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Fluorescence probe for detecting hydrogen sulfide as well as preparation method and application method of fluorescence probe

A fluorescent probe and hydrogen sulfide technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve problems such as unfavorable detection, achieve the effects of simple operation, easy promotion and application, and improved sensitivity

Active Publication Date: 2015-05-13
菏泽益驰化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, most of the reported hydrogen sulfide probes are fluorescent "off-on" type (see L.A.Montoya and M.D.Pluth, Selective Turn-on Fluorescent Probes for Imaging Hydrogen Sulfide in Living cells, Chem.Commun., 2012, 48: 4767-4769), easily affected by the detection environment, such as detection temperature, probe concentration and other conditions; or there are biologically susceptible groups in the probe molecule (see X.-L.Liu, X.-J.Du , C.-G.Dai, and Q.-H.Song, Ratiometric Two-Photon Fluorescent Probes for Mitochondrial Hydrogen Sulfide in Living Cells, J.Org.Chem., 2014, 79:9481-9489.), not conducive to its Assays in complex organisms

Method used

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  • Fluorescence probe for detecting hydrogen sulfide as well as preparation method and application method of fluorescence probe
  • Fluorescence probe for detecting hydrogen sulfide as well as preparation method and application method of fluorescence probe
  • Fluorescence probe for detecting hydrogen sulfide as well as preparation method and application method of fluorescence probe

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Experimental program
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Effect test

Embodiment 1

[0052] Such as figure 1 Shown, the preparation of embodiment 1, fluorescent probe Nap-S

[0053] 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 reaction temperature of 50°C 5 hours. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.20 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (80% yield).

[0054] Step b): Under an inert atmosphere, cut 2.00g of sodium metal into filaments and add it to 100mL of anhydrous tert-butanol. After the sodium filaments are dissolved, add 3.72g of N-n-butyl-4-bromo to the system -1,8-naphthalimide, at a reaction temperature of 0°C, reflux for 10 hours. After the reaction was complete, 500mL of 1N cold dilute hydrochloric acid was added to the system, a large amount of yellow solids precipitated, filtered, ...

Embodiment 2

[0058] Embodiment 2, the preparation of fluorescent probe Nap-S

[0059] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride to 100mL of anhydrous methanol, then inject 5.0mL of n-butylamine, and reflux at a reaction temperature of 80°C 1 hour. After the reaction was complete, needle crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.00 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (yield 76%).

[0060] Step b): Under an inert atmosphere, cut 4.00g of sodium metal into filaments and add it to 100mL of anhydrous tert-butanol. After the sodium filaments are dissolved, add 3.72g of N-n-butyl-4-bromo to the system -1,8-naphthalimide, at a reaction temperature of 50°C, reflux reaction for 1 hour. After the reaction was complete, 500 mL of 1N cold dilute hydrochloric acid was added to the system, a large amount of yellow solids precipitated, filtered, washed, and dried in...

Embodiment 3

[0064] Embodiment 3, the preparation of fluorescent probe Nap-S

[0065] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride to 100mL of anhydrous ethylene glycol monomethyl ether, then inject 5.0mL of n-butylamine, and react at 120°C Temperature, reflux reaction for 20 hours. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.50 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (86% yield).

[0066] Step b): Under an inert atmosphere, cut 8.00g of sodium metal into filaments and add it to 100mL of anhydrous isopropanol. After the sodium filaments are dissolved, add 3.72g of N-n-butyl-4-bromo to the system -1,8-naphthalimide, at a reaction temperature of 100°C, reflux for 20 hours. After the reaction was complete, 500mL of 1N cold dilute hydrochloric acid was added to the system, a large amount of yellow solids precipitated, ...

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Abstract

The invention discloses a fluorescence probe for detecting hydrogen sulfide as well as a preparation method and application method of the fluorescence probe. A classic ICT system is constructed by 4-oxhydryl-1,8-naphthalimides; an azide benzyl part is directly introducd at 4-bite, so that the ICT system has biological and optical stability. An azide group is restored into amino by the hydrogen sulfide in presence of the hydrogen sulfide, so that a 4-toluidine part is separated by 1,6-removal, so as to obtain the 4-oxhydryl-1,8-naphthalimides. A 'ratio meter' type hydrogen sulfide probe of naphthalimides dyes and a special detection kit for the hydrogen sulfide probe have good response to a hydrogen sulfide solution; detection of hydrogen sulfide in a cell can be achieved; and the fluorescence probe has the advantages of being simple and convenient to operate, low in cost, sensitive in response, easy to popularize and apply and the like.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a naphthalimide-p-azidobenzyl alcohol derivative used as a hydrogen sulfide fluorescent probe material and a preparation method and use method thereof. Background technique [0002] Hydrogen sulfide (H 2 S) is the third largest gas signaling molecule in the human body after nitric oxide (NO) and carbon monoxide (CO). In the living body, hydrogen sulfide participates in intracellular redox reactions and various signal transduction processes, including vasodilation, myocardial contraction, neurotransmission, and insulin secretion. When intracellular hydrogen sulfide is at an abnormal level, it will lead to a series of physiological diseases, such as Alzheimer's, liver cirrhosis, gastric mucosal injury, arterial and pulmonary hypertension, etc. (see B.D.Paul, and S.H.Snyder, H 2 S signaling through protein sulfhydration and beyond, Nat. Rev. Mol. Cell Biol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D221/14G01N21/64
Inventor 韩益丰杨成玉陈宇
Owner 菏泽益驰化工有限公司
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