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ATP (adenosine triphosphate) fluorescent probe based on TPE (tetraphenyl ethylene) as well as preparation method and application of fluorescence probe

A fluorescent probe, alkyl technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low specificity, high detection cost, low sensitivity, etc., and achieve fewer synthesis steps and short reaction time. , The effect of purification and convenience

Active Publication Date: 2018-04-17
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

High-performance liquid chromatography requires a large amount of organic solvents, causing great environmental pollution, high detection costs, and it is difficult to achieve trace detection levels; while the currently widely used luciferase-based ATP detection method has high sensitivity, but its accuracy is limited by the matrix. The influence of fluorescence quenching of middle components is greater; and low specificity and low sensitivity have always been difficult problems in the design of electrochemical biosensors

Method used

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  • ATP (adenosine triphosphate) fluorescent probe based on TPE (tetraphenyl ethylene) as well as preparation method and application of fluorescence probe
  • ATP (adenosine triphosphate) fluorescent probe based on TPE (tetraphenyl ethylene) as well as preparation method and application of fluorescence probe
  • ATP (adenosine triphosphate) fluorescent probe based on TPE (tetraphenyl ethylene) as well as preparation method and application of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of 4,4'-bis(trimethylethynyl)-benzophenone (compound 3)

[0049]

[0050]Under argon protection, bistriphenylphosphine palladium dichloride (619mg, 0.88mmol), copper iodide (223mg, 1.17mmol), triphenylphosphine (154mg, 0.59mmol), 4,4'-bis Bromobenzophenone (10.0g, 29.4mmol) was dissolved in a mixed solvent of tetrahydrofuran and triethylamine, and trimethylethynyl silicon (16.6mL, 117.6mmol) was added to react at 70°C for 12h. Then, the reaction was quenched with 200 ml of saturated aqueous ammonium chloride. Extracted with dichloromethane, the organic phase was spin-dried. The crude product was passed through a silica gel column with the developer petroleum ether / dichloromethane to obtain a white solid (10.8g, 98%) MALDI-TOF (C 23 h 26 OSi 2 ): [M]=374.1. 1 H-NMR (400MHz, CDCl3, TMS): δ: 7.71 (d, J = 8.4Hz, 4H), 7.56 (d, J = 8.4Hz, 4H), 0.27ppm (s, 18H, Si(CH 3 ) 3 ).

Embodiment 2

[0052] Preparation of 4,4'-bis(bromoethoxy)-benzophenone (compound 4)

[0053]

[0054] Under argon protection, 1,2-dibromoethane (35.1g, 186.7mmol), 4,4'-dihydroxybenzophenone (10.0g, 46.7mmol), K 2 CO 3 (38.7 g, 280.1 mmol) was dissolved in DMF. Reaction at 90°C for 48h. The reaction solution was filtered, and the organic phase was spin-dried, and the crude product was passed through a silica gel column with the developing solvent dichloromethane / petroleum ether to obtain a white solid (8g, 40%). MALDI-TOF (C 17 h 16 Br 2 o 3 ):[M-1]=427.1. 1 HNMR (400MHz, DMSO): δ: 7.70 (d, J = 8.4Hz, 4H), 7.10 (d, J = 8.4Hz, 4H), 4.43 (t, J = 5.2Hz, 4H), 3.84ppm (t, J=5.2Hz, 4H).

Embodiment 3

[0056] Preparation of 1,2-bis(4,4'-bromoethoxy)-diphenyl-1,2-bis(4,4'-trimethylsilylethynyl)-diphenylethylene. (compound 5)

[0057]

[0058] Under the protection of argon, compound 3 (2.37g, 6.3mmol), compound 4 (4.51g, 10.5mmol), zinc powder (10.95g, 168.5mmol), titanium tetrachloride (9.5mL, 84.3mol) were dissolved in tetrahydrofuran In the reaction at 65°C for 12h, with 10% saturated K 2 CO 3 The aqueous solution was used to quench the reaction, the reaction solution was filtered, the organic phase was extracted with dichloromethane, and the organic phase was spin-dried. The crude product was chromatographed on a silica gel column with the developer petroleum ether / dichloromethane to obtain a yellow solid (1.47g, 30%). MALDI-TOF (C 40 h 42 Br 2 o 2 Si 2 ):[M-1]=770. 1 HNMR (400MHz,C 3 D. 6 O), δ: 7.21(d, 4H, J=4Hz), 7.00-6.94(m, 8H), 6.74(d, 4H, J=8.8Hz), 4.30(t, 4H, J=5.6Hz), 3.74 (t, 4H, J=5.6Hz), 0.20(s, 18H).

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Abstract

The invention relates to a fluorescence probe shown in general formula (I) and a preparation method of the fluorescence probe. The probe takes TPE (tetraphenyl ethylene) as a fluorescence parent, andwhen the probe is completely dissolved in an aqueous solution, the fluorescence signal is weak; when the probe gathers or forms a solid state, the fluorescence signal is significantly enhanced. The probe has good selectivity for ATP (adenosine triphosphate) and can be used as an ATP fluorescence probe. The probe can be used for detecting in-vitro ATP when prepared in an aqueous solution or a buffer solution. The compound can automatically permeate cell membranes to enter cells without any vectors and can be used for intracellular ATP imaging. The fluorescence probe has the advantages of high specifity, light stability, wide response range and the like.

Description

technical field [0001] The invention relates to a tetraphenylethylene-based ATP fluorescent probe and its preparation method and application, belonging to the technical field of organic small molecule fluorescent probes. Background technique [0002] Adenosine triphosphate (ATP) is the smallest energy unit in living organisms and directly participates in various life activities. It is called the molecular currency in cells. ATP is the energy source for living cells to survive. The content of ATP in the body has a very important relationship with cell metabolism and apoptosis. Many diseases such as cardiovascular disease, Parkinson's syndrome and Alzheimer's disease are accompanied by Abnormal ATP content. Therefore, the detection of ATP is of great significance in life science and medical clinical research. [0003] At present, the detection methods of ATP include high performance liquid chromatography, capillary electrophoresis, bioluminescence, electrochemistry, and fluo...

Claims

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Application Information

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IPC IPC(8): C07D233/60C09K11/06G01N21/64
CPCC07D233/60C09K11/06C09K2211/1044G01N21/6428G01N21/6486
Inventor 杨国强张欣王双青胡睿
Owner INST OF CHEM CHINESE ACAD OF SCI
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