Colorimetric ratio-type acid-base fluorescent probe and preparation method and application thereof

A fluorescent probe and ratio-based technology, applied in the field of fluorescent probes, can solve the problems of inability to apply fluorescent probes, and achieve the effects of high product yield, mild reaction conditions and sensitive response.

Active Publication Date: 2017-12-19
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most fluorescent probes only exhibit ratiometric properties in the acidic or alkaline range, and the existing fluorescent probes cannot be applied when there is an acid-base conversion in the intracellular environment.

Method used

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  • Colorimetric ratio-type acid-base fluorescent probe and preparation method and application thereof
  • Colorimetric ratio-type acid-base fluorescent probe and preparation method and application thereof
  • Colorimetric ratio-type acid-base fluorescent probe and preparation method and application thereof

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Embodiment 1

[0038] The colorimetric ratiometric acid-base fluorescent probe of this embodiment is prepared by the following steps:

[0039] 1) Add p-hydroxyphenethyl alcohol (2.0g, 14.5mmol) and triethylamine (5.29mL, 0.4mmol) into a 100mL round bottom flask, add solvent dimethyl sulfoxide (DMSO) 20mL, and then divide it into three times within 30min Add sulfur trioxide-pyridine (4.54g, 28.5mmol), react at room temperature for 1 hour, add 100mL of ice water, extract three times with 200mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, distill off the solvent, and the obtained liquid is washed with silica gel Column (petroleum ether: ethyl acetate=5:1, V:V) separates p-hydroxyphenylacetaldehyde;

[0040] 2) Add 2,3,3-trimethyl-3H-indole (0.3g, 32.8mmol) into iodoethane (12.9g, 82.5mmol), heat to 75°C under nitrogen protection, and react for 4h, After cooling to room temperature, the solid phase was washed with 5 mL of ether to obtain purple crystals, the structur...

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Abstract

The invention relates to a colorimetric ratio-type acid-base fluorescent probe and a preparation method and an application thereof. The colorimetric ratio-type acid-base fluorescent probe has a conjugated structure of hemicyanine and p-hydroxy phenylacetaldehyde shown as a formula 1, a formula 2, or a formula 3. The colorimetric ratio-type acid-base fluorescent probe has good water-soluble performance, observation is carried out by naked eyes in a pH scope of 6.0-8.0, the liquid is yellow when the pH value is less than 7.0, the color is darker when the pH value is smaller, the liquid is red when the pH value is greater than 7.0, and the color is darker when the pH value is larger. The fluorescence detection test shows that 455 nm wavelength excitation is employed, in the pH scope of 6.6-8.0, the pH change and the fluorescence intensity ratio I530 nm/I557 nm change has a good linear relation, the fluorescent probe has colorimetric ratio characteristics under acid-base response, and the colorimetric ratio-type acid-base fluorescent probe has good application in autophagy process detection of tumor cells.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a colorimetric ratio type acid-base fluorescent probe and its preparation method and application. Background technique [0002] The fluorescent probe analysis method has the characteristics of high sensitivity, strong selectivity, real-time in situ detection and visual detection. Fluorescent probes are more advantageous in the analysis of biological samples due to the non-destructive nature of the sample during the analysis. At present, a lot of research work is being carried out around the biological imaging characteristics of fluorescent probes. Among them, for biologically active small molecules related to living organisms (active sulfur, active nitrogen, active oxygen, etc.), important ions associated with biochemical processes (Zn 2+ 、Gu 2+ , Hg 2+ , and H + / OH - etc.) and other detectors as the target of the research work of new structural fluorescent probes are bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/12G01N21/64
CPCC07D209/12C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 王建红牛林强王佳敏齐建国李明朱新科黄静周晓敏闫志杰
Owner HENAN UNIVERSITY
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