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High-brightness high-stability fluorescent dye containing active ester as well as synthesis and application of the fluorescent dye

A technology containing active esters and fluorescent dyes, applied in luminescent materials, organic dyes, azo dyes, etc., can solve the problems of reduced quantum yield, difficulty penetrating cell membranes, affecting molecular labeling performance, stability, compatibility, etc. , to achieve the effect of low-cost synthetic raw materials, simple and universal method, and maintaining accuracy

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such dye molecules themselves will be charged, which seriously affects the labeling performance, stability, and compatibility of the molecules. For example, the anion of the fluorescein molecule is easily oxidized to quench, and it is difficult to penetrate the cell membrane; the polymethine chain of the cyanine dye It is very easy to be attacked by singlet oxygen, and the twisting of olefins leads to a decrease in quantum yield, etc.

Method used

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  • High-brightness high-stability fluorescent dye containing active ester as well as synthesis and application of the fluorescent dye
  • High-brightness high-stability fluorescent dye containing active ester as well as synthesis and application of the fluorescent dye
  • High-brightness high-stability fluorescent dye containing active ester as well as synthesis and application of the fluorescent dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of NHSM-DAze

[0041] Synthesis of Intermediate 2-(N-(4-bromo-5-nitro-1,8-naphthalimide))aminoacetate (COMe-NBr)

[0042]

[0043] 4-Bromo-5-nitro-1,8-naphthalimide (1.00g, 3.11mmol) was dissolved in 80mL of ethanol, and ethyl glycine hydrochloride (1000mg, 7.17mmol) and 1.00g tris Ethylamine. After reacting at 90°C for 24 hours, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 962 mg of a white solid with a yield of 76%. Its nuclear magnetic spectrum data are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 )δ8.73(d, J=7.8Hz, 1H), 8.53(d, J=7.9Hz, 1H), 8.24(d, J=7.9Hz, 1H), 7.94(d, J=7.8Hz, 1H) ,4.92(s,2H),4.26(q,J=7.1Hz,2H),1.31(t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3)δ167.36, 162.48, 161.75, 151.56, 136.06, 132.66, 131.64, 130.74, 125.26, 124.71, 123.60, 122.00, 121.35, 61.94, 41.64, 14.16.

[0045] Its high-resolution mass spectrometry...

Embodiment 2

[0065] Synthesis of NHSM-DAC

[0066] Synthesis of Intermediate 2-(N-(4-bromo-5-nitro-1,8-naphthalimide))aminoacetate (COMe-NBr)

[0067]

[0068] 4-Bromo-5-nitro-1,8-naphthoimide (1.00g, 3.11mmol) was dissolved in 20mL of ethanol, and glycine ethyl ester hydrochloride (3000mg, 21.5mmol) and 3.00g tris Ethylamine. After reacting at 40°C for 1 h, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 418 mg of a white solid with a yield of 33%.

[0069] Synthesis of intermediate COOH-DAC

[0070]

[0071] (1) Synthesis of COMe-DAC

[0072] COMe-NBr (200 mg, 0.49 mmol) was dissolved in 20 mL of ethylene glycol methyl ether, and 400 mg of 1,2-cyclohexanediamine was added thereto. The reaction solution was slowly heated to 100°C and reacted for 12h. Ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica ge...

Embodiment 3

[0088] Synthesis of NHSB-DAC

[0089] Synthesis of Intermediate 6-(N-(4-bromo-5-nitro-1,8-naphthalimide))aminobutyric acid ethyl ester (BCOMe-NBr)

[0090]

[0091] 4-Bromo-5-nitro-1,8-naphthalimide (1.00g, 3.11mmol) was dissolved in 80mL ethanol, and 4-aminobutyric acid ethyl ester hydrochloride (1.00g, 6.21mmol ) and 3.00g triethylamine. After reacting at 80°C for 10 h, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:petroleum ether=3:1, V / V) to obtain 608 mg of a white solid with a yield of 45%. Its H NMR spectrum and C spectrum data are as follows:

[0092] 1 H NMR (400MHz, CDCl 3 )δ8.71(d, J=7.8Hz, 1H), 8.52(d, J=7.9Hz, 1H), 8.22(d, J=7.9Hz, 1H), 7.93(d, J=7.8Hz, 1H) ,4.25(t,J=7.1Hz,2H),4.10(q,J=7.1Hz,2H),2.44(t,J=7.4Hz,2H),2.09(p,J=7.3Hz,2H),1.24 (t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ172.72, 162.85, 162.09, 151.33, 136.00, 132.40, 131.30, 130.57, 125.65, 124.24, 123.56, 122.3...

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Abstract

The invention provides high-brightness high-stability fluorescent dye containing active ester as well as synthesis and application of the fluorescent dye. With the introduction of the 4,5-position rigid ring into naphthalimide, the fluorescence stability and brightness are substantially improved. The structural formula is represented by the formula (1), the highest fluorescence quantum yield of the dye in water can achieve 0.80 or above, the fluorescence emission wavelength is about 495 nm, the half-peak width is less than 35 nm, and the cross-color phenomenon can be effectively avoided. The dye can maintain the stability of fluorescence signals in different microenvironments, and is insensitive to temperature, polarity and the like. In addition, due to the existence of the active ester, the dye can be used for marking biomolecules such as antibodies and polypeptides, and monitoring and fluorescence imaging of a target object are realized.

Description

technical field [0001] The invention belongs to the field of fluorescent labeling, in particular to a class of high-brightness and high-stability fluorescent dyes containing active esters and their synthesis and application. Background technique [0002] Due to the advantages of high sensitivity, in-situ real-time response, and short detection cycle, fluorescence analysis has been widely used in identification and labeling in various research fields (such as: fluorescent PCR detection, antibody labeling, etc.), which can convert microscopic Information changes are displayed in a macroscopic form. The application of fluorescence analysis also promotes the development of fluorescent molecules to higher brightness and higher stability. Among them, organic small molecule fluorescent dyes are favored by researchers due to their characteristics of easy modification, multiple selectivity, and rich colors. . With the help of the active ester group, the covalent connection between ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D471/06C09K11/06C09B57/08C09B57/00G01N21/64
CPCC07D401/14C07D471/06C09K11/06C09B57/08C09B57/00G01N21/6428G01N21/6486C09K2211/1029C09K2211/1044G01N2021/6439
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI