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Use of BODIPY analog fluorescent reagent in biological large molecule marking

A biomacromolecule and fluorescent reagent technology, applied in the field of biomacromolecule labeling, achieves the effects of simple fluorescent labeling reaction, stable label product properties, and improved detection sensitivity

Inactive Publication Date: 2011-05-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no BODIPY-type fluorescent labeling reagent with epoxy ring as the active reactive group, which is applied to the fluorescent labeling of macromolecular substances such as proteins

Method used

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  • Use of BODIPY analog fluorescent reagent in biological large molecule marking
  • Use of BODIPY analog fluorescent reagent in biological large molecule marking
  • Use of BODIPY analog fluorescent reagent in biological large molecule marking

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) The specific steps of the synthesis and labeling method of the fluorescent reagent TMEPBODIPY are as follows:

[0035] (1) First, 2,4-dimethylpyrrole and p-hydroxybenzaldehyde are used as raw materials to generate hydroxyl BODIPY (1,3,5,7-tetramethyl-8-phenyl-(4-hydroxyl)-difluoro Boronide-dipyrromethane). Add 200 mg of p-hydroxybenzaldehyde, 115 mg of 2,4-dimethylpyrrole and 1 mg of trifluoroacetic acid (Lewis acid) into a 500 mL round-bottomed flask containing 100 mL of dichloromethane. Electromagnetic stirring at 40°C for 10-12h. After the reaction is complete, evaporate the solvent to dryness, dissolve the residue in toluene, add 110 mg of chlorobenzoquinone, stir and react at room temperature for 2 hours, the solution turns dark brown, then add 242 mg of triethylamine and stir for 5 minutes, and immediately add 0.5 mL of boron trifluoride (including 263 mg of boron trifluoride) ether solution (47%, w / w), stirred and reacted at room temperature for 25-35 minut...

Embodiment 2

[0055] In the general formula [1], R represents the preparation method of the compound represented by the aryl group with an epoxy group,

[0056] The preparation of such compounds can be carried out by using aryl formaldehyde compounds (such as: p-hydroxybenzaldehyde) and 2,4-dimethylpyrrole under heating in a nitrogen water bath, using tetrachlorobenzoquinone as a dehydrogenating agent, and using triethyl Amine reaction terminator, finally add the ether solution of boron trifluoride to complete the complexation reaction.

[0057] The reaction formula is as follows:

[0058]

[0059] In the formula, R2 represents an aryl group.

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Abstract

The invention relates to a mark of biology macromolecule, in particular to an application of BODIPY fluorescence agent in the mark of biology macromolecule, wherein the agent is composed of a 1, 3, 5, 7-4-methyl-boron fluoride-2-pyrrolylmethane skeleton, and a replace group with an active epoxy group which can be combined with the object material, and the structure is as the formula [1] while R is the aryl, heterocyclic radical or hydrocarbon radical with epoxy radicals. The invention uses the active epoxy group in the mother molecule of BODIPY, to realize the fluorescence mark on the proteinin buffer solution, which can be used the fluorescence mark agent before column or electrophoresis to be used in high-effect liquid spectrum, plate electrophoresis (SDS-PAGE), capillary electrophoresis, or the like to separate and check the biological macromolecule.

Description

technical field [0001] The invention relates to the labeling of biological macromolecules, in particular to the application of a BODIPY fluorescent reagent in the labeling of biological macromolecules. Background technique [0002] Existing fluorescent dyes for labeling proteins such as: fluorescein isothiocyanate (FITC), 4-fluoro-7-nitrobenzoxadiazole (NBD-F), 3-furoylquinoline-2-carbonyl Aldehydes (FQ), dansyl chloride, fluorescamine, and o-phthalaldehyde (OPA). Although these reagents can also perform fluorescent labeling on proteins, most of the labeling reactions lack selectivity, and too many labeling sites cause a large change in the molecular weight of the protein, which brings difficulties to the separation and characterization of the protein. In addition, some fluorescent reagents are very sensitive to the pH value of the solution, such as fluorescein isothiocyanate (FITC), and some fluorescent reagent labeling reactions need to be protected from light, such as da...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N33/52G01N21/00C07F5/02
Inventor 张玉奎张琳张维冰张丽华乔晓强
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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