Cationic fluorescent probe for dansyl biimidazole derivatives as well as synthesis method and application of cationic fluorescent probe

A technology of bisimidazole dansyl derivatives and diethylenetriamine dansyl derivatives, which is applied in the field of fluorescent probes and their synthesis, can solve the problems of large errors, long analysis time, and low sensitivity, and achieve low detection Limit detection, good chemical stability, and fast response

Inactive Publication Date: 2014-11-19
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the chemical method consumes a lot of reagents and the measurement cycle is long
Spectrophotometry is easy to operate and takes a short time, but it has large errors and cumbersome calculations
Chromatographic instruments are complex, expensive, single-purpose, long analysis time (currently reduced to about 1 hour), destroy the inherent structure of amino acids, and relatively low sensitivity

Method used

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  • Cationic fluorescent probe for dansyl biimidazole derivatives as well as synthesis method and application of cationic fluorescent probe
  • Cationic fluorescent probe for dansyl biimidazole derivatives as well as synthesis method and application of cationic fluorescent probe
  • Cationic fluorescent probe for dansyl biimidazole derivatives as well as synthesis method and application of cationic fluorescent probe

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0035] 1. Synthesis of diethylenetriamine protected by tert-butoxycarbonyl groups at both ends

[0036] Add 1mL (9.3mmol) diethylenetriamine, 4.0mL (22mmol) tert-butylphenyl carbonate, 0.3mL (2.2mmol) ) triethylamine (TEA), stirred for 12 hours under nitrogen protection and ice-bath conditions, the reaction solution was poured into 1L0.025mol / L K 2 HPO 4 and 0.025mol / L NaH 2 PO 4 In the buffer solution, use 2mol / L H 2 SO 4Adjust the pH of the solution to 3, then extract with ether, take the water layer, adjust the pH of the water layer to 10 with 9mol / L NaOH aqueous solution, extract three times with dichloromethane, take the dichloromethane layer, wash with anhydrous sodium sulfate Drying, dichloromethane is distilled off by rotary evaporation to obtain the diethylenetriamine protected by tert-butoxycarbonyl groups at both ends shown in formula I. The reaction equation is as follows:

[0037]

[0038] 2. Synthesis of diethylenetriamine dansyl derivatives protected by...

Embodiment 2

[0051] In step 2 of the synthesis of diethylenetriamine dansyl derivatives protected by both ends of the tert-butoxycarbonyl group in Example 1, 2.0 g (7 mmol) of dansyl chloride and 3.4 mL (24.5 mmol) of triethylamine were added to a container containing In a three-necked flask of 70 mL of chloroform, stir and dissolve, then add 2.1 g (7 mmol) of diethylenetriamine protected by tert-butoxycarbonyl groups at both ends, and stir for 12 hours under nitrogen protection and normal temperature conditions. Other steps are the same as in Example 1. Similarly, a cationic fluorescent probe of the bis-imidazole dansyl derivative was obtained with a yield of 38%.

Embodiment 3

[0053] In the step 4 of the synthesis of diethylenetriamine dansyl derivatives with brominated ends in Example 1, 0.25g (0.7mmol) of diethylenetriamine dansyl derivatives with amino groups at both ends and 0.4mL (18mmol) three Ethylamine was added to a three-necked flask containing 50 mL of chloroform, stirred and dissolved, and 0.176 mL (1.75 mmol) of bromoacetyl bromide and 12 mL of chloroform were placed in a constant-pressure dropping funnel, under nitrogen protection and ice bath conditions. Add it dropwise into a three-necked flask and stir for 48 hours. Other steps are the same as in Example 1 to obtain a cationic fluorescent probe of bis-imidazolyl dansyl derivative with a yield of 59%.

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Abstract

The invention discloses a cationic fluorescent probe for dansyl biimidazole derivatives as well as a synthesis method and application of the cationic fluorescent probe. The cationic fluorescent probe has the structural formula as shown in the specification. The synthesis method comprises the steps of with dansyl which is high in fluorescence quantum yield and extremely sensitive to a microenviroment as a signal output group, protecting two ends of diethylenetriamine to introduce dansyl; then, deprotectnig two ends of diethylenetriamine, and reacting diethylenetriamine with bromoacetyl bromide; and finally, enabling the reaction product to be covalently bound with N-methylimidazole to synthesize the cationic fluorescent probe for the dansyl biimidazole derivatives. The cationic fluorescent probe is good in chemical stability, capable of realizing real-time and online measurement of amino acid, rapid in response to aspartic acid or glutamic acid, high in sensitivity, wide in response range and capable of detecting amino acid with high selectivity, high sensitivity and low detection limit, wherein the detection limits can respectively reach 1.6 micromoles/liter and 6.0 micromoles/liter.

Description

technical field [0001] The invention belongs to the technical field of amino acid detection, and in particular relates to a fluorescent probe for determining amino acid in water, a synthesis method and a detection method thereof. Background technique [0002] Amino acid is the basic unit of biological functional macromolecular protein, which is of great significance to biochemistry and the whole life science research as well as product development, quality control and production management. Therefore, amino acid analysis is one of the very important technologies in industry, medicine, agricultural production, food processing and life science research. Among them, aspartic acid promotes the tricarboxylic acid cycle through deamination to generate oxaloacetate, and is closely related to the ornithine cycle, and is responsible for part of the work of converting ammonia in the blood into urea for excretion. At the same time, aspartic acid is also a raw material for the synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56C09K11/06G01N21/64
CPCC07D233/56C09K11/06C09K2211/1044G01N21/64
Inventor 丁立平曹建华王世怀胡雯婷薛思琪陈霄
Owner SHAANXI NORMAL UNIV
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