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化学进展 2020, Vol. 32 Issue (5): 594-603 DOI: 10.7536/PC190819 前一篇   后一篇

• 综述 •

基于生物素的荧光有机小分子及其应用

张继东1,**(), 刘阿晨1, 陈娇2, 袁光辉1, 金华峰1   

  1. 1.安康学院化学化工学院 新型材料研究中心 陕西省富硒食品质量监督检验中心 安康 725000
    2.西北大学化学与材料科学学院 合成与天然功能分子化学教育部重点实验室 西安 710127
  • 收稿日期:2019-08-19 修回日期:2019-12-03 出版日期:2020-05-15 发布日期:2020-02-20
  • 通讯作者: 张继东
  • 基金资助:
    陕西省科技厅重点项目(2018PT-31); 陕西省科技厅青年基金项目(2019JQ-504); 陕西省自然科学基金项目(2019JM-229); 安康学院博士科研启动基金(2018AYQDZR06); 农业部富硒产品开发国家地方联合工程实验室开放课题资助项目(Se-2018B02)
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Fluorescent Organic Small Molecule Based on Biotin and Their Applications

Jidong Zhang1,**(), Achen Liu1, Jiao Chen2, Guanghui Yuan1, Huafeng Jin1   

  1. 1.Department of Chemistry and Chemical Engineering, Research Centre of New Materials, Quality Supervision and Inspection Centre of Se-enriched Food of Shaanxi Province, Ankang Univerisity, Ankang 725000, China
    2.Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an 710127, China
  • Received:2019-08-19 Revised:2019-12-03 Online:2020-05-15 Published:2020-02-20
  • Contact: Jidong Zhang
  • About author:
    ** e-mail:
  • Supported by:
    Key Projects of Shaanxi Provincial Science & Technology Department(2018PT-31); Youth Foundation of Shaanxi Provincial Science & Technology Department(2019JQ-504); Natural Science Foundation of Shaanxi Province(2019JM-229); Doctor’s Initial Funding of Ankang University(2018AYQDZR06); Key Laboratory of Se-Enriched Products Development and Quality control, Ministry of Agriculture(Se-2018B02)

生物素是一种水溶性维生素,在人体中作为一种重要的羧酸酶辅酶起作用,近年来受到化学家和生物学家的广泛青睐。此外,其在各种生理和病理过程中表现出低毒性,可以被设计成具有靶向选择性的药物载体,能将抗癌药物有效地传递给肿瘤细胞。如今含生物素的小分子已发展成一类具有显著应用价值的生物功能分子。该类化合物具有合成简便、易功能化和特异性强等优点。本文综述了生物素及其衍生物在生物传感、药物释放和其他领域的研究进展,并对其发展趋势做出了展望。

关键词： 生物素, 荧光探针, 生物成像, 药物释放

Biotin is a water-soluble vitamin and serves as a coenzyme for carboxylases in human body. It is widely favored by chemists and biologists in recent years. In addition, it exhibits low toxicity in various physiological and pathological processes, and can be designed as a selectivity targeting drug carriers, which can efficiently deliver therapeutic drugs to cells. Nowadays, small molecules containing biotin have developed into a class of biofunctional molecules of high utility value. These compounds have the advantages of simple synthesis, easy functionalization, and high specificity. In this paper, the progress of biotin and its derivatives in biosensors, drug release and other fields are systematically reviewed, and the prospects for their development are presented.

Contents

1 Introduction

2 Fluorescent probe based on biotin structure

3 Targeted diagnostic and therapeutic molecular system based on biotin structure

4 Other biomolecules containing based on biotin structure

5 Conclusion

Key words: biotin, fluorescent probe, biological imaging, drug delivery
()
图1 基于生物素的荧光探针1的合成过程[19]
Fig. 1 Synthesis route of fluorescent probe 1 based on biotin[19]
图2 荧光探针2对硫醇的识别机理图[20]
Fig. 2 Schematic sensing mechanism of the fluorescent probe 2 toward thiols[20]
图3 荧光探针3的合成过程[22]
Fig. 3 Synthesis procedure of fluorescent probe 3[22]
图4 荧光探针4与FA的传感机理[23]
Fig. 4 The proposed sensing mechanism of fluorescent probe 4 with FA[23]
图5 荧光探针5对pH的响应机理[24]
Fig. 5 Proposed response mechanism of fluorescent probe 5 to pH[24]
图6 荧光探针6对H2S的响应机理[25]
Fig. 6 Proposed response mechanism of fluorescent probe 6 to H2S[25]
图7 荧光探针7对Zn(Ⅱ)的检测机理[26]
Fig. 7 Proposed sensing mechanism of fluorescent probe 7 to Zn(Ⅱ)[26]
图8 基于生物素结构的荧光分子8、9、10和11的化学结构[27,28]
Fig. 8 The chemical structure of fluorescent molecular 8, 9, 10 and 11 based on biotin[27,28]
图9 生理条件下12与谷胱甘肽的反应机理[29]
Fig. 9 Reaction mechanism of 12 with GSH under physiological conditions[29]
图10 前药13的化学结构[30]
Fig. 10 The chemical structure of prodrug 13[30]
图11 治疗诊断学前药物14的化学结构[31]
Fig. 11 The chemical structure of theranostic prodrug 14[31]
图12 生理条件下15与硫醇的反应机理[32]
Fig. 12 Reaction mechanism of 15 with thiols under physiological conditions[32]
图13 16的化学结构及与细胞内谷胱甘肽的反应机理[33]
Fig. 13 The reaction mechanism of chemical structure 16 with intracellular GSH[33]
图14 17的化学结构和在肿瘤细胞中作用的示意图[34]
Fig. 14 The chemical structure of prodrug 17 and inllustration of interactions in tumor cells[34]
图15 18的化学结构[35]
Fig. 15 The chemical structure of prodrug 18[35]
图16 化合物19的合成过程[36]
Fig. 16 The synthesis procedure of compound 19[36]
图17 化合物20和21的化学结构[37]
Fig. 17 Chemical structures of compounds 20 and 21[37]
图18 肿瘤-细胞器靶向诊疗策略示意图和光热剂22结构[38]
Fig. 18 Illustration of the tumor- and organelle targeted theranostic strategy and the structure of photothermal agent 22[38]
图19 探针23的化学结构(A);三元复合物作用说明图(B)[39]
Fig. 19 Chemical structures of probe 23(A); illustration interaction of the ternary complex(B)[39]
图20 生物素衍生物24的化学结构(A);生物素结合袋图[40]
Fig. 20 The chemical structure of biotin derivatives 24(A); illustrations of the biotin-binding pocket(B)[40]
图21 化合物25和26的结构[41]
Fig. 21 Chemical structures of compounds 25 and 26[41]
图22 Am580生物素偶联物27和28的化学结构[42]
Fig. 22 Chemical structures of Am580-biotin conjugates 27 and 28[42]
图23 生物素-Gd-DOTA配合物29和30[43]
Fig. 23 Biotin Gd-DOTA complexes 29 and 30[43]
图24 生物素偶联配合物31和32的化学结构[44]
Fig. 24 Chemical structures of the biotin-conjugated metal complexes 31 and 32[44]
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