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A kind of high-brightness, high-stability fluorescent dye excited by 488nm and its synthesis method

A fluorescent dye and high-stability technology, applied in the field of fluorescent dyes, can solve the problems that fluorescent dyes cannot meet the needs of fluorescence imaging and detection, fluorescence signal reading errors, etc.

Active Publication Date: 2022-05-06
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, Alexa 488 is affected by the alkaline environment, and the form of positive ions makes it easy to non-specifically label to mitochondria
However, uncharged neutral fluorescent dyes are usually polarity-sensitive fluorescent dyes, which are often accompanied by huge wavelength changes during labeling, which will cause huge errors in fluorescent signal reading
Therefore, fluorescent dyes excited at 488nm still cannot meet the needs of fluorescence imaging and detection, and the stability and environmental insensitivity of dyes still need to be further improved

Method used

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  • A kind of high-brightness, high-stability fluorescent dye excited by 488nm and its synthesis method
  • A kind of high-brightness, high-stability fluorescent dye excited by 488nm and its synthesis method
  • A kind of high-brightness, high-stability fluorescent dye excited by 488nm and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of N-butyl-4,5-diazetidinyl-1,8-naphthalimide (BuAN-DAze):

[0045] Synthesis of intermediate N-butyl-4-bromo-5-nitro-1,8-naphthalimide (BuAN-NBr):

[0046]

[0047]4-Bromo-5-nitro-1,8-naphthalimide (1.0 g, 3.11 mmol) was dissolved in 20 mL of ethanol, and n-butylamine (250 mg, 3.43 mmol) was added dropwise thereto. After 1 h at 70°C, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (petroleum ether: dichloromethane = 2:1, V / V) to obtain 620 mg of off-white solid with a yield of 53%.

[0048] 1 H NMR (400MHz, CDCl 3 )δ8.72(d, J=7.8Hz, 1H), 8.52(d, J=7.9Hz, 1H), 8.21(d, J=7.9Hz, 1H), 7.95(d, J=7.8Hz, 1H) ,3.66(t,J=6.5Hz,2H),1.68(m,2H),1.40(m,J=7.8Hz,2H),0.94(t,J=7.9Hz,3H).

[0049] Synthesis of N-butyl-4,5-diazetidinyl-1,8-naphthalimide (BuAN-DAze):

[0050]

[0051] Dissolve N-butyl-4-bromo-5-nitro-1,8-naphthalimide (100mg, 0.26mmol) in 20mL of ethylene glycol methyl ether, and add azeti...

Embodiment 2

[0059] Synthesis of N-butyl-4,5-bis(azacyclopentyl)-1,8-naphthalimide (BuAN-DAzo):

[0060]

[0061] N-butyl-4-bromo-5-nitro-1,8-naphthalimide (50 mg, 0.13 mmol) was dissolved in 5 mL of ethylene glycol methyl ether, and 200 mg of tetrahydropyrrole was added thereto. The reaction solution was slowly heated to 140°C and reacted for 10h. Ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=100:1, V / V) to obtain 38 mg of a yellow solid with a yield of 75%. The NMR spectrum and carbon spectrum of the BuAN-DAzo prepared in Example 2 are as follows: image 3 , 4 As shown, the specific data are:

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.32(d, J=8.7Hz, 2H), 6.65(d, J=8.7Hz, 2H), 4.18(t, J=7.0Hz, 2H), 3.60(s, 2H), 3.37(d, J=4.9Hz, 1H), 3.28(d, J=4.2Hz, 2H), 2.67(d, J=8.0Hz, 2H), 2.19(s, 2H), 1.97(s, 4H), 1.70(dt, J=15.2,7.6Hz,2H), 1.57(s,2H),1.45(dt,J=15.1,7.4Hz,2H),0.96(t,J=7.3Hz,3H). ...

Embodiment 3

[0070] Synthesis of N-butyl-4,5-ethylenediamino-1,8 naphthalimide (BuAN-EDA):

[0071]

[0072] N-butyl-4-bromo-5-nitro-1,8-naphthalimide (100 mg, 0.27 mmol) was dissolved in 25 mL of ethylene glycol methyl ether, and 100 mg of ethylenediamine was added thereto. The reaction solution was slowly heated to 50°C and reacted for 24h. Ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=70:1, V / V) to obtain 71 mg of a yellow solid with a yield of 87%. The NMR spectrum hydrogen spectrum of the BuAN-EDA prepared by embodiment 3 is as Figure 5 As shown, the specific data are:

[0073] 1 H NMR (400MHz, DMSO-d 6 )δ8.29(s,2H),8.03(d,J=8.6Hz,2H),6.67(d,J=8.7Hz,2H),4.01–3.92(m,2H),3.51(s,4H), 1.54(dt,J=14.9,7.5Hz,2H),1.31(dt,J=14.8,7.4Hz,2H),0.90(t,J=7.3Hz,3H). 13 C NMR (101MHz, DMSO-d 6 )δ163.36, 155.59, 135.28, 133.35, 110.27, 107.36, 105.79, 46.73, 38.97, 30.40, 20.35.

[0074] Af...

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Abstract

The invention provides a fluorescent dye with high brightness and high stability excited at 488nm and a synthesis method thereof. The fluorescent dye is a series of high brightness, high Stability Fluorescent dyes excited at 488nm, whose structural formula is shown in (1); Compared with existing commercial 488nm dyes FITC, Alexa488, etc., this series of dyes have higher photostability, and are sensitive to microenvironments such as pH, viscosity, temperature, and polarity. Both are insensitive and can maintain the accuracy of fluorescent signals in complex environments. The fluorescence half-peak width of this kind of dye is narrower in different solvents (<30nm), the fluorescence quantum yield in different solvents is greater than 0.80 (in water), and the molar extinction coefficient is greater than 4×10 4 m ‑1 cm ‑1 . The 488nm series dyes invented in this project are easy to be derived, and have good application prospects in the fields of fluorescence imaging and fluorescent labeling.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, and in particular relates to a fluorescent dye with high brightness and high stability excited by 488nm and a synthesis method thereof. Background technique [0002] Fluorescence imaging technology has been widely used in the monitoring of many basic physiological processes in life sciences, and with the development of high-resolution technology, fluorescence imaging technology can provide nanoscale and single-molecule resolution. The realization of this technology is based on fast, sensitive, reliable and stable fluorescence signal feedback. Among them, the unique parameter factors of the fluorescent signal seriously affect the selection of imaging methods and the quality of imaging results, such as: excitation (λ ex ) and emission wavelength (λ em ), intensity, fluorescence lifetime and emission anisotropy, etc. Fluorescence intensity and fluorescence stability are the most important factors ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/08C09B57/00C09K11/06G01N21/64
CPCC09B57/08C09B57/00C09K11/06G01N21/6428C09K2211/1029C09K2211/1044
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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