Cysteine detection reagent and preparation method thereof

A detection reagent, cysteine ​​technology, applied in the fields of chemical synthesis and biological analysis and detection, can solve the problems of complex preparation, difficult to meet commercial application requirements, and low sensitivity of detection reagents, and achieve the effect of high sensitivity

Active Publication Date: 2016-06-15
SHENZHEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a cysteine ​​detection reagent and its preparation method, aiming at solving the problems of low sensitivity, complicated preparation, obvious biological toxicity and difficulty in the detection of existing detection reagents. The problem of meeting the requirements of commercial application

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  • Cysteine detection reagent and preparation method thereof
  • Cysteine detection reagent and preparation method thereof
  • Cysteine detection reagent and preparation method thereof

Examples

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Effect test

Embodiment 1

[0038] Synthesis of FL-Cys-1: Add 10 mmoles of hydroxyacetophenone and 10 mmoles of 2-formylthiophene to 20 ml of ethanol, then dropwise add 20 ml of 30% potassium hydroxide solution , stirred at room temperature for 10 hours after the dropwise addition; after stirring, the reaction solution was cooled, and 15 milliliters of hydrogen peroxide solution with a mass fraction of 30% was slowly added dropwise, stirred at room temperature for 24 hours, and neutralized with dilute hydrochloric acid with a concentration of 1 mol / liter. After the precipitate was filtered and dried, it was recrystallized in ethanol to obtain an intermediate product; then 5 mmoles of the intermediate was added to 10 ml of dry dichloromethane, 1 ml of triethylamine was added, and 3 ml of it was slowly added dropwise in an ice-water bath Acryloyl chloride, after reacting for half an hour, continue to react at room temperature for 4 hours, add 20 ml of saturated aqueous solution of sodium carbonate, extract ...

Embodiment 2

[0040] Synthesis of FL-Cys-2: Add 10 millimoles of 1-hydroxy-3,4-dichloroacetophenone and 10 millimoles of 2-formylthiophene to 20 milliliters of ethanol, then dropwise add 20 milliliters of 30% potassium hydroxide solution, after the dropwise addition, stir at room temperature for 10 hours; after stirring, cool the reaction solution, slowly add 15 ml of hydrogen peroxide solution with a mass fraction of 30%, stir at room temperature for 24 hours, and use a concentration of 1 mol / L neutralize the dilute hydrochloric acid, filter and dry the precipitate, and recrystallize in ethanol to obtain the intermediate product; then add 5 mmol of the intermediate to 10 ml of dry dichloromethane, add 2 ml of triethylamine, and Slowly add 2 ml of acryloyl chloride dropwise in the water bath, react for half an hour, continue to react at room temperature for 4 hours, add 20 ml of saturated aqueous solution of sodium carbonate, extract with dichloromethane, add anhydrous sodium sulfate to dry,...

Embodiment 3

[0042]Synthesis of FL-Cys-3: Add 10 millimoles of 1-hydroxy-4-hydroxymethylacetophenone and 10 millimoles of 2-formylthiophene to 20 milliliters of ethanol, then dropwise add 20 milliliters of 30% potassium hydroxide solution, stirred at room temperature for 10 hours after the dropwise addition; after stirring, the reaction solution was cooled, slowly added dropwise 15 ml of 30% hydrogen peroxide solution, stirred at room temperature for 24 hours, and diluted hydrochloric acid with a concentration of 1 mol / liter Neutralize, filter and dry the precipitate, recrystallize in ethanol to obtain the intermediate product; then add 5 mmoles of the intermediate to 10 ml of dry dichloromethane, add 1 ml of triethylamine, and slowly Add 2 ml of acryloyl chloride dropwise, react for half an hour, continue to react at room temperature for 12 hours, add 20 ml of saturated aqueous solution of sodium carbonate, extract with dichloromethane, add anhydrous sodium sulfate to dry, concentrate and ...

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Abstract

The invention discloses a cysteine detection reagent and a preparation method thereof. The cysteine detection reagent has the general structure as shown in the formula (please see the formula in the description), wherein R1 is H, Cl or OCH3, R2 is H, Cl or OCH3. The detection reagent does not have biological toxicity and is high in sensitivity to cysteine, cysteine can be selectively detected, fluorescent detection can be performed on cysteine in cells, and the cysteine detection reagent meets the commercialized application requirement.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and biological analysis and detection, in particular to a cysteine ​​detection reagent and a preparation method thereof. Background technique [0002] As one of the essential amino acids in the human body, cysteine ​​is one of more than 20 amino acids involved in protein synthesis. At the same time, cysteine, as an important thiol in organisms, can undergo reversible reduction reactions in cells and Plays a crucial role in the metabolism of toxicants. Therefore, maintaining a reasonable cysteine ​​concentration at the cellular level is one of the criteria for measuring the normal metabolism of living organisms. Low concentrations of cysteine ​​in the human body are often closely related to many diseases, such as decreased hematopoietic function, skin damage, and even cancer. [0003] Traditional cysteine ​​detection methods mainly include high performance liquid chromatography, capillary elect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C09K11/06G01N21/64
CPCC07D409/04C09K11/06C09K2211/1088C09K2211/1092G01N21/6486
Inventor 刘斌
Owner SHENZHEN UNIV
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