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Copper ion fluorescence probe and synthetic method thereof

A fluorescent probe, copper ion technology, applied in the field of analytical chemistry, can solve the problems of large fluorescence influence, cytotoxicity, difficult to accurately measure metal ions, etc., and achieve the effect of good application prospect and low toxicity

Inactive Publication Date: 2014-07-30
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these probes have low stability in vivo, their fluorescence is greatly affected by the environment, and they have certain cytotoxicity, making it difficult to accurately measure metal ions in cells.

Method used

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  • Copper ion fluorescence probe and synthetic method thereof
  • Copper ion fluorescence probe and synthetic method thereof
  • Copper ion fluorescence probe and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add CH 2 Cl 2 100ml, react at 40°C for 4h; then add boron trifluoride (BF 3 ) 0.58ml (0.46mmol), react at 40°C for 6h; then add bis(2-pyridylmethyl)amine (83mg, 0.45mmol), triethylamine (378mg, 0.45mmol), nitrogen protection, 80°C oil bath reflux for 8h ; After the reaction, use 3 × 30ml saturated sodium chloride solution to extract and wash, use 3 × 30ml dichloromethane to extract the aqueous phase, combine the organic phases, dry over anhydrous sodium sulfate, and rotary evaporate the solvent to obtain a brown oil; Silica gel column Chromatographic separation, eluting with ethyl acetate, gave dark red viscous solid 8-[bis(2-pyridylmethyl)amine-3-benzyl]-4,4-difluoro-1,3,5, 7-tetramethyl-4-boron-3a,4a-dipyrrole (BODIPY-DPA) 75mg, yield 73%. Molecular formula C 32 h 32 BF 2 N 5 Elemental analysis measured value C, 71.81; H, 6.03; N, 13.06, theoretical value C, 71.78; H, 6.02; N, 13.08%; 1 HNMR (400MHz, CDCl 3 )δ H 8.54(2H,d),7.68(2H,t),7.54(3H,d),7.45(2H,d),7....

Embodiment 2

[0033] Add CH 2 Cl 2 200ml, react at 40°C for 8h; then add boron trifluoride (BF 3 ) 0.58ml (0.46mmol), react at 40°C for 6h; then add bis(2-pyridylmethyl)amine (83mg, 0.45mmol), triethylamine (378mg, 0.45mmol), nitrogen protection, 80°C oil bath reflux for 8h ; After the reaction, use 3 × 30ml saturated sodium chloride solution to extract and wash, use 3 × 30ml dichloromethane to extract the aqueous phase, combine the organic phases, dry over anhydrous sodium sulfate, and rotary evaporate the solvent to obtain a brown oil; Silica gel column Chromatographic separation, eluting with ethyl acetate, gave dark red viscous solid 8-[bis(2-pyridylmethyl)amine-3-benzyl]-4,4-difluoro-1,3,5, 7-Tetramethyl-4-boron-3a,4a-dipyrrole (BODIPY-DPA) 21mg, yield 22%.

Embodiment 3

[0035] Add CH 2 Cl 2 100ml, react at 40°C for 4h; then add boron trifluoride (BF 3 ) 0.58ml (0.46mmol), react at 40°C for 6h; then add bis(2-pyridylmethyl)amine (83mg, 0.45mmol), triethylamine (378mg, 0.45mmol), nitrogen protection, 80°C oil bath reflux for 8h ; After the reaction, use 3 × 30ml saturated sodium chloride solution to extract and wash, use 3 × 30ml dichloromethane to extract the aqueous phase, combine the organic phases, dry over anhydrous sodium sulfate, and rotary evaporate the solvent to obtain a brown oil; Silica gel column Chromatographic separation, eluting with ethyl acetate, gave dark red viscous solid 8-[bis(2-pyridylmethyl)amine-3-benzyl]-4,4-difluoro-1,3,5, 7-Tetramethyl-4-boron-3a,4a-dipyrrole (BODIPY-DPA) 34mg, yield 33%.

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Abstract

The invention belongs to the technical field of analysis chemistry and relates to a copper ion fluorescence probe and a synthetic method of the copper ion fluorescence probe. The copper ion fluorescence probe disclosed by the invention has a chemical name of 8-[di(2-picolyl)amine-3-benzyl]-4, 4-difluoro-1,3,5,7-tetramethyl-4-boron-3a, 4a-dipyrrole (called BODIPY-DPA for short). The synthetic method of the copper ion fluorescence probe comprises the steps of: mixing 2, 4-dimethylpyrrole with 3-chloromethyl benzoyl chloride, then adding CH2Cl2 into the mixture, then adding boron trifluoride for reaction, and then orderly adding di(2-picoly)amine and triethylamine for reaction, at last, obtaining the copper ion fluorescence probe. The BODIPY-DPA shows light yellow in the solution, has high fluorescence emission at 590 nm, can enter HepG-2 to show green fluorescence imaging, and has a lowest limit of detection of 2.78 muM on copper ions in water solution. The copper ion fluorescence probe prepared by the synthetic method is characterized in low toxicity and the inhibition rate of 100 muM of HepG-2 is smaller than 10%, so the copper ion fluorescence probe can be used for detection of living cell imaging and copper irons in the cell, and has a very good application prospect in environment monitoring and detection of copper irons in a biologic system.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a copper ion fluorescent probe and a synthesis method thereof. Background technique [0002] In recent years, the use of artificially synthesized probes to selectively sense and recognize important ions in the environment and in biological systems, especially heavy metal ions, has attracted great interest. Copper ions are widely used in industrial production, and it acts as a cocatalytic factor in human enzymes such as superoxide dismutase, cytochrome C oxidase, and tyrosinase. Although it plays an important role in organisms, excessive accumulation of copper ions and abnormal metabolism can lead to a series of diseases, such as Alzheimer's disease, Parkinson's disease, cardiovascular disease, etc. Therefore, it is particularly important to detect copper ions easily and rapidly in the environment and in biological systems. [0003] Currently rhodamine series and fluo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 陈秋云李赞
Owner JIANGSU UNIV
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