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Near-infrared selenocysteine fluorescent probe as well as preparation method and application thereof

A technology of selenocysteine ​​and fluorescent probes, which is applied in the field of near-infrared selenocysteine ​​fluorescent probes and its preparation, can solve the problems affecting the sensitivity and accuracy of detection and analysis, unfavorable living body and deep tissue imaging, Weak penetrability and other problems, to achieve the effect of low detection limit, fast reaction speed and high sensitivity

Pending Publication Date: 2021-08-20
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ultraviolet-visible light has weak penetration in tissues and is easily absorbed by substances such as hemoglobin and melanin in tissues; on the other hand, under the excitation of visible light, organisms have fluorescence background, which seriously affects the sensitivity and sensitivity of its detection and analysis. Accuracy, not conducive to imaging in vivo and deep tissue

Method used

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  • Near-infrared selenocysteine fluorescent probe as well as preparation method and application thereof
  • Near-infrared selenocysteine fluorescent probe as well as preparation method and application thereof
  • Near-infrared selenocysteine fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of compound YZ-M3

[0031] In a 50 mL round bottom flask, add 15 mL concentrated H 2 SO 4 , and then in concentrated H 2 SO 4 Cyclohexanone (2.94 g, 0.03 mol) was added dropwise to the mixture, and after cooling to room temperature, 4-(diethylamino) salicylaldehyde (3.86 g, 0.02 mol) was added, and the reaction was vigorously stirred at 90° C. for 2.0 h. After the reaction was complete, it was cooled and poured into 200 mL of ice water, then 1.5 mL of 70% perchloric acid was added and allowed to stand overnight, a red precipitate precipitated, filtered, washed with cold water (50 mL×3), and dried. Obtained compound YZ-M3 red solid 5.05g, yield 71%.

Embodiment 2

[0033] Preparation of Compound YZ-M4

[0034] Compound YZ-M3 (711 mg, 2 mmol) and p-hydroxybenzaldehyde (366 mg, 3 mmol) were dissolved in acetic acid (20 mL). The reaction mixture was heated to 110°C for 2h. After the reaction was complete, the solvent was distilled off under reduced pressure. The crude product was purified by using silica gel column chromatography (DCM:MeOH=20:1, v / v) to obtain 598 mg of a black solid with a yield of 65%. 1 H NMR (400MHz,d6-DMSO)δ10.33(s,1H),8.48(s,1H),8.03(s,1H),7.87(d,J=9.4Hz,1H), 7.58(d,J= 8.6Hz, 2H), 7.43(dd, J=9.4, 1.9Hz, 1H), 7.27(s, 1H), 6.93(d, J=8.6Hz, 2H), 3.70(q, J=7Hz, 4H), 2.87(dd,J=18.3,13.0Hz,4H),1.89-1.77(m,2H),1.26(t,J=7Hz,6H). 13 C NMR(100MHz,d6-DMSO)δ191.42,163.49,160.15,158.85,156.04,148.68,137.56, 133.97,132.55,132.29,126.90,125.49,123.43,118.80,118.45,116.43,116.29,95.85,45.95,27.23,21.48 , 13.01. HRMS (C 24 h 26 NO 2 ) + :360.1956, calcd for (C 24 h 26 NO 2 ) + :360.1958.

Embodiment 3

[0036] Preparation of fluorescent probe YZ-M5

[0037]Add compound YZ-M4 (230mg, 0.5mmol) and anhydrous potassium carbonate (138mg, 1mmol) into DCM (10 mL) solution, cool down to 0°C, then add 2,4-dinitrobenzenesulfonyl chloride (192mg, 0.75 mmol) was dissolved in 10 mL of anhydrous DCM, and added dropwise to the above reaction solution. After the reaction was complete, the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (DCM:MeOH=30:1, v / v) to obtain 234 mg of fluorescent probe YZ-M5 as a black solid, with a yield of 68%. 1 H NMR (400MHz, d6-DMSO) δ9.14 (d, J = 2Hz, 1H), 8.64 (dd, J = 9, 2Hz, 1H), 8.58 (s, 1H), 8.32 (d, J = 9Hz, 1H),8.03(s,1H),7.94(d,J=9Hz,1H),7.70(d,J=9Hz,2H),7.53(dd,J=9,2Hz,1H), 7.35(d,J =9Hz, 2H), 7.30(d, J=2Hz, 1H), 3.73(q, J=7Hz, 4H), 2.89(t, J=6Hz, 4H), 1.89– 1.80(m, 2H), 1.26( t,J=7Hz,6H). 13 C NMR(100MHz,d6-DMSO)δ161.23,159.18,156.80, 152.05,149.38,148.89,148.60,135.68,134.04,13...

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Abstract

The invention discloses a near-infrared selenocysteine fluorescent probe as well as a preparation method and application thereof. The structure of the near-infrared fluorescent probe for detecting selenocysteine is shown as (I), and the near-infrared fluorescent probe has the advantages of high reaction speed, good selectivity, high sensitivity and low detection limit. Under the physiological pH value, after the fluorescent probe reacts with selenocysteine with different concentrations, the fluorescence intensity and concentration show a good linear relationship, and the fluorescent probe is suitable for quantitative detection of selenocysteine, is used for fluorescence imaging of selenocysteine in human lung cancer cells A549, and can quantitatively detect selenocysteine in cells.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a near-infrared selenocysteine ​​fluorescent probe and its preparation method and application. Background technique [0002] Selenium is a micronutrient essential to human health. Insufficient intake of selenium can cause Keshan disease, Kaschin-Beck disease, diabetes and other diseases, but excessive intake of selenium can lead to selenium poisoning, hair loss, nail loss, liver damage, etc. The main form of selenium compounds in cells is selenocysteine ​​(Sec). Sec is called the 21st amino acid in protein synthesis and is an important component of selenoprotein (Selenoprotein, SeP). SeP has high enzyme catalytic activity, and SeP enzyme is involved in the metabolism of physiological functions such as antioxidant defense, fertility, muscle development, thyroid hormone regulation and immune function in the human body. Sec is specifically used as the reactive site of S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64A61K49/00
CPCC07D311/82C09K11/06A61K49/0021G01N21/6428C09K2211/1088C09K2211/1007C09K2211/1014
Inventor 蒋玉仁王宗成杨顺杨婷婷韩婷
Owner CENT SOUTH UNIV
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