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Fluorescent probe for high-selectivity detection of formaldehyde, and synthesis method and application thereof

A fluorescent molecular probe, formaldehyde technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low biocompatibility, high preparation cost, complicated synthesis, etc., and achieve strong anti-interference ability, Low-cost, easy-to-synthesize effects

Active Publication Date: 2020-05-01
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently developed probe molecules for the detection of biological aldehyde-based compounds have some defects, such as low sensitivity, cumbersome synthesis, high preparation cost and low biocompatibility (document DongB.Angew.Chem.Int.Ed., 2016, 55, 3356; Cheng H. Chem. Commun., 2016, 52, 11247.)

Method used

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  • Fluorescent probe for high-selectivity detection of formaldehyde, and synthesis method and application thereof
  • Fluorescent probe for high-selectivity detection of formaldehyde, and synthesis method and application thereof
  • Fluorescent probe for high-selectivity detection of formaldehyde, and synthesis method and application thereof

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Embodiment 1

[0022] Example 1: Synthesis of Fluorescent Molecular Probes

[0023] Aldehylated benzothiazole fluorescent molecule (compound 2) (0.269g, 1mmol) and allylboronic acid pinacol ester (0.201g, 1.2mmol) were added to methanol (10mL) and ammonia methanol (5mL, the concentration of ammonia 5mol·L -1 ) in a mixed solution at a controlled temperature of 0° C. for 1 h, and the reaction solution was moved to room temperature to continue the reaction for 5 h. The reaction was stopped, the reaction solution was spin-dried under reduced pressure, and the obtained crude product was separated by chromatography to obtain the probe molecule (0.274 g, 88.4%). The characterization of the probe molecules is as follows: 1 H NMR (400MHz, DMSO): δ8.03(d, J=7.4Hz, 1H), 7.99(d, J=1.6Hz, 1H), 7.93(d, J=7.9Hz, 1H), 7.45(dd, J=11.1,4.1Hz,1H),7.33(t,J=7.0Hz,1H),6.94(d,J=2.2Hz,1H),5.80(td,J=17.1,7.0Hz,1H),5.16– 5.04(m, 2H), 4.17(t, J=6.9Hz, 1H), 2.67–2.53(m, 2H), 2.26(s, 3H) (Fig. S1). 13 C NMR (100MH...

Embodiment 2

[0024] Embodiment 2 Probe of the present invention is to the detection of formaldehyde in the solution

[0025] The molecular probe prepared above was dissolved in a mixed buffer solution (H 2 O / DMSO=1 / 1, v / v, 10mM PBS, pH 7.4)), prepared to 10μmol L -1 probe solution. Add 2 mL of prepared 10 μmol L to a 3 mL cuvette -1 Probe solution of the present invention, then add formaldehyde of different concentrations respectively and mix uniformly, test its fluorescence spectrum, the result is as follows: image 3 shown. The ratio of the fluorescence emission intensity of the solution at 552nm and 492nm is plotted against the concentration of formaldehyde, and the concentration of formaldehyde is 0-500μmol L -1 In the range, there is a good linear relationship between the two ( Figure 4 ), according to the standard diagram, the quantitative detection of formaldehyde in the sample to be tested within this concentration range is realized, and the solution changes from colorless to...

Embodiment 3

[0026] Embodiment 3 Probe of the present invention is to the test of formaldehyde in the cell

[0027] After cultured human gastric cancer cells (MGC-803) were cultured in 10 μM PBS solution of the probe of the present invention at 37° C. for 2 hours, the cell images obtained had no fluorescence. However, the MGC-803 cells were cultured in PBS solution of 1mM formaldehyde at 37°C for 2h, then cultured in PBS solution of 10μM probe of the present invention at 37°C for 2h, and washed with PBS buffer solution to obtain Fluorescence imaging of cells. This shows that the probe of the present invention has good cell membrane permeability and can be used for cell imaging analysis in the field of biomedicine.

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Abstract

The invention discloses a novel fluorescent probe for high-selectivity detection of formaldehyde and a preparation method and application thereof, belonging to the technical field of chemical analysisand detection. The molecular structural formula of the probe is as shown in the specification. The fluorophore of the probe is of a benzothiazole skeleton structure, and a group responsive to formaldehyde is alkylamine. The individual probe emits blue fluorescence in a solution, and the emission wavelength of the probe is 492 nm. After the probe reacts with formaldehyde, the fluorescence emissionof the probe is redshifted to 552 nm. The probe has high selectivity and sensitivity to formaldehyde, has a detection range of 0-500 [mu]mol / L, and has a detection limit is 0.58 [mu]mol / L. The probecan be used for detecting formaldehyde in a water body and a biological system.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a molecular probe for detecting formaldehyde by a fluorescence method, a preparation method thereof and an application in detecting formaldehyde. Background technique [0002] Formaldehyde is not only a chemical raw material but also an important biologically active carbon-containing molecule. As an important single-carbon raw material in cells, formaldehyde can participate in the synthesis of important biomolecules and is closely related to certain physiological functions (such as cognitive ability and spatial memory ability). However, excessive levels of formaldehyde can lead to various diseases, including dementia, diabetes (including diabetes), cancer and neurodegenerative diseases. Therefore, the development of highly sensitive and highly selective methods for the detection of aldehyde groups is of great benefit to the effective detection...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/643C09K2211/1037C09K2211/1007G01N2021/6419
Inventor 郝远强张银堂董辉韩华博韦秀华朱旭瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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