Synthesis and application of fluorescence molecular probe containing cyanogens ions by naked eyes and fluorescence ratio detection

A technology of fluorescent molecular probe and cyanide ion, which is applied in the field of chemical analysis and detection, can solve the problems of poor selectivity, expensive equipment, complicated processing, etc., and achieve the effects of low detection limit, wide detection range and simple synthesis

Inactive Publication Date: 2014-05-21
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these traditional methods have disadvantages such as time-consuming, poor selectivity, complex processing, and expensive instruments.

Method used

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  • Synthesis and application of fluorescence molecular probe containing cyanogens ions by naked eyes and fluorescence ratio detection
  • Synthesis and application of fluorescence molecular probe containing cyanogens ions by naked eyes and fluorescence ratio detection
  • Synthesis and application of fluorescence molecular probe containing cyanogens ions by naked eyes and fluorescence ratio detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of diethylaminocoumarin aldehyde

[0026]Under the protection of argon, 2mL of N,N-dimethylformamide was cooled in an ice bath and vigorously stirred, slowly added dropwise with 2mL of phosphorus oxychloride, and continued to stir for 1 hour after the dropwise addition; then diethylcoumarin The element (1.33g.6.12mmol) was dissolved in 10mL of anhydrous N,N-dimethylformamide, added dropwise to the above solution, and the temperature was raised to 70°C for 18 hours. After the reaction was completed, it was lowered to room temperature, poured into 100 mL of ice water, stirred vigorously, and an orange-yellow solid was precipitated. Suction filtration, washing with water and ethanol, and recrystallization with absolute ethanol to obtain 0.6 g of yellow needle-like crystals, namely diethylaminocoumarin aldehyde (40%).

[0027] 1 HNMR (300MHz, CDCl 3 ):δ ppm =10.11 (1H, d, J4.5), 8.24 (1H, d, J4.7), 7.41 (1H, dd, J9.0, 2.8), 6.64 (1H, d, J9....

Embodiment 2

[0028] Embodiment 2: Preparation of molecular fluorescent probe

[0029] Dissolve diethylaminocoumarin aldehyde (25 mg.0.1 mmol) and benzothiazole-2-acetonitrile (18 mg.0.1 mmol) in 10 mL of absolute ethanol, add 1 drop of piperidine, and stir at room temperature for 3 hours. After the reaction, filter with suction, wash with ethanol, and separate by column chromatography (petroleum ether / dichloromethane=1:2) to obtain 28 mg (70%) of the product, which is the molecular fluorescent probe.

[0030] 1 HNMR (400MHz, DMSO-d6): δ ppm =8.91(1H, s), 8.43(1H, d, J0.4), 8.12-8.08(1H, m), 7.90-7.88(1H, m), 7.52-7.42(3H, m), 6.61(1H, s), 6.60 (1H, s), 3.49 (4H, dd, J9.4, 9.6), 1.28 (6H, d, J9.6).

Embodiment 3

[0031] Example 3: Application of naked-eye and fluorescence-enhanced detection of thiol-containing amino acid fluorescent probes

[0032] Dissolve the fluorescent probe in dimethyl sulfoxide solution to a concentration of 2.0×10 -5 mol / L and 1.0×10 -5 mol / L solution, add the corresponding anion, respectively measure the change of ultraviolet absorption spectrum and fluorescence emission spectrum. Figure 1-Figure 5 It shows that in the ultraviolet absorption spectrum and the fluorescence emission spectrum, the fluorescent probe shows high selectivity to cyanide ion, and with the increase of the concentration of cyanide ion, the ultraviolet absorption peak and the fluorescence emission peak both appear larger blue. shift, while the obvious color change is also suitable for naked eye detection. And the fluorescent probe is not affected by other anions such as: AcO - , H 2 PO 4 2- , NO 3 - , ClO 4 - , HSO 4 - , F - , Cl - , Br - , I - The effect of plasma shows th...

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Abstract

The invention relates to a preparation method of a fluorescence molecular probe contanining cyanogens ions and having naked eye identification and fluorescence ratio detection as well as an application of the fluorescence molecular probe in detection of cyanogen ions. The fluorescent molecules provided by the invention are synthesized with benzothiazole-2-acetonitrile under the condition that taking piperidine is taken as an alkali by taking diethylin coumarin as a raw material. The synthesizing method is simple and convenient and mild in reaction condition. The probe provided by the invention is high in molecular sensitivity, stable in fluorescent performance, high in synthesizing yield, good in selectivity, wide in response range, low in limit of detection and suitable for naked eye detection. The fluorescence probe is not affected by anions such as AcO<-1>, H2PO4<2->, NO3<-1>, ClO4<-1>, HSO4<-1>, F<-1>, Cl<-1>, Br<-1> and I<-1>. The ratio type fluorescence probe can overcome external errors caused by strength of exciting light, concentration of probe and environmental factors, so that the fluorescence molecular probe has an actual application value in the fields of biochemistry, environmental sciences and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a method for preparing a fluorescent molecular probe for naked eye and fluorescence ratio detection of cyanide ion and the application of the fluorescent molecular probe in the detection of cyanide ion. Background technique [0002] As an alkaline reagent, cyanide is widely used in production activities such as plastics, fibers, gold, dyes, water treatment, and medicines, and is of great significance; however, cyanide is a very dangerous chemical that can pass through the lungs. , gastrointestinal tract and skin enter the body and combine with the active site of cytochrome c oxidase in heme, causing damage to the mitochondrial electron transport chain, inhibiting the normal respiration process, and the inhalation of cyanide will increase the concentration of calcium ions, Inducing a series of enzymatic reactions increases the content of active oxygen speci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/07G01N21/64G01N21/78
CPCC07D417/06C09K11/07C09K2211/1037C09K2211/1077G01N21/643G01N21/78G01N2021/6417G01N2021/7786
Inventor 宋相志陈颂
Owner SUZHOU ROWLAND BIOTECH
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