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A kind of 450nm excited high-brightness, high-stability fluorescent dye and its synthesis method

A high-stability, fluorescent dye technology, applied in the field of fluorescent dyes, can solve problems such as difficult to meet imaging, and achieve the effects of low-cost synthetic raw materials, high fluorescence quantum yield, and high fluorescence brightness

Active Publication Date: 2021-11-09
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

[0003] In the current fluorescence imaging technology, the most commonly used fluorescent dyes are respectively matched with 405nm, 488nm, 560nm, 640nm and other lasers, and it is difficult to satisfy more color imaging.

Method used

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  • A kind of 450nm excited high-brightness, high-stability fluorescent dye and its synthesis method
  • A kind of 450nm excited high-brightness, high-stability fluorescent dye and its synthesis method
  • A kind of 450nm excited high-brightness, high-stability fluorescent dye and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of intermediate N-butyl-4-bromo-5-azetidinyl-1,8-naphthalimide (BuAN-BrAze):

[0041]

[0042] N-butyl-4-bromo-5-nitro-1,8-naphthalimide (100 mg, 0.26 mmol) was dissolved in 10 mL of ethylene glycol methyl ether, and 100 mg of azetidine was added thereto. After the reaction solution was stirred at 50°C for 3 h, ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=200:1, V / V) to obtain 43 mg of a brown solid with a yield of 42%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0043] 1 H NMR (400MHz, CDCl 3 )δ8.46(d, J=8.5Hz, 1H), 8.30(d, J=7.9Hz, 1H), 7.82(d, J=7.9Hz, 1H), 6.77(d, J=8.5Hz, 1H) ,4.24(t,J=7.5Hz,4H),4.15(dd,J=10.0,5.0Hz,2H),2.54–2.36(m,2H),1.69(dt,J=15.2,7.6Hz,2H), 1.51–1.35(m,2H),0.96(t,J=7.3Hz,3H).

[0044] Synthesis of BuAN-AzeBu:

[0045]

[0046] BuAN-BrAze (80 mg, 0.21 mmol) was dissolved in 10 mL of ethylene gl...

Embodiment 2

[0050] Synthesis of intermediate N-butyl-4-bromo-5-azetidinyl-1,8-naphthalimide (BuAN-BrAze):

[0051]

[0052] N-butyl-4-bromo-5-nitro-1,8-naphthalimide (100 mg, 0.26 mmol) was dissolved in 2 mL of ethylene glycol methyl ether, and 10 mg of azetidine was added thereto. After the reaction solution was stirred at 70°C for 1 h, ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=200:1, V / V) to obtain 91 mg of a brown solid with a yield of 89%.

[0053] Synthesis of BuAN-AzeMe:

[0054]

[0055] BuAN-BrAze (100 mg, 0.26 mmol) was dissolved in 2 mL of ethylene glycol methyl ether, and 100 mg of methylamino alcohol solution was added to the reaction solution, and then the reaction solution was slowly heated to 90° C. and reacted for 6 h. Ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:met...

Embodiment 3

[0059] Synthesis of BuAN-AzeAzi:

[0060]

[0061] BuAN-BrAze (50 mg, 0.13 mmol) was dissolved in 10 mL of ethylene glycol methyl ether and 200 mg of aziridine was added to the reaction solution, and then the reaction solution was slowly heated to 120° C. and reacted for 10 h. 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 22 mg of a dark yellow solid with a yield of 47%. The NMR spectrum and carbon spectrum of the BuAN-AzeBu prepared in embodiment 3 are as follows: figure 2 , image 3 As shown, the specific data are:

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.43(d, J=5.9Hz, 1H), 8.41(d, J=6.3Hz, 1H), 7.02(d, J=8.1Hz, 1H), 6.53(d, J=8.5Hz, 1H) ,4.28–4.08(m,6H),2.38(dt,J=15.0,7.5Hz,2H),2.26(s,4H),1.68(dt,J=15.2,7.6Hz,2H),1.43(dq,J =14.7,7.3Hz,2H),0.95(t,J=7.3Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ164.41,164.31,159.01,155.45,132.87,132.52,132.33,115.99,11...

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Abstract

The invention provides a high-brightness and high-stability fluorescent dye excited at 450 nm and a synthesis method thereof. The fluorescent dye is a series of high-quantum dyes designed and synthesized based on naphthalimide through the limitation of the four-membered ring structure to the intramolecular twist. A fluorescent dye excited at 450 nm with high yield and high stability, the structural formula of which is shown in (1). The rigid structure of azetidine can greatly restrict the transition of naphthalimide molecules to the TICT (twisted intramolecular charge transfer) state, thereby reducing the non-radiative relaxation and increasing the fluorescence quantum yield. This series of fluorescent dyes can satisfy laser excitation around 450nm, and can match different fluorescent dyes to meet multi-color fluorescence imaging. In addition, this series of fluorescent dyes are easy to functionalize and have good application prospects in the field of fluorescent labeling and detection.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, in particular to a fluorescent dye with high brightness and high stability excited by 450nm and a synthesis method thereof. Background technique [0002] With the coordinated development of photophysics and precise design of fluorescent dyes, bioluminescent imaging has gradually become an indispensable tool for monitoring biological macromolecules and deciphering physiological processes at high spatial and temporal resolution. This in-depth exploration of biological systems is largely determined by the visualization and quantification of target molecules at the cellular level. However, the monitoring of physiological processes in vivo requires simultaneous real-time labeling and fluorescence localization of multiple target molecules. Therefore, more-color fluorescence imaging is particularly important in deciphering more complex and more component-involved physiological processes. [0003] In th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14
CPCC09B57/08C09K11/06C09K2211/1029G01N21/6428
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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