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ATP (adenosine triphosphate) multisite binding fluorescence-enhanced type probe molecule and preparation method and application thereof

A technology of fluorescent molecular probes and derivatives, applied in the field of fluorescent probes, can solve the problems of high response concentration and poor mitochondrial targeting, and achieve the effects of simple synthesis method, easy large-scale synthesis, and good application value

Active Publication Date: 2019-03-12
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current fluorescent probes for ATP lack selectivity to specific biological anions, require high response concentrations, and have poor mitochondrial targeting.

Method used

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  • ATP (adenosine triphosphate) multisite binding fluorescence-enhanced type probe molecule and preparation method and application thereof
  • ATP (adenosine triphosphate) multisite binding fluorescence-enhanced type probe molecule and preparation method and application thereof
  • ATP (adenosine triphosphate) multisite binding fluorescence-enhanced type probe molecule and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A method for synthesizing an ATP fluorescent probe containing a secondary amine segment and a rhodamine derivative (Rh-NH-PBA) modified with phenylboronic acid, the specific preparation steps of which are:

[0042] (1) Add 1.0mmol Rhodamine 6G (0.48g) into a 100mL three-neck flask filled with 15mL of absolute ethanol and stir to dissolve completely, then add 1g of diethylenetriamine (10.0mmol) dropwise, and stir and reflux at 90°C for 32h , until the color of the solution becomes lighter, the reaction is terminated, and the solvent is removed by rotary evaporation after cooling to room temperature, then water and dichloromethane are added for extraction and washing 2 times (20mL water and 30mL dichloromethane are shared), and organic matter after 2 extractions and washings is collected. phase, and the solvent was removed by rotary evaporation, and the mixture of dichloromethane and ethanol with a volume ratio of 6:0.2 to 6:0.8 (gradient elution, adjust the volume ratio of ...

Embodiment 2

[0047] A method for synthesizing an ATP fluorescent probe containing a secondary amine segment and a rhodamine derivative (Rh-NH-PBA) modified with phenylboronic acid, the specific preparation steps of which are:

[0048] (1) Add 1.0mmol Rhodamine B (0.48g) into a 100mL three-necked flask filled with 15mL of absolute ethanol and stir to dissolve completely, then add 1g of diethylenetriamine (10.0mmol) dropwise, and stir and reflux at 90°C for 32h , until the color of the solution becomes lighter, the reaction is terminated, and the solvent is removed by rotary evaporation after cooling to room temperature, then water and dichloromethane are added for extraction and washing 3 times (20mL water and 30mL dichloromethane are shared), and the organic matter after 3 times of extraction and washing is collected. phase, and the solvent was removed by rotary evaporation, and the mixture of dichloromethane and ethanol with a volume ratio of 6:0.2 to 6:0.8 (gradient elution, adjust the vo...

Embodiment 3

[0053] Rhodamine derivatives Rh6G-NH-PBA and RhB-NH-PBA containing secondary amine segments and phenylboronic acid modification prepared in Examples 1 and 2 were used as ATP fluorescent probes for research.

[0054] Rh6G-NH-PBA and RhB-NH-PBA were respectively dissolved in EtOH to prepare Rh6G-NH-PBA stock solution and RhB-NH-PBA stock solution with a concentration of 1 mM. Dissolve adenosine triphosphate (ATP), guanosine monophosphate (GMP), sodium pyrophosphate (SDP), adenosine-5-phosphate (AMP), uridine 5'-triphosphate (UTP) in distilled water , adenosine (ADS), sodium dihydrogen phosphate (H 2 PO 4 - ), disodium hydrogen phosphate (HPO 4 2- ), sodium phosphate (PO 4 3- ), sodium chloride (Cl - ), sodium sulfate (SO 4 2- ), sodium nitrate (NO 3 - ), sodium carbonate (CO 3 2- ) to make a stock solution with a concentration of 10 mM. A certain volume (can be 0, that is, no addition) of stock solution of at least one analyte was added to 50 μL Rh6G-NH-PBA stock s...

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly discloses a ATP (adenosine triphosphate) multisite binding fluorescence-enhanced type probe molecule based on rhodamine derivatives and a preparation method and application thereof. The preparation method comprises the following steps of introducing a polyamine compound and aldehyde-containing boric acid into a rhodamine system, so as to obtain multiple ATP multisite binding fluorescent probes with simple structures. The synthesized fluorescent probe has the advantages that by the ATP multisite binding (interaction of ions, interaction of other hydrogen bonds, action of covalence bonds, and stacking action of phi-phi), the spiral structure of the rhodamine is induced for ring opening at high efficiency, the strong fluorescence can be produced, and the fluorescent probe can be used for selectively identifying the ATP at high efficiency, without the interference by other phosphate ions; the fluorescent probe can be used for selectively marking A375 cell mitochondria, and be used as a specific mitochondria targeting fluorescent probe; the synthesized fluorescent probe can be used for monitoring the change of ATP concentration of the A375 cell mitochondria in real time via the fluorescence imaging.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to an ATP multi-site binding fluorescence-enhanced probe molecule and its preparation method and application. Background technique [0002] ATP plays a very important role in many biological processes, especially mitochondrial ATP concentration is essential in the regulation of cellular energy status. ATP concentration is widely used in food quality and cell viability detection. Therefore, the selective recognition of ATP in mitochondria and the real-time monitoring of ATP concentration have become particularly important, and have become one of the important topics studied by the majority of scientific researchers. However, most of the current fluorescent probes for ATP lack selectivity to specific biological anions, require high response concentrations, and have poor mitochondrial targeting. For this reason, few fluorescent probes have been successfully used for mitoch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/6456
Inventor 许泽军刘亚楠张道洪张俊珩程娟
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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