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Chlorochromone acylhydrazone derivative based on rhodamine B as parent and application of derivative as fluorescence probe

A chromone acylhydrazone, fluorescent probe technology, applied in biological testing, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of long copper ion time, shorten detection time, etc., achieve high sensitivity, speed up detection, penetration Sex-enhancing effects

Inactive Publication Date: 2012-01-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The inventor’s prior patent [201110087413.4] contained 6-methoxy-4-oxo-4H-3-formyl-benzopyran and rhodamine B acylhydrazone derivatives as fluorescent probes to detect HeLa cells Insufficient copper ion time is long, further modification is needed to improve its membrane permeability and shorten the detection time

Method used

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  • Chlorochromone acylhydrazone derivative based on rhodamine B as parent and application of derivative as fluorescence probe
  • Chlorochromone acylhydrazone derivative based on rhodamine B as parent and application of derivative as fluorescence probe
  • Chlorochromone acylhydrazone derivative based on rhodamine B as parent and application of derivative as fluorescence probe

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Experimental program
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Embodiment 1

[0023] The reaction process of the chlorochromone acylhydrazone derivatives of rhodamine B synthetic rhodamine B is shown in the following formula:

[0024]

[0025] The specific preparation method is as follows:

[0026] Add 1g Rhodamine B (1) (2.1mmol) and 2.7g 80wt% hydrazine hydrate (43mmol) into 12mL of absolute ethanol, heat to reflux, and continue the reaction for about three hours. After the reaction is complete, reduce the temperature and concentrate under reduced pressure to remove the solvent. Add 40mL of water and 40mL of ethyl acetate to the mixture, shake and extract, continue to extract the water phase twice with ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter with suction, and concentrate under reduced pressure to remove the solvent to obtain khaki-yellow Rhodamine B Hydrazide (2) 0.95g, melting point: 166-170°C, yield: 97%.

[0027] H NMR spectrum determination: 1 H NMR (CDCl 3 , 400MHz), δ (ppm): 1.17 (t, 12H, NCH...

Embodiment 2

[0033] Add 10 equiv. Na + , Mg 2+ , Al 3+ , K + , Ca 2+ , Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ , Zn 2+ , Ag + , Cd 2+ , Ba 2+ , Pb 2+ , Hg 2+ and Cu 2+ The ionic water solution was tested by UV-Vis spectrophotometry and fluorescence spectrophotometry respectively.

[0034] The results show that the chlorochromone acylhydrazone derivatives of rhodamine B show better selectivity to divalent copper ions, and the contrast before and after adding copper ions shows a stronger fluorescence enhancement effect (see image 3 ).

Embodiment 3

[0036] Intracellular fluorescence imaging test:

[0037] A: use copper chloride, B: use copper nitrate. Control group 1 in each group of A and B: HeLa cells added with 10 μM rhodamine B chlorochromone acylhydrazone derivatives were cultured at 37°C for one hour; control group 2: HeLa cells added with 50 μM copper ions in the culture medium Incubate at 37°C for two hours, and then treat with the chromone acylhydrazone derivative of rhodamine B under the same conditions as the control group. Fluorescence imaging showed that the chlorochromone acylhydrazone derivatives of rhodamine B penetrated into cells well. Control group 1 showed no fluorescence, and control group 2 showed strong fluorescence in cells.

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Abstract

The invention discloses a chlorochromone acylhydrazone derivative based on rhodamine B as a parent and application of the derivative as a fluorescence probe. The structure formula of the chlorochromone acylhydrazone derivative related in the invention is shown in a formula (I). Compared with the existing similar compounds, the chlorochromone acylhydrazone derivative in the invention is enhanced in membrane permeability, can selectively act with a cupric ion so as to turn colorless to red, has fluorescence enhancement effect, can realize naked eye discrimination and detection, and can also be used for analysis through ultraviolet absorption and fluorophotometric methods. According to the invention, the trace detection of the cupric ion can be realized, thus the chlorochromone acylhydrazone derivative has high sensitivity.

Description

technical field [0001] The invention relates to a chlorochromone acylhydrazone derivative with rhodamine B as a matrix and its application as a fluorescent probe in detecting divalent copper ions. Background technique [0002] Rhodamine B has a large molar extinction coefficient and a high quantum yield, and is often modified for fluorescent probe research and used as a labeled biomolecule. In recent years, the use of fluorescence enhancement effect to detect metal ions in living cells has been continuously developed. [0003] Divalent copper ion is a heavy metal ion widely present in the environment and living organisms, and is an essential trace element for the human body. The existence of appropriate amount of copper ions can maintain the normal function of important proteins such as cytochrome oxidase, zinc, copper superoxide dismutase, lysyl oxidase and so on. Disruption of the metabolic balance of copper ions in human cells may lead to diseases such as Menkes syndrom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N33/52
Inventor 赵宝祥苗俊英刘为永李海英
Owner SHANDONG UNIV
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