Fluorescent probe for specifically distinguishing different thiol

A fluorescent probe and specific technology, which is applied in the field of fluorescent probes, can solve the problems of poor selectivity, few reports on fluorescent probes, inability to selectively distinguish thiophenols, etc., and achieve simple synthesis routes and simple operations , low cost effect

Active Publication Date: 2018-08-03
CENT SOUTH UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, due to the chemical similarity between biothiols and thiophenols, as well as the similar nucleophilicity, most of these probes are not very selective.
Studies have shown that thiophenols are more nucleophilic than biothiols under physiological conditions and cannot selectively distinguish thiophenols from biothiols
However, there are few reports on fluorescent probes that simultaneously distinguish and detect cysteine / homocysteine, glutathione, and thiophenol

Method used

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  • Fluorescent probe for specifically distinguishing different thiol
  • Fluorescent probe for specifically distinguishing different thiol
  • Fluorescent probe for specifically distinguishing different thiol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: the synthesis of intermediate product 2

[0038] Compound 1 (500mg, 2.6mmol) was dissolved in 15mL of toluene, then cyanoacetic acid (440mg, 5.2mmol) was added, the reaction was refluxed for 3h, and the reaction was stopped. The reaction liquid was cooled to room temperature, filtered with suction, and the filter cake was washed with dichloromethane to obtain 490 mg of beige powder as Compound 2 with a yield of 73.1%. HRMS(ESI)m / z: theoretical value C 13 h 8 NO 5 [M-H] + , 258.0408; experimental value, 258.0420. 1 H NMR (400MHz, DMSO) δ7.59(d, J=8.7Hz, 1H), 6.81(dd, J=8.7, 2.1Hz, 1H), 6.76(d, J=2.1Hz, 1H), 6.31(s ,1H), 5.44(s,2H), 4.23(s,2H), 3.86(s,1H). 13 C NMR (101 MHz, DMSO) δ 166.2, 164.5, 161.9, 160.6, 155.5, 150.1, 126.5, 113.6, 109.4, 108.6, 102.9, 63.2, 25.0.

Embodiment 2

[0039] Embodiment 2: the synthesis of compound CQ

[0040] Compound 3 (102 mg, 0.25 mmol) and piperidine (20 μL) were dissolved in 7.5 mL of dichloromethane, compound 2 (97 mg, 0.37 mmol) was dissolved in 7.5 mL of ethanol, and the two solutions were mixed. The reaction was carried out at 45° C. for 10 h under the protection of argon. After the reaction was finished, the solvent was spin-dried, and the residue was separated and purified by column chromatography. First, dichloromethane and ethyl acetate were used as eluent (V:V=15:1), and then dichloromethane and methanol were used as eluent (V : V=15:1) to perform column chromatography to obtain 50 mg of red powder as compound CQ, with a yield of 30.1%. HRMS(ESI)m / z: theoretical value C 32 h 26 N 5 o 10 [M-H] + , 640.1680; experimental value, 640.1666. 1 H NMR(400MHz,DMSO)δ10.61(s,1H),8.83(d,J=2.4Hz,1H),8.42(dd,J=9.3,2.4Hz,1H),8.14(s,1H),7.62 (s,1H),7.52(d,J=9.3Hz,1H),7.14(d,J=9.3Hz,1H),6.82–6.67(m,2H),6.61(s,1H),6.12(...

Embodiment 3

[0041] Embodiment 3: the synthesis of probe

[0042] Compound CQ (64 mg, 0.1 mmol) was dissolved in 10 mL of acetone, then NBD-Cl (40 mg, 0.2 mmol) and potassium carbonate (60 mg, 0.4 mmol) were added, and stirred at room temperature for 3 h. The reaction was stopped, the solvent was spin-dried, and the residue was separated and purified by column chromatography, using dichloromethane and ethyl acetate (V:V=20:1) as eluents to obtain 21 mg of purple-red powder as probe NCQ. The yield was 26.4%. HRMS(ESI)m / z: theoretical value C 38 h 27 N 8 o 13 [M-H] + , 803.1698; experimental value, 803.4059. 1 H NMR (400MHz, DMSO) δ8.86(d, J=2.8Hz, 1H), 8.67(d, J=8.3Hz, 1H), 8.43(dd, J=9.3, 2.8Hz, 1H), 8.17(s ,1H),7.93(d,J=8.8Hz,1H),7.65–7.57(m,2H),7.40(dd,J=8.8,2.4Hz,1H),7.16(d,J=9.3Hz,1H) ,7.03(d,J=8.3Hz,1H),6.63(s,1H),6.42(s,1H),5.54(s,2H),3.59(d,J=4.9Hz,2H),3.43(dd, J=14.1, 7.0Hz, 2H), 1.31–1.22(m, 4H), 1.18(t, J=7.0Hz, 3H), 1.06(t, J=7.0Hz, 3H). 13 C NMR (101MHz, DMSO) δ163.3,...

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Abstract

The invention relates to a fluorescent probe for specifically distinguishing different thiol and belongs to the field of fluorescent probes. A molecular structure of the fluorescent probe is as follows: a formula is shown in the description. A probe molecule has no fluorescent light; after the probe molecule responds with thiophenol, a solution produces blue light and red light; after the probe molecule responds with GSH (glutathione), the solution produces the blue light; after the probe molecule responds with Hcy / Cys, the solution produces the blue light and green light. The probe molecule provided by the invention can be used for distinguishing different types of the thiol and can be used for rapidly and quantitatively detecting different types of the thiol, and has important application value in the fields of biochemistry, environment monitoring and the like.

Description

technical field [0001] The invention relates to the preparation of a fluorescent probe for specifically distinguishing different thiols and its application in detecting biological thiols and thiophenols in cells, belonging to the field of fluorescent probes. Background technique [0002] Thiol is the general term of biothiol and thiophenol, which is an important class of compounds in living organisms and chemical industry. Biothiols include cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH), which play important roles in living organisms. Cysteine ​​deficiency can lead to liver damage, growth retardation, skin lesions, hair loss and lethargy; high levels of homocysteine ​​in the blood can cause cardiovascular disease, mental illness and Alzheimer's disease; glutathione in biological The content in the body is the most abundant, maintaining cell function, maintaining cell homeostasis, intracellular signal transduction, foreign body metabolism and gene regulation. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C09K11/06G01N21/64
CPCC07D413/14C09K11/06C09K2211/1007C09K2211/1044C09K2211/1048C09K2211/1088G01N21/6486
Inventor 宋相志杨雷苏远安熊海青耿娅妮沙占魁
Owner CENT SOUTH UNIV
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