Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe

A glutathione and fluorescent probe technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as difficult to achieve specific detection of glutathione, and achieve easy promotion and application, excellent Responsive sensitivity, responsive effects

Inactive Publication Date: 2015-06-03
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, most of the reported glutathione probes are interfered by amino acids that also contain sulfhydryl groups in organisms, such as cysteine ​​(Cysteine, Cys) and homocysteine ​​(Homocysteine, Hcy) (see J. Bouffard, Y.Kim, T.M.Swager, etc., A Highly Selective Fluor

Method used

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  • Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe
  • Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe
  • Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Such as figure 1 Shown, the preparation of embodiment 1, fluorescent probe Nap-G

[0058] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride to 100mL of absolute ethanol, then inject 2.5mL of n-butylamine, and reflux at a temperature of 50°C for 6 Hour. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.20 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (80% yield).

[0059] Step b): Under an inert atmosphere, add 1.00g of N-n-butyl-4-bromo-1,8-naphthalimide and 1.87g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of Alcohol monomethyl ether and 2.1 mL of triethylamine were reacted under reflux for 5 hours at a temperature of 0°C. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo ...

Embodiment 2

[0063] Embodiment 2, the preparation of fluorescent probe Nap-G

[0064] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalic anhydride to 100mL of anhydrous methanol, then inject 5.0mL of n-butylamine, and reflux at a temperature of 80°C for 1 Hour. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.40 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (yield 84%).

[0065] Step b): Under an inert atmosphere, add 1.00g of N-butyl-4-bromo-1,8-naphthalimide and 3.94g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of butanol and 2.5 mL of diisopropylethylamine was refluxed at 100°C for 1 hour. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo to obtain N-n-butyl-4-(p-methylphenylsulfanyl)-1,8-naphthalene Amine 1.0 g (...

Embodiment 3

[0069] Embodiment 3, the preparation of fluorescent probe Nap-G

[0070] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalic anhydride to 100mL of anhydrous n-propanol, then inject 7.5mL of n-butylamine, and reflux at a temperature of 120°C React for 5 hours. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.60 g of intermediate N-n-butyl-4-bromo-1,8-naphthoimide (yield 87%).

[0071] Step b): Under an inert atmosphere, add 1.00g of N-n-butyl-4-bromo-1,8-naphthalimide and 0.38g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of diethyl Glycol monomethyl ether and 2.9 g of potassium carbonate were refluxed for 48 hours at a temperature of 140°C. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo to obtain N-n-butyl-4-(p-...

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Abstract

The invention discloses a fluorescence probe for detecting glutathione and a preparation method and a use method of the fluorescence probe. A classical ICT system is constructed by utilizing 1,8-naphthalimides, a benzene sulfoxide part is introduced at 4-position, and the ICT effect of probe molecules is adjusted and controlled by utilizing a classical ICT system constructed by 1,8-naphthalimide and introducing benzene sulfoxide part at the fourth position. Under the condition that no glutathione exists, the probe molecules do not emit fluorescence light because of strong electron-withdrawing effect of 4-position benzene sulfoxide; under the condition that glutathione exists, the benzene sulfoxide part can be replaced by the glutathione, and thus intramolecular electron transfers from a 4-position sulphur atom (from the glutathione) to the 1,8-naphthalimides, and the probe molecules emit hyperfluorescence because of the ICT effect. According to the invention, the detection of the intracellular glutathione can be realized, and the fluorescence probe has the advantages of convenient operation, low cost, sensitive response, easy promotion and application and the like.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a naphthalimide-phenylsulfoxide derivative used as a glutathione fluorescent probe material and a preparation method and use method thereof. Background technique [0002] Glutathione (GSH) is a tripeptide molecule composed of glutamic acid, cysteine ​​and glycine, and is the most abundant thiol-containing amino acid in the human body. In the living body, glutathione plays an important role in maintaining intracellular redox balance, metabolism of exogenous substances, intracellular signal conversion and gene regulation. Abnormality of intracellular glutathione concentration will lead to a series of physiological diseases, such as leukocyte loss, psoriasis, liver damage, cancer and AIDS, etc. Survival in HIV disease, Proc. Natl. Acad. Sci. USA., 1997, 94: 1967-1972). Therefore, quantitative and real-time monitoring of glutathione content in organisms has...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/14G01N21/64
Inventor 韩益丰杨成玉
Owner ZHEJIANG SCI-TECH UNIV
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