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Near-infrared fluorescent probe for hydrogen polysulfides, and preparation method and application of near-infrared fluorescent probe

A fluorescent probe and near-infrared technology, which is applied in the field of chemistry and analysis and detection, can solve the problems of lack of fluorescent probes, detection difficulties, dynamic changes, etc., and achieve the effect of good selectivity and high sensitivity

Active Publication Date: 2019-10-08
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is an urgent need for probes with the following characteristics in the field of polyhydrogen sulfide detection: (1) There are various reactive sulfides (RSS) in complex organisms, such as hydrogen sulfide, glutathione (GSH), cysteine Amino acids (Cys) and inorganic sulfides will interfere with the detection and bring difficulties to the detection. Therefore, we need to improve the selectivity of the probe to ensure that the probe can quickly and accurately identify polyhydrogen sulfide in complex biological samples.
(2) Although the current fluorescent probes for detecting polyhydrogen sulfide have high sensitivity, the content of polyhydrogen sulfide is very low and changes dynamically under physiological conditions
(3) Near-infrared fluorescent probes have high tissue penetration ability and are suitable for fluorescence imaging of polyhydrogen sulfide in living mice, but there is still a lack of fluorescent probes for detecting endogenous polyhydrogen sulfide in vivo
(4) At present, the Stokes shifts of the reported polyhydrogen sulfide fluorescent probes are mostly small, which easily leads to fluorescence self-quenching and detection errors caused by excitation scattering effects

Method used

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  • Near-infrared fluorescent probe for hydrogen polysulfides, and preparation method and application of near-infrared fluorescent probe
  • Near-infrared fluorescent probe for hydrogen polysulfides, and preparation method and application of near-infrared fluorescent probe
  • Near-infrared fluorescent probe for hydrogen polysulfides, and preparation method and application of near-infrared fluorescent probe

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Experimental program
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Embodiment approach

[0071] 1. Materials and instruments

[0072] LPS (lipopolysaccharide from Escherichia coli 026B6); MTT cell proliferation / toxicity detection kit (Biosharp); Gibco DMEM high glucose medium (US Life Technologies); Gibco fetal bovine serum (US Life Technologies); penicillin (100 μg / mL) and streptomycin (100 μg / mL) (Life Technologies, USA); TLC using GF 254 Silica gel plate (250 μm), column chromatography using 300-400 mesh silica gel (Qingdao Ocean Chemical); the rest of the reagents are domestic analytical grade.

[0073] cell:

[0074] Species and strains: human breast cancer MCF-7 cell line.

[0075] Experimental animals:

[0076] Species and strains: healthy male Kunming mice, weighing 20-25 g. Source: Experimental Animal Center of Xuzhou Medical University.

[0077] instrument:

[0078] ECZ-400S nuclear magnetic resonance instrument (Japan JEOL company); FV1000 laser confocal scanning microscope (Olympus, Japan); F4600 fluorescence spectrophotometer (Hitachi, Japan); ...

Embodiment 1

[0109] Preparation of Compound Ⅰ: Under ice-bath conditions, cyclohexanone (508 μL, 4.92 mmol) was slowly added dropwise to concentrated sulfuric acid (6.7 mL, 125.05 mmol), and 4-diethylamino ketoacid (0.5 g, 1.59 mmol). The mixed solution was reacted at 90° C. for 2 h, cooled to room temperature, and poured into ice water. Perchloric acid (620 μL, 10.86 mmol) was slowly added, and a red solid was precipitated, which was filtered by suction and washed with water (3×20 mL) to obtain 369.81 mg of compound with a yield of 48.9%. TLC (silica, CH 2 Cl 2 :CH 3 OH, 20:1v / v): R f = 0.4.

Embodiment 2

[0111] Preparation of 2-fluoro-5-nitrobenzoyl chloride: 2-fluoro-5-nitrobenzoic acid (0.5 g, 2.70 mmol) was dissolved in thionyl chloride (20 mL), and refluxed at 80° C. for 5 h. Distillation under reduced pressure gave 0.49 mg of solid, with a yield of 90.7%. TLC (silica, CH 2 Cl 2 :CH3 OH, 20:1v / v): R f = 0.5.

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Abstract

The invention relates to a near-infrared fluorescent probe for hydrogen polysulfides, and a preparation method and application of the near-infrared fluorescent probe, and belongs to the field of chemistry and analysis detection. The near-infrared fluorescent probe NIR-CPS for detecting hydrogen polysulfides has relatively large stokes shift (100nm), and has the advantages of good selectivity, highsensitivity, low limit of detection (18nM) and good biocompatibility. In a phosphate buffer saline (PBS), fluorescence intensity shows a good linear relation with the concentration of hydrogen polysulfides, so that the probe is suitable for quantitatively detecting hydrogen polysulfides. The probe NIR-CPS also realizes fluorescence imaging of hydrogen polysulfides in MCF-7 cells. More importantly, the probe NIR-CPS also realizes sensitive detection of endogenous hydrogen polysulfides generated by induction of lipopolysaccharide at a living body level, and is relatively high in response and relatively stable in fluorescence intensity.

Description

technical field [0001] The invention belongs to the field of chemistry and analysis and detection, and in particular relates to a near-infrared fluorescent probe for detecting polyhydrogen sulfide in living organisms, a preparation method and application thereof. Background technique [0002] Sulfurane sulfur compounds (sulfane sulfur) refers to S with six valent electrons but no charge 0 , which mainly includes persulfides (RSSH), polyhydrogen sulfides (hydrogen polysulfides, H 2 S n , n>1), polysulfides (polysulfides, RSS n SR) and protein-bound elemental sulfur (S 8 )Wait. Among them, hydrogen sulfide (Hydrogen sulfide, H 2 S) is an important gas signal molecule in the human body. It can affect the transmission of neurotransmitters, regulate vasodilation, insulin secretion, promote colonic peristalsis, and have anti-inflammatory effects; it has protective effects on the heart and nerves, and is an effective neuromodulator substance. The abnormal production and m...

Claims

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Application Information

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IPC IPC(8): C07D311/82C09K11/06G01N21/64A61K49/00
CPCC07D311/82C09K11/06G01N21/6428A61K49/0043C09K2211/1007C09K2211/1088
Inventor 张玲刘云萍盛志佳刘慧珍腾杨欣开晓宁
Owner XUZHOU MEDICAL UNIV
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