Photosensitive compound, preparation method and application thereof, and photosensitive protein immobilized gel containing photosensitive compound

Abstract

The invention discloses a photosensitive compound, a preparation method and application thereof, and photosensitive protein immobilized gel containing the photosensitive compound, wherein the structural formula of the photosensitive compound is shown as a formula (I), and R is an electron withdrawing group. The preparation method of the photosensitive compound comprises the following steps: dissolving N-(3-aminopropyl) methacrylate hydrochloride in an organic solvent, adding an electron withdrawing group-containing tetrazole compound and triethylamine into the organic solvent, carrying out a stirring reflux reaction for 10-20 h, and carrying out purification treatment to obtain the photosensitive compound. According to the invention, the photosensitive compound takes a tetrazole ring as aphotosensitive group, and the photosensitive protein immobilized gel comprises the compound as a photosensitive component; and a protein separation function and a protein immobilization function are integrated, protein can be immobilized in situ and stably in the gel, the gel is more powerful and efficient, and protein loss caused by elution is not likely to happen.

Description

technical field

[0001] The invention relates to the technical field of chemistry and biology, in particular to a photosensitive compound, its preparation method and application, and a photosensitive protein immobilized gel containing it. Background technique

[0002] In the field of tumor research, tumor cells are highly heterogeneous, and targeted cancer therapy needs to provide quantitative and highly specific target protein detection at the single-cell resolution level. The study of cell heterogeneity can provide rich and key genetic expression information for individualized treatment, and lay the foundation for the formulation of treatment plans and the selection and development of targeted drugs. In the field of stem cell research, the study of gene expression differences in different cells will help to deepen the understanding of genetic development and the regulation of gene expression in different tissues and cells. Protein is the material basis of life, an organic ...

Examples

Embodiment 1

[0060] According to the molar ratio of 1:11:200, weigh methyl-1 hydrogen-pyrrole, iodobenzene diacetate, and trifluoroethanol, first dissolve methyl-1 hydrogen-pyrrole in trifluoroethanol, and then Add iodobenzene diacetate and stir for 3h under nitrogen protection. The stirred mixture was concentrated to a black oil which was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed in a molar ratio of 3:1:13 were added thereto; stirred at room temperature for 24 h under nitrogen protection. The obtained substance was washed with saturated ammonium chloride and brine respectively, then dried with anhydrous magnesium sulfate, finally filtered, and further purified by silica gel chromatography (eluent: PE:EA=8:1) to obtain a brown oily intermediate Product, its structural formula is shown in following formula (1).

[0061]

[0062] Wherein, the yield rate of the above preparation method is 9.6%. Su...

Embodiment 2

[0070] A photosensitive compound whose structural formula is shown in the following formula (4) is prepared.

[0071]

[0072] Weigh pyrrole, iodobenzene diacetate and trifluoroethanol according to the molar ratio of 1:10:170, first dissolve pyrrole in trifluoroethanol, then add iodobenzene diacetate at –40°C, and stir for 3 h under nitrogen protection. The stirred mixture was concentrated to a black oil which was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed according to the molar ratio of 4:1:15 were added thereto; stirred at room temperature for 24 h under nitrogen protection. The obtained substance was washed with saturated ammonium chloride and brine respectively, dried with anhydrous magnesium sulfate, filtered, and further purified by silica gel chromatography (eluent: PE:EA=7:1) to obtain a brown oily intermediate product.

[0073] Weigh the intermediate product and lithium hydr...

Embodiment 3

[0076] A photosensitive compound whose structural formula is shown in the following formula (5) is prepared.

[0077]

[0078] Weigh thiophene, iodobenzene diacetate and trifluoroethanol according to the molar ratio of 1:12:150, first dissolve thiophene in trifluoroethanol, then add iodobenzene diacetate at –40°C, and stir for 4 h under nitrogen protection. After the stirred mixture was concentrated to a black oil, it was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed according to the molar ratio of 5:1:16 were added thereto; stirred at room temperature for 27 h under nitrogen protection. The obtained material was washed with saturated ammonium chloride, dried over anhydrous magnesium sulfate, finally filtered, and further purified by silica gel chromatography (eluent: PE:EA=6:1) to obtain a brown oily intermediate product.

[0079] Weigh the intermediate product and lithium hydroxide accor...

technical field

[0001] The invention relates to the technical field of chemistry and biology, in particular to a photosensitive compound, its preparation method and application, and a photosensitive protein immobilized gel containing it. Background technique

[0002] In the field of tumor research, tumor cells are highly heterogeneous, and targeted cancer therapy needs to provide quantitative and highly specific target protein detection at the single-cell resolution level. The study of cell heterogeneity can provide rich and key genetic expression information for individualized treatment, and lay the foundation for the formulation of treatment plans and the selection and development of targeted drugs. In the field of stem cell research, the study of gene expression differences in different cells will help to deepen the understanding of genetic development and the regulation of gene expression in different tissues and cells. Protein is the material basis of life, an organic ...

Examples

Embodiment 1

[0060] According to the molar ratio of 1:11:200, weigh methyl-1 hydrogen-pyrrole, iodobenzene diacetate, and trifluoroethanol, first dissolve methyl-1 hydrogen-pyrrole in trifluoroethanol, and then Add iodobenzene diacetate and stir for 3h under nitrogen protection. The stirred mixture was concentrated to a black oil which was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed in a molar ratio of 3:1:13 were added thereto; stirred at room temperature for 24 h under nitrogen protection. The obtained substance was washed with saturated ammonium chloride and brine respectively, then dried with anhydrous magnesium sulfate, finally filtered, and further purified by silica gel chromatography (eluent: PE:EA=8:1) to obtain a brown oily intermediate Product, its structural formula is shown in following formula (1).

[0061]

[0062] Wherein, the yield rate of the above preparation method is 9.6%. Su...

Embodiment 2

[0070] A photosensitive compound whose structural formula is shown in the following formula (4) is prepared.

[0071]

[0072] Weigh pyrrole, iodobenzene diacetate and trifluoroethanol according to the molar ratio of 1:10:170, first dissolve pyrrole in trifluoroethanol, then add iodobenzene diacetate at –40°C, and stir for 3 h under nitrogen protection. The stirred mixture was concentrated to a black oil which was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed according to the molar ratio of 4:1:15 were added thereto; stirred at room temperature for 24 h under nitrogen protection. The obtained substance was washed with saturated ammonium chloride and brine respectively, dried with anhydrous magnesium sulfate, filtered, and further purified by silica gel chromatography (eluent: PE:EA=7:1) to obtain a brown oily intermediate product.

[0073] Weigh the intermediate product and lithium hydr...

Embodiment 3

[0076] A photosensitive compound whose structural formula is shown in the following formula (5) is prepared.

[0077]

[0078] Weigh thiophene, iodobenzene diacetate and trifluoroethanol according to the molar ratio of 1:12:150, first dissolve thiophene in trifluoroethanol, then add iodobenzene diacetate at –40°C, and stir for 4 h under nitrogen protection. After the stirred mixture was concentrated to a black oil, it was dissolved in dichloromethane. Then, 5-ethyl tetrazolium carboxylate, copper (II) trifluoromethanesulfonate and triethylamine weighed according to the molar ratio of 5:1:16 were added thereto; stirred at room temperature for 27 h under nitrogen protection. The obtained material was washed with saturated ammonium chloride, dried over anhydrous magnesium sulfate, finally filtered, and further purified by silica gel chromatography (eluent: PE:EA=6:1) to obtain a brown oily intermediate product.

[0079] Weigh the intermediate product and lithium hydroxide accor...

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