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Fluorescence molecular probe and application thereof in hydrogen sulfide detection

A technology of fluorescent molecular probes and hydrogen sulfide, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of reducing the molecular performance of fluorescent probes

Active Publication Date: 2014-06-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Detection in these media will greatly degrade the performance of fluorescent probe molecules

Method used

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  • Fluorescence molecular probe and application thereof in hydrogen sulfide detection
  • Fluorescence molecular probe and application thereof in hydrogen sulfide detection
  • Fluorescence molecular probe and application thereof in hydrogen sulfide detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] (1) Synthesis of AIE active tetraphenylethylene azide derivatives:

[0047] Weigh diphenylmethane (5.5g, 32.8mmol) into a 500mL double-necked round-bottomed flask, place it in a liquid nitrogen acetone bath, evacuate nitrogen for three times, add 100mL freshly distilled tetrahydrofuran to dissolve, and slowly drop n-butyllithium ( 18.75mL, 30mmol), 4-bromobenzophenone (7.8g, 30mmol) was dissolved in an appropriate amount of freshly distilled tetrahydrofuran, added to the reaction system, and the system returned to room temperature overnight. The reaction was terminated with saturated ammonium chloride, and the crude product of intermediate 9 obtained after extraction was dissolved in an appropriate amount of toluene, 500 mg of p-toluenesulfonic acid was added, and refluxed overnight. The solvent was spin-dried, and the crude product obtained after extraction and washing was separated and purified by silica gel column chromatography (petroleum ether as eluent) to obtain ...

Embodiment 2

[0068] (1) The synthesis of tetraphenylethylene azide and aminotetraphenylethylene is the same as in Example 1

[0069] (2) Tetraphenylethylene azide qualitatively detects the presence of hydrogen sulfide as in Example 1

[0070] (3) The specificity and anti-interference identification of the detection of hydrogen sulfide by tetraphenylethylene azide in the aggregated state are the same as in Example 1.

[0071] (4) Quantitative detection of hydrogen sulfide in aggregated state with different concentrations of tetraphenylethylene azide.

[0072] The quantitative detection process of hydrogen sulfide is as follows: prepare 2×10 -4 M tetraphenylethylene azide dimethyl sulfoxide solution, take 1mL and add it to a 10mL volumetric flask, then take 1mL dimethyl sulfoxide and add it to the volumetric flask, use a pipette to draw different volumes of 2×10 -2 Add the NaHS aqueous solution of M into the volumetric flask, adjust the pH to 7.4 with the HEPES buffer solution to set the v...

Embodiment 3

[0074] (1) The synthesis of tetraphenylethylene azide and aminotetraphenylethylene is the same as in Example 1

[0075] (2) Tetraphenylethylene azide qualitatively detects the presence of hydrogen sulfide as in Example 1

[0076] (3) The specificity and anti-interference identification of tetraphenylethylene azide in the aggregation state for the detection of hydrogen sulfide in this example are the same as those in Example 1.

[0077] (4) Quantitative detection of hydrogen sulfide in the aggregated state of tetraphenylethylene azide.

[0078] The quantitative detection process of hydrogen sulfide is as follows: prepare 5×10 -4 M tetraphenylethylene azide dimethyl sulfoxide solution, take 1mL and add it to a 10mL volumetric flask, then take 1mL dimethyl sulfoxide and add it to the volumetric flask, and use a pipette to draw different volumes of 5×10 -2 Add the NaHS aqueous solution of M into the volumetric flask, adjust the pH to 7.4 with the HEPES buffer solution to set the...

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Abstract

The invention discloses a fluorescence molecular probe and application thereof in hydrogen sulfide detection. The structure of the fluorescence molecular probe is R1-N3, wherein R1 is a gene with aggregated and induced luminescence property. The principle is as follows: the molecule containing a nitrine functional group does not shine in a solution or an aggregation state due to the quenching effect of nitrine while the molecule containing amino generated after reduction of the nitrine functional group by using hydrogen sulfide displays the characteristics of an adaptive image enhancer (AIE). Thus, detection of the hydrogen sulfide concentration in the aggregation state is achieved. The principle is as follows: the fluorescence quenching of the overall aggregation is caused by azide groups left in the aggregation state. Therefore, luminescence of the probe molecule just can be opened after most of azide groups are reduced. Thus, the detection limit and the effective detection range are regulated and controlled by regulating and controlling the concentration of the probe molecule.

Description

technical field [0001] The invention relates to the fields of chemical detection and biological detection, in particular to a novel fluorescent molecular probe and its application in hydrogen sulfide detection. Background technique [0002] Hydrogen sulfide (H 2 S) As an endogenous gas signal molecule, it participates in many physiological processes in organisms and is related to many diseases. Hydrogen sulfide is involved in numerous physiological processes, including vasodilation, angiogenesis, oxygen sensing, apoptosis, tissue inflammation, neuromodulatory processes, and trauma and ischemic protection. At the same time, the level of hydrogen sulfide in the human body may indicate the existence of some diseases in the human body, including Alzheimer's disease, Down's syndrome, diabetes and liver cirrhosis. However, the role and mechanism of hydrogen sulfide in living organisms are still inconclusive, so it is particularly important to detect and determine the concentrati...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64C07D241/12C07C247/16C07F7/10
Inventor 蔡云波秦安军唐本忠孙景志
Owner ZHEJIANG UNIV
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