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Synthetic method of 8,8'-2- phenylamino-5,5'2-naphthyl-1,1'-2-sulphonate

A synthetic method, the technology of aniline, applied in the field of synthesis of protein fluorescent probes, can solve the problems of poor solubility and the like

Inactive Publication Date: 2011-04-20
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention utilizes the characteristics of ionic liquids, adopts several self-synthesized imidazolium cationic ionic liquids as solvents for the reaction, solves the problem of poor solubility of the reaction raw material 8-anilino-1-naphthalenesulfonate in common organic solvents, and improves bis-ANS yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-3

[0039] Provide the concrete implementation condition of embodiment 1-3 below:

[0040] In the first step, as mentioned above, in the synthesis of imidazolium cationic ionic liquid, the parameter conditions are respectively:

[0041] Alkyl imidazole and haloalkane are mixed in molar ratios of 1:1.0; 1:1.2; 1:1.5;

[0042] Alkyl imidazoles and haloalkanes are dissolved in 20; 25; 30 times the volume ratio of 1,1,1-trichloroethane;

[0043] The reaction stirring and reflux time are respectively 2; 2.5; 3 hours;

[0044] Reaction temperature 70°C; 75°C; 80°C.

[0045] Gained imidazolium cationic ionic liquid product is respectively:

[0046] 1. 1,3-dimethyl-imidazole iodide (MMIMI - ), 2, 1-ethyl-3-methylimidazole bromide (EMIMBr - ), 3, 1-propyl-3-methylimidazole bromide (PMIMBr - ), 4, 1-butyl-3-methylimidazole chloride (BMIMCl - ), 5, 1,3-diethylimidazole bromide (EEIMBr - ), 6, 1-propyl-3-ethylimidazole bromide (PEIMBr - ), 7, 1-butyl-3-ethylimidazole chloride (BEIMCl...

Embodiment 4

[0058] In the synthesis of 8,8'-di-phenylamino-5,5'-di-naphthyl-1,1'-di-sulfonate potassium, the prepared seven ionic liquids were mixed with acetone as the reaction solvent, Under other identical reaction conditions (0.2M sodium nitrite solution 8ml, 36% concentrated hydrochloric acid 10ml, reaction temperature 60 ℃, reaction time 2 hours), examine their respective productive rates respectively, the result is as follows.

[0059] 1. 1,3-dimethyl-imidazole iodide (MMIMI - )-yield 14.8%, 2, 1-ethyl-3-methylimidazole bromide (EMIMBr - )-yield 12.5%, 3, 1-propyl-3-methylimidazole bromide (PMIMBr - )-yield 9.6%, 4, 1-butyl-3-methylimidazole chloride (BMIMCl - )-yield 19.2%, 5, 1,3-diethylimidazole bromide (EEIMBr - )-yield 10.8%, 6, 1-propyl-3-ethylimidazole bromide (PEIMBr - )-yield 16.3%, 7, 1-butyl-3-ethylimidazole chloride (BEIMCl - ) - 23.4% yield.

Embodiment 5

[0061] In the synthesis of 8,8'-two-phenylamino-5,5'-two-naphthyl-1,1'-two-sulfonate potassium, in order to investigate the impact of the amount of sodium nitrite on the yield, according to the implementation The result of example 4, has selected the highest ionic liquid---7 chloride 1-butyl-3-ethyl imidazoles (BEIMCl - ) and acetone as mixed solvent, other reaction conditions are consistent with the description in embodiment 4, in the above case, investigated respectively the productive rate situation using 0.2M sodium nitrite solution under 8ml, 10ml, 15ml different consumptions is:

[0062] 0.2M sodium nitrite solution in 8ml-yield 23.1%, 0.2M sodium nitrite solution in 10ml-yield 26.0%, 0.2M sodium nitrite solution in 12ml-yield 25.7%.

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Abstract

The invention relates to a method to synthesize 8,8`-2-phenylamino-5,5`-2- naphthyl-1,1`2- sulfonate(bis-ANS) which is used as protein fluorescent probe in biological engineering field. The method takes alkyl-imidazole and alkyl halide as material and 1,1,1-trichloroethane as solvent; the phegma is stirred for reaction to get corresponding imidazole cation solution; after that 8-anilino-1-naphthalenesulfonic acid(ANS), as material, reacts with potassium hydroxide to produce 8-anilino-1-naphthalenesulfonic potassium; under the catalysis of hydrochloric acid and sodium nitrite, the imidazole cation solution is mixed with acetone to be used as solvent and the reaction begins under reflux temperature; after the reaction, the products are separated through silica gel column, obtaining 8,8`-2-phenylamino-5,5`-2- naphthyl-1,1`2- sulfonate(bis-ANS), with a yield up to 26%.

Description

technical field [0001] The invention relates to a method for synthesizing protein fluorescent probes in the technical field of bioengineering, in particular to a 8,8'-di-phenylamino-5,5'-di-naphthyl-1,1'-di-sulfonate salt synthesis method. Background technique [0002] Fluorescent probe technology is a highly sensitive analytical method for studying proteins in solution at the molecular weight level by using the photophysical and photochemical properties of substances. Fluorescent probes for protein molecules can be divided into fluorescent probes emitting in the ultraviolet-visible region and near-infrared fluorescent probes according to the fluorescence wavelength. [0003] 8-anilino-1-naphthalenesulfonate (ANS) has been the most widely used probe in the UV-vis region of protein molecules. Studies have shown that ANS is non-covalently bound to the protein at the 2DPG2 binding site in the central cavity of human hemoglobin. The fluorescence intensity is greatly enhanced,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/47C07C303/02B01J31/02
Inventor 刘文陆张健存傅磊彭英丹
Owner SHANGHAI JIAOTONG UNIV
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