed]
[16] Cai, Y., Shen, H., Zhan, J., et al. (2017) Supramolecular “Trojan Horse” for Nuclear Delivery of Dual Anticancer Drugs. Journal of the American Chemical Society, 139, 2876-2879.
[Google Scholar] [CrossRef] [PubMed]
[17] Mori, M., Fujikawa, Y., Kikkawa, M., et al. (2019) A Highly Selective Fluorogenic Substratefor Imaging Glutathione S-Transferase P1: Development and Cellular Applicability in Epigenetic Studies. Chemical Communications, 55, 8122- 8125.
[Google Scholar] [CrossRef] 
[18] Zhang, B., Ge, C., Yao, J., et al. (2015) Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications. Journal of the American Chemical Society, 137, 757-769.
[Google Scholar] [CrossRef] [PubMed]

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