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Polarity-sensitive fluorescence probe and preparation method and application thereof

A fluorescent probe and sensitive technology, applied in the field of fluorescent sensors, can solve the problems of being unsuitable for biological detection and short emission wavelength, and achieve the effects of convenient detection operation, simple preparation method and fast response

Inactive Publication Date: 2015-04-22
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the defect that existing rhodamine-based fluorescent dyes have short excitation and emission wavelengths and are not suitable for biological detection, the purpose of the present invention is to provide a polarity-sensitive fluorescent probe, preparation method and application

Method used

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  • Polarity-sensitive fluorescence probe and preparation method and application thereof
  • Polarity-sensitive fluorescence probe and preparation method and application thereof
  • Polarity-sensitive fluorescence probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The polarity sensitive fluorescent probe of the present invention, structural formula is:

[0036]

[0037] Among them, R 1 = H, R 2 =CH 3 ,

[0038] The reaction equation is as follows:

[0039]

[0040] The preparation method is as follows:

[0041] (1) Dissolve 5.00g (25mmol) of compound a-1 in 5ml of formaldehyde solution with a volume concentration of 37% and 40ml of acetic acid mixed solution, stir at 60°C for 30 minutes, after natural cooling, distill off the acetic acid under reduced pressure at 100°C, Then add saturated NaHCO 3 solution. The resulting solution was extracted with 3 times the volume of ethyl acetate to extract the organic phase, and the organic phase was washed three times with deionized water and three times with brine successively, and then washed with Na 2 SO 4 Dry, remove the solvent by distillation under reduced pressure at 60°C to obtain a solid, which is separated by silica gel column chromatography (the eluent is a mixed sol...

Embodiment 2

[0046] The polarity sensitive fluorescent probe of the present invention, structural formula is:

[0047]

[0048] Among them, R 1 =CH 3 CH 2 , R 2 =CH 3 CH 2 .

[0049] The reaction equation is as follows:

[0050]

[0051] The preparation method is as follows:

[0052] (1) 5.66g (25mmol) of compound a-2 was dissolved in 5ml of a volume concentration of 37% formaldehyde solution and 40ml of acetic acid mixed solution, stirred at 60°C for 30 minutes, after natural cooling, acetic acid was distilled off under reduced pressure at 100°C, Then add saturated NaHCO 3 solution. The resulting solution was extracted with 3 times the volume of ethyl acetate to extract the organic phase, and the organic phase was washed three times with deionized water and three times with brine successively, and then washed with Na 2 SO 4 Dry, remove the solvent by distilling under reduced pressure at 60°C, and separate by silica gel column chromatography (the eluent is a mixed solution...

Embodiment 3

[0057] (1) Preparation of probe solution:

[0058] Two parts of compound f-1 (2.3mg) prepared in Example 1 were fixed in a 25ml volumetric flask with 1,4-dioxane and methanol as solvent to obtain 2×10 -4 mol / L f-1 solution, take 2.5ml of two solutions respectively, dilute and constant volume in a 100ml volumetric flask to obtain 5μmol / L f-1 solution (solvent is 1,4-dioxane), weigh It is solution I, and 5 μmol / L f-1 solution (solvent is methanol), called solution II.

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Abstract

The invention discloses a polarity-sensitive fluorescence probe and a preparation method and application thereof. A structural formula of the probe is as shown in the specification, wherein R1 is H, CH3, CH3CH2 or COOH; and R2 is CH3, CH3CH2 or CH3CH2CH2. The preparation method comprises the following steps: reacting a reactant 1 and a reactant 2 at a low temperature in an anhydrous anoxic reactor; and adding a reactant 3, reacting at a room temperature, and carrying out treatment such as skimming and purification, so as to obtain the probe. The probe has the specific fluorescence response on the solvent polarity, and is fast in response; the fluorescence wavelength is relatively large during response; the preparation method is simple; and the response detection on the solvent polarity is convenient.

Description

technical field [0001] The invention relates to a polarity-sensitive fluorescent probe, a preparation method and an application, in particular to the preparation of a polarity-sensitive fluorescent material and the fluorescence intensity response in different polar solvents, and belongs to the field of fluorescence sensors. Background technique [0002] Fluorescence spectroscopy is a very important tool in the identification of ions, detection of small molecules, and biochemical studies of biological processes such as protein folding, protein-protein interactions, and phosphorylation. [0003] We live in an environment that is closely related to polarity. The natural environment we live in, the internal environment of organisms, cells, and organelles are all subtly related to the polarity of the environment in which we live. Fluorescent probes sensitive to polar environments are a special class of fluorescent probes whose spectral properties change with changes in the surrou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/30G01N21/64
Inventor 张小玲雷蕾聂海亮杨文敬静
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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