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Near-infrared fluorescent molecular probe, synthesizing method and use thereof

A fluorescent molecular probe, near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, biochemical equipment and methods, etc. The effect of increased compatibility, extended cycle time

Inactive Publication Date: 2009-05-27
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But for now, the number of near-infrared fluorescent organic probes that can be used in vivo is still very limited, especially the number of near-infrared fluorescent dyes that can be used in water systems is even less, which is also one of the bottleneck problems to be solved in promoting this technology one

Method used

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  • Near-infrared fluorescent molecular probe, synthesizing method and use thereof
  • Near-infrared fluorescent molecular probe, synthesizing method and use thereof
  • Near-infrared fluorescent molecular probe, synthesizing method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0056] Preparation of ICG-Der-01

[0057] 1. Dissolve 4g of 1,1,2-trimethyl[1H]-benzindole and 6g of 3-bromopropionic acid in 30mL of 1,2-dichlorobenzene solution, and keep stirring at 130°C Heat for 16 hours. After the reaction solution was cooled to room temperature, dichloromethane was added to the reaction system to precipitate the product, and the product was washed three times with dichloromethane to remove unreacted substances, and finally the relatively pure product 1,1,2-trimethyl Base [1H]-benzoindole-3-propionic acid (dark purple).

[0058] 2. Dissolve 4g of 1,1,2-trimethyl[1H]-benzindole and 8g of iodocaproic acid in 30mL of acetonitrile, heat to boiling under constant stirring, and reflux for 4 days. After the reaction is finished, cool to room temperature, add dichloromethane to the reaction system to precipitate the product, and wash the product with dichloromethane three times to remove unreacted substances, and finally obtain the relatively pure product 1,1,...

Embodiment 2

[0061] Preparation of ICG-Der-02

[0062] 1. Add 30mL of glacial acetic acid to a mixture of p-hydrazinobenzenesulfonic acid (6g), methyl isopropyl ketone (7mL) and sodium acetate (2g). The obtained brown suspension was heated to boiling and refluxed for 16 hours. Then filter while hot with a sintered glass filter to remove unreacted suspended matter. After the filtrate was cooled to room temperature, the product was precipitated with dichloromethane, and the product was brown (2,2,3-trimethyl[3H]-indole-5-sulfonic acid).

[0063] 2. Take 50 mL o-dichlorobenzene and add to 2,2,3-trimethyl[3H]-indole-5-sulfonic acid (15 g) and 1,3-propane sultone (4 mL). The mixture was heated to 130°C and held for 15 hours. The resulting solid was triturated with dichloromethane to finally give the product 2,2,3-trimethyl-5-sulfonic acid-1-(3-sulfonic acid-propyl)-[3H]-indole.

[0064] 3. Add 20mL of absolute ethanol to 2,2,3-trimethyl-5-sulfonic acid-1-(3-sulfonic acid-propyl)-[3H]-indole...

Embodiment 3

[0067] Preparation of Folic Acid-Coupled ICG-Der-01 Near-infrared Fluorescent Probe Complex

[0068] Weigh 18 mg of folic acid (Folic acid) and dissolve it in 5 mL of anhydrous dimethylsulfoxide (DMSO), add 15 mg of 1-ethyl-3 (3-dimethylpropylamine) carbodiimide and 7 mg of N-hydroxysuccinyl Imine (EDCI / NHS) was activated for 2 hours, and the activation solution was added dropwise to an anhydrous dimethyl sulfoxide (DMSO) solution containing 200 mg of bisaminopolyethylene glycol (PEG-bis-amine, molecular weight 4,000), avoiding React at room temperature for 8 hours; Folate-PEG was obtained by separation and purification on a silica gel column. Take 2 mg of ICG-der-01 near-infrared dye containing carboxyl functional groups, dissolve it in 1 mL of anhydrous DMSO, add the catalyst EDCI / NHS to activate for 2 hours, and then add the activated solution dropwise to polyethylene glycol (Folate- PEG) in pH 9.4 carbonate buffer and reacted in the dark for 12 hours. The reaction soluti...

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Abstract

The invention relates to the field of specific molecular identification and diagnosis reagent and in particular discloses a near infrared fluorescent dye with structural formulas I and II; and the invention also discloses a near infrared molecular probe which is obtained through covalent bonding between the near infrared fluorescent dye with the structural formulas I and II and a ligand of specific molecules. The near infrared molecular probe can be used for early diagnosis of turmour diseases.

Description

technical field [0001] The invention relates to the field of specific molecular recognition diagnostic reagents, in particular to a diagnostic reagent complex composed of near-infrared fluorescent dyes and ligands of specific molecules. Background technique [0002] The light waves in the near-infrared band (700-900nm) avoid the absorption of main absorbers such as water, aerobic and anoxygenated hemoglobin in the body, and its propagation characteristics are mainly determined by light scattering, so it has a deep penetration into biological tissues ( up to ten centimeters). Moreover, this band has no ionization, no radiation, and no harm to biological tissues, which endows it with the potential of non-destructive on-site continuous monitoring of various parameters in the living body, and also makes it have a huge application prospect in the field of biomedical detection. The recognition of specific molecules in vivo, especially the diagnosis of tumor-specific molecules, pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B23/08C09B23/12C12Q1/68G01N21/64
Inventor 顾月清刘飞陈新洋邓大伟钱志余
Owner CHINA PHARM UNIV
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