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A kind of near-infrared polyhydrogen sulfide fluorescent probe and its preparation method and application

A fluorescent probe, near-infrared technology, used in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of small Stokes shift, lack of fluorescent probes, difficult detection, etc., and achieve stable fluorescence intensity. , the effect of good selectivity and high sensitivity

Active Publication Date: 2022-04-29
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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  • A kind of near-infrared polyhydrogen sulfide fluorescent probe and its preparation method and application
  • A kind of near-infrared polyhydrogen sulfide fluorescent probe and its preparation method and application
  • A kind of near-infrared polyhydrogen sulfide fluorescent probe and its preparation method and application

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Experimental program
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Embodiment approach

[0071] 1. Materials and instruments

[0072] LPS (lipopolysaccharide from Escherichia coli 026 B6); 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. instrument:

[0077] ECZ-400S nuclear magnetic resonance instrument (Japan JEOL company); FV1000 laser confocal scanning microscope (Olympus, Japan); F4600 fluorescence spectrophotometer (Hitachi, Japan); LB983 Ni...

Embodiment 1

[0108] 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

[0110] 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 :CH 3 OH, 20:1v / v): R f = 0.5.

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Abstract

The invention relates to a near-infrared polyhydrogen sulfide fluorescent probe and a preparation method and application thereof, belonging to the field of chemistry and analysis and detection. The near-infrared fluorescent probe NIR-CPS for detecting polyhydrogen sulfide provided by the invention has a large Stokes shift (100nm), good selectivity, high sensitivity, low detection limit (18nM) and good biocompatibility The advantages. In PBS buffer, the fluorescence intensity showed a good linear relationship with the concentration of polyhydrogen sulfide, indicating that the probe is suitable for quantitative detection of polyhydrogen sulfide; the probe NIR-CPS also realized the fluorescence imaging of polyhydrogen sulfide in MCF-7 cells; more Importantly, the probe NIR‑CPS also achieves sensitive detection of endogenous polyhydrogen sulfide induced by lipopolysaccharide in vivo, with fast response and stable 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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Patent Type & Authority Patents(China)
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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