Two-photon fluorescent probe as well as preparation method and application thereof

A two-photon fluorescence and probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of low sensitivity and detection concentration, and achieve the effect of low detection concentration, high sensitivity and simple operation

Active Publication Date: 2016-08-17
ANHUI UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims to provide a two-photon fluorescent probe and its preparation method and application. The technical problem to be solved is to select a suitable fluorescent probe structure through molecular design, so as to realize the qualitative detection of palladium ions in cells by two-photon imaging (II ), has the advantages of specific selectivity, high sensitivity, and low detection concentration, and the cytotoxicity test shows that the fluorescent probe of the present invention has almost no toxic effect on cells

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  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof
  • Two-photon fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: Fluorescent probe molecule RN 3 Synthesis

[0022] 1. Mix 7-((4-methoxyphenyl)acetylene)-3-carboxylic acid-coumarin (1g, 3mmol), 1-hydroxybenzotriazole (0.65g, 4.5mmol) and EDC·HCl (0.65g, 3.3mmol) into the Shrek bottle, add 30mL N,N-dimethylformamide under anhydrous and anaerobic conditions, stir at room temperature for 24h; after the reaction, add 50mL dichloromethane to dissolve the reactant , and then extracted 3 times with 30 mL of water to obtain an organic phase, which was distilled under reduced pressure and spin-dried to obtain intermediate 1;

[0023] 2. Put rhodamine B (2g, 4.16mmol) in a three-necked flask, add 100ml of ethanol and heat to reflux, after the rhodamine is completely dissolved, slowly add diethylenetriamine (0.646g, 6.26mmol) dropwise, and heat to reflux reaction for 24h; after the reaction is completed and down to room temperature, the intermediate 1 prepared in step 1 is added to the reaction solution, and stirred at room tempera...

Embodiment 2

[0024] Embodiment 2: Fluorescence test of fluorescent probe molecule

[0025] Dissolve the fluorescent probe molecule of the present invention in DMSO to prepare a 1 mM mother solution, take 250 μL of the mother solution in a 10 mL volumetric flask, and then dilute to volume with DMSO to prepare a 25 μM detection reagent. Add 1 times the equivalent of palladium ion (II) to the detection reagent, and visible ultraviolet light has an obvious absorption at about 550nm ( figure 2), detect the change of fluorescence spectrum in the range of 415-700nm, as time changes, it can be observed that the emission peak at 515nm is gradually weakened, and the emission peak at 575nm is gradually enhanced ( image 3 ).

[0026] When the flexible chain region is not chelated with palladium ion (II), the excitation wavelength of 395nm can provide energy for the coumarin group to fluoresce at 515nm. After chelating with palladium ion (II), the rhodamine group undergoes a ring-opening reaction du...

Embodiment 3

[0027] Example 3: Cell Imaging Test

[0028] 293FT cells were cultured with DEME (invitrogen) medium. One day before imaging, HeLa cells were placed in a flat-bottomed surface dish. During imaging, HeLa cells and 10 μM fluorescent probe RN 3 DMSO solution at 37°C, containing 5% CO 2 Incubate in a cell culture box for 0.5 hours, wash fully with neutral PBS buffer solution or culture medium, and use fluorescent confocal imaging to obtain Figure 4 . Add (10 μM) palladium ion (II) solution to the above-mentioned cell culture medium containing the fluorescent probe, at 37°C, containing 5% CO 2 Incubate in a cell culture incubator for 0.5 hours, wash thoroughly with neutral PBS buffer solution or culture medium, and perform two-photon fluorescence confocal imaging. It can be seen from the figure that before adding palladium ion (II), there is fluorescence at 515nm; after adding palladium ion (II), the fluorescence at 575nm is obviously enhanced, and the maximum emission peak of ...

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Abstract

The invention discloses a two-photon fluorescent probe as well as a preparation method and application thereof. The two-photon fluorescent probe takes coumarin and rhodamine as a matrix. The structure of the two-photon fluorescent probe is described in the specification. Molecules of the two-photon fluorescent probe show relatively high selectivity and sensitivity in a system in which palladium ions (II) and other positive ions coexist. A cytotoxicity test shows that the two-photon fluorescent probe disclosed by the invention has hardly any toxic effect on cells, and a two-photon fluorescence microscopy imaging experiment shows that the two-photon fluorescent probe has good HeLa cell permeability and is applicable to detection of distribution of palladium ions (II) in cells.

Description

1. Technical field [0001] The invention relates to a two-photon fluorescent probe, its preparation method and application. 2. Background technology [0002] Palladium and its compounds are effective catalysts for the synthesis of drug molecules, and palladium's excellent catalytic ability makes it widely used as a catalyst in organic synthesis. Palladium-catalyzed reaction is an effective catalyst for the synthesis of drug molecules and has been widely used, but a large amount of palladium will remain in the final product, which will enter the human body with the administration of drugs. In automotive catalytic converters, palladium is used to catalyze the conversion of harmful gases and reduce waste emissions. Unfortunately, palladium will also be released into the environment along with the exhaust gas, increasing the content of palladium in the environment, thereby increasing the risk of entering the human body. At the same time, palladium ions can interact with biomacr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1088G01N21/6428
Inventor 孟祥明韦新洁朱满洲邵宗龙
Owner ANHUI UNIVERSITY
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