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Formaldehyde fluorescent probe, and preparation method and application thereof

A fluorescent probe, formaldehyde technology, applied in the field of analytical chemistry, to achieve the effect of high selective detection, high sensitivity and high yield

Inactive Publication Date: 2016-03-02
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently reported formaldehyde fluorescent probes are all based on the first type of enhanced fluorescent probes, and no ratiometric formaldehyde probes have been reported.

Method used

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  • Formaldehyde fluorescent probe, and preparation method and application thereof
  • Formaldehyde fluorescent probe, and preparation method and application thereof
  • Formaldehyde fluorescent probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 : compound RFFP Synthesis:

[0030]

[0031] Dissolve 86mg of 6-hydroxy-2-naphthaldehyde (0.5mmol) in 5mL of methanol, add 378μL of 25% ammonia water (5mmol) in an ice bath and keep stirring for 30 minutes. Subsequently, 101 mg of allylboronic acid pinacol ester (0.6 mmol) was added, the ice bath was removed and the reaction was stirred overnight (over 10 h). After the reaction, remove the solvent from the reaction liquid by a vacuum rotary evaporator to obtain a crude product, and use a silica gel (200-300 mesh) chromatography column to purify with dichloromethane and ethanol at a volume ratio of 10:1 as the eluent , to obtain 70 mg of white solid (66% yield). 1 HNMR (400MHz, CDCl 3 ),(ppm):2.47-2.63(m,2H),4.10-4.13(t, J =6.8Hz,1H),5.09-5.18(m,2H),5.69-5.79(m,1H),6.94-6.95(1H),6.98-7.01(dd, J =8.8,2.4Hz,1H),7.31-7.34(dd, J =8.8,1.6Hz,1H),7.43-7.45(d, J =6.8Hz,1H),7.54-7.56(d, J =8.8Hz,1H),7.60(s,1H); 13 CNMR (100MHz, CDCl 3): δ (ppm): 43.34, 55...

Embodiment 2

[0032] Example 2 :probe RFFP The change of fluorescence spectrum with the addition of different amounts of formaldehyde

[0033] Get the probe prepared in Example 1 RFFP Dissolve in acetone to make a concentration of 1mol / L probe mother solution (probe RFFP The concentration of formaldehyde is 1mol / L); the formaldehyde solution with a mass fraction of 37% is added to distilled water to prepare formaldehyde mother liquors with formaldehyde concentrations of 1mmol / L, 50mmol / L and 500mmol / L respectively. Take 30μL from the probe mother solution and add it to a 5mL centrifuge tube, add different equivalents (1-300eq) of formaldehyde mother solution (referring to the formaldehyde content in the added formaldehyde mother solution is the probe mother solution RFFP content of 1-300 times), diluted to 3mL with potassium dihydrogen phosphate aqueous solution (concentration 25mmol / L, pH7.4), and configured as a test solution with a probe concentration of 10μmol / L and 1% acetone. Use...

Embodiment 3

[0034] Example 3 :probe RFFP Calculation of lower limit of detection of formaldehyde

[0035] According to the fluorescence spectrogram of example 2, the fluorescence intensity at 451nm place and the fluorescence intensity ratio at 359nm place (I 451 / I 359 ) and the corresponding formaldehyde concentration. Depend on Figure 4 Visible, when formaldehyde concentration is 20-300 equivalent, I 451 / I 359 Good linearity with formaldehyde concentration. According to the formula Dl=3σ / k (Dl is the lower limit of detection, σ is the standard deviation of the intercept, and k is the slope), the lower limit of detection can be calculated as 5.53×10 -5 mmol / L.

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Abstract

The invention relates to a preparation method and application of a formaldehyde fluorescent probe, and belongs to the technical field of analytical chemistry. The formaldehyde fluorescent probe is a ratio-type fluorescent probe with double emission bands. The excitation wavelength is 318 nm; and the fluorescence peak at 359nm decreases gradually with the increasing of the concentration of formaldehyde, and at the same time a new emission band is produced at 451 nm and the fluorescence peak gradually increases. The formaldehyde fluorescent probe can resist the interference of acetaldehyde, glyoxal, methylglyoxal, benzaldehyde, alanine, glycine, serine, arginine, cysteine, glutathione and glucose, has high detection accuracy, high sensitivity and strong anti-interference capability. In addition, the formaldehyde fluorescent probe of the invention can detect the formaldehyde in a biological sample (cell environment), realizes formaldehyde fluorescence imaging in living cell level, and has potential practical application value. The synthesis of the formaldehyde fluorescent probe only needs a one-step reaction, which is simple and high in yield.

Description

Technical field [0001] The invention involves a formaldehyde fluorescent probe, which is the field of preparation and application, which is the field of analytical chemistry. Background technique [0002] In recent years, substances with active cymbals have received widespread attention, such as carbon monoxide, ethyletedehyde, tither acetaldehyde, and acrylic.Aldehyde is the product of the metabolism process of human body, and is usually considered toxic to the human body.That is because the cymbal group has high activity, which can react with the amino group at the end of the protein and the end of the DNA to destroy its original biological activity. It has proven that the aldosum substances are related to diabetes, cardiovascular disease, cerebral infarction, liver disease, and cancer.EssenceAs the simplest aldehyde, formaldehyde can not only be generated through natural activities and human production activities, but also catalyze through dehuminase and oxidase in the organis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C09K11/06
CPCC09K11/06G01N21/6402
Inventor 林伟英何隆薇杨雪玲
Owner UNIV OF JINAN
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