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Fluorescent probe for identifying heme protein and application thereof

A technology of fluorescent probes and metalloproteins, applied in the field of fluorescent probes, can solve problems such as limited applications

Pending Publication Date: 2022-07-22
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods are often slow and require nonphysiological concentrations of proteins, which limits their utility for characterizing the dynamics and equilibrium of protein-membrane interactions

Method used

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  • Fluorescent probe for identifying heme protein and application thereof
  • Fluorescent probe for identifying heme protein and application thereof
  • Fluorescent probe for identifying heme protein and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: Synthesis of Fluorescent Probes for Identifying Heme Proteins

[0072] Pyrene (4 g, 19.77 mmol) and 3-chloropropionyl bromide (2.04 g, 11.86 mmol) were dissolved in 40 mL of anhydrous DCM, cooled to 10 °C under nitrogen, and AlCl was added in portions within 20 min 3 (2.64 g, 19.77 mmol). The reaction mixture was darkened. The reaction mixture was allowed to slowly reach room temperature. The reaction mixture was stirred overnight. Cool excess aluminum chloride with crushed ice. The resulting aqueous phase was saturated with solid sodium chloride. 100-200 mL of fresh DCM was added and the layers were separated. The organic phase was washed with saturated sodium chloride. The mixture was dried over magnesium sulfate. Filter and concentrate in vacuo. The crude product was purified by silica gel (petroleum ether-DCM=7:3) column chromatography to obtain compound 3-chloro-1-pyrenylacetone.

[0073] A solution of 3-chloro-1-pyrenylacetone (0.51 g, 1.58 mmo...

Embodiment 2

[0077] Example 2: Fluorescent Probe Synthesis Method for Identifying Heme Proteins

[0078] Pyrene (4 g, 19.77 mmol) and 3-chloropropionyl bromide (2.72 g, 15.82 mmol) were dissolved in 40 mL of anhydrous DCM, cooled to 10 °C under nitrogen, and AlCl was added in portions within 20 min 3 (5.28 g, 39.54 mmol). The reaction mixture was darkened. The reaction mixture was allowed to slowly reach room temperature. The reaction mixture was stirred overnight. Cool excess aluminum chloride with crushed ice. The resulting aqueous phase was saturated with solid sodium chloride. 100-200 mL of fresh DCM was added and the layers were separated. The organic phase was washed with saturated sodium chloride. The mixture was dried over magnesium sulfate. Filter and concentrate in vacuo. The crude product was purified by silica gel (petroleum ether-DCM=7:3) column chromatography to obtain compound 3-chloro-1-pyrenylacetone.

[0079] A solution of 3-chloro-1-pyrenylacetone (0.51 g, 1.58 ...

Embodiment 3

[0083] Example 3: Synthesis of Fluorescent Probes for Identifying Heme Proteins

[0084] Pyrene (4 g, 19.77 mmol) and 3-chloropropionyl bromide (2.38 g, 13.84 mmol) were dissolved in 40 mL of anhydrous DCM, cooled to 10 °C under nitrogen, and AlCl was added in portions within 20 min 3 (3.96 g, 29.66 mmol). The reaction mixture was darkened. The reaction mixture was allowed to slowly reach room temperature. The reaction mixture was stirred overnight. Cool excess aluminum chloride with crushed ice. The resulting aqueous phase was saturated with solid sodium chloride. 100-200 mL of fresh DCM was added and the layers were separated. The organic phase was washed with saturated sodium chloride. The mixture was dried over magnesium sulfate. Filter and concentrate in vacuo. The crude product was purified by silica gel (petroleum ether-DCM=7:3) column chromatography to obtain compound 3-chloro-1-pyrenylacetone.

[0085] A solution of 3-chloro-1-pyrenylacetone (0.51 g, 1.58 mmo...

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Abstract

The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe for identifying heme protein and application of the fluorescent probe. The invention provides a fluorescent probe with a chemical structure as shown in a formula (I), the fluorescent probe is simple, convenient and economical to synthesize and has a good heme protein recognition effect, rapid response is provided based on a fluorescence method, protein-membrane interaction is allowed to be studied under micromole protein concentration, and the fluorescent probe has a good application prospect. The method can be used for characterizing the interaction between the protein and the cell membrane under the condition of no dyeing, and is suitable for research on protein-membrane binding balance and dynamics.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe used for identifying heme proteins and applications thereof. Background technique [0002] Protein is one of the basic substances that constitute life and plays a vital role in the activities of living organisms. Heme protein is a metalloprotein with heme as a cofactor, and the heme cofactor is a complex composed of iron ion and protoporphyrin IX or its derivatives. Heme protein plays an important role in living organisms due to its characteristics as carrier, transport, regulation and catalysis. Myoglobin is a type of hemoglobin and is a typical oxygen carrier protein. It has the functions of storing oxygen and transporting molecular oxygen in biological systems. It can also directly react with reactive oxygen species (ROS) and play a protective role in physiology. Cytochrome c is involved in important biological functions such as electron transp...

Claims

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Application Information

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IPC IPC(8): C07D233/60C09K11/06G01N21/64
CPCC07D233/60C09K11/06G01N21/643G01N21/6428C09K2211/1011C09K2211/1044G01N2021/6439Y02A50/30
Inventor 龙双双林英武袁彬彬
Owner NANHUA UNIV
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