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Progress in Chemistry 2020, Vol. 32 Issue (5): 594-603 DOI: 10.7536/PC190819 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • 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)
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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
Fig. 1 Synthesis route of fluorescent probe 1 based on biotin[19]
Fig. 2 Schematic sensing mechanism of the fluorescent probe 2 toward thiols[20]
Fig. 3 Synthesis procedure of fluorescent probe 3[22]
Fig. 4 The proposed sensing mechanism of fluorescent probe 4 with FA[23]
Fig. 5 Proposed response mechanism of fluorescent probe 5 to pH[24]
Fig. 6 Proposed response mechanism of fluorescent probe 6 to H2S[25]
Fig. 7 Proposed sensing mechanism of fluorescent probe 7 to Zn(Ⅱ)[26]
Fig. 8 The chemical structure of fluorescent molecular 8, 9, 10 and 11 based on biotin[27,28]
Fig. 9 Reaction mechanism of 12 with GSH under physiological conditions[29]
Fig. 10 The chemical structure of prodrug 13[30]
Fig. 11 The chemical structure of theranostic prodrug 14[31]
Fig. 12 Reaction mechanism of 15 with thiols under physiological conditions[32]
Fig. 13 The reaction mechanism of chemical structure 16 with intracellular GSH[33]
Fig. 14 The chemical structure of prodrug 17 and inllustration of interactions in tumor cells[34]
Fig. 15 The chemical structure of prodrug 18[35]
Fig. 16 The synthesis procedure of compound 19[36]
Fig. 17 Chemical structures of compounds 20 and 21[37]
Fig. 18 Illustration of the tumor- and organelle targeted theranostic strategy and the structure of photothermal agent 22[38]
Fig. 19 Chemical structures of probe 23(A); illustration interaction of the ternary complex(B)[39]
Fig. 20 The chemical structure of biotin derivatives 24(A); illustrations of the biotin-binding pocket(B)[40]
Fig. 21 Chemical structures of compounds 25 and 26[41]
Fig. 22 Chemical structures of Am580-biotin conjugates 27 and 28[42]
Fig. 23 Biotin Gd-DOTA complexes 29 and 30[43]
Fig. 24 Chemical structures of the biotin-conjugated metal complexes 31 and 32[44]
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