Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes

doi:10.6023/cjoc202305030

Abstract

Selenocysteine (Sec) is important in maintaining the functioning of living systems and its abnormal concentration will lead to a variety of physiological disorders. Fluorescent probes offer the advantages of high sensitivity, high spatial and temporal resolution, nondestructive and visual detection. However, the construction of highly selective selenocysteine probes for in vivo imaging is challenging due to the interference of biothiols. In recent years, various design strategies have been adopted to improve probe selectivity, accuracy and fluorescence properties. The research progress of Sec fluorescent probes in terms of design principles, performance characteristics and imaging applications based on the type of recognition mechanism is reviewed, and the challenges and development trends in this field are predicted.

Key words: selenocysteine, fluorescent probe, design strategies, selectivity, bioimaging

Cite this article

Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.

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Fig. & Tab. 28

Figure 1. Reaction mechanism based on 2,4-dinitrophenylsulfonyl with Sec

Figure 2. Mechanism of selective recognition of Sec by fluorescein backbone based probe 1

Figure 3. Recognition mechanism and imaging of Sec by probe 2 under physiological conditions[26]

Figure 4. Identification of Sec by colorimetric/fluorescent dual signal probe 3

Figure 5. Identification of Sec by probe 4 with high fluorescence quantum yield

Figure 6. Probes 5 and 6 based on tetrahydronaphthalene-oxanthene dyestuff backbone

Figure 7. Isomeric probes 7 and 8 for regional differences in recognition sites

Figure 8. Identification and imaging of Sec by NIR dye skeleton probe 9[32]

Figure 9. NIR probe 10 based on xanthene dye backbone

Figure 10. NIR probes 11 and 12 with large Stokes shifts

Figure 11. NIR probe 13 based on ICT effect

Figure 12. NIR ratio probe 14 based on heptamethanocyanine backbone

Figure 13. Identification of Sec by dual response ratio probe 15

Figure 14. Identification of Sec by two-photon probe 16 [39]

Figure 15. Synthesis of carbon dot probe 17 and recognition of Sec[40]

Figure 16. Based on the reaction mechanism of selenolysis between phenyl ether and Sec

Figure 17. Selective recognition of Sec by probes 18 and 19 based on the B-Bodipy backbone

Figure 18. Identification of Sec by colorimetric/fluorescent dual signal probe 20

Figure 19. Two-photon ratio probe 21 based on FRET mechanism for Sec identification

Figure 20. Mechanism of addition-cyclization-cleavage tandem reaction based on acrylate and Sec

Figure 21. Recognition mechanism of Sec by ratio probe 22 based on ICT mechanism

Figure 22. Identification of Sec by ratio probe 23 based on NIR heptamethanocyanine skeleton and imaging[46]

Figure 23. Recognition of Sec and cystine uptake by diacrylate-based probe 24[47]

Figure 24. Mechanism of selenolysis of disulfide bond and cleavage of N—Se bond

Figure 25. Mechanism of disulfide bond-based probe 25 for Sec recognition and cell imaging applications [50]

Figure 26. Identification and cellular imaging of Sec based on two-photon fluorescent probe 26 [51]

Figure 27. Probe 27 based on 2,1,3-benzoselenadiazole

识别机制	探针编号	荧光骨架	线性范围/(μmol•L^－1)	检测限(LOD)/(nmol•L^－1)	响应时间/min	参考文献
芳香亲核取代反应	1	荧光素	—	—	10	[25]
	2	香豆素	0.5~100	—	3	[26]
	3	香豆素	0~80	47	30	[27]
	4	香豆素	0~100	18	6	[28]
	5	四氢萘-氧杂蒽	0~50	17	2	[29]
	6	四氢萘-氧杂蒽	0~32	11.2	3	[30]
	7	菲并咪唑	0~50	65.4	4	[31]
	8	菲并咪唑	0~50	84.7	3.5	[31]
	9	染料HD-NH₂	0~40	_—	10	[32]
	10	氧杂蒽染料	0~40	18.5	5	[33]
	11	二氰基甲基苯并吡喃荧光素	0.2~80	60	10	[34]
	12	二氰基槐酮	0~100	10	20	[35]
	13	染料NN	0~1	22	2.5	[36]
	14	七甲基花菁素	0~7	—	4	[37]
	15	香豆素	0~45	6.9	4	[38]
	16	2-(2-萘基)苯并噻唑	0~10	10.6	10	[39]
	17	黄绿色发光碳点	0~30	—	12	[40]
苯醚硒解反应	18	硼-二苯并吡喃甲烷染料	0~25	16	10	[41]
	19	硼-二苯并吡喃甲烷染料	0~10	9	10	[41]
	20	二腈基亚甲基苯并吡喃	0.2~80	62	5	[42]
	21	香豆素	0~50	7.88	10	[43]
加成-环化-裂解串联	22	4-羟基萘酰亚胺骨架	0~30	12	1	[45]
	23	七甲基花菁素	0~15	92	5	[46]
	24	荧光素	—	—	—	[47]
其他反应	25	七甲基花菁素	0~20	90	3	[50]
	26	TP-NN	—	—	—	[51]
	27	半花菁素染料	0~20	7	—	[53]

Table 1. Comparison of the performance of various Sec probes

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