Two-photon fluorescence probe, and preparation method and application thereof

A two-photon fluorescence and probe technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of unfavorable modification, increase and expand its application, single use of two-photon fluorescent probes, etc., to achieve the improvement of molecular Planarity, expanding the scope of application, enhancing the effect of two-photon fluorescence

Active Publication Date: 2019-04-30
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In view of the deficiencies in the prior art above, the purpose of the present invention is to provide a two-photon fluorescent probe and its preparation method and application, aiming to solve the problem that the existing two-photon fluorescent probe has single use and is not conducive to increasing its expansion through modification. application problem

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  • Two-photon fluorescence probe, and preparation method and application thereof
  • Two-photon fluorescence probe, and preparation method and application thereof
  • Two-photon fluorescence probe, and preparation method and application thereof

Examples

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Embodiment 1

[0050] Example 1 Preparation, characterization and performance testing of the two-photon fluorescent probe 7-(diethylamino)-3-(4-hydroxyquinazolin-2-yl)coumarin.

[0051] (1) According to the reaction formula To prepare, the specific steps are: under air conditions, in a 100mL round bottom flask, add 10mmol of anthranilamide, 10mmol of 7-(diethylamino)coumarin-3-carbaldehyde, and then add wet dimethyl Sulfoxide (DMSO) 50mL, the reaction temperature is 100°C, after 10h, the materials in the reaction solution are poured into water, static phase separation, suction filtration, the obtained solid is further recrystallized with a mixed solvent of ethanol and water to obtain Two-photon fluorescent probe 7-(diethylamino)-3-(4-hydroxyquinazolin-2-yl)coumarin with a yield of 80%.

[0052] (2) According to the reaction formula To prepare, the specific steps are: under air conditions, in a 100mL round bottom flask, add 10mmol of anthranilamide, 10mmol of 7-(diethylamino)coumarin-3-ca...

Embodiment 2

[0059] The preparation, characterization and Performance Testing.

[0060] (1) According to the reaction formula Simply modify the two-photon fluorescent probe 7-(diethylamino)-3-(4-hydroxyquinazolin-2-yl)coumarin to prepare 7-(diethylamino)-3- (4-((4-nitrobenzyl)oxy)quinazolin-2-yl)coumarin, the specific steps are: in a 50mL round bottom flask, add two-photon fluorescent probe 7-(diethyl Amino)-3-(4-hydroxyquinazolin-2-yl)coumarin (0.5mmo, 180.7mg), p-nitrobenzyl bromide (1.0mmol, 216mg) and CsCO 3 (0.75mmol, 244.4mg), then add the solvent N,N-dimethylformamide (DMF) 3mL, stir under ice bath for 3h, then react at room temperature for 24h, TLC monitoring, until the reaction is complete, the reaction mixture Pour into ice water, filter with suction, dry, and then separate by column chromatography to obtain a two-photon probe with a yield of 20%.

[0061] (2) carry out NMR test to the two-photon fluorescent probe that this embodiment makes, its 1 H NMR spectrum as Figure...

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Abstract

The invention discloses a two-photon fluorescence probe, and a preparation method and an application thereof. The structural formula of the two-photon fluorescence probe is shown in the description; and in the structural formula, each of R1 and R2 is one selected from the hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, a hydroxyl group, an alkoxy group, an aminogroup, a dialkylamino group, a nitro group, a cyano group, an acyl group, a sulfonyl group, a phenyl group, a benzyl group, an aryl group, a substituted aryl group, a heterocyclic ring, an aromatic heterocyclic ring and a substituted aromatic heterocyclic ring, and R3 is one selected from the hydrogen atom, a benzyl group, a substituted benzyl group, alkyl silicon, a substituted acyl group, a sulfonyl group, a thioacyl group, an alkyl group, an allyl group, a propargyl group, an aryl group and an aromatic heterocyclic ring. The two-photon fluorescence probe adopts a quinazoline-coumarin structure as the center, so the molecular planarity is improved, and the two-photon fluorescence intensity and the two-photon imaging resolution are improved; the two-photon fluorescence probe can detect exogenous fluoride ions in cells; and the two-photon fluorescence probe can be simply modified to locate mitochondrial cell imaging and detect nitroreductase in the cells, so the application range is enlarged.

Description

technical field [0001] The invention relates to the technical field of organic functional molecular fluorescent probe imaging, in particular to a two-photon fluorescent probe and its preparation method and application. Background technique [0002] Bioimaging technology, especially bioluminescent imaging technology, has been widely used in life science research. Among them, the development of bioluminescent probe materials with high resolution and low toxicity is a current research hotspot in the field of bioimaging. The excitation wavelength of traditional single-photon fluorescent probes is usually in the visible region, which makes it prone to photobleaching when used in biological imaging, and is also interfered by autofluorescence in biological systems, while having a small tissue penetration depth (<100 μm ). Secondly, due to the low transmittance of short-wavelength light in vivo, the imaging resolution is relatively low, which affects the application of these si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/64
CPCC07D405/04C09K11/06C09K2211/1044C09K2211/1088G01N21/643
Inventor 黄静宋智彬李国瑞杨吉焕张雅雅
Owner HUNAN UNIV
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