Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof

A fluorescent probe and sulfite technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of long reaction time and limited application, and achieve high detection sensitivity, high selectivity, and easy identification Effect

Inactive Publication Date: 2017-05-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are few fluorescent probes for the ratiometric detection of sulfite, and most of the reported probes are based on the nucleophilic reaction to aldehyde groups. These probes often require a long reaction time, which greatly limits their potential. application

Method used

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  • Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof
  • Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof
  • Novel ratio type sulfite fluorescent probe as well as preparation method and biological application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of Compound 1

[0037] React m-N-diethylaminophenol (0.50g, 3.03mmol) with phthalic anhydride (0.49g, 3.33mmol) in 180mL of toluene at 110°C for 24 hours to obtain a white solid, then add the white solid to 20mL containing 6ml of propane in 98wt% concentrated sulfuric acid was reacted at 50°C for 3 hours, and the solid was recrystallized from ethanol to obtain compound 1 (0.22g, 0.45mmol).

[0038] The synthetic route is as follows:

[0039]

Embodiment 2

[0041] Preparation of a New Fluorescent Probe for Detecting Sulfite

[0042] The reaction scheme is as follows:

[0043]

[0044] The preparation process comprises steps as follows:

[0045] Compound 1 (0.377g, 1.0mmol) prepared in Example 1 was reacted with 4-dimethylaminobenzaldehyde (0.178g, 1.2mmol) in 20ml of acetic acid at 110°C for 5h to obtain a dark solution, which was removed by rotary distillation. Solvent, the solid was dissolved in dichloromethane, and separated by column chromatography with a mixed solvent of dichloromethane and methanol to obtain the target compound CS-NMe; yield: 50%. 1 HNMR(400MHz,MeOD)δ8.05(d,J=15.5Hz,2H),8.00–7.91(m,2H),7.63(d,J=8.9Hz,5H),7.60–7.54(m,4H), 7.39(d,J=9.4Hz,2H),7.37–7.31(m,2H),7.08(d,J=2.9Hz,3H),7.05(d,J=2.4Hz,1H),7.01(d,J =2.3Hz, 2H), 6.94(d, J=15.5Hz, 2H), 6.74(d, J=9.0Hz, 4H), 3.62(q, J=7.2Hz, 9H), 3.07(s, 12H), 1.27(d,J=7.1Hz,14H). 13 C NMR(101MHz,MeOD)δ166.57,162.66,158.37,154.69,153.53,146.02,134.19,131.86,129.81,1...

Embodiment 3

[0047] The preparation method of sulfite fluorescent probe as described in embodiment 2, difference is:

[0048] The amount of 4-dimethylaminobenzaldehyde was 3 mmol, acetic acid was replaced by acetic anhydride, the amount of acid was 20 mL, the reaction temperature was 60° C., and the reaction time was 12 h.

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Abstract

The invention discloses a novel ratio type sulfite fluorescent probe as well as a preparation method and biological application thereof. The structural formula of the probe is shown as a formula in the description. The probe has very high fluorescent light; after the probe is added into water or an organic solvent, an obtained solution is blue; after the probe acts with sulfite, the color of the solution is gradually faded and the color of the solution becomes green fluorescent. A synthesis process of the probe is simple and the yield of a prepared product is high. The novel ratio type sulfite fluorescent probe can be applied to a water body system, an organic solvent system or a biological system, and the sulfite is detected in a manner of enhancing and weakening fluorescent light of two wave bands and obviously changing the color; the novel ratio type sulfite fluorescent probe is high in selectivity and high in sensitivity.

Description

technical field [0001] The invention relates to a novel fluorescent probe for detecting sulfite, its preparation method and biological application. The probe is a ratio type and has a high degree of recognition for sulfite, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] SO 2 It is not only a major air pollutant, but also closely related to the health of animals and humans. SO 2 In organisms, it mainly exists in the form of sulfite and bisulfite. A small amount of SO in the air 2 It can promote the opening of the stomata of plant leaves to increase the photosynthesis rate of plants. Studies have shown that SO in the air 2 When the concentration is too high, it will significantly affect the growth of plants and even reduce crop yield. Sulfite is also a widely used food preservative, and it can also be produced in the human body through the metabolism of sulfur-containing amino acids. Although studies have shown that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58C09K11/06G01N21/64
CPCC07D311/58C09K11/06C09K2211/1007C09K2211/1088G01N21/6428G01N21/6486
Inventor 林伟英刘克印尚慧明
Owner UNIV OF JINAN
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