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A kind of fluorescent dye for lysosome labeling and its synthesis method and application

A technology of a fluorescent dye and a synthesis method, which is applied in the field of lysosome-labeled fluorescent dye and its synthesis, can solve the problems of high phototoxicity, poor structural stability and photostability, limited application, etc., and achieves a simple synthesis method and high efficiency. Fluorescence stability, cheap and easily available raw materials

Active Publication Date: 2021-12-21
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, most lysosomal fluorescent dyes on the market have many defects in biological imaging, such as poor structural stability and photostability, high phototoxicity, etc., which largely limit their use in lysosomes. Applications in Imaging

Method used

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  • A kind of fluorescent dye for lysosome labeling and its synthesis method and application
  • A kind of fluorescent dye for lysosome labeling and its synthesis method and application
  • A kind of fluorescent dye for lysosome labeling and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of Lyso-DAze, a lysosomal dye.

[0029] Synthesis of intermediate Lyso-NBr:

[0030]

[0031] 4-Bromo-5-nitro-1,8-naphthalimide (0.50g, 1.56mmol) was dissolved in 40mL of ethanol, and N-(2-aminoethyl)morpholine (0.609g, 4.68 mmol). After reacting at 70°C for 3 hours, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=200-50:1, V / V) to obtain 1.12 g of a khaki solid with a yield of 55%. Its H NMR spectrum is as figure 1 As shown, the specific data are as follows:

[0032] 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) ,4.33(t,J=6.6Hz,2H),3.71–3.57(m,4H),2.70(t,J=6.5Hz,2H),2.57(s,4H).

[0033] Synthesis of the dye Lyso-DAze:

[0034]

[0035] The intermediate Lyso-NBr (50 mg, 0.12 mmol) was dissolved in 10 mL of ethylene glycol methyl ether, and 100 mg of azetidine was added thereto. The reaction ...

Embodiment 2

[0044] Synthesis of Lyso-DAze, a lysosomal dye.

[0045] Synthesis of intermediate Lyso-NBr:

[0046]

[0047]4-Bromo-5-nitro-1,8-naphthalimide (0.75g, 2.34mmol) was dissolved in 30mL ethanol, and N-(2-aminoethyl)morpholine (0.45g, 3.46 mmol). After reacting at 140°C for 10 h, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=200-50:1, V / V) to obtain 0.47 g of a khaki solid with a yield of 46%.

[0048] Synthesis of the dye Lyso-DAze:

[0049]

[0050] The intermediate Lyso-NBr (75 mg, 0.18 mmol) was dissolved in 75 mL of ethylene glycol methyl ether, and azetidine (75 mg, 1.31 mmol) was added thereto. The reaction solution was slowly heated to 160°C and reacted for 30h. Ethylene glycol methyl ether was removed under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=50:1, V / V) to obtain 7 mg of a yellow solid, with a yield of 10%...

Embodiment 3

[0054] Synthesis of Lyso-DAze, a lysosomal dye.

[0055] Synthesis of intermediate Lyso-NBr:

[0056]

[0057] 4-Bromo-5-nitro-1,8-naphthalimide (0.9g, 2.81mmol) was dissolved in 108mL ethanol, and N-(2-aminoethyl)morpholine (2.16g, 16.60 mmol). After reacting at 120°C for 8 hours, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (dichloromethane:methanol=200-50:1, V / V) to obtain 0.51 g of a khaki solid with a yield of 42%.

[0058] Synthesis of the dye Lyso-DAze:

[0059]

[0060] The intermediate Lyso-NBr (100 mg, 0.24 mmol) was dissolved in 40 mL of ethylene glycol methyl ether, and azetidine (400 mg, 7 mmol) was added thereto. The reaction solution was slowly heated to 140°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=50:1, V / V) to obtain 8 mg of a yellow solid with a yield of ...

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Abstract

The invention provides a fluorescent dye for lysosome labeling and its synthesis method and application. The fluorescent dye uses naphthalimide as a fluorophore and introduces an N-(2-aminoethyl) at its N position. Phyloline substituents, two azetidine substituents were introduced at the 4,5-position, and a new type of lysosome fluorescent dye—Lyso-DAze was designed and synthesized. Its structural formula is shown in (1). The fluorescence of the dye The emission wavelength is 498nm, and it has very excellent fluorescence stability and high fluorescence intensity, and can realize the specific labeling of lysosomes in living cells under the condition of relatively low concentration (500nM). The Lyso-DAze dye satisfies the high stability and high brightness requirements of the current super-resolution technology for fluorescent dyes, making lysosome visualization have a very broad application prospect in basic research on the occurrence and development of diseases.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, and in particular relates to a fluorescent dye used for lysosome labeling, a synthesis method and application thereof. Background technique [0002] Lysosome is a kind of organelle in eukaryotic cells. It is a vesicular structure covered by a single membrane, with a size and diameter of about 0.025-0.8 μm. It is involved in various life activities of cells such as material metabolism, cell membrane cycle, and apoptosis all play a very important role. Therefore, the visualization of lysosomes plays a very important role in the detection of active species and the monitoring of key physiological processes. Research is very important. [0003] With the rapid development of laser confocal and high-resolution technology, the application of fluorescence imaging technology has provided a better way for the visualization of lysosomes. At present, fluorescent dyes applied to lysosome imaging an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06C09B57/08G01N21/64
CPCC07D401/14C09K11/06C09B57/08G01N21/6428G01N21/6458C09K2211/1029C09K2211/1033G01N2021/6441
Inventor 徐兆超许宁乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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