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A kind of pH-sensitive ratio type semicyanine-rhodamine dye and preparation method thereof

A semi-cyanine, ratio-type technology, applied in the direction of organic dyes, styrene-based dyes, chemical instruments and methods, etc., can solve the problems of inaccuracy, low quantum yield, insensitive detection of fluorescent dyes, etc., and achieve high yield , the synthesis method is simple, the effect of good application prospect

Active Publication Date: 2022-05-17
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a pH-sensitive ratiometric hemicyanine-rhodamine dye (Hcy-Rh) and a preparation method thereof, to solve the problems of insensitive and inaccurate detection of traditional fluorescent dyes, and lower quantum yields.

Method used

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  • A kind of pH-sensitive ratio type semicyanine-rhodamine dye and preparation method thereof
  • A kind of pH-sensitive ratio type semicyanine-rhodamine dye and preparation method thereof
  • A kind of pH-sensitive ratio type semicyanine-rhodamine dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of pH sensitive ratio dyes

[0030] (1) Weigh 2.0 g of 1,1,2-trimethylbenzo[e]indole into a 100 ml flask, and add 30 ml of dry acetonitrile. After being dissolved, 3.73 g of 6-bromohexanoic acid was added, and the mixture was reacted at 80° C. under reflux for 36 hours. After the reaction was completed, it was cooled to room temperature, and most of the acetonitrile was removed under reduced pressure distillation. The product was dropped into anhydrous ether, and a gray-blue solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain the pure product 3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo[e]indole (compound 1), Yield 88%.

[0031] (2) Weigh 1 g of 3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo[e]indole in step (1) and dissolve it in 30 ml of absolute ethanol, After dissolving, add 0.41 g of p-hydroxybenzaldehyde, then add 2-3 drops of piperidine dropwise, and heat to reflux for 18 hou...

Embodiment 2

[0035] Embodiment 2 configures the Britton-Robinson-Ethanol (BRE) buffer solution of different pH values

[0036] (1) Weigh 1.96 grams of phosphoric acid, 1.2 grams of acetic acid, and 1.24 grams of boric acid and dissolve them in 250 milliliters of double-distilled water and 250 milliliters of ethanol to obtain a mixed solution of the three acids.

[0037] (2) After the pH three composite electrodes are calibrated, adjust the three-acid mixed solution prepared in step (1) with 1.0M NaOH solution or 1.0M HCl solution to obtain BRE buffer solutions with different pH values.

Embodiment 3

[0038] Example 3 Test the UV absorption and fluorescence emission spectra of the dye molecules in the BRE buffer at different pH values

[0039] (1) Configure a 1.0mM dye stock solution, add 10 microliters of the stock solution to the quartz cuvette, use BRE buffers of different pH to make the dye concentration 20µM, and then use a UV-visible spectrophotometer to test 320- UV absorption spectrum under different pH conditions in the range of 650nm, such as figure 1 shown.

[0040] (2) After adding 10 microliters of the stock solution of the dye prepared in step (1) to the quartz cuvette, the concentration of the dye is 20 μM after constant volume with BRE buffer solution of different pH, and then tested with a fluorescence spectrometer at 390 Fluorescence emission spectra under different pH conditions in the range of -700nm, the excitation wavelength of the fluorescence spectrum is 380nm, and the emission wavelengths are 450nm and 580nm, such as figure 2 shown.

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Abstract

The invention discloses a pH-sensitive ratio-type hemicyanine-rhodamine dye (Hcy-Rh) and a preparation method thereof, belonging to the field of organic dye synthesis. The prepared hemicyanine-rhodamine dye has a brown-red solid appearance. It has good photostability, high fluorescence quantum yield, wide detection pH range and high sensitivity, low cytotoxicity, and is beneficial to cell imaging analysis. The pH-sensitive ratiometric dye prepared by the present invention can avoid being affected by microenvironmental factors such as the change of the concentration of the detected substance, the intensity of the excitation light, and photobleaching through the change of the ratio fluorescence, and has the advantage of high accuracy. It provides a good application prospect.

Description

technical field [0001] The invention relates to a pH-sensitive ratiometric dye, which belongs to the field of organic dye synthesis, in particular to a pH-sensitive ratiometric hemicyanine-rhodamine dye (Hcy-Rh) and a preparation method thereof. Background technique [0002] As one of the important parameters of metabolism in organisms, pH is closely related to physiological processes such as cell growth, proliferation, metabolism and apoptosis. Under normal physiological conditions, different regions of the cell have different pH fluctuation ranges. For example, the pH in the lysosome is about 4.5-5.0, the pH in the Golgi apparatus is about 6.0-6.7, and the pH in the cytoplasm is 6.8-7.2, which is slightly alkaline. The mitochondrial matrix is ​​around 8.0. Abnormal pH in cells can cause many diseases, such as cancer, neurodegenerative diseases, osteoporosis, etc. Therefore, accurate and sensitive monitoring of intracellular pH changes is of great significance for underst...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09B23/14C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09B23/145G01N21/6456G01N21/6428G01N2021/6439Y02E10/542
Inventor 王琦白庆庆杨超杰杨马骏吴丽冀海伟周晓波李国吴铭敏
Owner NANTONG UNIVERSITY
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