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Synthesis and application of novel fluorescence probe for detecting hydrogen peroxide

A technology of hydrogen peroxide and fluorescent probes, applied in the field of chemical analysis and detection, to achieve the effects of high yield, large Stokes shift and good selectivity

Inactive Publication Date: 2017-05-31
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Red-near-infrared fluorescent probes with large Stokes shifts for the detection of hydrogen peroxide are rarely reported

Method used

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  • Synthesis and application of novel fluorescence probe for detecting hydrogen peroxide
  • Synthesis and application of novel fluorescence probe for detecting hydrogen peroxide
  • Synthesis and application of novel fluorescence probe for detecting hydrogen peroxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of 3-hydroxyphthalonitrile

[0025] Take 3-nitrophthalonitrile (1.0g, 5.8mmol), potassium carbonate (0.9g, 6.35mmol) and sodium nitrite (0.4g, 5.8mmol) in a 25ml round bottom flask, add 15mL of dimethyl Dissolve in sulfoxide, heat the oil bath to 130°C, stir and reflux, analyze the progress of the reaction by TLC thin-layer chromatography, cool to room temperature after 30 minutes of reaction, slowly add distilled water (45mL) to dilute the reaction solution, dilute hydrochloric acid (2M) to adjust the pH to 3. The precipitate was precipitated, then filtered under reduced pressure, the filter cake was washed three times with distilled water, recrystallized in glacial acetic acid to obtain brown needle-shaped crystals, filtered by suction to obtain all crystals, and dried overnight in a vacuum desiccator to obtain the product 3- Hydroxyphthalonitrile. Yield: 0.51 g. Yield 60%.

Embodiment 2

[0026] Embodiment 2: the preparation of dyestuff

[0027] Take 3-hydroxyphthalonitrile (288mg, 2mmol), 2-aminopyridine (385mg, 4.1mmol) and calcium chloride (46mg, 0.41mmol) in a 25mL round bottom flask, add 6mL n-butanol to dissolve. Under the protection of argon, the oil bath was heated to 110°C and stirred and refluxed. TLC thin-layer chromatography was used to detect the reaction progress. After 5 days, the reaction was completed. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The cake was placed in a vacuum desiccator overnight, further purified by column chromatography, and the obtained orange powder was dried in vacuum overnight. Yield: 150.8 mg. Yield 26.6%. 1 H NMR (400MHz, CDCl 3 )δ H 13.70(s, 1H), 8.62(m, 2H), 7.78(t, J=7.9Hz, 2H), 7.60(s, 1H), 7.52(d, J=7.3Hz, 2H), 7.38(d, J =8.0Hz, 1H), 7.19-7.09(m, 3H). 13 C NMR (101MHz, CDCl 3 )δ c 160.10, 159.34, 155.81, 155.59, 153.70, 147.98,...

Embodiment 3

[0028] Embodiment 3: the preparation of probe molecule

[0029] Take the dye (48mg, 0.15mmol) obtained in the previous step, potassium carbonate (400mg, 3mmol), potassium iodide (80mg, 0.5mmol) in a 100mL round bottom flask, add 30mL acetonitrile to dissolve, stir at room temperature for 30 minutes, then add 4-bromomethyl Phenylboronic acid pinacol ester (47.6mg, 1.6mmol), then the oil bath was heated to 61°C and stirred and refluxed, TLC thin layer chromatography was used to detect the progress of the reaction, the reaction was completed after 30 minutes, the reaction solution was cooled to room temperature, and removed by rotary evaporation under reduced pressure. The solvent was acetonitrile, and purified by flash column chromatography to obtain a yellow powder. Yield: 59 mg. Yield: 73.8%.

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Abstract

The invention discloses a fluorescence probe for detecting hydrogen peroxide, as well as a preparation method and application of the fluorescence probe. The chemical structural formula of the fluorescence probe is as shown in the specification. The raw materials of the probe disclosed by the invention are low in cost and readily available, and the probe is easy and convenient to synthesize. The probe does not emit fluorescence; after the probe reacts with hydrogen peroxide, the fluorescence intensity of the probe is gradually enhanced (enhanced to 77.8 times of the original fluorescence intensity to the maximum extent); the maximum emission wavelength is at the near infrared, and has the Stokes shifts which is 217 nm. The detection limit is low (6.6 nM), the sensitivity is high, and the detection range is wide; the fluorescence probe is extremely high in selectivity and interference resistance to identification of the hydrogen peroxide, can detect the hydrogen peroxide in vitro and in living cells, and has a wide application prospect in the field of chemical analysis detection.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a novel red light-near-infrared fluorescent probe for identifying hydrogen peroxide and its application in detecting hydrogen peroxide in vitro and in living cells. Background technique [0002] Active oxygen includes superoxide radicals (O 2 ), hydrogen peroxide radical (HO 2 ), hydroxyl radical (HO ), peroxyl radical (RO 2 ), singlet oxygen ( 1 o 2 ) and hypochlorous acid (HOCl), etc. As an indispensable member of the reactive oxygen species, hydrogen peroxide plays an important role in the physiology, metabolism and pathology of living organisms. Elevated levels of hydrogen peroxide in cells have the potential to cause DNA damage, mutation and genetic instability. It is also an indicator of oxidative stress associated with aging and disease, a second messenger in cell signaling, and a deoxidizer produced by immune cells in ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096G01N21/6486
Inventor 宋相志田惠惠刘兴江张子涵谭倩齐风佩
Owner CENT SOUTH UNIV
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