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Biotin derivative of phenylephrine and preparation method and application thereof

A technology of phenylephrine and biotin derivatives, which is applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of inability to visualize the dynamic process of cells, lack of such problems, and achieves reduction of intermediate steps, reduction of steric hindrance, and simple operation. Effect

Inactive Publication Date: 2013-04-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous studies, probes composed of prazosin derivatives and quantum dots were synthesized for localizing cell surface α in living cells. 1 - Epinephrine, but cannot visualize dynamic processes inside cells
The lack of probes that can track dynamic processes in receptor cells limits the study of receptor mechanism of action

Method used

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  • Biotin derivative of phenylephrine and preparation method and application thereof
  • Biotin derivative of phenylephrine and preparation method and application thereof
  • Biotin derivative of phenylephrine and preparation method and application thereof

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preparation example Construction

[0037] A preparation method of a biotin derivative of phenylephrine, the reaction scheme is as follows:

[0038]

Embodiment 1

[0040] Diisomeric Polyethylene Glycol H 2 Synthesis of N-PEG-COOH

[0041] Add 2.2mL of potassium hexamethyldisilazide and 4.5mL of ethylene oxide into a dry and sealed one-necked bottle, dissolve in 18mL of anhydrous tetrahydrofuran, stir, and react in ice bath for 24 hours, then add 0.50g of succinic anhydride , continue to react for 5-6 hours, finally add excess glacial acetic acid, avoid light and stir for 3-4 hours, drop the reaction solution into a large amount of ether to settle three times, and dry the obtained solid in vacuum at 40°C for 24 hours to obtain a brown solid 3.64 g, yield 95.6%.

Embodiment 2

[0043] Synthesis of t-Boc-phenylephrine

[0044] Protect the amino group of phenylephrine: add 1.21g (6mmol) of phenylephrine hydrochloride to a 25mL single-necked bottle, dissolve with 7mL of 2M NaOH solution, stir with a magnet for 20 minutes and put it in an ice bath. Dissolve 1.47g (6.7mmol) of di-tert-butyl dicarbonate in 1mL of tetrahydrofuran to form a solution, and slowly drop the solution into a one-necked flask with a constant pressure dropping funnel, and accelerate the stirring. Remove the ice bath after the dropwise addition, stir at room temperature, follow the reaction by TLC (thin-layer chromatography analysis), and complete the reaction in 24 hours. Adjust the reaction solution to pH=7 with glacial acetic acid, extract with 15mL×3 dichloromethane, and evaporate to dryness In the dichloromethane layer, 1.39 g of a yellow viscous product was obtained, yield: 91.6%.

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Abstract

The invention discloses a biotin derivative of phenylephrine and a preparation method and application thereof. The method includes: firstly, the synthetization of double-different-end polyethylene glycol; and secondly, the synthetization of piperazine derivative of phenylephrine; and thirdly, the synthetization of biotinylation of piperazine derivative of phenylephrine. The biotin derivative of phenylephrine and preparation method and application thereof discloses the application of the biotin derivative of phenylephrine as a fluorescence probe. The method firstly synthetizes the biotin derivative capable of being used to be connected with the biotin derivative of phenylephrine of alpha I adrenergic receptor agonist of streptavidin quantum dots, reserves the pharmaceutical activity part of the biotin derivative, and provides a tool for the future application of quantum dots in the research field of alpha I adrenergic receptor. Using PEG to connect alpha I adrenergic receptor agonist with biotin, the nonspecific adsorption of quantum dots and the steric hindrance generated after connected with the agonist are reduced. Because of continuous charging, the method is simple and effective, simple in operation, and good in purification effect. The structural formula is shown in the description, and n=25-60.

Description

technical field [0001] The present invention relates to a biotin derivative, in particular to an α 1 A biotin derivative of an adrenergic receptor agonist phenylephrine and its preparation method and application, especially a method of using polyethylene glycol to connect the agonist phenylephrine and biotin, belongs to medicinal chemistry, organic synthesis chemistry, field of polymer chemistry. Background technique [0002] Receptors are therapeutic targets for many drugs. The study of the interaction mechanism between receptors and drugs is of great significance for the interpretation of pathogenesis and the development of drugs. The interaction between receptors and drugs mainly occurs inside the cell or in the process of entering the interior from the cell surface. The study of these processes requires tracing the receptors in living cells. Early studies used radioligand labeling or fluorescent labeling methods to track receptors. Although these labeling methods ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/334C08G65/26C09K11/06
Inventor 王磊姜玮周国桁马婧
Owner SHANDONG UNIV
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