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Active near infrared fluorophore as well as preparation method and application thereof

A fluorophore, near-infrared technology, applied in chemical instruments and methods, luminescent materials, pharmaceutical formulations, etc., can solve problems such as no near-infrared fluorescent probe reports, and achieve suitable fluorescence wavelength, stable labeling, absorption coefficient and The effect of high quantum yield

Inactive Publication Date: 2015-06-03
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] To sum up, the review of domestic and foreign literature shows that there is no report on this kind of near-infrared fluorescent probe that can be used for bioactive molecular labeling.

Method used

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  • Active near infrared fluorophore as well as preparation method and application thereof
  • Active near infrared fluorophore as well as preparation method and application thereof
  • Active near infrared fluorophore as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of compound 1

[0036]

[0037]Dissolve DMF (8mL) in DCM (8mL) in an ice-water bath to obtain solution ; and dissolve POCl3 (7.2mL) in DCM (7mL) to obtain solution ; when solution When is cooled to zero, slowly drop into to obtain solution . Dissolve cyclohexanone (2g) in DCM (5mL), and drop it into under the same ice bath condition to obtain solution . After is completely dissolved, move to 65°C oil Bath, reflux 3h. After the reaction is complete, cool it down to room temperature, carefully pour it into ice (50g), let it melt at room temperature, and transfer it to a separatory funnel to stand and separate layers. The bottom layer was discarded. The upper solution was filtered to obtain a yellow precipitate, which was washed with ice water to obtain dialdehyde, compound 1, with a yield of 78%.

Embodiment 2

[0039] Synthesis of Compound 2

[0040]

[0041] 2.3.3-Trimethylindole (2g) and butane sultone (5.6g) were dissolved in o-dichlorobenzene (5mL), stirred in an oil bath at 120°C, and refluxed for 12h. After the reaction was completed, after cooling to room temperature, it was dropped into diethyl ether (450 mL) to precipitate, and the crude product was obtained by filtration. After dissolved in water, it was extracted three times with chloroform to obtain an aqueous layer solution, which was lyophilized to obtain pure indolesulfonic acid group, compound 2, with a yield of 74%.

Embodiment 3

[0043] Synthesis of Compound IR783

[0044]

[0045] Compound 2 (1.4 mmol), compound 1 (0.7 mmol) and sodium acetate (1.41 mmol) were dissolved in acetic anhydride (13 mL), and heated in an oil bath at 70°C for 40 min. After the reaction was completed and cooled, diethyl ether precipitated to obtain a green solid product. The product was purified by column chromatography (CH2Cl2:CH3OH=10:3) to obtain compound IR783 with a calculated yield of 84%.

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Abstract

The invention belongs to the field of molecular imaging reagents ad relates to an active near infrared fluorophore for rapidly marking bioactive molecules. A general formula of the active near infrared fluorophore is IRP-B-NHS, wherein IRP is an anthocyanin near infrared fluorophore; B is an aromatic group introduced to the secondary position of the anthocyanin fluorophore by virtue of a carbon-carbon bond; NHS is N-hydroxysuccinimide eater. A preparation method of the active near infrared fluorophore comprises the following steps: with the anthocyanin fluorophore as a parent, introducing benzene carboxylic acid into the fluorophore by virtue of the carbon-carbon bond through Suzuki-Miyaura reaction, modifying phenyl carboxylic acid to produce the N-hydroxysuccinimide eater, reacting with primary amine in a biomolecule under the physiological condition, and marking the biomolecule with the near infrared fluorophore to realize noninvasive tracing. The active near infrared fluorophore is capable of rapidly, safely, effectively and stably marking the bioactive molecules including polypeptide, proteins, antibodies or polymer molecules and has important significance of noninvasively monitoring and quantifying distribution of target active molecules in vivo.

Description

technical field [0001] The invention belongs to the field of molecular imaging reagents, relates to a class of active near-infrared fluorescent groups that can rapidly label bioactive molecules, and specifically relates to the synthesis, characterization, optical properties and application of such active near-infrared fluorescent groups in biomolecular labeling Applications. This type of fluorophore has the characteristics of high labeling efficiency, mild labeling conditions, high fluorophore absorption coefficient and quantum yield, and stable photochemical properties. The non-invasive monitoring and quantification of the distribution of target bioactive molecules in vivo can be realized through the labeling of such fluorescent groups. Background technique [0002] The optical microscope in the sixteenth century changed people's understanding of biology and promoted the rapid development of biomedicine. It is known in the art that the size and shape of cells, organelles,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D403/14A61K49/00
Inventor 李聪张静烨黄翠云
Owner FUDAN UNIV
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