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No-clean aggregation-induced cell membrane targeted dyeing reagent based on purine skeleton, preparation method and application thereof

A technology of aggregation induction and dyeing reagents, applied in the preparation of test samples, styrene-based dyes, chemical instruments and methods, etc., can solve the problems of low accuracy of imaging results, complicated operation process, and inability to connect sensing, etc., to achieve Avoid the interference of background light, the raw materials are economical and easy to obtain, and the overall cost is low

Active Publication Date: 2019-05-07
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a purine skeleton-based no-wash aggregation-inducible cell membrane targeting staining reagent and its preparation method and application to solve the problem of the existing cell membrane phospholipid molecular layer targeting dyes due to the need for multiple washings. The process is complicated, time-consuming, the accuracy of imaging results is low, and the problem of inability to connect to sensing

Method used

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  • No-clean aggregation-induced cell membrane targeted dyeing reagent based on purine skeleton, preparation method and application thereof
  • No-clean aggregation-induced cell membrane targeted dyeing reagent based on purine skeleton, preparation method and application thereof
  • No-clean aggregation-induced cell membrane targeted dyeing reagent based on purine skeleton, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] The preparation method of the purine skeleton-based aggregation-inducible cell membrane targeting staining reagent of this embodiment comprises the following steps:

[0068] (1) Synthesis of the first intermediate: 2,6-dichloro-9-n-propyl-9-hydrogen-purine

[0069] The synthetic route is as follows:

[0070]

[0071] 2,6-Dichloropurine (1.0 mmol), 1-bromopropane (1.5 mol) and potassium carbonate (3.0 mmol) were mixed and stirred in DMSO (5 mL) for 6 hours, then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extracts were washed with brine and treated with Na 2 SO 4 dry. After the solvent was removed and distilled under reduced pressure, it was purified by 200-300 mesh silica gel column chromatography. Elution with petroleum ether / ethyl acetate (3:2) gave the first intermediate as a white solid with a yield of 57%. The eluent is ethyl acetate / petroleum ether=2:3 (V / V). Fi...

Embodiment 2

[0090] This example is basically the same as Example 1, except that the third intermediate R is changed 3 The substituent, its synthetic route is as follows:

[0091]

[0092]After adding the third intermediate (381 mg, 1 mmol) and 1,4-lutidine-1-iodide (235 mg, 1 mmol) in ethanol (10 mL), piperidine (0.05 mL) was dropped into the stirring liquid. Then the mixture was stirred at room temperature for about 12 hours. After the completion of the reaction was monitored by thin-layer chromatography, the solvent was removed by rotary evaporation, and then dissolved with saturated potassium hexafluorophosphate acetone solution (10 mL). After stirring at room temperature for 2 hours, the acetone was distilled off under reduced pressure, and then the crude product was obtained by filtration. The crude product was purified by neutral alumina column chromatography. Elution with methanol / dichloromethane=20 / 1 (V:V) gave a yellow solid with a yield of 37%.

[0093] 1 H NMR (400MHz, D...

Embodiment 3

[0096] This example is basically the same as Example 1, except that the picoline salt in step (4) is changed to 4-methyl-1-(3-(trimethylammonium) propyl)pyridinium-1-ammonium bromide , its synthetic route is as follows:

[0097]

[0098] A dark brown solid was obtained in 33% yield. 1 H NMR (400MHz, DMSO-d 6 )δ9.23-9.20(d,1H),9.09-9.03(m,3H),8.71-8.69(s,1H),8.62-8.57(d,2H),8.37-8.33(d,2H),8.20- 8.14(d,1H),8.02-7.98(d,2H),7.74-7.67(m,2H),7.47-7.42(t,1H),7.34-7.28(t,1H),6.95-6.93(d,1H ),4.65-4.60(t,2H),4.40-4.34(t,2H),3.11-3.7(s,9H),1.99-1.92(m,2H),0.89-0.83(t,3H). 13 C NMR (101MHz, DMSO-d 6 )δ157.08,154.10,153.50,149.06,146.25,145.04,140.83,139.78,137.37,135.68,130.69,129.15,129.00,128.93,124.83,124.58,124.36,123.26,121.57,121.29,116.71,109.99,108.61,62.25,57.24 ,52.91,45.50,24.47,23.06,11.51.HRMS(ESI):m / z:Calcd for C 35 h 39 f 6 N 7 P + :702.2903; [M-PF 6 ] + Found: 702.2902.

[0099] The hydrogen spectrum, carbon spectrum and high-resolution mass spectrum of t...

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Abstract

The invention discloses a no-clean aggregation-induced cell membrane targeted dyeing reagent based on a purine skeleton, a preparation method and application thereof. According to the invention, the purine skeleton is adopted as the basis of a cell membrane dye, and through reasonable regulation design of lipid-soluble end and hydrophilic end, the cell membrane targeted dyeing reagent based on thepurine skeleton can be obtained. The reagent can stagnate on the cell membrane for a long time at the same time of targeted dyeing, and is beneficial to long-term monitoring. In addition, as the dyeing reagent has the characteristics of aggregation-induced compounds, emits weak or no light in good solvents and emits strong fluorescence in poor solvents, the dye also has the specific performance of no clean. The preparation method provided by the invention has the characteristics of high yield and mild reaction conditions, and the prepared dyeing reagent has large Stokes shift and high targeting ability.

Description

technical field [0001] The invention relates to the field of biochemistry, in particular to the technical field of biomembrane targeted staining, in particular to a purine skeleton-based wash-free aggregation-inducible cell membrane targeted staining reagent and its preparation method and application. Background technique [0002] The cell membrane (also known as the plasma membrane or cytoplasmic membrane), consisting of a phospholipid bilayer with intercalated proteins, is a biological membrane that separates the interior of a cell from its external environment and protects the cell from its environment. important components of cells. It has been shown to be involved in various cellular processes and biological functions, such as cell migration, cell spreading, phagocytosis, endocytosis, exocytosis, and selective permeability of substances. Cell membrane abnormalities are important markers of poor cell status and various diseases. Therefore, the development of highly sel...

Claims

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Application Information

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IPC IPC(8): C09B23/14C09K11/06G01N1/30G01N21/64
CPCC07D473/00C07D473/34C09B23/14C09K11/06G01N1/30G01N21/64
Inventor 李坤石磊余孝其刘艳红于抗抗
Owner SICHUAN UNIV
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