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Fluorescent dye for lipid droplet labeling, and synthesis method and application thereof

A technology of fluorescent dye and synthesis method, which is applied in the field of lipid droplet-labeled fluorescent dye and its synthesis, can solve the problems that are not conducive to in vivo fluorescence imaging, and achieve the effects of photostability and brightness improvement, simple purification, and convenient operation

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

AI Technical Summary

Problems solved by technology

In addition, since the scattering power is inversely proportional to the fourth power of the wavelength, it is not conducive to intravital fluorescence imaging

Method used

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  • Fluorescent dye for lipid droplet labeling, and synthesis method and application thereof
  • Fluorescent dye for lipid droplet labeling, and synthesis method and application thereof
  • Fluorescent dye for lipid droplet labeling, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis method of lipid droplet fluorescent dye MLD-DAzi.

[0041] Synthesis of intermediate N-methyl-9,10-dibromo-1,6,7,12-tetrachloroperylimide (MLD-DBr):

[0042]

[0043] Dissolve 1,6,7,12-tetrachloro-9,10-dibromo-3,4-perylene anhydride (1.2 g, 1.96 mmol) in 50 mL of a mixture of acetic acid and N-methylpyrrolidone (1:1, V / V), and then dropwise added methylamine 120mg therein. After reacting at 100°C for 3 h, the reaction solution was poured into 200 mL of ice water, settled and filtered to obtain a black solid. The black solid was separated through a silica gel column (petroleum ether:dichloromethane=1:1, V / V) to obtain 482 mg of a red solid with a yield of 39%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 )δ8.59(s,2H),8.14(s,2H),4.33(s,3H).

[0045] Synthesis of the dye N-methyl-9,10-di-aziridinyl-1,6,7,12-tetrachloroperylimide:

[0046]

[0047] N-butyl-1,6,7,12-tetrachloro-9,10-dibromo-3,4-pe...

Embodiment 2

[0051] Synthesis method of lipid droplet fluorescent dye BuLD-DAze.

[0052] Synthesis of intermediate N-butyl-9,10-dibromo-1,6,7,12-tetrachloroperyleneimide:

[0053]

[0054] Dissolve 1,6,7,12-tetrachloro-9,10-dibromo-3,4-perylene anhydride (1.2g, 1.96mmol) in 144mL of a mixture of acetic acid and N-methylpyrrolidone (4:1, V / V), and then add n-butylamine (428mg, 5.86mmol) dropwise thereto. After reacting at 140°C for 1 h, the reaction solution was poured into 200 mL of ice water, settled and filtered to obtain a black solid. The black solid was separated through a silica gel column (petroleum ether:dichloromethane=1:1, V / V) to obtain 600 mg of a red solid with a yield of 46%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0055] 1 H NMR (400MHz, CDCl 3 )δ8.59(s,2H),8.14(s,2H),4.38–4.11(m,2H),1.94–1.66(m,2H),1.56–1.38(m,2H),0.99(t,J= 7.1Hz, 3H).

[0056] Synthesis of the dye N-butyl-9,10-di-azetidinyl-1,6,7,12-tetrachloroperylimide:

[0057...

Embodiment 3

[0062] Synthesis method of lipid droplet fluorescent dye OLD-DAze.

[0063] Synthesis of intermediate N-(2-(2-hydroxy)-ethoxy)ethyl-9,10-dibromo-1,6,7,12-tetrachloroperyleneimide:

[0064]

[0065] Dissolve 1,6,7,12-tetrachloro-9,10-dibromo-3,4-perylene anhydride (1.2g, 1.96mmol) in 24mL of a mixture of acetic acid and N-methylpyrrolidone (2:1, V / V), and then added diglycolamine (303mg, 8.79mmol) dropwise thereto. After reacting at 100°C for 6 h, the reaction solution was poured into 150 mL of ice water, settled and filtered to obtain a black solid. The black solid was separated through a silica gel column (petroleum ether:dichloromethane=1:1-1:4, V / V) to obtain 380 mg of a red solid with a yield of 55%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0066] 1 H NMR (400MHz, CDCl 3 )δ8.60(s,2H),8.13(s,2H),4.67–4.41(m,2H),3.88(d,J=5.3Hz,2H),3.71(d,J=4.5Hz,2H), 3.67(d,J=3.6Hz,2H),2.38(s,1H).

[0067] Dye N-(2-(2-hydroxy)-ethoxy)ethyl-9,10-di-aze...

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Abstract

The invention provides a fluorescent dye for lipid droplet marking as well as a synthesis method and application of the fluorescent dye. The fluorescent dye is based on perylene bisimide. Two amino substituents are introduced into one electron donating group end for design and synthesis; the structural formula of the dye is shown as (1). Compared with commercial lipid droplet dyes, the light stability of the series of dye is greatly improved, and the fluorescence emission wavelength in different solvents reaches a near infrared region (680-730 nm), the brightness (phi) is greater than 0.4, thehalf-peak width (less than 60 nm) is narrow, and the biocompatibility is good. The fluorescent dye can be used for quickly and accurately dyeing lipid droplets in various living cells and oleaginousyeasts at low concentration. Besides, the fluorescence emission wavelength of the lipid droplet fluorescent dye in a triglyceride environment reaches 711nm, the tissue and living body penetrability ishigh, and the lipid droplet fluorescent dye has high biological applicability and can be widely applied to detection and imaging of lipid in a living body.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes used for lipid droplet labeling, and in particular relates to a class of fluorescent dyes used for lipid droplet labeling and a synthesis method and application thereof. Background technique [0002] In recent years, lipid droplets are considered to be an important organelle that exists in both bacteria and human cells. The hydrophobic core of neutral lipid (TAG) or sterol lipid (SE) is wrapped by a single layer of phospholipid membrane, and the phospholipid head group The group is exposed to the cytoplasm while the acyl group interacts with TAG. However, in different tissues and cells, lipid droplets are specific, and their number, size, and distribution are different, ranging from 100nm to 100μm in size. The number and size of lipid droplets in the same cell change rapidly with the change of its physiological environment. When lipid droplets serve as storage sites for neutral lipids, they gener...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06C09B57/00C09B57/08A61K49/00G01N21/64
CPCC09K11/06C07D401/14C09B57/08C09B57/00G01N21/64A61K49/0021C09K2211/1029
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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