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Rhodamine fluorescent probe sensitive to pH change, synthetic method and application

A fluorescent probe and synthesis method technology, applied in the field of rhodamine fluorescent probes, can solve problems such as changing the water solubility of rhodamine, unfavorable pH monitoring, etc., and achieve the effects of avoiding autofluorescence interference, reducing light damage, and good water solubility

Inactive Publication Date: 2012-09-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these structural modifications change the water solubility of rhodamine, making it unsuitable for monitoring the pH of living biological samples

Method used

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  • Rhodamine fluorescent probe sensitive to pH change, synthetic method and application
  • Rhodamine fluorescent probe sensitive to pH change, synthetic method and application
  • Rhodamine fluorescent probe sensitive to pH change, synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] a. Dissolve dibromofluorescein in anhydrous toluene, add four times the amount of N-methylpiperazine, 20% palladium acetate, 20% BINAP, heat and reflux for 20 hours, evaporate the reaction solution to dryness under reduced pressure, and column Separate the target product, productive rate 60%, HRMS (M + ) 496.25

[0023] b. Dissolve the internal salt product obtained above in methanol, add 2 times the amount of concentrated hydrochloric acid dropwise and stir for 1 h, spin the methanol to dryness and purify to obtain a purple solid.

example 2

[0025]

[0026] c. Dissolve the product Example 1 in methanol, dropwise add 2 times the amount of thionyl chloride to raise the temperature and reflux for reaction, cool down and spin the methanol to dry and purify to obtain a purple powder solid. Yield 90%, HRMS(M + ) 511.2703

example 3

[0028]

[0029] Replace methyl alcohol with ethanol in c operation, all the other are with example 2. Yield 90%, HRMS (M + )525.2860

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PUM

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Abstract

The invention relates to a class of rhodamine fluorescent probe sensitive to pH change. The fluorescent probe has the following structural general formula, the molecules of the fluorescent probe have a simple synthetic process and better chemical and light stability, fluorescence is sensitive to pH change, and the fluorescent probe has different protein kinase A (pKa) values by introducing different amine groups. Meanwhile, the rhodamine fluorescent probe sensitive to the pH change has very good water solubility and biological compatibility and higher fluorescent quantum yield and has the function of cellular localization. Meanwhile, the pH value of a cellular microenvironment can be detected.

Description

technical field [0001] The invention relates to a class of rhodamine fluorescent probes sensitive to pH changes. Background technique [0002] Rhodamine is a class of fluorescent molecules widely used in biosensing and material science. Due to its large molar absorptivity, high fluorescence quantum yield, and long absorption and emission wavelengths, it is widely used as Laser dyes, biolabeling reagents, and designing fluorescence-enhanced probes. Rhodamine exists in the form of a colorless rocyclic lactone and a purple zwitterion, usually in the form of a deep red zwitterion in acutely protic solvents. Many of the metal ion probes designed in the form of rhodamine lactim respond to metal ions through the fluorescence of rhodamine ring opening and the non-fluorescence of ring closing. [0003] Compared with fluorescein, rhodamine has better photostability and wider spectral tunable range (500-680 nm). Although rhodamine has better photophysical and photochemical properties...

Claims

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Application Information

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IPC IPC(8): C07D311/80C09K11/06G01N21/64
CPCC09B11/24G01N21/643G01N21/80G01N2021/6439
Inventor 肖义郭海英
Owner DALIAN UNIV OF TECH
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