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A dual-functional near-infrared fluorescent molecular probe for detecting hypochlorous acid and its preparation method

A fluorescent molecular probe, a technology for detecting hypochlorous acid, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of photoinstability, photobleaching performance, etc., achieve omission of pretreatment process, good selectivity , significant effect

Inactive Publication Date: 2015-09-30
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although several cyanine dyes have been reported in the literature for the detection of hypochlorous acid, hydrogen peroxide, and enzymes, their research and application have been limited due to the photoinstability or photobleaching properties of the cyanine dyes themselves. sex

Method used

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  • A dual-functional near-infrared fluorescent molecular probe for detecting hypochlorous acid and its preparation method
  • A dual-functional near-infrared fluorescent molecular probe for detecting hypochlorous acid and its preparation method
  • A dual-functional near-infrared fluorescent molecular probe for detecting hypochlorous acid and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: fluorescent probe CyN(CH 2 R 1 )(CH 2 R 2 ) (R 1 =2-furyl, R 2 =2-pyridyl) preparation

[0047] Add 6ml of ethyl acetate to a 25ml single-necked round-bottomed flask, then add 2-aminopicoline (270mg, 2.5mmol) and furfural (200mg, 2.0mmol) in turn, and react at room temperature to obtain a brown solution, continue at room temperature Stir for 10 hours, remove the solvent ethyl acetate by rotary evaporation to obtain a brown substance which is the intermediate, add 5mL of anhydrous methanol to the obtained intermediate to dissolve, add sodium borohydride (150mg, 4.0mmol) under ice-water bath conditions, room temperature 2.5 hours under stirring, then add 10mL of saturated brine to quench the reaction, the aqueous phase was extracted 3 times with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed to obtain a brown oily crude product; 150 mg of the crude product was dissolved in In 10mL of ...

Embodiment 2

[0052] Embodiment 2: fluorescent probe CyN(CH 2 R 1 )(CH 2 R 2 ) (R 1 =2-furyl, R 2 = phenyl) for the preparation of

[0053] Add 6ml of ethyl acetate to a 25ml single-necked round-bottom flask, then add benzylamine (268mg, 2.5mmol) and furfural (200mg, 2.0mmol) successively, react at room temperature to obtain a brown solution, continue to stir at room temperature for 10 Hours, the solvent ethyl acetate was removed by rotary evaporation to obtain a brown substance which was an intermediate, and 5 mL of anhydrous methanol was added to the obtained intermediate to dissolve, and sodium borohydride (150 mg, 4.0 mmol) was added under ice-water bath conditions, and stirred at room temperature for 2.5 hour, then add 10mL of saturated brine to quench the reaction, the aqueous phase was extracted 3 times with dichloromethane, the organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was removed to obtain a brown oily crude product; 150 mg of the crude p...

Embodiment 3

[0056] Embodiment 3: fluorescent probe CyN(CH 2 R 1 )(CH 2 R 2 ) (R 1 =5-methyl-2-furyl, R 2 =2-pyridyl) preparation

[0057] Add 6ml of ethyl acetate to a 25ml single-necked round-bottom flask, then add 2-aminopicoline (270mg, 2.5mmol) and 5-methylfurfural (220mg, 2.0mmol) in sequence, and react at room temperature to obtain a brown solution , continue to stir at room temperature for 10 hours, remove the solvent ethyl acetate by rotary evaporation to obtain a brown substance which is the intermediate, add 5 mL of anhydrous methanol to the obtained intermediate to dissolve, add sodium borohydride (150 mg, 4.0 mmol), stirred at room temperature for 2.5 hours, then added 10 mL of saturated brine to quench the reaction, the aqueous phase was extracted 3 times with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed to obtain a brown oily crude product; 150mg of the crude product was dissolved in 10mL of anhydro...

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Abstract

The invention discloses a difunctional near-infrared fluorescence molecular probe for detecting hypochlorous acid and a preparation method for the same. The difunctional near-infrared fluorescence molecular probe has the structure general formula defined in the specification, wherein R1 and R2 independently represent 2-pyridyl, 2-furyl, substituted 2-pyridyl, substituted 2-furyl, aryl or substituted aryl respectively; R3 is selected from methyl, ethyl or propyl; and X- is selected from Cl-, Br- or I-. The changes of the fluorescence intensity and the colour of the probe are caused due to the breakage of the double bonds of the fluorescence probe at the end of a chain under the oxidation of hypochlorous acid, so that the fluorescence probe can be used for visual detection for hypochlorous acid in an aqueous solution, and is suitable for detection for hypochlorous acid generated by enzymatic reaction in the condition of a physiological environment simultaneously, and a detection line can achieve 0.70mu mol / L. The method disclosed by the invention has the advantages of being capable of detecting hypochlorous acid with a fast speed and high selectivity, suitable for bioimaging, and the like.

Description

1. Technical field [0001] The invention relates to an analysis and detection method of hypochlorous acid, specifically a method for visually detecting hypochlorous acid in water and hypochlorous acid produced under the catalysis of active enzymes in a physiological environment based on a near-infrared fluorescent molecular probe. 2. Background technology [0002] Hypochlorous acid or hypochlorite is widely used in our daily life as a bleach, disinfectant and anti-infective agent. At the same time, hypochlorous acid, as an important active oxygen molecule, participates in a large number of physiological activities, such as the immune defense in the body and the occurrence and development of inflammation. In organisms, hypochlorous acid is generated through the oxidation of hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase. It is very necessary and important to keep the content of hypochlorous acid in the organism within a certain range. The lack or ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
Inventor 王素华孙明泰
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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