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Cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye and preparation method thereof

A cytoplasmic protein and fluorescent dye technology, which is applied in the field of synthesis and preparation of cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dyes, can solve the problems of poor stability and secondary processability, achieve enhanced fluorescence intensity, realize detection and Imaging, improve the effect of the output signal

Inactive Publication Date: 2019-11-15
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the anthocyanin dyes reported in the literature are poor in stability and secondary processing, which poses a great challenge to the detection of targets under complex environmental conditions in cells and in vivo

Method used

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  • Cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye and preparation method thereof
  • Cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye and preparation method thereof
  • Cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of n=0 anthocyanin fluorescent dye (PAF-1).

[0027] The specific synthetic route of the described class of cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye PAF is as follows

[0028] The synthesis route of the n=0 cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye is as follows:

[0029]

[0030] Weigh 9-formaldehyde-8-hydroxyjulolidine (217 mg, 1 mmol) and 5-methoxy-1-indanone (162 mg, 1 mmol), dissolve in 2 mL methanesulfonic acid, and Under the protection of nitrogen, react in an oil bath at 90°C for 6 hours to obtain a reaction solution. After the reactant is cooled to room temperature, slowly add the reactant dropwise to 100 g of ice water, and keep stirring. At the same time, add 1 mL of perchloric acid and stir well. , the bottom of the dye ice-water mixture was formed and there was a large amount of precipitation, extracted 4-5 times with dichloromethane-methanol (volume ratio: 25:1) mixture, 30...

Embodiment 2

[0031] Example 2: Synthesis of anthocyanin-like fluorescent dyes (PAF-2, PAF-3, PAF-4, PAF-5) with n=1.

[0032]

[0033] Weigh the reactant reactant 1 as 4-(diethylamino) salicylaldehyde (R1 is nitrogen nitrogen diethylamino) (193 mg, 1 mmol), and reactant 6-(methylamino)-3, 4,-Dihydro-1-naphthalenone (compound 1) (175 mg, 1 mmol) was dissolved in 2 mL of methanesulfonic acid, and reacted for 6 hours under nitrogen protection, 90°C oil bath to obtain a reaction solution, which was then The reaction solution was cooled to room temperature, and the reactant was slowly added dropwise to 100 g of ice water, and kept stirring, and at the same time, 1 mL of perchloric acid was added dropwise, and the stirring was sufficient, and a large amount of precipitation was formed at the bottom of the dye ice water mixture, and dichloromethane- Methanol (volume ratio (10-30): 1) was extracted 4-5 times from the mixed solution, 30 mL each time, the extract was dried with anhydrous sodium s...

Embodiment 3

[0035] Example 3: Histogram of fluorescence intensity ratios of dyes in cell lysates and buffers of different cells.

[0036]Take 495 uL of PBS buffer (10 mM, pH=7.2) and add 5 uL of different PAF dyes respectively, and use a fluorescence spectrophotometer to detect the fluorescence intensity of different dyes. Then the buffer solution was replaced with the cell lysate of HepG-2, Hela, and MCF-7 cells respectively, and the fluorescence intensity of different dyes in the cell lysate was measured under the same conditions, and the fluorescence intensity value of the dye in the cell lysate was Compared with the fluorescence intensity value in PBS buffer, get as image 3 The histogram shown.

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Abstract

The invention discloses cytoplasmic protein-assisted enhanced anthocyanin-like fluorescent dye and a preparation method thereof. The main structure of the dye is shown in the description, wherein R1 and R2 are different substituent groups, and a value of n is 0 or 1. The dye provided by the invention has an excitation wavelength and emission wavelength of 550 nm or more and stable optical performance, and the fluorescence intensity value of the dye is significantly enhanced in the presence of a cytoplasmic protein; the dye and method provided by the invention have the following technical effects: the synthetic method of the dye is simple, raw materials are easy to obtain, the yield is high, and products are easy to separate and purify; at the same time, the structure of the dye is simple and stable, the dye is easily used for design of a probe, and detection of low-abundance targets in cells and living bodies by the probe can be effectively realized by utilizing the advantage that fluorescence of the dye is significantly enhanced in the presence of the cytoplasmic protein; and the dye has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of fluorescent organic dyes and applications, in particular to a method for synthesizing and preparing anthocyanin-like fluorescent dyes assisted by cytoplasmic proteins. Background technique [0002] At present, there are many kinds of organic fluorescent dyes, such as common coumarins, fluoresceins, rhodamines, cyanines, anthocyanins, fluorobodipyrroles, squaraines, etc. Most of the dyes are based on the combination of dyes and fluorescence imaging technology, so they have a wide range of applications in many fields such as chemistry, biology, material science, and clinical medicine. However, when most of the current dyes are applied to cell and in vivo imaging, the fluorescence intensity of the dye is easily interfered by the autofluorescence in vivo, so it is necessary to develop a fluorescent dye with a longer wavelength; at the same time, the fluorescence of the dye The intensity is also easily partia...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/16C09B57/00G01N21/64
CPCC09K11/06C07D491/16C09B57/00G01N21/6428C09K2211/1088C09K2211/1029
Inventor 杨盛杨荣华文锡旦
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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