Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO)

doi:10.6023/cjoc202206044

Abstract

1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) is an excellent near-infrared fluorescent dye with near-infrared emission, low pK_a (≈5.0), high water solubility and high quantum yield (Φ=0.39), which has attracted much attention in recent years in the field of fluorescent probes. The researches prove that the fluorescent probes designed and synthesized based on this dye can work in mild aqueous solutions, and have excellent sensing performance, such as rapid reaction, high selectivity and sensitivity, low detection limit and obvious colorimetric signal change. In addition, the low cytotoxicity of this class of probes is of significant application for the detection of living cells and organisms. The research progress of fluorescent probes based on DDAO and its derivatives, mainly including the molecular design, action mechanism and application of probes in the recognition and detection of biological enzymes, reactive oxygen species, reactive nitrogen species, proteins and Pd⁰, is reviewed, and the development prospect of this type of fluorescent probes is prospected.

Key words: 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO), fluorescent probe, near infrared, detection

Cite this article

Yanhui Ma, Yuqian Wu, Xiaoxu Wang, Gui Gao, Xin Zhou. Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO)[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 94-111.

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Fig. & Tab. 34

Scheme 1. Probe 1 response diagram

Scheme 2. Schematic diagram of the synthesis and response of Probe 2 and Probe 3

Scheme 3. Schematic diagram of the synthesis and response of Probe 4, Probe 5, Probe 6 and Probe 7

Scheme 4. Schematic diagram of the synthesis and response of Probe 8 and Probe 9

Scheme 5. Schematic diagram of the synthesis and response of Probe 10~Probe 12

Scheme 6. Schematic diagram of the synthesis and response of Probe 13

Scheme 7. Schematic diagram of the synthesis and response of Probe 14

Figure 1. Confocal fluorescence images of SKOV-3 cells[56] (a~d) Cells treated with Probe 14 (20 μmol/L) and Hoechst 33342 (nuclear stain, 2 μmol/L) at 37 ℃ for 20 min; (e~g) Cells pretreated with BNPP (CE2 inhibitors, 100 μmol/L) and further stained with Probe 14 (20 μmol/L) and Hoechst 33342 (2 μmol/L).

Scheme 8. Probe 15response diagram

Scheme 9. Probe 16response diagram

Scheme 10. Probe 17response diagram

Figure 2. (A) Fluorescence images of intestinal bacteria in platemedium and (B) confocal fluorescence images of intetinal bacteria[81] Staining with Probe 17 (DDAO-GLU, 20 μmol/L) for 1 h at 37 ℃ to determine intracellular GLU activity. Baicalin as the inhibitor of GLU was pretreated for bacteria before Probe 17 incubation

Scheme 11. Probe 18 response diagram

Figure 3. Absorbance (A) and fluorescence (B) spectra of Probe 18 and DDAO (λex=600 nm)

Scheme 12. Schematic diagram of the synthesis and response of Probe 19

Figure 4. In-situ visualization of endogenous PL in varous rat organs [the organs were stained with Probe 19 (100 μmol/L) for 30 min under physiological conditions][57]

Scheme 13. Schematic diagram of the synthesis and response of Probe 20

Figure 5. (A) Absorbance spectra and (B) fluorescence spectra of Probe 20 and DDAN (λex=600 nm)

Scheme 14. Schematic diagram of the synthesis and response of Probe 21

Scheme 15. Schematic diagram of the synthesis and response of Probe 22

Scheme 16. Schematic diagram of the synthesis and response of Probe 23

Figure 6. Changes in the absorption (A) and fluorecence (B) of Probe 23 (DAND)

Scheme 17. Schematic diagram of the synthesis and response of Probe 24

Scheme 18. Schematic diagram of the synthesis and response of Probe 25

Scheme 19. Schematic diagram of the synthesis and response of Probe 26

Scheme 20. Schematic diagram of the synthesis and response of Probe 27

Figure 7. In vivo imaging of exogenous/endogenous H2O2 in the peritoneal cavity of mice using Probe 27

Scheme 21. Schematic diagram of the synthesis and response of Probe 28

Figure 8. Confocal imaging of exogenous HClO in zebrafish using Probe 28 (5 μmol/L) by co-incubation with different concentrations of HClO

Scheme 22. Schematic diagram of the synthesis and response of Probe 29

Scheme 23. Schematic diagram of the synthesis and response of Probe 30

Scheme 24. Schematic diagram of the synthesis and response of Probe 31

Scheme 25. Schematic diagram of the synthesis and response of Probe 32

Scheme 26. Probe 32response diagram

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基于1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)的近红外荧光探针研究进展