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Fluorescent probe for detecting biological thiols

A biological thiol and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of expensive instruments and equipment, cumbersome processing, complicated operation process, etc., and achieve the effects of low cost and simple synthesis route.

Inactive Publication Date: 2018-08-24
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these conventional methods usually have disadvantages such as the need for expensive instruments and equipment, complicated operation procedures, cumbersome sample pretreatment, etc.

Method used

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  • Fluorescent probe for detecting biological thiols
  • Fluorescent probe for detecting biological thiols
  • Fluorescent probe for detecting biological thiols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of intermediate product 2

[0026] Add 10.0mL acetone to a 50mL single-necked round bottom flask, then dissolve compound 1 (0.2173g, 1.0mmol) and 3-bromopropyne (0.2380g, 2.0mmol) in acetone, then add anhydrous potassium carbonate (0.2764g , 2.0mmol), then heated to reflux for 12 hours, stopped the reaction, filtered the reaction solution to remove the filter residue, spin-dried to obtain a solid crude product, and finally column chromatography (silica gel 200-300 mesh, eluent: V 乙酸乙酯 / V 石油醚 =1 / 3) 0.2002 g of yellow solid was isolated with a yield of 78.4%. 1 H NMR (500MHz, CDCl 3 )δ H :10.03(s,1H),7.34(s,1H),4.63(d,J=2.4Hz,2H),3.52-3.05(m,4H),2.81(t,2H),2.73(t,2H), 2.55(t,1H),2.01-1.82(m,4H). 13 C NMR (125MHz, CDCl 3 )δ C :187.8,157.8,148.8,127.5,117.5,117.0,112.6,78.7,76.1,62.1,50.0,49.7,27.3,21.4,21.3,20.7.

Embodiment 2

[0027] Embodiment 2: the synthesis of intermediate product 3

[0028] Compound 2 (0.2552g, 1.0mmol) and 4-aminophenol (0.1308g, 1.2mmol) were added to a 25mL single-necked round bottom flask containing 5.0mL of anhydrous DMF, reacted at 110°C for 4h, stopped the reaction, and cooled to room temperature. The reaction solution was poured into 50 mL saturated brine, extracted with dichloromethane (25.0 mL×4), washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried under reduced pressure to obtain a crude product, which was then subjected to column chromatography (eluent: V 石油醚 / V 乙酸乙酯 =6 / 1 to 3 / 1) isolated the product 0.0689 g; yield 20%. 1 HNMR (400MHz, DMSO-d 6 )δ H9.85(s,1H),7.78(d,J=9.2Hz,2H),7.65(s,1H),7.22(dd,J=9.0,2.6Hz,1H),7.06(d,J=2.6Hz,1H ),5.19(s,2H),3.19–3.06(m,4H),2.72(t,J=6.2Hz,2H),2.60(t,J=6.4Hz,2H),2.52-2.47(m,1H) ,1.86(m,4H). 13 C NMR (100MHz, DMSO-d 6 )δ C 155.0, 153.7, 147.2, 145.6, 143.3, 130.0, 129.2, 128.2, 125.2, 122.4, 121...

Embodiment 3

[0029] Embodiment 3: the synthesis of intermediate product 4

[0030] Add compound 3 (0.1801g, 0.52mmol) and 5mL of anhydrous dichloromethane into a 20mL thick-walled pressure bottle, then add iodomethane (0.0863g, 0.6mmol), react at 90°C for 12h in the dark, and stop the reaction. Cool to room temperature, remove solvent under reduced pressure to obtain crude product, finally through column chromatography (eluent: V 二氯甲烷 / V 甲醇 =50 / 1 to 33 / 1) isolated the product 0.0932 g, yield 87%. 1 H NMR (500MHz, DMSO-d 6 )δ H 10.64(s,1H),8.45(s,1H),8.12(d,J=9.3Hz,1H),7.61-7.42(m,2H),7.36(s,1H),5.19(s,2H),4.35 (s,3H),2.72(d,J=49.8Hz,4H),1.92-1.89(m,4H),1.40-1.12(m,4H). 13 C NMR (400MHz, DMSO-d 6 )δ C 157.5,157.0,149.2 147.7,135.3135.0,130.5,128.7,127.8,124.5,121.2,117.2,111.3,107.5,103.3,67.9,50.1,49.5,44.5,27.3,21.3,203.6,2

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Abstract

The invention discloses a fluorescent probe for detecting biological thiols. The molecular structural formula of the fluorescent probe is shown in the description. The fluorescent probe has weak fluorescence, and after the fluorescent probe responds to biological thiols, a liquor emits red light. The probe molecule not only can be applied to a pure water system for detecting biological thiols, butalso can rapidly identify and quantitatively detect biological thiols in cells. The fluorescent probe has important application value in the field of biochemistry.

Description

technical field [0001] The invention relates to the field of fluorescent probes, and relates to the preparation and application of a fluorescent probe for detecting biological thiols. Background technique [0002] Biothiols promote the function of enzymes in organisms and are important signaling molecules in physiological activities. At the same time, they can also regulate the normal redox state of cells and have important functions in the physiological activities of organisms. [0003] Conventional methods for the detection of biothiols include chromatography, electrochemical methods, and gas chromatography. However, these conventional methods usually have disadvantages such as the need for expensive instruments and equipment, complicated operating procedures, and cumbersome sample pretreatment. Compared with conventional detection methods, fluorescence analysis has the advantages of simple operation, good selectivity, and high sensitivity, and can be used for cell and bi...

Claims

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Application Information

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IPC IPC(8): C07D491/22C09K11/06G01N21/64
CPCC07D491/22C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643G01N21/6486
Inventor 宋相志熊海青苏远安杨雷张赟韩金梁
Owner CENT SOUTH UNIV
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