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Preparation and application of a two-photon fluoride ion fluorescent probe compound

A technology of fluorescent probes and fluoride ions, which is applied in the field of fluorescent probes, can solve the problems of non-quantitative determination of fluoride ion content, the probe does not report the working curve, autofluorescence will interfere, etc., to achieve good sensitivity and selectivity, good Promotion prospect, good water solubility effect

Inactive Publication Date: 2019-04-30
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, CN104449677A provides a preparation method and application of a fluoride ion fluorescent probe based on benzothiazole, which can be applied to the detection of fluoride ions in cells, but it has the following disadvantages: 1. The probe is a quenching fluorescent probe, which is not conducive to the observation of biological imaging; 2. The excitation wavelength of the probe is 300nm, which has a certain harmful effect on organisms, and the autofluorescence of intracellular substances will interfere; 3 , The probe does not report a working curve, and cannot quantitatively determine the content of fluoride ions
In addition, CN104845611A provides a method for preparing a fluoride ion fluorescent probe based on coumarin and fluorescein. The fluorescent probe can be applied to the detection of fluoride ions in water, but the probe cannot be applied to the detection of fluoride ions in cells and cell imaging studies

Method used

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  • Preparation and application of a two-photon fluoride ion fluorescent probe compound
  • Preparation and application of a two-photon fluoride ion fluorescent probe compound
  • Preparation and application of a two-photon fluoride ion fluorescent probe compound

Examples

Experimental program
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Embodiment 1

[0037] Embodiment 1, the synthesis of probe molecule compound I

[0038] (a) Take 1.106g of 2,4-dihydroxybenzaldehyde and 0.816g of imidazole in a three-necked flask under nitrogen protection. Take 1.3mL of cyclohexenone and add it into the flask; add 6mL of tetrahydrofuran and 6mL of water into the flask. React at ℃ for 72h, then add 20mL of 1M dilute hydrochloric acid, extract the aqueous phase with ethyl acetate, evaporate the solvent, use the mixture of ethyl acetate and n-hexane with a volume ratio of 1:6 as the developing solvent, and separate by column chromatography to obtain 0.46 g compound II, yield 19%;

[0039] (b) Dissolve 0.1g of compound II, 0.331g of tert-butyldimethylchlorosilane, and 0.163g of imidazole in 10mL of dichloromethane, react for 8 hours at room temperature under nitrogen atmosphere, distill off the solvent, and use a volume ratio of 10:1 A mixed solvent of petroleum ether and ethyl acetate was used as a developer and separated by column chromatog...

Embodiment 2

[0040] Embodiment 2, fluorescence experiment

[0041] Take the fluorescent probe compound prepared in Example 1, dissolve it in an aqueous solution containing 5% ethanol, adjust the pH=7.4 with HEPES buffer solution; obtain the fluorescent probe solution, and set aside;

[0042] 1. Take the fluorescent probe solution and divide it into 11 groups, 10mL in each group. Among them, 1 group does not add anion, and 10 groups add CO 3 2‒ , SO 4 2‒ , NO 3 ‒ , Cl ‒ , I ‒ 、Br ‒ 、CH 3 COO ‒, N 3 ‒ 、PO 4 3‒ , F ‒ solution, so that the concentration of the probe compound contained in each group of solutions is 10 μM, and the anion concentration is 300 μM, so that the molar ratio of the anion to the probe compound is 30:1; the excitation wavelength is 422 nm, and the fluorescence intensity is tested by a fluorescence photometer. The invention probe solution itself has no fluorescence. Once fluoride ions are added, the fluorescence of the solution at 511nm increases rapidly, b...

Embodiment 3

[0044] Embodiment 3, cell imaging experiment

[0045] MCF-7 cells were cultured in 1 mL cell culture medium containing 10% bovine fetal serum for 12 hours, then treated with 100 μM fluoride ion for 10 minutes, and then treated with 10 μM fluorescent probe of the present invention for 30 minutes. Cells were excited with a light source with an excitation wavelength of 534 nm and imaged under a confocal microscope. Such as image 3 A picture of MCF-7 cells cultured with the addition of fluoride ions for the fluorescent probe of the present invention.

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Abstract

The invention relates to a preparation method and application of a double-photon fluorine ion fluorescent probe compound. The formula of the double-photon fluorine ion fluorescent probe compound is as shown in formula I. The preparation method includes: allowing 2, 4-dihydroxy benzaldehyde and cyclohexenone to react under nitrogen protection by using imidazole as the catalyst; allowing the product obtained by separation to react with tert-butyldimethylsilyl chloride to obtain the pure fluorine ion fluorescent probe compound. The fluorine ion fluorescent probe compound has the advantages that the probe compound has good selectivity and sensitivity to fluorine ions and is nontoxic to cells; probe molecules can be stimulated by double photons to avoid an ultraviolet region, so that the probe molecules are applicable to detection of the fluorine ions in water and detection and imaging of the fluorine ions in cells.

Description

technical field [0001] The invention relates to a fluoride ion fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Fluorine is a non-metallic element and an essential trace element for the human body. A small amount of fluorine can replace phosphorus to build teeth and make them stronger. Drinking water and toothpaste contain appropriate amounts of fluoride ions that can effectively prevent dental caries. Too much fluorine in the human body Too much fluoride can lead to dental fluorosis and bone disease, and too little fluoride in the human body can lead to osteoporosis and dental caries. Therefore, the qualitative and quantitative detection of fluoride ion is of great significance. [0003] Due to its advantages of high sensitivity, good selectivity, and fast response, fluorescent probe detection has attracted the attention of researchers in recent years. The excitation wavel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/188C09K11/06C09K2211/1088G01N21/6428G01N21/6486
Inventor 吕正亮史孝民范春华
Owner UNIV OF JINAN
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