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Near-infrared molecular probe capable of reversibly responding to ClO-/GSH oxidation reduction as well as preparation method and application of near-infrared molecular probe

A molecular probe and near-infrared technology, applied in the field of near-infrared molecular probes and their preparation, can solve the problems that it is difficult to reveal the oxidation-reduction state, and the probe cannot monitor oxides and reduced substances synchronously, achieving good results and easy The effect of promotion and high productivity

Pending Publication Date: 2022-05-24
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most probes cannot simultaneously monitor oxides and reductions through one response signal, so it is difficult to reveal the true redox state

Method used

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  • Near-infrared molecular probe capable of reversibly responding to ClO-/GSH oxidation reduction as well as preparation method and application of near-infrared molecular probe
  • Near-infrared molecular probe capable of reversibly responding to ClO-/GSH oxidation reduction as well as preparation method and application of near-infrared molecular probe
  • Near-infrared molecular probe capable of reversibly responding to ClO-/GSH oxidation reduction as well as preparation method and application of near-infrared molecular probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Preparation of Example 1 Compound 1:

[0062] Dissolve 3,5-di-tert-butyl-4-hydroxybenzaldehyde (0.02mol) and 4-methoxyacetophenone (0.02mol) in 20 mL of ethanol and add 3 g of potassium hydroxide (0.05mol), the resulting mixture After stirring at room temperature for 1 h, the precipitated product was filtered, washed with 20 mL of ethanol and dried under reduced pressure to obtain compound 1 (565 mg, yield 33%) as a pale yellow solid.

[0063] The hydrogen nuclear magnetic spectrum and carbon spectrum of compound 1 prepared in Example 1 are as follows figure 1 , 2 shown, figure 1 for the hydrogen spectrum results. 1 H NMR (400MHz, CDCl 3 , 25℃, TMS), δ=8.07-8.01(m, 2H), 7.79(d, J=15.6Hz, 1H), 7.58-7.51(m, 2H), 7.49(s, 1H), 7.23(d, J=8.0Hz, 2H), 7.01-6.96 (m, 2H), 3.89 (s, 3H), 2.39 (s, 3H) ppm; figure 2 For the carbon spectrum results, 13 C NMR (101 MHz, CDCl 3 , 25°C, TMS), δ=188.8, 163.4, 144.1, 140.8, 132.3, 131.2, 130.8, 129.7, 128.4, 120.9, 113.8, 55.5, 21...

Embodiment 2

[0064] Preparation of Example 2 Compound 2:

[0065] Compound 1 (20 mmol), nitromethane (10 mL) and diethylamine (10 mL) were dissolved in methanol (30 mL) and heated to reflux for 10 h. After cooling at room temperature, the solvent was removed in vacuo and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated to give compound 2 (565 mg, yield 33%) as a yellow oil.

[0066] Compound 2 prepared in Example 2 has a hydrogen nuclear magnetic spectrum and a carbon spectrum such as image 3 , 4 shown, image 3 for the hydrogen spectrum results. 1 H NMR (400MHz, CDCl 3 , 25℃, TMS), δ=7.94-7.87(m, 2H), 7.15(q, J=8.2Hz, 4H), 6.94-6.89(m, 2H), 5.29(s, 1H), 4.82(dd, J=12.4, 6.5Hz, 1H), 4.65 (dd, J=12.4, 8.2Hz, 1H), 4.22-4.13 (m, 1H), 3.86 (s, 3H), 3.40-3.33 (m, 1H), 2.31 (s, 3H) ppm; Figure 4 For the carbon spectrum results, 13 C NMR (101 MHz, CDCl 3 , 25°C, TMS), δ=195.5, 163.8, 137.4, 136.4, 130.4, 129.6, 127.0, 113.9, 79.8, 55.5, 53....

Embodiment 3

[0067] Example 3 Synthesis of near-infrared molecular probe AzaBDP-DiOH:

[0068] Compound 2 (1.0 mmol) and ammonium acetate (20 mmol) were dissolved in ethanol (20 mL) at reflux for 9 h, cooled to room temperature and concentrated to about 5 mL. The precipitate was washed with ethanol and filtered to obtain the blue-black solid product azadipyrrolene, which was used directly without purification. To toluene (100 mL) was added the obtained azabipyrrolidine (0.23 mmol, 100 mL), and triethylamine (4 mL) and boron trifluoride diethyl ether (6 mL) were added. The mixture was stirred at 60 °C for 2 h. After cooling to room temperature, the solvent was removed under vacuum. The residue was washed with ethanol and filtered to obtain a red solid, which is the near-infrared photoacoustic probe AzaBDP-DiOH (83% yield).

[0069] The hydrogen nuclear magnetic spectrum, carbon nuclear magnetic spectrum and mass spectrum of the probe prepared in Example 3 are as follows: Figure 5 , 6 ...

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Abstract

The invention discloses a near-infrared molecular probe capable of reversibly responding to ClO <-> / GSH oxidation reduction as well as a preparation method and application of the near-infrared molecular probe. According to the invention, the near-infrared probe aza-BODIPY (AzaBDP-DiOH) is obtained through preparation methods such as aldol condensation, Michael addition and cyclization reaction, and the molecular formula of the aza-BODIPY (AzaBDP-DiOH) is C50H56BF2N3O4. The near-infrared probe AzaBDP-DiOH prepared by the method disclosed by the invention can be specifically oxidized into AzaBDP-DiO by ClO <->, the ultraviolet absorption of the near-infrared probe AzaBDP-DiO at 682nm is weakened, and the ultraviolet absorption of the near-infrared probe AzaBDP-DiO at 965nm is enhanced; azaBDP-DiO can be specifically reduced into AzaBDP-DiOH by GSH, the ultraviolet absorption of the AzaBDP-DiOH at 965nm is weakened, and the ultraviolet absorption at 682nm is enhanced, so that the probe shows good selectivity and sensitivity on ClO- / GSH, meanwhile, the probe is successfully used for in-vivo renal ischemia reperfusion mouse model visual imaging, and the probe has good application prospects in the aspect of monitoring ClO- / GSH oxidation reduction.

Description

technical field [0001] The invention belongs to near-infrared molecular probe technology, and specifically relates to a ClO - / GSH redox reversible near-infrared molecular probe and preparation method and application thereof. Background technique [0002] Renal ischemia-reperfusion injury is common in kidney transplantation, renal trauma surgery, extracorporeal shock wave lithotripsy, etc., and is one of the main causes of acute renal failure. At present, there is a lack of effective early diagnosis in clinical practice, and most patients are diagnosed after the disease has already occurred and developed, which leads to further deterioration of the underlying kidney disease and greatly increases the mortality rate of patients. Therefore, it has important clinical significance for the early diagnosis of renal ischemia-reperfusion injury. [0003] Kidney tissue produces a large amount of reactive oxygen species (ROS) in the process of ischemia-reperfusion, which exceeds the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02G01N21/33G01N21/17A61K49/22
CPCC07F5/022G01N21/33G01N21/1702A61K49/22
Inventor 田蒋为余伯阳张王宁沈卓霞
Owner CHINA PHARM UNIV
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