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Two-photon formaldehyde fluorescent probe and preparation and application thereof

A fluorescent probe and two-photon technology, applied in the field of preparation of new two-photon formaldehyde-based fluorescent probes, can solve few problems, and achieve the effects of strong penetrating ability, reducing fluorescent background, and small cell damage.

Active Publication Date: 2016-09-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the formaldehyde detection methods at the present stage, most of them are to detect formaldehyde in the air, and there are still very few probes for detecting formaldehyde in cells reported at home and abroad.

Method used

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  • Two-photon formaldehyde fluorescent probe and preparation and application thereof
  • Two-photon formaldehyde fluorescent probe and preparation and application thereof
  • Two-photon formaldehyde fluorescent probe and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthesis of embodiment 1 probe (I)

[0035] In a 50mL round bottom flask, add 148mg of compound 4 (0.5mmol) dissolved in 5mL of methanol, ice-bath to 0°C, add 0.72mL ammonia methanol solution (7mol / L 5mmol), react at 0°C for half an hour, then add 168 mg o-di-tert-alcohol propenyl borate (1 mmol). The reaction was brought to room temperature overnight, the mixture was evaporated under reduced pressure to remove the solvent, and the concentrate was separated on a silica gel column (eluted with a mixture of dichloromethane:methanol at a volume ratio of 20:1) to obtain 118 mg of the product with a yield of 70% . H NMR spectrum see figure 1 , see C NMR figure 2 .

[0036] 1 H NMR (500MHz, d 6 -DMSO) δ: 8.43 (d, J = 7.8, 1H), 8.25 (d, J = 7.0, 1H), 8.03 (s, 1H), 7.35 (t, J = 7.6, 1H), 5.72 (ddt, J =13.8,10.1,6.8,1H),5.06(dd,J=25.4,13.6,2H),4.50-4.32(m,1H),4.09-3.94(m,2H),2.88-2.75(m,1H), 2.74-2.63 (m, 1H), 1.64-1.49 (m, 2H), 1.39-1.26 (m, 2H), 0.92 (t, J = 7.4,...

Embodiment 2

[0037] Embodiment 2 probe (I) adds the ultraviolet absorption spectrometry of 0mM and 5mM formaldehyde concentration under the condition of pH 7.4

[0038]Accurately weigh a certain amount of probe (I), prepare a probe stock solution with a concentration of 1mM with dimethyl sulfoxide, pipette 2μL into 394μL phosphate buffer (10mM pH=7.4), add 4μL respectively Ultrapure water and 4μL, 500mM formaldehyde aqueous solution were reacted at 37°C for 3 hours, and the ultraviolet absorption spectra of the two mixed solutions were measured. The results are shown in image 3 .

[0039] Experiments have shown that the difference in the ability of the 3-position of naphthalimide dyes to push up and pull electrons can affect the absorption spectrum of the compound. Since the aldehyde group has a relatively strong electron-pull ability, the product of the reaction between probe (I) and formaldehyde The absorption spectrum has a blue-shift process, and the maximum absorption wavelength dro...

Embodiment 3

[0040] Example 3 Detection of the fluorescence effect of probe (I) under the condition of pH 7.4 and excitation wavelength 450nm by adding different equivalent formaldehyde concentrations.

[0041] Accurately weigh a certain amount of probe (I), prepare a probe stock solution with a concentration of 1mM with dimethyl sulfoxide, pipette 2μL into 394μL phosphate buffer (10mM pH=7.4), add 4μL respectively Formaldehyde aqueous solutions with different concentrations (final concentration of formaldehyde in water are 0mM, 0.25mM, 0.5mM, 1mM, 2mM, 5mM respectively) were reacted at 37°C for 3 hours, and their fluorescence values ​​were measured. The excitation wavelength is 450nm, the emission wavelength is 480-740nm, see the fluorescence spectrum Figure 4 .

[0042] Experiments have shown that when the formaldehyde equivalent is increased, due to the strong electron-pulling ability of the aldehyde group, when the excitation wavelength is 450nm, the emission spectrum of the product ...

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Abstract

The invention discloses a two-photon formaldehyde fluorescent probe and preparation and application thereof. The probe is a novel formaldehyde probe taking 1,8-naphthalimide as a two-photon fluorogen on the basis of an intramolecular charge transfer mechanism. Probe molecules have good light stability and a large Stoke's shift, the probe can well detect the formaldehyde concentration in a neutral buffer solution, and meanwhile compared with other aldehyde compounds, the probe has good specificity on formaldehyde. It is well proved through two-photon confocal fluorescence microscopic imaging experiments that the probe can permeate through a cell membrane to enter cells and can detect a change of the formaldehyde concentration in the cells, and an effective research tool for researching the physiological action of formaldehyde in the cells is provided.

Description

(1) Technical field [0001] The invention relates to a two-photon fluorescent dye for detecting intracellular formaldehyde, in particular to a preparation method and application of a novel two-photon formaldehyde fluorescent probe based on 1,8-naphthalimide. (2) Background technology [0002] As a recognized carcinogen, formaldehyde has three main sources: one is from industrial production, the other is from the release of nature, and the other is from endogenous formaldehyde, such as oxidase, neutrophil marrow, etc. Biological reactions such as peroxidase can release formaldehyde. In normal human blood, the concentration of formaldehyde can reach about 0.1mM. However, excessive formaldehyde in the body can cause chronic respiratory diseases, embryonic deformities, Alzheimer's disease and cancer, etc. Among the formaldehyde detection methods at the present stage, most of them are to detect formaldehyde in the air, and there are still very few probes for detecting formaldehy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6486
Inventor 朱勍谢振达
Owner ZHEJIANG UNIV OF TECH
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