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A novel fluorescent probe with an asymmetric semicyanine structure and its preparation method and application

A fluorescent probe and semicyanine technology, applied in the field of fluorescent probes, can solve the problems of poor biocompatibility of dyes and susceptibility to biological internal environmental factors, etc.

Inactive Publication Date: 2020-06-05
刘东雨
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its structure also has certain limitations, such as the fluorescence emission wavelength region is easily affected by biological internal environmental factors, and the biocompatibility of dyes is poor.

Method used

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  • A novel fluorescent probe with an asymmetric semicyanine structure and its preparation method and application
  • A novel fluorescent probe with an asymmetric semicyanine structure and its preparation method and application
  • A novel fluorescent probe with an asymmetric semicyanine structure and its preparation method and application

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Embodiment 1

[0030] (1) Synthesis of compound 1

[0031] 4-Dimethylaminoacetophenone (1.63 g, 0.1 mol) and Fisher’s aldehyde (2.01 g, 0.1 mol) were added to 10 mL of toluene, and then sodium hydroxide (0.4 g, 0.1 mol) was added to the reaction solution ), install a water separator, and heat to reflux for 12 hours. The solvent was evaporated, and silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) was separated to obtain compound 1 (bright orange solid 2.52 g, yield 73%). 1 H NMR (300 MHz, Methanol- d 4 ) δ 8.21 (t, J = 13.3 Hz, 1H), 7.93 (d, J = 9.0 Hz, 2H), 7.30 -7.17 (m, 2H), 7.02-6.82 (m, 3H), 6.82-6.66 (m, 2H), 5.78 (d, J = 12.8 Hz, 1H), 3.29 (s, 3H), 3.08 (s, 6H), 1.64 (s, 6H).

[0032] (2) Synthesis of compound 2

[0033] Compound 1 (1.73 g, 0.05 mol) was dissolved in 20 mL of dichloromethane, 0.3 mL of triethylamine was added, and the temperature was controlled in an ice-water bath to 0˚C. Under nitrogen protection, acryloyl chloride (8.13 mL, 0.1 mol) dissolved...

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Abstract

The invention discloses a novel fluorescent probe with an asymmetrical hemicyanine structure as well as a preparation method and application thereof. The structural formula of the novel fluorescent probe with the asymmetrical hemicyanine structure is shown in the description. A novel fluorescent compound with a hemicyanine-4-dimethylaminobenzene structure is designed based on a hemicyanine and substituted aniline structure, and preparation of the compound is realized by a simple and efficient chemical method. The compound designed by the invention is a near-infrared fluorescent probe with a novel structure. The compound has high water solubility, the excitation wavelength is 475nm, the fluorescence emission of the probe at 549nm is only enhanced by Cys (the fluorescence strength is increased by about 78 times); under the same condition, when Hcy and GSH are added separately, the probe almost has no fluorescent emission at 547nm. The compound can be taken as a novel fluorescent probe for selectively detecting Cys.

Description

Technical field [0001] The invention belongs to the technical field of fluorescent probes, and specifically relates to a preparation method of a compound with an asymmetric hemicyanine structure and its application as a cysteine-responsive fluorescent probe. Background technique [0002] Fluorescent molecular probe technology has many advantages such as convenient operation, no damage to samples, high selectivity, high sensitivity, and the ability to realize in-situ and visual detection of biological samples. At present, analysis methods based on fluorescent probe technology have been widely used in important fields such as analytical chemistry, environmental detection, biological imaging, and disease diagnosis. [0003] Biological thiols, such as cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH), participate in a variety of biochemical processes in the organism, especially in maintaining the redox state of the biological internal environment Play a key role. Abnormal ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C09B23/14G01N21/64
CPCC09B23/145C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 刘东雨张宏牛林强王佳敏闫志杰门玉辉王建红
Owner 刘东雨