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Preparation method of fluorescent dye and water-soluble near-infrared fluorescent probe

A technology of fluorescent probes and fluorescent dyes, applied in the field of chemical synthesis, can solve problems such as large damage to the human body and fine imaging of biological tissues, achieve good biocompatibility, high fluorescence quantum efficiency, and improve biocompatibility and specificity The effect of the recognition function

Inactive Publication Date: 2018-05-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently existing imaging technologies, such as computerized tomography (CT), magnetic resonance imaging (MRI) and ultrasonic positioning imaging, are difficult to perform fine imaging of biological tissues, and technologies such as CT use high-dose radiation rays, Greater harm to the human body

Method used

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  • Preparation method of fluorescent dye and water-soluble near-infrared fluorescent probe
  • Preparation method of fluorescent dye and water-soluble near-infrared fluorescent probe
  • Preparation method of fluorescent dye and water-soluble near-infrared fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] This embodiment is based on the method of step 1 and step 3 described in the present invention, such as figure 1N,N'-4-PEG(pentamer)phenyl-1,7-bis(4-(1,2,2-triphenyl)vinyl)benzene was prepared by replacing amine-terminated haloalkane with amine-terminated PEG as shown Base-3,4:9,10-tetracarboxylic perylenediamide.

[0051]

[0052] Perylene dianhydride (1.0 g) and 10 mL of concentrated sulfuric acid (98%) were added to a three-neck round bottom flask, and the mixture was stirred at 40° C. for 2 days. Bromine (1.3 mL) was added dropwise to the mixture over 30 minutes, followed by stirring at 100°C for 8 hours. After cooling to 40°C, the excess bromine was purged with argon with stirring. The mixture was then poured into ice water, the precipitate was separated by filtration, and the precipitate was washed with water several times until the filtrate was nearly neutral.

[0053] Preparation of cpd2. Trimethyltin-tetraphenylethylene (550mg), cpd1 (300mg) and Pd (PPh ...

Embodiment 2

[0056] In this example, based on the methods of step 1 and step 3 of the present invention, N, N'-2,4,6-tripolyvinyl alcohol phenyl-1,7-di (4-(1,2,2-Triphenyl)vinyl)phenyl-3,4:9,10-tetracarboxylic perylenediamide.

[0057]

[0058] Perylene dianhydride (10.0 g) and 20 mL of concentrated sulfuric acid (98%) were added to a three-neck round bottom flask, and the mixture was stirred at 60° C. for 2 days. Bromine (1.3 mL) was added dropwise to the mixture over 30 minutes, followed by stirring at 80°C for 8 hours. After cooling to 40°C, excess bromine was purged with nitrogen with stirring. The mixture was then poured into ice water, the precipitate was separated by filtration, and the precipitate was washed with water several times until the filtrate was nearly neutral.

[0059] Preparation of cpd2. Trimethyltin-tetraphenylethylene (2.15g), cpd1 (1.80g) and Pd(PPh 3 ) 4 (380 mg) was added to a double necked round bottom flask. The flask was evacuated under vacuum and flus...

Embodiment 3

[0062] In this example, based on the methods of step 1 and step 3 of the present invention, N, N'-2,4,6-pentapolyvinyl alcohol phenyl-1,7-di (4-(1,2,2-Triphenyl)vinyl)phenyl-3,4:9,10-tetracarboxylic perylenediamide.

[0063]

[0064] Preparation of 1,7-dibromo-3,4:9,10-tetracarboxylic perylene dianhydride (cpd1). Perylene dianhydride (5.0 g) and 15 mL of concentrated sulfuric acid (98%) were added to a three-neck round bottom flask, and the mixture was stirred at 60° C. for 3 days. Bromine (3.3 mL) was added dropwise to the mixture over 30 minutes, followed by stirring at 80°C for 5 hours. After cooling to 40°C, the excess bromine was purged with argon with stirring. The mixture was then poured into ice water, the precipitate was separated by filtration, and the precipitate was washed with water several times until the filtrate was nearly neutral.

[0065] Preparation of cpd2. Trimethyltin-tetraphenylethylene (4.34g), cpd1 (1.6g) and Pd(PPh 3 ) 4 (250 mg) was added to...

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Abstract

The invention provides a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent probe, and belongs to the technical field of chemical synthesis. The invention provides aperylene diimide derivative, wherein R1 is a conjugated group with aggregation-induced emission characteristics, and R2 is pyridinium salt with alkyl chains of different lengths, PEG (polyethylene glycol) with different chain lengths or tri-PEG benzene. The derivative is prepared from 3,4,9,10-perylenetetracarboxylic dianhydride as a raw material through the following chemical reactions: (1) 3,4,9,10-perylenetetracarboxylic dianhydride and bromine are subjected to a reaction in a molar ratio of 1 to (1 to 10) to obtain 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride; (2) 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride and trimethyl tin-tetraphenyl ethylene are subjected to a reaction under the catalysis of Pd(PPh3)4 to obtain a coupling product; and (3) the coupling product and an amine-terminated compound are subjected to a reaction, and the reaction product is bonded with hydrophilic pyridine bromide onium salt or PEG in an anhydride position to obtain the target product. The obtained water-soluble fluorescent material can be used for near-infrared cell imaging.

Description

technical field [0001] The invention relates to a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent probe, in particular to a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent probe with high fluorescence quantum efficiency, belonging to the technical field of chemical synthesis. Background technique [0002] Bioimaging technology for early diagnosis and precision medicine is an extremely important technology in tumor diagnosis and treatment. Currently existing imaging technologies, such as computerized tomography (CT), magnetic resonance imaging (MRI) and ultrasonic positioning imaging, are difficult to perform fine imaging of biological tissues, and technologies such as CT use high-dose radiation rays, The damage to the human body is relatively large. Utilizing fluorescent labeling and computer-aided imaging, not only can the precise imaging of larger tissues be achieved, but also the imaging of small...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06C09B57/00G01N21/64
CPCC07D471/06C09B57/00C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 宋波吴成凤
Owner SUZHOU UNIV
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