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Ratiometric fluorescence probe for reversibly detecting sulfur dioxide/formaldehyde, preparation method and application thereof

A fluorescent probe, sulfur dioxide technology, applied in the field of fluorescent probes, can solve problems such as the lack of reversible ratio fluorescent probes, and achieve the effects of convenient qualitative analysis, high sensitivity and high selectivity

Active Publication Date: 2021-03-16
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, fluorescent probes with reversible ratios for sulfur dioxide / formaldehyde detection in living organisms are relatively lacking, and exploring a new type of highly efficient fluorescent probe for rapid detection of formaldehyde and sulfur dioxide in the environment and living cells is still a hot issue.

Method used

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  • Ratiometric fluorescence probe for reversibly detecting sulfur dioxide/formaldehyde, preparation method and application thereof
  • Ratiometric fluorescence probe for reversibly detecting sulfur dioxide/formaldehyde, preparation method and application thereof
  • Ratiometric fluorescence probe for reversibly detecting sulfur dioxide/formaldehyde, preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0057] Embodiment 1: the synthesis of formula (II) compound

[0058] The synthetic design route is as follows:

[0059]

Embodiment approach 1

[0060] Embodiment 1: 204 mg (1 mmol) (Ⅴ) compound of formula and 193 mg (1 mmol) 4-(diethylamino) salicylaldehyde were dissolved in 5 mL methanesulfonic acid, refluxed at 90°C for 6 hours, after the reaction was completed, cooled to room temperature, Pour into ice water, add 6mL of perchloric acid, and filter with suction to obtain a crude product; the crude product is further separated by a chromatographic column with dichloromethane as the eluent to obtain 258 mg of a blue product with a yield of 56%.

Embodiment approach 2

[0061] Embodiment 2: Dissolve 204 mg (1 mmol) of compound (Ⅴ) and 386 mg (2 mmol) of 4-(diethylamino) salicylaldehyde in 5 mL of methanesulfonic acid, and reflux at 90° C. for 6 h. After the reaction is complete, cool to room temperature, Pour into ice water, add 6mL of perchloric acid, and filter with suction to obtain a crude product; the crude product is further separated by a chromatographic column with dichloromethane as the eluent to obtain 295 mg of a blue product with a yield of 64%.

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Abstract

The invention relates to a ratiometric fluorescent probe for reversibly detecting sulfur dioxide / formaldehyde as well as a preparation method and an application thereof, and particularly relates to the ratiometric fluorescent probe which can be used for measuring, detecting or screening sulfur dioxide / formaldehyde and living cell fluorescence imaging, especially reversible colorimetric ratio detection of sulfur dioxide / formaldehyde. The probe can achieve at least one of the following technical effects: reversible detection of sulfur dioxide / formaldehyde, colorimetric ratio detection, high-selectivity recognition of sulfur dioxide / formaldehyde, rapid response to sulfur dioxide / formaldehyde, sensitive analysis of sulfur dioxide / formaldehyde, detection of sulfur dioxide / formaldehyde under physiological level conditions, and detection of sulfur dioxide / formaldehyde under physiological level conditions. The product has the advantages of simple synthesis and stable properties.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a fluorescent probe for reversible detection of sulfur dioxide / formaldehyde based on coumarin compounds and its application in measuring, detecting or screening sulfur dioxide / formaldehyde and live cell fluorescence imaging methods; the present invention Also provided are methods of preparing the fluorescent probes. Background technique [0002] In living systems, formaldehyde, as an active carbonyl substance, plays an important role in the process of maintaining carbon cycle metabolism. Formaldehyde is produced endogenously by demethylases and oxidases, such as lysine-specific demethylation enzymes, amino-sensitive amine oxidase, etc. The concentration level of formaldehyde in organisms is related to spatial memory and cognitive ability, however, the abnormal accumulation of formaldehyde may cause protein and DNA damage, and then lead to a variety of diseases, including Alzhei...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/6428G01N21/6456G01N21/6458G01N2021/6417C09K2211/1088
Inventor 蔡昕宇曲乐扬高娜彭艺媛王梦琪张雪柳彩云白健朱宝存
Owner UNIV OF JINAN
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