Ratiometric fluorescent molecular probe for detecting hypochlorite ion, preparation method and application thereof

A fluorescent probe, ratiometric technology, applied in the field of chemical fluorescent materials, can solve the problem of less ClO-specific detection, and achieve remarkable effects and strong selectivity

Active Publication Date: 2022-04-26
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is known from the literature that the current small molecule fluorescent probes with lysosome-targeting effect on ClO - Relatively few specific tests

Method used

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  • Ratiometric fluorescent molecular probe for detecting hypochlorite ion, preparation method and application thereof
  • Ratiometric fluorescent molecular probe for detecting hypochlorite ion, preparation method and application thereof
  • Ratiometric fluorescent molecular probe for detecting hypochlorite ion, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] (1) Synthesis of compound 1:

[0068] A mixture of 5.0g (28.4mmol) of 7-hydroxy-4-methylcoumarin and 9.2g (65mmol) of hexamethylenetetramine was dissolved in glacial acetic acid (55mL), heated to 90°C and stirred at reflux for 5.5h. Then hydrochloric acid (20 mL) was added dropwise to the solution, and the reaction solution was heated for 50 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a light yellow solid was obtained, that is, compound 1 (0.84 g in total), with a yield of 14.5%.

[0069] Compound 1 1 H NMR picture as figure 1 Shown: 1 H NMR(400MHz,DMSO)δ(ppm):11.86(s,1H),10.38(s,1H),7.88(d,1H),6.92(d,1H),6.26(d,1H),2.33(d ,3H). After verifi...

Embodiment 2

[0088] (1) Synthesis of compound 1:

[0089] A mixture of 1.0 g of 7-hydroxy-4-methylcoumarin and 7.2 g of hexamethylenetetramine was dissolved in glacial acetic acid (40 mL), heated to 80° C. and stirred at reflux for 6.5 h. Then hydrochloric acid (10 mL) was added dropwise to the solution, and the reaction solution was heated for 60 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a light yellow solid was obtained, that is, compound 1 (0.84 g in total).

[0090] (2) Synthesis of Compound 2:

[0091] Weigh 0.56 g of 4-bromo-1,8-naphthalic anhydride and 0.35 g of 2-aminoethylmorpholine and dissolve them in absolute ethanol (10 mL), then heat the reaction s...

Embodiment 3

[0097] (1) Synthesis of compound 1:

[0098] A mixture of 10.0g 7-hydroxy-4-methylcoumarin and 11.2g hexamethylenetetramine was dissolved in glacial acetic acid (70mL), heated to 100°C and stirred at reflux for 4h. Then hydrochloric acid (30 mL) was added dropwise to the solution, and the reaction solution was heated for 40 min under the same conditions. After the reaction was cooled, ice-cold water (100 mL) was added to the solution, extracted with ether several times, and dried by rotary evaporation to obtain a crude product, which was washed with Al 2 o 3 The crude product was purified by column chromatography (petroleum ether:dichloromethane=10:1). After rotary evaporation and drying, a pale yellow solid, Compound 1, was obtained.

[0099] (2) Synthesis of Compound 2:

[0100] Weigh 1.67g of 4-bromo-1,8-naphthalic anhydride and 0.95g of 2-aminoethylmorpholine and dissolve in absolute ethanol (30mL), then heat the reaction solution to 80°C under reflux and stir for 3h. ...

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Abstract

The invention relates to a ratio-type fluorescent molecular probe for detecting hypochlorite ions and its preparation method and application, belonging to the technical field of chemical fluorescent materials; the invention uses compound 6-bromo-2-(2-morpholinoethyl) ‑1H‑benzo[iso]quinoline‑1,3(2H)‑diketone and coumarin aldehyde are used as raw materials to obtain the probe described in the present invention; the present invention is based on coumarin and naphthalimide A fluorophore constructed a novel lysosome-localized fluorescent probe, and used it for the ratiometric detection of ClO‑, realizing the detection of endogenous or exogenous ClO ‑ fluorescence imaging.

Description

technical field [0001] The invention relates to a ratio-type fluorescent molecular probe for detecting hypochlorite ions, a preparation method and application thereof, and belongs to the technical field of chemical fluorescent materials. Background technique [0002] A certain concentration of hypochlorite ion has the effect of sterilization and disinfection, but abnormal concentration of hypochlorous acid can also cause many problems, such as strong irritation and damage to the human respiratory system, making the human body suffer from various diseases or interacting with other substances Combined to produce carcinogens, which seriously endanger human health. [0003] Hypochlorite (ClO - ) as active oxygen with high reactivity, plays an important role in the environment, water weight and immune defense system of biological organisms. endogenous ClO - It can be produced by the catalytic reaction of peroxidase, which can destroy invading pathogens, but if it is overproduc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06G01N21/6428G01N21/643G01N21/6447C09K2211/1029C09K2211/1033C09K2211/1088
Inventor 沈玉婷魏文雅木开热木马新楠刘学明管伟民韩娟
Owner JIANGSU UNIV
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