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BODIPY derivative BDO-N3 and synthetic method and usage thereof

A BDP-N3, fluoroboron dipyrrole technology is applied in the field of fluoroboron dipyrrole derivatives to achieve the effects of obvious detection signal, convenient operation and high sensitivity

Active Publication Date: 2018-11-06
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While methods for measuring bulk macroscopic viscosity are well developed, imaging local microviscosity remains a challenge

Method used

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  • BODIPY derivative BDO-N3 and synthetic method and usage thereof
  • BODIPY derivative BDO-N3 and synthetic method and usage thereof
  • BODIPY derivative BDO-N3 and synthetic method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] BDP-N 3 Preparation and Characterization of

[0038] 1) Stir 4-pyridinecarbaldehyde (9.0mmol, 0.96g) and 2,4-dimethylpyrrole (19.4mmol, 1.85g) in deoxymethylene chloride (150ml). A drop of trifluoroacetic acid was added and the mixture was stirred at room temperature under argon. The combined solution was treated with dichlorodicyanobenzoquinone (9.0 mmol, 2.04 g), stirring was continued for 4 hours, then triethylamine (15 mL) was added. Add BF after 15 minutes 3 ·Et 2O (15 mL), and the mixture was stirred at room temperature for 3 hours, and after washing with saturated sodium bicarbonate solution, the organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was subjected to silica gel column chromatography (CH 2 Cl 2 / petroleum ether, 1 / 1, V / V, eluting) purification, obtain desired compound 1 as red powder (0.35g, 12%);

[0039] 2) Compound 1 (0.06 mmol, 0.02 g) and 1-azido-4-(bromomethyl)benzene (0.6 mmol, 0.10 g...

Embodiment 2

[0042] In a cuvette, add 2 mL of DMSO, 0.5 μM BDP-N 3 DMSO solution, add hydrogen sulfide solution in volumes of 0, 4, 8, 12, 16, 20, 24, and 28 μL respectively, and measure the fluorescence intensity at 515 nm on a fluorescence spectrometer after 15 minutes as 125.8, 213.7, 342.1, 438.2, 579.4, 714.3, 837.6, 967.9, the fluorescence intensity gradually increased. Fluorescence emission diagram see Figure 4 .

Embodiment 3

[0044] Prepare a PBS buffer solution with a pH=7.4 and a concentration of 10mM, prepare 2mM BDP-N 3 DMSO solution, prepare 0.2M hydrogen sulfide aqueous solution; in the fluorescence cuvette, add 2mL of DMSO and 0.5μM BDP-N 3 DMSO solution, and then add 10 times the equivalent of other analytes and hydrogen sulfide: SO 3 2- ,S 2 o 3 2- ,SCN - ,PO 4 3- ,NO 3 - ,NO 2 - , HSO 3 - , HCO 3 - , AcIO - ,F - , Cl - ,Br - , I - ,,CO 3 2- ,SCN - , SO 4 2- ,ClO - , Cys, GSH, and the aqueous solution of Hcy are detected on a fluorescence spectrophotometer, and the fluorescence intensity histogram at 515nm corresponding to different analytes is drawn (see Figure 5 ). Hydrogen sulfide makes the fluorescence intensity of the detection system increase significantly at 515nm, and other analytes basically do not cause changes in the fluorescence intensity of the detection system.

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Abstract

The invention provides a BODIPY derivative BDO-N3 and a synthetic method and the usage thereof. The English name of the derivative is 1-(4-azidobenzy1)-4-(5,5-difluoro-1,3,7,9-tetramethy1-5H-4lambda<4>,5lambda<4>-dipyrrolo[1,2-c:2',1'-f][1,3,2]diaz aborinin-10-y1)pyridin-1-ium. The invention further provides a method for detecting hydrogen sulfide through specificity of being sensitive to viscosity, and in DMSO (dimethyl sulfoxide), the content of hydrogen sulfide is detected through a fluorospectrophotometer. In addition, in a methanol and glycerol system, with the increase of viscosity, BDP-N3 is used for detecting viscosity change through the fluorospectrophotometer. The detecting is simple in process, sensitive and quick, and the detecting results are accurate.

Description

technical field [0001] The present invention relates to fluoroboron dipyrrole derivatives, in particular to a fluoroboron dipyrrole derivative BDP-N 3 and its synthesis method, and BDP-N 3 Application in detection of hydrogen sulfide and viscosity. Background technique [0002] Studies have shown that hydrogen sulfide is related to various physiological and pathological functions. As a third gaseous signaling molecule, hydrogen sulfide is considered a bioactive gas that modulates the immune, endocrine, cardiovascular, nervous, and gastrointestinal systems. In general, in most mammalian tissues and organisms, hydrogen sulfide can be passed through at least some specific enzymes such as cystathionine γ-lyase (CSE), cystathionine β-synthase (CBS) and 3 - Mercaptopyruvate sulfur transferase (MST)) endogenous metabolism. Abnormally low or high levels of endogenous hydrogen sulfide can lead to serious diseases such as diabetes, Alzheimer's disease, Down's syndrome, liver cirrh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C07F5/02
CPCC07F5/022G01N21/6486
Inventor 阴彩霞赵琪霍方俊
Owner SHANXI UNIV
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