Azido-containing naphthalimide compound and applications thereof in detecting hydrogen sulfide

A nitrogen-based naphthalimide and compound technology, which is applied to the application field of azide-containing naphthalimide compounds and hydrogen sulfide detection, can solve problems such as unfavorable detection of hydrogen sulfide content, achieve the expansion of linear detection range, change Response time, fast response effect

Inactive Publication Date: 2013-01-02
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some hydrogen sulfide fluorescent sensors currently developed usually require a response time of more than half an hour, and their detection limit is usually at the μM level, which is not conducive to real-time detection of hydrogen sulfide content in tissues or cells

Method used

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  • Azido-containing naphthalimide compound and applications thereof in detecting hydrogen sulfide
  • Azido-containing naphthalimide compound and applications thereof in detecting hydrogen sulfide
  • Azido-containing naphthalimide compound and applications thereof in detecting hydrogen sulfide

Examples

Experimental program
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Effect test

Embodiment 1

[0029]

[0030] Synthesis of N-(n-butyl)-4-azido-1,8-naphthalimide (compound 1):

[0031] (1) Add 50mL of ethanol, 5.54g of 4-bromo-1,8-naphthalene anhydride (20mmol) and 2.5g of n-butylamine (34.3mmol) in a 100mL three-necked flask, heat the mixture under reflux for 4 hours, and remove solvent. The reaction product was recrystallized twice with absolute ethanol to obtain a light yellow solid with a yield of 85%.

[0032] (2) Weigh 0.50 g of the product synthesized by step (1) and 0.20 g of sodium azide, mix and dissolve it in 20 mL of N,N-methylformamide (DMF), and heat the mixture to 80°C under nitrogen protection. For 12 hours, the reaction was followed by thin-plate chromatography until the reaction was complete. After the reaction, the solution was poured into 100 mL of deionized water, and the above solution was extracted three times with dichloromethane, the organic phases were combined, and the solvent was distilled off under pressure. The resulting solid was sep...

Embodiment 2

[0034] Synthesis of N-(diethylene glycol)-4-azido-1,8-naphthalimide (compound 2)

[0035] Except that diglycolamine is used to replace n-butylamine, other synthesis and purification methods are the same as in Example 1. The product (compound 2) was obtained with a yield of 55%.

[0036] 1 H-NMR (400MHz, CDCl 3 ): 8.64(d, J=7.2Hz, 1H, ArH), 8.58(d, J=8.0Hz, 1H, Ar-H), 8.44(d, J=8.4Hz, 1H, Ar-H), 7.75( t, J=7.6Hz, 1H, Ar-H), 7.47(d, J=8.0Hz, 1H, Ar-H), 4.44(t, J=5.6Hz, 2H, CH 2 ), 3.86(t, J=5.6Hz, 2H, CH 2 ), 3.68 (m, 4H, 2CH 2 ); LC-MS (ESI): m / z 327.31 (M+H) + , calculated 327.40

[0037] Determination of hydrogen sulfide in buffer solution and surfactant system:

[0038] Accurately weigh a certain amount of compound 1 or 2 and dissolve it in 10mL ethanol to prepare a 1mM stock solution and store it in the dark; accurately weigh a certain amount of Na 2 Dissolve S in 10 mL of water to make 1 mM Na 2 S stock solution. Accurately pipette 100 μL stock solution of compo...

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Abstract

The invention relates to an azido-containing naphthalimide compound and applications of the azido-containing naphthalimide compound in detecting hydrogen sulfide, wherein the azido-containing naphthalimide compound is constituted by a novel fluorescence molecular probe and three different detection systems. The fluorescence molecular probe makes use of reducibility of the hydrogen sulfide; the spectrum of the compound is obviously changed before and after the fluorescence molecular probe reacts with the hydrogen sulfide, and the color is changed to be yellow from nearly colorless; different surfactants are added into the solution, so that the response time can be changed and the linear detection range on the hydrogen sulfide is expanded. The technology is characterized by sensitive reaction, fast response speed and wide linear range, and is particularly suitable for detecting the content of the hydrogen sulfide in organisms.

Description

【Technical field】 [0001] The invention relates to the technical field of hydrogen sulfide detection, in particular to an azide-containing naphthalimide compound and its application in the detection of hydrogen sulfide. 【Background technique】 [0002] Hydrogen sulfide is considered to be the third gas signaling molecule after nitric oxide and carbon monoxide, which plays a very important role in many physiological and pathological processes, including participating in the relaxation of vascular smooth muscle, as a regulator of the central nervous system, Inhibits insulin signaling and has anti-inflammatory and antioxidant effects. However, abnormal hydrogen sulfide concentrations in the body are associated with Down syndrome and Alzheimer's disease. It is reported in the literature that the concentration of hydrogen sulfide in the body can vary by up to 10 5 order of magnitude, that is, from nM to mM; at the same time, the metabolism of hydrogen sulfide in the body is very ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14G01N21/64G01N21/25
Inventor 钱俊红张凌怡王智聪张维冰田海玉柏红燕孙倩
Owner EAST CHINA UNIV OF SCI & TECH
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