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Synthesis and application of near infrared fluorescence probe for detecting hydrogen polysulfide

A fluorescent probe, hydrogen polysulfide technology, applied in the field of synthesis of near-infrared fluorescent probes, can solve problems such as poor selectivity, difficult popularization and application, and complicated measurement operations

Active Publication Date: 2017-09-22
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional determination method of hydrogen polysulfide mainly relies on GC method, which has certain defects, such as poor selectivity, complicated determination operation, high cost, and difficult to be popularized and applied.

Method used

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  • Synthesis and application of near infrared fluorescence probe for detecting hydrogen polysulfide
  • Synthesis and application of near infrared fluorescence probe for detecting hydrogen polysulfide
  • Synthesis and application of near infrared fluorescence probe for detecting hydrogen polysulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Preparation of compound III:

[0017] Under nitrogen protection, accurately weigh pyranonitrile compound II (500mg, 2.27mmol), p-hydroxybenzaldehyde (335g, 2.72mmol), dissolve in 20mL of acetonitrile, then add 1 drop of piperidine dropwise to the mixed solution, and reflux The reaction was stirred for 6 hours. TLC detected that the reaction was complete, the reaction was stopped, the solvent was distilled off under reduced pressure, and separated and purified by column chromatography to obtain a red product (480 mg, yield 67.5%). 1 H NMR (400MHz, DMSO-d 6 )δ10.29(s, 1H), 8.70(d, J=8.0Hz, 1H), 7.91(t, J=7.8Hz, 1H), 7.78(d, J=8.0Hz, 1H), 7.70-7.54( m,4H),7.23(d,J=16.0Hz,1H),6.95(s,1H),6.85(d,J=8.5Hz,2H). 13 C NMR (100MHz, DMSO-d 6 )δ160.0, 158.9, 152.8, 152.0, 139.3, 135.2, 130.3, 126.1, 126.0, 124.6, 118.9, 117.4, 117.1, 116.0, 115.9, 105.7, 59.1. For the synthetic steps of compound II, see RSC Adv., 2014, 4 ,46561-46567.

Embodiment 2

[0019] Preparation of compound I:

[0020] Under nitrogen protection, accurately weigh hydroxypyranonitrile compound II (300mg, 0.95mmol), 2-fluoro-5-nitrobenzoic acid (209mg, 1.15mmol), 1-ethyl-(3-dimethylamino Propyl)carbodiimide hydrochloride (363mg, 1.90mmol), 4-dimethylaminopyridine (12mg, 0.95mmol) were dissolved in 20mL of dichloromethane, and stirred at room temperature for 8 hours. TLC detected that the reaction was complete, the reaction was stopped, washed with saturated sodium chloride solution, the solvent was distilled off under reduced pressure, and separated and purified by column chromatography to obtain a light yellow product (180 mg, yield 39.6%). 1 H NMR (400MHz, DMSO-d 6 )δ8.70(d,J=12.0Hz,1H),8.63-8.60(m,1H),8.52-8.48(m,1H),7.90(t,J=8.0Hz,1H),7.76(d,J =8.0Hz, 2H), 7.66-7.57(m, 4H), 7.25(d, J=16.0Hz, 1H), 6.92(s, 1H), 6.85(d, J=8.0Hz, 2H). 13 C NMR (100MHz, DMSO-d 6 )δ166.2, 163.8, 160.5, 159.3, 153.2, 152.5, 144.1, 139.7, 135.7, 132.6, 130.8, 130.4, 12...

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Abstract

The invention relates to a synthesis method and application of a novel high-selectivity and high-sensitivity near infrared fluorescence probe for visually detecting hydrogen polysulfide. The method comprises the steps of making benzopyran carbonitrile and p-hydroxy benzaldehyde react to obtain a precursor, and then conducting an esterification reaction with 2-fluoro-5-nitrobenzoic acid to obtain the fluorescence probe. The probe reacts with sodium polysulfide to generate a strengthened fluorescence change, which is that the fluorescence at the 682 nm is strengthened remarkably. Besides, a dynamic experiment result shows that the reaction time of the compound and hydrogen polysulfide is shorter than 5 min, and the interference rejection is strong. Thus, the pyran carbonitrile compound can serve as the application of the near infrared fluorescence probe for detecting hydrogen polysulfide.

Description

technical field [0001] The invention relates to a synthesis method and application of a near-infrared fluorescent probe with high selectivity, high sensitivity, near-infrared and visual detection of hydrogen polysulfide. Background technique [0002] Active sulfur-containing compounds (such as thiol-containing amino acids, hydrogen sulfide, hydrogen persulfide, etc.) play an important role in biological redox reactions. Among these sulfur compounds, H 2 As a key biological signaling molecule, S is involved in a series of physiological and pathological events. Recent studies have shown that intracellular signaling may be via H 2 S n (biologically active oxygen oxidizes H 2 S produced) and H 2 S cooperating to achieve. SO in relation to cysteine ​​disability and persulfate 2 In the reaction, H 2 S n exhibited higher biological reactivity. However, for intracellular H 2 S n The study of biological function is still in the development stage. Therefore, for H 2 S n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/04C09K11/06G01N21/64
CPCC07D311/04C09K11/06C09K2211/1088G01N21/6428
Inventor 厉凯彬韩得满
Owner TAIZHOU UNIV
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