Unlock instant, AI-driven research and patent intelligence for your innovation.

Malachite green derivatives with double protein activation sites as well as synthesis method and application of malachite green derivatives

A technology of malachite green and derivatives, applied in the field of dyes, can solve the problems of reducing non-specific labeling, inability to complete and eliminate

Pending Publication Date: 2021-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two types of compounds can reduce the background fluorescence of non-specific labeling to a certain extent when applied to cell labeling imaging, but they still cannot completely eliminate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Malachite green derivatives with double protein activation sites as well as synthesis method and application of malachite green derivatives
  • Malachite green derivatives with double protein activation sites as well as synthesis method and application of malachite green derivatives
  • Malachite green derivatives with double protein activation sites as well as synthesis method and application of malachite green derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Malachite green derivatives (R 1 =N,N-Dimethyl, R 2 = R 4 = H, R 3 =methoxy group, X=O, Y=carbonyl) preparation, the basic synthesis process is as follows:

[0067] Mix 180mg of 2-formyl-5-methoxybenzoic acid, 485mg of N,N-dimethylaniline, and 22mg of copper bromide, stir and react at 120°C for 5 hours, then cool down to room temperature, and purify by silica gel column chromatography to obtain 150mg target compound. The H NMR spectrum of the synthesized dye is as figure 1 Shown; NMR spectrum as figure 2 As shown, the specific data are as follows:

[0068] 1 H NMR (400MHz, CDCl 3 )δ7.39(d, J=8.5Hz, 1H), 7.33(d, J=2.4Hz, 1H), 7.25(d, J=8.6Hz, 5H), 6.94(d, J=8.5Hz, 4H) ,3.87(s,3H),3.01(s,12H). 13 C NMR (101MHz, CDCl 3 )δ169.88, 160.73, 147.99, 144.75, 133.21, 128.50, 126.94, 124.78, 123.04, 114.80, 107.62, 91.62, 55.85, 42.23.

[0069]

[0070] After detection, the structure of the product is shown in the above structural formula.

Embodiment 2

[0072] Malachite Green Dye (R 1 =N,N-Dimethyl, R 2 = carboxylic acid, R 3 = R 4 =H, X=O, Y=carbonyl), the basic synthesis process is as follows:

[0073] Mix 194mg of 2-formyl-4-carboxybenzoic acid, 363mg of N,N-dimethylaniline, and 22mg of copper bromide, stir and react at 150°C for 2 hours, then cool down to room temperature, and purify by silica gel column chromatography to obtain 120mg of the target compound . The H NMR spectrum of the synthesized dye is as image 3 As shown, the specific data are as follows:

[0074] 1 H NMR (400MHz, DMSO-d 6 )δ8.14(d, J=7.8Hz, 1H), 8.03–7.94(m, 2H), 7.04(d, J=8.9Hz, 4H), 6.70(d, J=8.9Hz, 4H), 2.89( s,13H).

[0075]

[0076] After detection, the structure of the product is shown in the above structural formula.

Embodiment 3

[0078] Malachite Green Dye (R 1 =N,N-Dimethyl, R 2 = R 3 = R 4 =H, X=O, Y=carbonyl), the basic synthesis process is as follows:

[0079] Mix 150mg of o-carboxybenzaldehyde, 484mg of N,N-dimethylaniline, and 22mg of copper bromide, stir and react at 100°C for 10 hours, cool down to room temperature, and purify by silica gel column chromatography to obtain 100mg of the target compound. The H NMR spectrum of the synthesized dye is as Figure 4 Shown; NMR spectrum as Figure 5 As shown, the specific data are as follows:

[0080] 1 H NMR (400MHz, CDCl 3 )δ7.89(d, J=7.6Hz, 1H), 7.63(t, J=7.3Hz, 1H), 7.53–7.44(m, 2H), 7.18(d, J=8.3Hz, 4H), 6.62( d,J=8.4Hz,4H),2.92(s,12H). 13 C NMR (101MHz, CDCl 3 )δ170.38, 153.38, 150.25, 133.80, 128.74, 128.54, 128.28, 125.77, 125.68, 124.00, 111.75, 92.69, 40.36.

[0081]

[0082] After detection, the structure of the product is shown in the above structural formula.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to malachite green derivatives with double protein activation sites as well as a synthesis method and application of the malachite green derivatives. The structural formula of the malachite green derivative is shown as (I). The synthetic method has the advantages of high total yield, simple reaction conditions, convenience in operation, large-scale preparation, wide substrate selection range and the like. The derivative has the characteristic of two protein activation sites, and can be applied to the fields of fluorescence imaging, fluorescent probes, stimulation response materials and the like.

Description

technical field [0001] The invention belongs to the field of dyes, and in particular relates to a class of malachite green derivatives with dual protein activation sites, their synthesis method and application. Background technique [0002] Fluorescence imaging, which can identify biomolecules in living organisms in real time and with high sensitivity, is an indispensable tool in life science research and is playing an increasingly important role. For example, super-resolution fluorescence imaging developed in recent years breaks through the spatial resolution below 20nm, making it possible to study single molecules in living cells. The special imaging method of super-resolution fluorescence imaging requires the labeling dye to have the following basic characteristics: (1) high enough brightness to meet the needs of single-molecule detection; (2) strong enough photostability to adapt to the high laser intensity during the imaging process; (3) Intelligent fluorescent respons...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88C07D209/46C07D333/72C07D307/87C09K11/06G01N21/64
CPCC07D307/88C07D209/46C07D333/72C07D307/87C09K11/06G01N21/6428C09K2211/1088C09K2211/1092C09K2211/1029
Inventor 徐兆超邓霏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI