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Thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent and its preparation and application

A technology of hydroxycoumarin and thiosemicarbazide, used in chemical instruments and methods, fluorescence/phosphorescence, instruments, etc.

Inactive Publication Date: 2018-12-28
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There have been many reports on the detection of single targets by fluorescent probes, but few of them can realize the selective recognition of cations and anions at the same time, especially for specific ion imaging in living cells to detect the water solubility and permeability of probes. and biological toxicity and other factors

Method used

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  • Thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent and its preparation and application
  • Thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent and its preparation and application
  • Thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment 1: Synthesis of thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent:

[0095] synthetic route:

[0096]

[0097] Specific steps:

[0098] 1. N 2 Under protection, add 120mL of dichloromethane, 7-hydroxycoumarin (9.3g, 57.3mmol) into a 250mL three-necked flask, stir to dissolve, then add acetic anhydride (11.7g, 114.6mmol), 7-8 drops of piperidine (0.3, g), reflux at room temperature, and react for 12 hours. After the reaction is completed, the solvent is distilled off under reduced pressure. After adding water, it is extracted with ethyl acetate. The ethyl acetate layer is washed with saturated brine, dried over sodium sulfate, filtered, and decompressed. The solvent was distilled off, and the crude product was separated by column chromatography using chloroform as the eluent to obtain 11.16 g of a white product, 7-acetoxycoumarin, with a yield of 95.4%. 1 H NMR (400MHz, CDCl 3 ), δ (ppm): 2.36 (s, 3H, CH 3 ), 6.41(d, 1H, J=9.6Hz, ArH), 7.07(...

Embodiment 2

[0102] The preparation methods of various reagents are:

[0103] 1. The preparation method of the probe reagent solution: weigh 26.3 mg of the probe reagent, dissolve it in DMF, and prepare a 100 mL solution with a concentration of 1 mM;

[0104] 2. Zn 2+ Reserve standard solution preparation method: weigh 74.4mg of analytically pure Zn(ClO 4 ) 2 , dissolved in acetonitrile, and prepared into 10 mL of a solution with a concentration of 20 mM; the preparation methods of the rest of the metal ions are the same as above;

[0105] 3. F -Stock solution preparation method: Weigh 52.8 mg of tetrabutylammonium fluoride, dissolve it in acetonitrile, and prepare 10 mL of a solution with a concentration of 20 mM. The preparation of other anion solutions is the same as above.

[0106] 4. 75% ethanol solution: add 75mL of absolute ethanol to 100mL with distilled water, mix well, and store at room temperature for later use;

[0107] 5. Phosphate buffer solution (D-hanks balanced salt ...

Embodiment 3

[0115] (1) Fluorescence spectrometry on Zn 2+ detection

[0116] Add (1mM, 100μL) to a 10mL volumetric flask, Zn 2+ (20mM, 0~100μL), with DMF / H 2 O (v / v, 1 / 4) was diluted to the mark, shaken up, and carried out fluorescence spectrum measurement;

[0117] Set the fluorescence excitation wavelength to 355nm, add 3ml of probe reagent (10μM concentration) in DMF / H to a 1cm cuvette 2 The O (v / v, 1 / 4) solution is subjected to spectral scanning, and the probe reagent has fluorescence emission at a wavelength of 475nm. Add 20 μM metal ion Li + , Na + , K + , Mg 2+ , Ca 2+ , Ba 2+ , Hg 2+ ,Sr 2+ , Al 3+ , Cd 2+ , Ni 2+ ,Co 2+ , Pb 2+ , Fe 3+ , Cr 3+ , Ag + , Cu 2+ , no obvious change in the fluorescence spectrum was observed, only Zn 2+ The addition of the probe reagent significantly enhanced the fluorescence peak at 475nm, such as figure 1 .

[0118] in DMF / H 2 In O(v / v, 1 / 4) solution, with 410nm as the fluorescence excitation wavelength, different concentratio...

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Abstract

The invention discloses a thiosemicarbazone 7-umbelliferone-8-aldehyde probe reagent which is prepared by enabling 7-hydroxyl-8-aldehyde coumarin and thiosemicarbazone to react. By adopting a probe disclosed by the invention, selective recognition of metal ions and anion can be achieved simultaneously, specific ions can be rapidly detected through visual colorimetric, the probe can be also applied to specific ion imaging detection in living cells, has double-mode detection with fluorescence enhancement and proportioning absorption, is relatively excellent in detection sensitivity and accuracy, has the advantages of high sensitivity, high selectivity, high yield and the like, and moreover is beneficial to quantitative and qualitative analysis on complex micro systems.

Description

technical field [0001] The invention relates to a probe reagent and its preparation method and application, in particular to a thiosemicarbazide 7-hydroxycoumarin-8-aldehyde probe reagent and its preparation method and application. Background technique [0002] Compared with other analytical methods, fluorescent probe technology has the advantages of good selectivity, high sensitivity, and real-time online. It is an ideal and cheap sensor and an important method in trace detection. Organic small molecule fluorescent probes have the advantages of simple structure, easy synthesis, low cost, good water solubility, and low cytotoxicity. Its application to ion detection in biological systems has high sensitivity, good selectivity, strong visibility, and rapid , Simple and other characteristics. [0003] The identification and detection of biologically relevant ions is particularly important in the research of life, food and environment. Zinc ions play an important role in biolo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/18G01N21/64G01N21/31C09K11/06
CPCC07D311/18C09K11/06C09K2211/1088G01N21/314G01N21/6428G01N2021/3155
Inventor 曾晞曾莉李钊牟兰
Owner GUIZHOU UNIV
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