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A kind of selenocysteine ​​near-infrared fluorescent probe and its preparation method and application

A technology of selenocysteine ​​and fluorescent probe, which is applied in the field of fluorescent probe for detecting selenocysteine ​​in vivo and its preparation, can solve problems such as lack of detection, and achieve fast response, good selectivity and fluorescent signal stable effect

Active Publication Date: 2022-05-13
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite some development of fluorescent probes for selenocysteine, there is still a lack of probes for the detection of endogenous selenocysteine ​​in vivo

Method used

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  • A kind of selenocysteine ​​near-infrared fluorescent probe and its preparation method and application
  • A kind of selenocysteine ​​near-infrared fluorescent probe and its preparation method and application
  • A kind of selenocysteine ​​near-infrared fluorescent probe and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment approach

[0072] 1. Materials and instruments

[0073] GIBCO DMEM high glucose medium (life technologies, USA); GIBCO fetal bovine serum (life technologies, USA); Penicillin Streptomycin Solution (100) ×) (Shanghai biyuntian Biotechnology Co., Ltd.); Phosphate buffer (PBS) (Beijing Zhongshan Jinqiao Biotechnology Co., Ltd.); Anhydrous sodium selenite (NA) 2 SeO 3 )(sanen Chemical Technology (Shanghai) Co., Ltd.); N - (4-formylphenyl) acetamide (Shanghai bide Pharmaceutical Technology Co., Ltd.); 2,4-dinitrobenzenesulfonyl (Shanghai TITAN Technology Co., Ltd.); Other reagents are domestic analytical pure.

[0074] Cells:

[0075] (1) Species and strain: human breast cancer MCF-7. Source: Cell Bank of Chinese Academy of Sciences.

[0076] Laboratory animals:

[0077] (2) Species and strains: healthy male Kunming mice, weighing 20-25g. Source: experimental animal center of Xuzhou Medical University.

[0078] (3) Species and strains: healthy female BALB / C nude (SPF grade), 5-6 weeks old. Source...

Embodiment 1

[0118] Preparation of compound II: freshly distilled cyclohexanone (508) μ 50. 4.9 mmol) dropwise added to concentrated H 2 SO 4 (6.7ml, 125.0mmol) and cooled to 0 ℃, then 4 - (diethylamino) - 2-hydroxybenzaldehyde (500mg, 2.6mmol) was added and stirred vigorously at 90 ℃ for 1.5h. After the reaction, cool and pour into ice water. Then add perchloric acid (620 μ 50. 10.8mmol) until red precipitates are precipitated, and cold water (40ml) is used × 3) Wash and dry. 600mg red solid was obtained with a yield of 65%. TLC(silica,DCM:MeOH,20:1v / v):R f =0.55.

Embodiment 2

[0120] NIR-MNH 2 Preparation: compound II (100mg, 0.28mmol) and N - (4-formylphenyl) acetamide (91.3mg, 0.56mmol) were dissolved in ethanol (20ml), and then piperidine (2.8) was added μ L,0.03mmol)。 The reaction mixture was heated to 85 ℃ for 12h. After the reaction, the solvent was removed by vacuum distillation. Reflux in the mixed solution of ethanol and hydrochloric acid (15ml, 2:1v / V) for 2h, and remove ethanol and Na under reduced pressure 2 CO 3 Adjust pH to neutral and precipitate dark green solid. The crude product was purified by silica gel column chromatography (silica, DCM: MeOH, 100:1v / V) to obtain 40 mg of blue-green solid with a yield of 40%. TLC(silica,DCM:MeOH,20:1v / v):R f =0.45; 1 H NMR(400MHz,DMSO-d 6 ): δ 8.36(s,1H),8.07(s,1H),7.82(d,J=9.6Hz,1H),7.56(d,J=8.8Hz,2H),7.33(dd,J=9.2,2.4Hz,1H),7.22(d,J=2.0Hz,1H),6.71(d,J=8.8Hz,2H),6.51(s,2H),3.64-3.69(m,4H),2.93(t,J=5.6Hz,2H),2.84(t,J=5.6Hz,2H),1.87(t,J=6.0Hz,2H),1.25(t,J=6.8Hz,6H); HRMS(ESI + ):(M) + calcd. forC...

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Abstract

The invention relates to a selenocysteine ​​near-infrared fluorescent probe and its preparation method and application, belonging to the field of chemistry and analysis and detection. The near-infrared fluorescent probe Fsec-3 for detecting selenocysteine ​​provided by the present invention has the advantages of good selectivity, high sensitivity, low detection limit (20nM) and good biocompatibility. In phosphate buffer, the fluorescence intensity has a good linear relationship with the concentration of selenocysteine ​​(0‑100 μM), indicating that the probe Fsec‑3 is suitable for the quantitative detection of selenocysteine; Fluorescence imaging of selenocysteine ​​in cancer cell MCF‑7; probe Fsec‑3 also achieved sensitive detection of endogenous selenocysteine ​​in vivo, with fast response and stable fluorescence signal. It can be seen that the fluorescent probe Fsec-3 prepared by the present invention is an effective tool for visual and quantitative detection of selenocysteine ​​content in cells, living bodies and tumor tissues.

Description

technical field [0001] The invention belongs to the field of chemistry and analysis and detection, in particular to a fluorescent probe for detecting selenium cysteine in organisms and a preparation method and application thereof. Background technology [0002] Selenium is a "double-edged sword", which is not only an essential trace element in the body, but also a chemical poison, which depends on the existing form and concentration of selenium in the body. Insufficient selenium intake can cause Kashin Beck disease, Keshan disease and other diseases, as well as low immune function, cognitive decline and increased risk of cancer. However, excessive selenium supplementation can lead to selenium poisoning and increase the risk of type 2 diabetes. Selenium exists in many forms in organisms, mainly including inorganic substances (selenite, SEO 3 2- ; Selenate, SEO 4 2- )And organic matter (seleno amino acid; selenoprotein). Selenocysteine (SEC) is one of the main forms of selenium i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/33G01N21/64A61K49/00
CPCC07D311/82C09K11/06G01N21/6428G01N21/33A61K49/0041G01N2021/6432G01N2021/6421G01N2021/6419C09K2211/1088C09K2211/1007
Inventor 薛运生张玲石艳芬刘云萍开晓宁张怡然
Owner XUZHOU MEDICAL UNIV
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