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Pyrene-based ratiometric fluorescent probe as well as preparation method and biological application thereof

A fluorescent probe, ratiometric technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high detection limit and poor photostability of fluorescent probes, and achieve low detection limit and time Short, good photostability effect

Inactive Publication Date: 2018-06-22
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problems of high detection limit and poor photostability of existing fluorescent probes, the present invention provides a pyrene-based ratiometric fluorescent probe and its preparation method and biological application, which are used for HSO in vivo 3 - Detection and Imaging

Method used

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  • Pyrene-based ratiometric fluorescent probe as well as preparation method and biological application thereof
  • Pyrene-based ratiometric fluorescent probe as well as preparation method and biological application thereof
  • Pyrene-based ratiometric fluorescent probe as well as preparation method and biological application thereof

Examples

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Effect test

Embodiment 1

[0021] Example 1: A ratiometric fluorescent probe based on pyrene, which is 1-(pyrene-1-yl)-3-(4,5-dibromothiophen-2-yl)propenone, its chemical The structural formula is as follows: .

[0022] The method for preparing the ratiometric fluorescent probe based on pyrene, using pyrene as a starting material, reacting with anhydrous aluminum trichloride and acetyl chloride according to a molar ratio of 4:5:7 to obtain 1-acetylpyrene, Mix and dissolve the obtained 1-acetylpyrene and 4,5-dibromothiophene-2-carbaldehyde in a molar ratio of 3:4, then add 10% NaOH solution and stir at room temperature to obtain 1-(pyrene-1 -yl)-3-(4,5-dibromothien-2-yl)propenone.

[0023] Specific steps are as follows:

[0024] (1) Synthesis of 1-acetylpyrene: Add 1.00g (4mmol) pyrene and 40mL dichloromethane to a dry 100mL single-necked round-bottom flask equipped with magnetic stirring, stir to dissolve (the solution turns light yellow), and then Quickly add about 0.67g (5mmol) of anhydrous alumi...

Embodiment 2

[0028] Example 2 HSO of fluorescent probe 3 - Varying UV Absorption Spectrum

[0029] Add 20.0 µL fluorescent probe stock solution to 2.0 mL water / absolute ethanol (9 / 1, v / v) system for HSO 3 - UV titration experiment, and record its UV absorption spectrum ( figure 1 ). With HSO 3 - The UV absorption at 332 nm and 411 nm both decreased with the increase of the amount.

Embodiment 3

[0030] Embodiment 3 Fluorescent probes with HSO 3 - Fluorescence titration plot of change

[0031] Add 20.0 µL fluorescent probe stock solution to 2.0 mL water / absolute ethanol (9 / 1, v / v) system for HSO 3 - Fluorescent titration experiment, detected on a spectrofluorometer, along with HSO 3 - With the increase of , the fluorescence intensity at 530nm gradually weakened, and a new peak appeared at 420nm and gradually increased ( figure 2 ). Instrument parameters: The slit widths of the excitation wavelength and emission wavelength are 5.0 nm and 10 nm respectively, the voltage is 600 V, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex is 366nm and the maximum emission wavelength is λ em 530nm. Fluorescence ratio I 420 / I 530 Plotting the graph for the ordinate gives the HSO 3 - The working curve of concentration, linear regression equation is: I 420 / I 530 = 0.18*[HSO 3 - ]+0.77, HSO 3 - The unit of concentration is 10 -6 mo...

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Abstract

The invention belongs to the technical field of synthesis of fluorescent probes, and provides a pyrene-based ratiometric fluorescent probe as well as a preparation method and a biological applicationthereof to solve the problems that the conventional fluorescent probes are high in detection limit, poor in light stability and the like. The pyrene-based ratiometric fluorescent probe is used for detection of HSO3<-> and imaging in a biological body, is 1-(pyrene-1-yl)-3-(4,5-dibromothiophene-2-yl)acrylketone, and is prepared through the following steps: pyrene taken as a starting material is subjected to a reaction with anhydrous aluminium trichloride and acetyl chloride in the mole ratio of 4:5:7, 1-acetylpyrene is obtained and is mixed and dissolved with 4,5-dibromothiophene-2-formaldehydein the mole ratio of 3:4, 10% NaOH solution is added, stirring reaction is performed at room temperature, and the fluorescent probe is obtained. Detection of HSO3<-> by the fluorescent probe is ratiometric, reaction is quick, selectivity and sensitivity are high, and the fluorescent probe can be used for detecting HSO3<-> in the biological body through combination with confocal laser scanning microscopy.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorescent probes, in particular to a pyrene-based ratiometric fluorescent probe, its preparation method and biological application, and the probe is applied to the detection of bisulfite in living organisms. Background technique [0002] Modern human activities such as mineral burning and processing produce large amounts of sulfur dioxide (SO 2 ), posing a threat to the ecological environment and human health. Human inhalation of SO 2 HSO is produced in the body 3 - and SO 3 2- . Sulfite is widely used in food, beverage and pharmaceutical industries due to its ability to inhibit oxidation, microbial growth and enzymatic reactions. However, excessive sulfurous acid can cause some diseases, such as allergic reactions, asthma and cardiovascular and nervous system diseases. WHO stipulates that the permissible intake of sulfite per person per day is 0-0.7mg / Kg (in SO 2 count). Therefor...

Claims

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Application Information

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IPC IPC(8): C07D333/28C09K11/06G01N21/64G01N31/16
CPCC07D333/28C09K11/06C09K2211/1011C09K2211/1092G01N21/6486G01N31/16
Inventor 钞建宾王小露张永斌徐苗赵明根孙金鱼
Owner SHANXI UNIV
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