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Targeting lysosome super-resolution self-flashing dye as well as synthesis method and biological application thereof

A synthetic method and lysosome technology, applied in the field of super-resolution fluorescent dyes, can solve problems such as capture difficulties

Active Publication Date: 2022-04-01
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, the capture of lysosome dynamics at the nanoscale still faces great difficulties.

Method used

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  • Targeting lysosome super-resolution self-flashing dye as well as synthesis method and biological application thereof
  • Targeting lysosome super-resolution self-flashing dye as well as synthesis method and biological application thereof
  • Targeting lysosome super-resolution self-flashing dye as well as synthesis method and biological application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of intermediate Rho530

[0047]

[0048]Put 3-N,N-bis(allyl)aminophenol (100mg, 0.53mmol) and phthalic anhydride (38mg, 0.26mmol) in 5mL of 1,2-dichlorobenzene, and then gradually heated up to 190°C , and reacted at this temperature for 10h. After the reaction solution was cooled to room temperature, the sample was wet-loaded and separated by silica gel column chromatography (developing solvent: dichloromethane: methanol volume ratio 20:1) to obtain 45 mg of a purple solid with a yield of 32%.

[0049] Its high-resolution mass spectrometry data are as follows:

[0050] HRMS(ESI)m / z[M] + : Calculated value: 491.2335, Experimental value: 491.2339.

[0051] Its NMR spectrum is as follows figure 1 As shown, the specific data are as follows:

[0052] 1 H NMR (400MHz, MeOD) δ8.05–7.97(m,1H),7.60–7.50(m,2H),7.12(t,J=8.8Hz,3H),6.85(dd,J=9.4,2.4Hz, 2H), 6.81(d, J=2.4Hz, 2H), 5.89–5.76(m, 4H), 5.17(d, J=1.1Hz, 2H), 5.14(dd, J=3.5, 1.3Hz, 4H), 5.09(d, J=1.2Hz,...

Embodiment 2

[0081] Synthesis of intermediate Rho530

[0082]

[0083] Put 3-N,N-bis(allyl)aminophenol (300mg, 1.59mmol) and phthalic anhydride (114mg, 0.77mmol) in 30mL of 1,2-dichlorobenzene, then gradually heat up to 190°C , and react at this temperature for 6h. After the reaction solution was cooled to room temperature, the sample was wet-loaded and separated by silica gel column chromatography (developing solvent: dichloromethane:methanol volume ratio 20:1) to obtain 194 mg of a purple solid with a yield of 46%.

[0084] After testing, its structure is shown in the above formula.

[0085] Synthesis of Dye LysoH-530

[0086]

[0087] Rho530 (200mg, 0.38mmol) was dissolved in 20mL of 1,2-dichloroethane, then 2mL of phosphorus oxychloride was added to the reaction solution, and reacted at 80°C for 2h. It was then removed under reduced pressure to obtain a purple crude product. The crude product was dissolved in 20 mL of acetonitrile, and 0.5 mL of triethylamine and 2-aminopyrid...

Embodiment 3

[0104] Synthesis of intermediate Rho530

[0105]

[0106] Put 3-N,N-bis(allyl)aminophenol (200mg, 1.06mmol) and phthalic anhydride (77mg, 0.56mmol) in 15mL of 1,2-dichlorobenzene, then gradually heat up to 190°C , and reacted at this temperature for 8h. After the reaction solution was cooled to room temperature, the sample was wet-loaded and separated by silica gel column chromatography (developing solvent: dichloromethane:methanol volume ratio 20:1) to obtain 118 mg of a purple solid with a yield of 42%.

[0107] After testing, its structure is shown in the above formula.

[0108] Synthesis of Dye LysoN-530

[0109]

[0110] Rho530 (100mg, 0.19mmol) was dissolved in 15mL of 1,2-dichloroethane, then 0.5mL of phosphorus oxychloride was added to the reaction solution, and reacted at 80°C for 4h. It was then removed under reduced pressure to obtain a purple crude product. The crude product was dissolved in 15 mL of acetonitrile, and 0.5 mL of triethylamine and 2-amino-5...

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Abstract

The invention relates to a super-resolution self-flashing dye targeting lysosome as well as a synthesis method and biological application thereof, and the dye is structurally characterized in that a 2-aminopyridine derivative is introduced for ring locking based on a rhodamine 110 parent. The fluorescent dye provided by the invention has the characteristics of pH gt; 5 in a dark state of a closed-loop structure; the pyridine group enables the dye to accurately locate lysosomes in living cells. In addition, the invention develops a novel method for introducing spiroamide into a rhodamine 110 parent, and the method can be applied to synthesis of various rhodamine 110 spiroamide molecules. The dye can realize self-flashing in the lysosome, so that the dye can be used for dynamically monitoring the lysosome for a long time at a nanoscale.

Description

technical field [0001] The invention belongs to the field of super-resolution fluorescent dyes, and in particular relates to a synthesis method of a lysosome-targeted super-resolution self-flashing dye and its application in the field of fluorescence imaging. Background technique [0002] Fluorescence imaging technology can present changes in the microcosm to researchers in a macroscopic form through fluorescent signals. With the help of this technology, researchers have realized the dynamic monitoring of fine cell structures. However, this research still faces the problem of low temporal and spatial resolution, in which the spatial resolution is only above the optical diffraction limit (>200nm), and it is impossible to analyze the trajectory of organelles and the interaction between organelles and cells at the nanoscale. The spatial resolution of the super-resolution fluorescence imaging technology that emerged in recent years can reach within 10nm, enabling the observat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09B11/24C09B57/00C09K11/06G01N21/64
CPCY02P20/55
Inventor 徐兆超乔庆龙尹文婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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