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

doi:10.6023/cjoc202206044

摘要/Abstract

1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO)是一种优异的近红外荧光染料, 具有近红外发射、低pK_a值(≈5.0)、高水溶性以及高量子产率(Φ=0.39), 近年来在荧光探针领域受到广泛关注. 研究证明, 以该染料设计合成的荧光探针可以在温和的水溶液中工作, 具有反应迅速、选择性和灵敏度高、检测限低以及比色信号变化明显等优异的传感性能. 此外, 该类探针的细胞毒性低, 对于活细胞和生物体的检测具有显著的应用价值. 综述了基于DDAO及其衍生物的荧光探针的研究进展, 主要包括探针在生物酶、活性氧、活性氮、蛋白质以及Pd⁰的识别检测中的分子设计、作用机理和应用, 并对该类荧光探针的发展前景进行了展望.

关键词: 1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(DDAO), 荧光探针, 近红外, 检测

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

引用此文

马延慧, 武宇乾, 王晓旭, 高贵, 周欣. 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[J]. 有机化学, 2023, 43(1): 94-111.

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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图/表 34

图式1. Probe 1响应示意图

Scheme 1. Probe 1 response diagram

图式2. Probe 2和Probe 3的合成及响应示意图

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

图式3. Probe 4、Probe 5、Probe 6和Probe 7的合成及响应示意图

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

图式4. Probe 8和Probe 9的合成及响应示意图

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

图式5. Probe 10~Probe 12的合成及响应示意图

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

图式6. Probe 13的合成及响应示意图

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

图式7. Probe 14的合成及响应示意图

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

图1. SKOV-3细胞共聚焦荧光图像[56]

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).

图式8. Probe 15响应示意图

Scheme 8. Probe 15response diagram

图式9. Probe 16响应示意图

Scheme 9. Probe 16response diagram

图式10. Probe 17响应示意图

Scheme 10. Probe 17response diagram

图2. (A)平板培养基中肠道细菌的荧光图像和(B)肠道细菌的共聚焦荧光图像[81]

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

图式11. Probe 18响应示意图

Scheme 11. Probe 18 response diagram

图3. Probe 18和DDAO的吸收(A)与荧光(B)光谱(λex=600 nm)[84]

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

图式12. Probe 19的合成及响应示意图

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

图4. 各种大鼠器官中内源性PL的原位可视化[器官在生理条件下用Probe 19 (100 μmol/L)染色30 min][57]

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]

图式13. Probe 20的合成及响应示意图

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

图5. Probe 20(DDAP)和DDAN的吸收光谱(A)及荧光光谱(B) (λex=600 nm)[53]

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

图式14. Probe 21的合成及响应示意图

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

图式15. Probe 22的合成及响应示意图

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

图式16. Probe 23的合成及响应示意图

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

图6. Probe 23(DAND)的吸收(A)和荧光(B)变化[55]

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

图式17. Probe 24的合成及响应示意图

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

图式18. Probe 25的合成及响应示意图

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

图式19. Probe 26的合成及响应示意图

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

图式20. Probe 27的合成及响应示意图

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

图7. Probe 27对小鼠腹膜腔内的外源性/内源性H2O2进行体内成像[102]

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

图式21. Probe 28的合成及响应示意图

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

图8. Probe 28(5 μmol/L)通过与不同浓度的HClO共孵育, 对斑马鱼中的外源HClO进行共聚焦荧光成像[105]

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

图式22. Probe 29的合成及响应示意图

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

图式23. Probe 30的合成及响应示意图

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

图式24. Probe 31的合成及响应示意图

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

图式25. Probe 32的合成及响应示意图

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

图式26. Probe 32响应示意图

Scheme 26. Probe 32response diagram

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