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Selenocysteine near-infrared fluorescent probe and preparation method and application thereof

The technology of selenocysteine ​​and fluorescent probe is applied in the field of fluorescent probe for detecting selenocysteine ​​in vivo and its preparation, which can solve problems such as lack of detection, and achieve the effects of high sensitivity and good selectivity

Active Publication Date: 2019-11-12
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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  • Selenocysteine near-infrared fluorescent probe and preparation method and application thereof
  • Selenocysteine near-infrared fluorescent probe and preparation method and application thereof
  • Selenocysteine near-infrared fluorescent probe and preparation method and application thereof

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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 buffered saline (PBS) (Beijing Zhongshan Jinqiao Biotechnology Co., Ltd.); anhydrous sodium selenite (Na 2 SeO 3) (Saen Chemical Technology (Shanghai) Co., Ltd.); N-(4-formylphenyl) acetamide (Shanghai Biide Pharmaceutical Technology Co., Ltd.); 2,4-Dinitrobenzenesulfonyl (Shanghai Titan Technology Co., Ltd. Co., Ltd.); the rest of the reagents were of domestic analytical grade.

[0074] cell:

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

[0076] Experimental animals:

[0077] (2) Species and strain: healthy male Kunming mice, weighing 20-25 g. Source: Experimental Animal Center of Xuzhou Medical University.

[0078] (3) Species and strain: healthy female BALB / ...

Embodiment 1

[0118] Preparation of compound II: Freshly distilled cyclohexanone (508 μL, 4.9 mmol) was added dropwise to concentrated H 2 SO 4 (6.7mL, 125.0mmol), and cooled to 0°C, then added 4-(diethylamino)-2-hydroxybenzaldehyde (500mg, 2.6mmol), stirred vigorously at 90°C for 1.5h. After the reaction was complete, it was cooled and poured into ice water. Then, perchloric acid (620 μL, 10.8 mmol) was added and allowed to stand until a red precipitate precipitated, washed with cold water (40 mL×3), and dried. 600 mg of red solid was obtained, yield 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), then piperidine (2.8μL, 0.03mmol ). The reaction mixture was heated to 85°C for 12h. After the reaction was completed, the solvent was distilled off under reduced pressure. Reflux in a mixed solution of ethanol and hydrochloric acid (15mL, 2:1v / v) for 2h, remove ethanol under reduced pressure, Na 2 CO 3 The pH was adjusted to neutral, and a dark green solid was precipitated. The crude product was purified by silica gel column chromatography (silica, DCM:MeOH, 100:1 v / 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 ):δ8.36(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...

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Abstract

The invention relates to a selenocysteine near-infrared fluorescent probe, and a preparation method and application thereof, belonging to the field of chemical analysis and detection. The near-infrared fluorescent probe Fsec-3 for detecting selenocysteine provided by the invention has the advantages of good selectivity, high sensitivity, low detection limit (20 nM) and good biocompatibility. In aphosphate buffer, the fluorescence intensity and the concentration of selenocysteine (0-100[mu]M) are in a good linear relationship, which indicates that the probe Fsec-3 is suitable for quantitativedetection of selenocysteine. The probe Fsec-3 achieves fluorescence imaging of selenocysteine in the human breast cancer cell MCF-7; and the probe Fsec-3 also achieves sensitive detection of endogenous selenocysteine in a living body, and is fast in response and stable in fluorescence signals. Thus, the fluorescent probe Fsec-3 prepared by the invention is an effective tool for visual and quantitative detection of the content of selenocysteine in cells, living bodies and tumor tissue.

Description

technical field [0001] The invention belongs to the field of chemistry and analysis and detection, and specifically relates to a fluorescent probe for detecting selenocysteine ​​in living organisms, a preparation method and application thereof. Background technique [0002] Selenium is a "double-edged sword". It is an essential trace element in the body and a chemical poison, which depends on the form and concentration of selenium in the body. Insufficient selenium intake can cause diseases such as Kashin-Beck disease and Keshan disease, and can also lead to low immune function, cognitive decline and increased risk of cancer. However, excessive supplementation of selenium can lead to selenium toxicity and increase the risk of developing type 2 diabetes. Selenium exists in various forms in organisms, mainly including inorganic substances (selenite, SeO 3 2- ; Selenate, SeO 4 2- ) and organic matter (selenoamino acids; selenoproteins). Selenocysteine ​​(Sec) is one of th...

Claims

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Application Information

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