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Formaldehyde fluorescence probe and preparation method and application thereof

A fluorescent probe and formaldehyde technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited detection sensitivity, destructive biological samples, etc., achieve high yield, realize detection, and achieve specificity and the effect of rapid detection

Inactive Publication Date: 2016-05-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are generally suitable for the detection of formaldehyde in aqueous solutions, textiles, and food, but are not suitable for the detection of formaldehyde in biological environments because of their limited detection sensitivity and are destructive to biological samples

Method used

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  • Formaldehyde fluorescence probe and preparation method and application thereof
  • Formaldehyde fluorescence probe and preparation method and application thereof
  • Formaldehyde fluorescence probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of Compound 1:

[0055] ;

[0056] 480mg rhodamine 6G (molecular formula: C 28 h 31 N 2 o 3 Cl) (1.0mmol) was dissolved in methanol, then 300mg of ethylenediamine (5.0mmol) was added dropwise, the reaction solution was heated to about 70°C, and the temperature was kept constant after some substances began to reflux, and the reaction was stirred for 6 hours, and the reaction was completed. After the reaction was completed, the solvent (methanol) was removed by distillation under reduced pressure with a rotary evaporator to obtain a crude product. Using dichloromethane and ethanol at a volume ratio of 3:1 as the eluent, the silica gel (200-300 mesh) chromatography column was used for purification to obtain 342 mg of a white solid (yield 75%). 1 HNMR (400MHz, CDCl 3 ),(ppm):1.31-1.34(t,J=7.2Hz,6H),1.90(s,6H),2.33-2.35(t,J=6.6Hz,2H),3.17-3.24(m,4H), 3.52(3H),6.22(s,2H),6.34(s,2H),7.05-7.07(1H),7.43-7.49(m,2H),7.92-7.94(1H); 13 CNMR (100MHz, CDCl 3 ): δ(pp...

Embodiment 2

[0060] Fluorescence spectrum changes of embodiment 2 probe II reacting with different equivalents of formaldehyde

[0061] Dissolve the probe II prepared in Example 1 in DMF to make a probe mother solution with a concentration of 0.5mmol / L (the concentration of probe II is 0.5mmol / L); add the formaldehyde solution with a mass fraction of 37% into distilled water, Formaldehyde mother liquor that formaldehyde concentration is 1mmol / L is prepared. Take 60μL from the probe mother solution and add it to a 5mL centrifuge tube, add different equivalents (0-2eq) of formaldehyde mother solution (the equivalent is the number of moles of formaldehyde in the mother solution of formaldehyde relative to the number of moles of probes in the mother solution of probe) Multiples of ), diluted to 3mL with 1.44mL DMF and different volumes of PBS aqueous solution (concentration 25mmol / L, pH 7.4), and configured as a test solution with a probe concentration of 10μmol / L and 50% DMF. Use a fluoresce...

Embodiment 3

[0062] Example 3 Fluorescence Changes of Probe II and Formaldehyde Over Time

[0063] Take 60 μL from the fluorescent probe mother solution in Example 2 and add it to a 5mL centrifuge tube, add 60 μL of formaldehyde mother solution with a concentration of 0.5mmol / L, then 1.44mL of DMF and 1.44mL of PBS aqueous solution (concentration 25mmol / L, pH7.4 ) was diluted to 3 mL, and prepared into a test solution with a probe concentration of 10 μmol / L, a formaldehyde concentration of 3 mmol / L, and 50% DMF. With an excitation wavelength of 530nm, its fluorescence spectrum changing with time was tested. Depend on Figure 7 It can be seen that as time increases, the fluorescence intensity at 560 nm gradually increases, and reaches the maximum value in about 10 seconds.

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Abstract

The invention relates to a formaldehyde fluorescence probe and a preparation method and an application thereof, and belongs to the technical field of preparation of formaldehyde probes. The formaldehyde fluorescence probe has the structural formula defined in the specification; the formaldehyde response time is about 10 seconds, and thus rapid detection is realized; the formaldehyde fluorescence probe can resist interference of acetaldehyde, glyoxal, methylglyoxal, benzaldehyde, alanine, glycine, serine, arginine, cysteine, glutathione, glucose, hydrogen peroxide and hypochlorous acid and has good specificity. The formaldehyde content in a solution can be determined through observing the change degree of spectra in a fluorescence spectrophotometer, and thus quantitative detection is achieved; the lower limit of detection is 7.7*10<-7> mol / L. Whether the solution contains formaldehyde and the general concentration of formaldehyde are determined through observing color changes of the solution via naked eyes. In addition, with use of the probe II, detection of formaldehyde in biological samples can be realized. The preparation method of the probe II is simple, and the yield is relatively high.

Description

technical field [0001] The invention relates to a formaldehyde fluorescent probe and its preparation method and application, belonging to the technical field of formaldehyde probe preparation. Background technique [0002] Formaldehyde is a colorless gas with a special pungent smell. It has been confirmed to have a strong carcinogenic and cancer-promoting effect, and it will cause damage to human eyes, nose, respiratory tract, skin and other easily exposed organs. At present, formaldehyde in the environment mainly comes from human production activities such as phenolic and urea-formaldehyde resins, textile auxiliaries and preservatives, as well as the metabolism and degradation of certain organic compounds. Formaldehyde is also an endogenous substance in the human body, which can be catalyzed by biological enzymes such as semicarbazide-sensitive amine oxidase and lysine-specific histone demethylase 1. Studies have found that formaldehyde plays an important role in the forma...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1088G01N21/6402G01N2021/6419
Inventor 林伟英何隆薇杨雪玲
Owner UNIV OF JINAN
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