Amide derivative neutral mitochondrial fluorescent marker and its preparation method and application

A technology of amide derivatives and fluorescent markers, applied in the field of fluorescent markers, achieves good biodescriptiveness, great scientific significance and commercial value, and solves the effect of uncertainty in organelle targeting ability

Active Publication Date: 2022-02-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the above-mentioned technical problems, the object of the present invention is to provide an amide derivative neutral mitochondrial fluorescent marker and its preparation method and application. The present invention provides an amide derivative with excellent mitochondrial targeting ability. Sexual dye targeting mitochondria does not depend on the negative charge on the inner mitochondrial membrane, which solves the shortcomings of existing cationic mitochondrial dyes

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  • Amide derivative neutral mitochondrial fluorescent marker and its preparation method and application
  • Amide derivative neutral mitochondrial fluorescent marker and its preparation method and application
  • Amide derivative neutral mitochondrial fluorescent marker and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] The general procedure for the synthesis of dyes 2a-e is as follows:

[0066] Take compound 2 (1.0 mmol, 357.2 mg), one of the amide compounds 1a-e (1.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride ( Pd(dppf)Cl 2 , 0.03 mmol, 22 mg) and potassium phosphate (K 3 PO 4 , 2.5 mmoles, 557.5 mg) were dissolved in 15.0 milliliters of 1,4-dioxane (1,4-dioxane) solvent; then the reaction system was replaced three times by nitrogen, then refluxed for 8 to 10 hours, and TLC detected the reaction progress; After cooling down to room temperature, the reacted mixture was suction filtered, and the filtrate was removed from the solvent by a rotary evaporator, and purified by column chromatography (eluent: dichloromethane / methanol (100 / 1, v / v)) after separation. Dye 2a-e.

[0067] Specifically, the specific synthetic raw materials, yields, and structural characterization results of each product are as follows:

[0068] Dye 2a (262.0 mg) was prepared from compoun...

Embodiment 2

[0074] The general procedure for the synthesis of dyes 3a-e is as follows:

[0075] Take compound 3 (0.5 mmol, 222.1 mg), one of the amide compounds 1a-e (0.6 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride ( Pd(dppf)Cl 2 , 0.015 mmol, 12 mg) and potassium acetate (AcOK, 1.5 mmol, 334.5 mg) were dissolved in 15.0 ml of 1,4-dioxane (1,4-dioxane) solvent; then the reaction system was replaced by nitrogen three times , heated at 95° C. for 10-12 hours, and TLC detected the reaction progress; after cooling down to room temperature, the reacted mixture was suction-filtered, and the filtrate was removed from the solvent by a rotary evaporator, and column chromatography (eluent: dichloromethane / Methanol (50 / 1, v / v)) gave pure dye after separation.

[0076] Specifically, the specific synthetic raw materials, yields, and structural characterization results of each product are as follows:

[0077] Dye 3a (65.5 mg) was prepared from compound 3 (0.5 mmol, 222.1 mg) a...

Embodiment 3

[0083] The above-mentioned prepared dyes 2a-2e, 3a-e (concentration is 10 μM) were tested for photostability, first weighed the corresponding mass of dyes 2a-2e, 3a-e and reference coumarin and Nile red, and weighed them They were respectively dissolved in acetonitrile (concentration: 10 μM), and all samples were irradiated with a Philips iodine-tungsten lamp (500 W), and the distance between the lamp and the sample was set at 25 cm. Place an 8cm thick NaNO between the lamp and the sample 2 (60g.L -1 ) cold trap to remove heat and short wavelength light. Continuous irradiation for 6 hours, in which a UV fluorescence test is performed every half hour. After six hours, the photostability is calculated according to the change of the absorption intensity at different times before and after irradiation to calculate the remaining absorption rate. like figure 2 and image 3 As shown, the residual absorption of coumarin after continuous irradiation for 6 hours is 94%, and the rel...

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Abstract

The invention relates to a series of neutral mitochondrial fluorescent markers of amide derivatives and their preparation methods and applications. The invention discloses for the first time that neutral dyes linked with amide compounds have excellent mitochondrial targeting ability. The invention solves the problem of the uncertainty of the organelle targeting ability of the existing neutral fluorescent dyes and the problems that the neutral dyes are commercial markers of lipid droplets in cells. While improving the optical performance of the fluorescent dye, the invention regulates the cell organelle targeting ability of the original dye through the creative modification of its structure, and the biological performance of the dye after being linked with an amide compound is obviously improved. Amide compounds are cheap and easy to obtain, which is beneficial to control the cost of new dyes, and has great scientific significance and commercial value.

Description

technical field [0001] The invention relates to fluorescent marker technology, in particular to an amide derivative neutral mitochondrial fluorescent marker and its preparation method and application. Background technique [0002] Mitochondria is an organelle surrounded by two membranes that exists in most cells. It is a structure that produces energy in cells and is the main place for cells to carry out aerobic respiration. In addition to serving as the main place for aerobic respiration and providing energy for cells, it also participates in important physiological activities such as cell genetic material transfer and cell differentiation, and has the ability to regulate cell growth and cell cycle. Therefore, in scientific research, real-time monitoring of mitochondria is particularly important. Among various technical means, fluorescent labeling technology stands out because of its advantages of simple operation and low preparation cost. Various fluorescent probes and d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C07D265/38C07D405/04C07D413/04C09K11/06G01N21/64
CPCC07D311/16C07D265/38C07D405/04C07D413/04C09K11/06G01N21/6458C09K2211/1088C09K2211/1033C09K2211/1029G01N33/533G01N33/582
Inventor 葛健锋马威孙如
Owner SUZHOU UNIV
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