Sulfhydryl group ion fuorescence probe and synthesis method thereof

A fluorescent probe and hydrogen sulfide technology, applied in the field of analytical chemistry, can solve the problems of processing a large number of biological tissue samples, expensive testing instruments, etc., and achieve the effect of low toxicity and rapid response

Inactive Publication Date: 2013-04-03
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional detection methods usually require a large number of biological tis

Method used

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  • Sulfhydryl group ion fuorescence probe and synthesis method thereof
  • Sulfhydryl group ion fuorescence probe and synthesis method thereof
  • Sulfhydryl group ion fuorescence probe and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0029]The compound DOBIPY-DPA (53.5mg, 0.1mmol) was mixed with CuCl 2 (13.5mg, 0.1mmol) were mixed at a molar ratio of 1:1, dissolved in methanol solution (30mL), and reacted at room temperature for 30min to obtain the compound dichloride [8-bis(2-pyridylmethyl)amine-3-benzyl Base-4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole]copper (abbreviated as DOBIPY-DPA-Cu). Yield 96%. ES-MS (CH 3 OH): m / z 633.42(100)[(DOBIPT-DPA-Cu)-Cl - ] + .

Embodiment 2

[0031] Compound DOBIPY-DPA (53.5mg, 0.1mmol) and CuCl 2 (6.8mg, 0.05mmol) were mixed at a molar ratio of 2:1, dissolved in methanol solution (60mL), and reacted at room temperature for 60min to obtain the compound dichloride [8-bis(2-pyridylmethyl)amine-3-benzyl Base-4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole]copper (abbreviated as DOBIPY-DPA-Cu). Yield, 60%.

Embodiment 3

[0033] Compound DOBIPY-DPA (53.5mg, 0.1mmol) and CuCl 2 (27mg, 0.2mmol) were mixed at a molar ratio of 1:2, dissolved in methanol solution (60mL), and reacted at room temperature for 5min to obtain the compound dichloride [8-bis(2-pyridylmethyl)amine-3-benzyl -4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole]copper (abbreviated as DOBIPY-DPA-Cu). Yield, 50%.

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Abstract

The invention belongs to the field of analytic chemistry technologies and relates to a sulfhydryl group ion fuorescence probe and a synthesis method thereof. The chemical name of the sulfhydryl group ion fuorescence probe is [8-di(2-picolyl)amine-3-benzyl-4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole] copperdichloride (BODIPY-DPA-Cu for short). The synthesis method of the sulfhydryl group ion fuorescence probe comprises the following steps: mixing 8-[di(2-(2-picolyl)amine-3-benzyl]-4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-dipyrrole] (BODIPY-DPA for short) with CuCl2 (copper chloride) to be dissolved in methanol; and reacting for 5-60 minutes at room temperature, thereby obtaining the sulfhydryl group ion fuorescence probe. The sulfhydryl group ion fuorescence probe can respond HS- in a buffering solution and living cell with a phenomenon of green fluorescence recovery, and has the characteristic of low toxicity; the inhibition ratio of 100 mu M HepG-2 is less than 10%; a living cell imaging experiment shows that the BODIPY-DPA-Cu system can detect the HS- in the HepG-2 cell, the detection limit reaches 1.12 mu M, so the sulfhydryl group ion fuorescence probe is an extremely sensitive detection system and can be used for the detection of the HS- in a living body and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to a fluorescent probe of sulfhydryl ion and a synthesis method thereof. Background technique [0002] Hydrogen sulfide is regarded as the third signaling molecule after nitric oxide and carbon monoxide. It is reported that the content of endogenous hydrogen sulfide in human blood is 10-100 μM. Endogenous hydrogen sulfide is involved in many aspects of physiological processes , such as soothing vascular smooth muscle, regulating neurotransmission, inhibiting insulin signaling, regulating inflammation in the body, and oxygen release. Considering the high diffusivity and activity of hydrogen sulfide, hydrogen sulfide mainly exists in the form of HS ions under physiological conditions. [0003] Many tests have been developed in recent years to detect immediate onset of HS - , such as colorimetric methods, electrochemical methods, chromatographic methods, etc. Qi JS, Cao K...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F1/08G01N21/64
Inventor 陈秋云李赞
Owner JIANGSU UNIV
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