Method for synthesizing mitochondria targeted spinning scavenger MitoPBNs (spinning probe)

A synthesis method and compound technology are applied in the field of synthesizing mitochondria-targeted spin trapping agent MitoPBN (spin probe) series compounds, which can solve the problems of low product purity, cumbersome preparation procedures, harsh reaction conditions and the like, and achieve cheap raw materials. The effect of easy availability, high product purity, and short synthesis steps

Inactive Publication Date: 2010-12-08
刘珊林
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0007] This route requires the use of iodo compounds and metal hydrides, which have the disadvantages of expensive raw materials, harsh reaction conditions, cumbersome preparation procedures, low yields, and low product purity, which severely limit the research in this field.
And there is no liposome treatment that can detect and intervene in the intracellular redox microenvironment

Method used

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  • Method for synthesizing mitochondria targeted spinning scavenger MitoPBNs (spinning probe)
  • Method for synthesizing mitochondria targeted spinning scavenger MitoPBNs (spinning probe)
  • Method for synthesizing mitochondria targeted spinning scavenger MitoPBNs (spinning probe)

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Embodiment M

[0022] Synthesis of Example MitoPBN

[0023] 1) Synthesis of 4-(4-bromobutoxy)benzaldehyde: Add 2.0 grams (16.4mmol) of p-hydroxybenzaldehyde in a 250mL reaction flask, 4.5 grams (32.8mmol, 2eq) of anhydrous potassium carbonate, and 2.5mL of 1,4-Dibromobutane and 50 ml of DMF were reacted for 12 hours, the reaction solution was poured into 150 ml of ice water, extracted with ethyl acetate (50 ml x 4), the organic phases were combined and washed once with 100 ml of water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain a concentrated crude product. The crude product was separated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether=1 / 3). 3.1 g of the product was obtained with a yield of 73%. 1 H NMR (400MHz, CDCl 3 ): δ9.84(s, 1H), 7.78(d, J=5.6Hz, 2H), 6.95(d, J=3.2Hz, 2H), 4.04(t, 2H), 3.46(t, 2H), 2.01 -2.05 (m, 2H), 1.93-1.97 (m, 2H).

[0024] 2) Synthesis of quate...

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Abstract

The invention discloses a method for preparing a mitochondria targeted spinning scavenger MitoPBNs (spinning probe). The structural formula of the MitoPBN is shown in a formula (I). A synthesis flow is shown in the formula (II), and comprises the following steps of: performing elimination reaction on 4-hydroxybenzaldehyde and dibromo-straight-chain paraffin under alkali condition to prepare a compound 3; reacting the compound 3 with triphenylphosphine to prepare the compound 4; in ethanol, mixing the compound 4, 2-nitro-2-methylpropane, a 4A molecular sieve and zinc powder in a solvent, adding dropwise a glacial acetic acid, stirring and reacting the mixed solution at room temperature, placing the mixed solution in a refrigerator for refrigeration, and performing separation and purification to prepare the spinning probe MitoPBN; and performing liposome packing treatment. The method has the characteristics of relatively fewer synthesis steps, low raw material cost, readily available raw materials and relatively higher product purity. The probe for scavenging free radical signals can enter cell mitochondria.

Description

technical field [0001] The invention relates to a simple and practical preparation method of MitoPBN series compounds. The invention has the characteristics of short synthesis steps, cheap and easy-to-obtain raw materials, and relatively high product purity. Its function can enter the probe that captures the free radical signal into the mitochondria of the cell, and through the detection of the probe conjugate, it can observe and analyze the change information of the redox microenvironment of the cell early, and can intervene early. Thus, the early warning of the lesion and the early prevention and treatment of the disease can be realized. Background technique [0002] Oxygen- and nitrogen-containing free radicals (ROS and RNS) are constantly produced in the body, and they play an extremely important role in life activities. Under physiological conditions, free radicals in the body are constantly produced and eliminated, so that the concentration of free radicals remains in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54G01N33/50
Inventor 施冬云王东林刘珊林
Owner 刘珊林
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