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Carbazolyl two-photon fluorescent probe and preparation method and application thereof

A two-photon fluorescence, carbazole-based technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of few reports of two-photon fluorescent probes, and achieve simple structure, high sensitivity, and detection limit. low effect

Active Publication Date: 2018-09-04
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One-photon fluorescent probes using carbazole as a fluorophore have been reported in many literatures, but there are relatively few literature reports as two-photon fluorescent probes

Method used

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  • Carbazolyl two-photon fluorescent probe and preparation method and application thereof
  • Carbazolyl two-photon fluorescent probe and preparation method and application thereof
  • Carbazolyl two-photon fluorescent probe and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of fluorescent probe molecule Lyso-DCHO

[0029] 1. Synthesis of Intermediate 1

[0030] A mixture of KOH (2.0g, 35.8mmol), KI (0.4g, 2.39mmol) and 1,4-dibromobutane (7.73g, 35.8mmol) was heated to 60°C, and 3,6 -diiodocarbazole (10g, 23.9mmol), continue to heat and reflux for 12 hours; cool to room temperature after the reaction, add 200mL H 2O, the mixture was extracted with dichloromethane (100 mL×2), and the organic phase was evaporated to give a crude residue, which was purified by column chromatography (petroleum / dichloromethane = 10:1 as eluent) to give intermediate 1, 6.8 g, yield 51.4%.

[0031] 2. Synthesis of Intermediate 2

[0032] Intermediate 1 (1g, 1.8mmol), 4-ethynylbenzaldehyde (0.7g, 5.4mmol), Pd 2 (PPh 3 ) 2 Cl 2 (5.1mg, 0.007mmol), CuI (2.7mg, 0.014mmol) and Et 3 N (5 mL) was stirred and reacted at 30° C. for 12 hours under anhydrous and anaerobic conditions. After the reaction was completed, it was cooled to room ...

Embodiment 2

[0036] Embodiment 2: the spectroscopic test of fluorescent probe molecule

[0037] Dissolve the two-photon fluorescent probe of the present invention in DMSO to prepare a 1mM mother solution, take 100 μL of the mother solution in a 10mL volumetric flask, and then use a solvent of DMSO:PBS (v / v)=1:1 to make up the volume to prepare 10 μM detection reagent. The detection reagents have absorption peaks at 313nm and 373nm respectively; with the addition of Cys, the absorption peak of Lyso-DCHO at 373nm gradually decreases, and the absorption peak at 313nm gradually increases. When Cys is added to 4.5 times the equivalent, the absorbance at 313nm reaches saturation ( figure 2 ). 10μM detection reagent added 8 times the equivalent of other amino acids, various anions and metal cations for 20min ( image 3 a), detection of fluorescence spectrum changes in the range of 350-700nm, it can be seen that Lyso-DCHO only has obvious fluorescence changes to Cys, and has a specific response...

Embodiment 3

[0038] Example 3: Two-photon performance test of fluorescent probe molecules before and after adding Cys

[0039] Using the two-photon induced fluorescence measurement technique, the two-photon effective absorption cross-section of the fluorescent probe molecule (Lyso-DCHO) was tested. Lyso-DCHO has a maximum two-photon effective absorption cross-section of 58GM at 760nm, and the maximum at 720nm after adding Cys The value becomes 45GM. It shows that the probe can be applied to two-photon confocal imaging.

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Abstract

The invention discloses a carbazolyl two-photon fluorescent probe and a preparation method and application thereof. The carbazolyl two-photon fluorescent probe uses carbazole as a matrix and adopts astructural formula as follows: FORMULA. The two-photon fluorescent probe molecule shows specific response and high sensitivity in a system in which cysteine (Cys) coexists with other interfering reagents. Cytotoxicity tests show that the probe has almost no toxic and side effects on cells; in addition, the two-photon confocal fluorescent microscopic imaging experiments show that the fluorescent dye Lyso-DCHO has good permeability to an MCF-7 cell, can effectively position a lysosome in the cell (positioning coefficient is 0.90), and is suitable for visual detection of the Cys in the cytolysosome.

Description

technical field [0001] The invention relates to a carbazole-based two-photon fluorescent probe and its preparation method and application, to realize two-photon confocal imaging to visually detect Cys in cell lysosomes, and has the advantages of high selectivity, high sensitivity and low detection limit . Background technique [0002] Amino acid is the most basic substance that constitutes the protein of organisms and is related to life activities, and has a close relationship with the life activities of organisms. Among them, cysteine ​​(Cys), as one of the essential amino acids for the human body, is one of the 20 amino acids involved in protein synthesis, and is also one of the three amino acids that build important glutathione. And Cys play important roles in many key cellular functions. For example, protein synthesis, detoxification and metabolism etc. Lysosome is an acidic organelle in eukaryotic cells, which can play a role in digestion, defense and regulation of h...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033G01N21/6486
Inventor 冯燕黄银亮王文娟李长虎汪啸周虎祖润奇
Owner ANHUI UNIVERSITY
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