Ratio-type two-photon formaldehyde fluorescent probe, preparation method therefor and use of ratio-type two-photon formaldehyde fluorescent probe

A fluorescent probe and two-photon technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of few reports of two-photon fluorescent probes, and achieve simple structure, specific selectivity, and simple operation Effect

Active Publication Date: 2017-07-14
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One-photon fluorescent probes using quinoline as a fluorophore have been reported in many literatures, but there are few reports on two-photon fluorescent probes.

Method used

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  • Ratio-type two-photon formaldehyde fluorescent probe, preparation method therefor and use of ratio-type two-photon formaldehyde fluorescent probe
  • Ratio-type two-photon formaldehyde fluorescent probe, preparation method therefor and use of ratio-type two-photon formaldehyde fluorescent probe
  • Ratio-type two-photon formaldehyde fluorescent probe, preparation method therefor and use of ratio-type two-photon formaldehyde fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of fluorescent probe molecule MQAP

[0035] Dissolve 288.09mg (1mmol) of compound MQ, 677.38mg (10mmol) of 25wt% ammonia water in methanol, stir and react at 0°C for 30min, then add 202mg of propenylboronic acid o-di-tert-alcohol ester after warming up to room temperature, and stir at 30°C Reaction for 24 hours; After the reaction, the reaction solution was rotary evaporated to remove the solvent to obtain a crude product, and the column chromatography was performed on 200-300 mesh silica gel, and the eluent was mixed with dichloromethane and methanol at a volume ratio of 10:1 to obtain the target product MQAP 148.12mg (0.45mmol), productive rate 45%;

[0036] The structural formula of the compound MQ is:

[0037]

[0038] 1 H NMR (600MHz, CDCl 3): δ8.07(d, J=8.5Hz, 1H), 8.00(d, J=8.7Hz, 1H), 7.96(d, J=1.3 Hz, 1H), 7.78(dd, J=8.7, 1.7Hz ,1H),7.51(d,J=8.7Hz,2H),7.46(d,J=8.5Hz,1H),6.90(d,J=8.7Hz,2H),5.87–5.74(m,1H),5.16 (dd,J=17.1,1.1Hz...

Embodiment 2

[0039] Example 2: Two-photon testing of fluorescent probe molecules

[0040] Fluorescent probe of the present invention is dissolved in DMSO and makes the mother liquor of 1mM, utilizes two-photon testing technique, test the two-photon absorption cross section of (MQ) after fluorescent probe molecule (MQAP) and fluorescent probe molecule react with formaldehyde, from Figure 4 It can be seen that the maximum absorption cross sections of the fluorescent probe molecules before and after the reaction with formaldehyde are 185 and 274 GM respectively, and the two-photon excitation wavelengths are both at 720 nm.

Embodiment 3

[0041] Example 3: Cytotoxicity Test

[0042] The MTT (3-(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) experiment was based on the reported articles to do some cytotoxicity tests. Add 0, 10, 20, and 30 μM fluorescent probes to the same batch of cells, and the conditions are 37 ° C, 5% CO 2 Incubate in a cell incubator for 24 hours, according to the formula of cell viability: cell viability% = OD 570 (sample) / OD 570 (control group)×100, the cell survival rate can be calculated ( Figure 5 ). from Figure 5 We can see that, when the concentration is 10 μM, the cell survival rate is still about 98%, which shows that the fluorescent probe of the present invention has no toxic effect on cells, so it can be used to detect formaldehyde in cells.

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Abstract

The invention discloses a ratio-type two-photon formaldehyde fluorescent probe, a preparation method therefor and use of the ratio-type two-photon formaldehyde fluorescent probe. The ratio-type two-photon formaldehyde fluorescent probe has a structure as follows shown in the description. Molecules of the fluorescent probe disclosed by the invention show relatively high selectivity and sensitivity to formaldehyde in a coexisting system of molecules of the formaldehyde and other aldehydes, amino acids and the like. Proven by cytotoxicity tests, the molecules of the fluorescent probe disclosed by the invention are almost free of toxic action on cells; and shown by two-photon fluorescence microscopy imaging experiments, the molecules of the fluorescent probe disclosed by the invention have good cell permeability to MCF-7 cells, so that the fluorescent probe is applicable to the detection of presence of formaldehyde molecules in the cells.

Description

[0001] 1. Technical field [0002] The invention relates to a two-photon fluorescent probe, in particular to a ratio-type two-photon formaldehyde fluorescent probe and its preparation method and application. [0003] 2. Background technology [0004] As an active carbonyl substance (RCS), formaldehyde is a protoplasmic poison that destroys biological cell proteins, can cause damage to human skin, respiratory tract and internal organs, anesthetize human central nervous system, and can cause pulmonary edema, hepatic coma, kidney exhaustion etc. The World Health Organization confirms that formaldehyde is a teratogenic, carcinogenic substance, and is a source of allergies. Long-term contact will cause gene mutation, and is a potential strong mutagen. High levels of formaldehyde may contribute to many diseases, including heart disease, Alzheimer's disease and cancer. Therefore, it is of great significance to monitor formaldehyde in biological environment. How to detect them is ve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/14C09K11/06G01N21/64
CPCC07D215/14C09K11/06C09K2211/1029G01N21/6486
Inventor 孟祥明倪永兴郭蒙蒙朱满洲
Owner ANHUI UNIVERSITY
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