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Six-membered spiro rhodamine pH fluorescent indicator containing urea structure and application thereof

A fluorescent indicator, the technology of six-membered spiro, which is applied in the field of six-membered spirocyclic rhodamine pH fluorescent indicator to achieve the effects of high sensitivity, good acid-base reversibility and rapid response

Active Publication Date: 2019-10-15
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the expansion of the helical ring may also improve the sensitivity of the indicator

Method used

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  • Six-membered spiro rhodamine pH fluorescent indicator containing urea structure and application thereof
  • Six-membered spiro rhodamine pH fluorescent indicator containing urea structure and application thereof
  • Six-membered spiro rhodamine pH fluorescent indicator containing urea structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Six-membered spirocyclic rhodamine pH fluorescent indicator containing urea structure——Rh-NH1

[0031] The reaction formula is as follows:

[0032]

[0033] Mix 1 mole of rhodamine B with 3 moles of POCl 3 Add it into dry 1,2-dichloroethane, heat and reflux at 90°C for 3-5 hours, cool to room temperature, remove the solvent 1,2-dichloroethane, then add sodium azide in acetone aqueous solution ( Dissolve 0.5 mL of an aqueous solution containing 1.3 moles of sodium azide in 30 mL of acetone), stir at room temperature for 24 hours, extract the reaction solution with dichloromethane, take the lower layer, dry it with anhydrous magnesium sulfate, and evaporate it under reduced pressure After solvent, dissolve the reactant with dry acetonitrile and move it into the reaction kettle, add excess ammonia water, react in an oil bath at 100°C for 10 hours, extract the resulting reaction liquid with dichloromethane, take the lower layer, dry it with anhydrous magnesium...

Embodiment 2

[0035] Example 2 Six-membered spirocyclic rhodamine pH fluorescent indicator containing urea structure——Rh-NH2

[0036]

[0037] Mix 1 molar amount of Rhodamine 6G with 3 molar amounts of POCl 3 Add it into dry 1,2-dichloroethane, heat and reflux at 90°C for 3-5 hours, cool to room temperature, remove the solvent 1,2-dichloroethane, then add sodium azide in acetone aqueous solution ( Dissolve 0.5 mL of an aqueous solution containing 1.3 moles of sodium azide in 30 mL of acetone), stir at room temperature for 24 hours, extract the reaction solution with dichloromethane, take the lower layer, dry it with anhydrous magnesium sulfate, and evaporate it under reduced pressure After the solvent, the reactant was dissolved in dry acetonitrile and moved into a reaction kettle, and excess ammonia water was added, and reacted in an oil bath at 100°C for 10 hours. The resulting reaction liquid was extracted with dichloromethane, and the lower layer was taken and dried with anhydrous ma...

Embodiment 3

[0038] Example 3 Six-membered spirocyclic rhodamine pH fluorescent indicator containing urea structure——Rh-NH3

[0039]

[0040] Add 1 mole of tetramethylrhodamine TMR and 3 moles of POCl3 into dry 1,2-dichloroethane, heat and reflux at 90°C for 3-5 hours, cool to room temperature, remove the solvent 1,2 -Dichloroethane, then add the aqueous acetone solution of sodium azide (dissolve 0.5 mL of the aqueous solution containing 1.3 molar amounts of sodium azide in 30 mL of acetone), stir at room temperature for 24 hours, and extract the reaction solution with dichloromethane , remove the lower layer, dry with anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, dissolve the reactant with dry acetonitrile and move it into a reaction kettle, add excess ammonia water, and react in an oil bath at 100°C for 10 hours. The reaction solution was extracted with dichloromethane, and the lower layer was taken and dried over anhydrous magnesium sulfate. Purify by si...

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PUM

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Abstract

The invention relates to a six-membered spiro rhodamine pH fluorescent indicator containing a urea structure and application thereof. The fluorescent indicator has a structure as shown in a general formula (I). The preparation method comprises the following steps: 1) adding a rhodamine compound and phosphorus oxychloride into 1,2-dichloroethane, carrying out heating reflux reaction, cooling the product to room temperature, and removing the solvent; 2) adding an acetone aqueous solution of sodium azide, stirring the mixture at room temperature, extracting the reaction solution with dichloromethane, drying the extract, and performing pressure reduced evaporation to remove the solvent; 3) dissolving the obtained reaction solution with dry acetonitrile, transferring into a reaction kettle, adding excessive ammonia water, and carrying out reaction in oil bath at 100 DEG C for 10 hours; and 4) extracting the obtained product with dichloromethane, drying the extract, and purifying the extractthrough silica gel column chromatography to obtain the target product Rh-NH. The indicator provided by the invention has good pH reversibility. After the indicator disclosed by the invention is usedfor dyeing the daphnia magna, the indicator Rh-NH1 can be positioned in the intestinal tract of the daphnia magna and indicates the acidity of the daphnia magna.

Description

technical field [0001] The invention relates to a six-membered spirocyclic rhodamine pH fluorescent indicator containing a urea structure. Background technique [0002] Any chemical reaction or biological activity requires precise control of related parameters, and pH value is one of the key indicator parameters. Under normal physiological conditions, the H of the extracellular fluid + The concentration is about 40nmol / L (pH=7.40), and the normal fluctuation range is about 0.1-0.2 pH units. Abnormal pH values ​​will interfere with cell function. At the same time, some diseases can also induce pH fluctuations before the onset of disease, such as colorectal cancer, cystic fibrosis and other diseases will have abnormal pH. Fluctuations in pH may also occur during the attack of organisms by foreign pollutants. Compared with other methods of detecting pH such as glass electrode method, nuclear magnetic resonance method, absorption spectroscopy, etc., measuring pH with the help...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B57/00C07D491/107C07D491/22G01N21/64A61K49/00
CPCC09K11/06C09B57/00C07D491/107C07D491/22G01N21/6428A61K49/0021C09K2211/1044C09K2211/1088C09K2211/1029Y02A40/81
Inventor 于海波李雅慧宋怡红闵蕾张铭琰隋然朱晓慧
Owner LIAONING UNIVERSITY
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