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Near infrared fluorescence molecular probe, and preparation method and application thereof

A fluorescent molecular probe and near-infrared technology, applied in the field of biochemical detection, can solve the problems of difficult separation and purification of products, many side reactions of synthesis, etc., and achieve the effects of high sensitivity, good optical stability, and avoiding interference

Inactive Publication Date: 2014-06-04
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the many side reactions in the synthesis of cyanine dyes, especially asymmetric cyanine dyes, the by-products have similar polarities, and the separation and purification of the products is quite difficult.

Method used

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  • Near infrared fluorescence molecular probe, and preparation method and application thereof
  • Near infrared fluorescence molecular probe, and preparation method and application thereof
  • Near infrared fluorescence molecular probe, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Add 0.25mmol of compound 5 into a 100mL reaction flask, add 50mL of anhydrous tetrahydrofuran (THF) and stir to dissolve, under the protection of argon, add 0.30mmol of compound 4 dropwise at 0°C, stir at 0°C for 2h, and the reaction ends. The product precipitated from the system, was filtered and dried to obtain 0.11 g of a white powdery solid. Yield: 61.11%. Mp=247-248°C.

[0042] Take 0.54mmol of compound 3 into a 50mL reaction flask, add 20mL of acetic anhydride and stir to dissolve, add 0.27mmol of compound 2 and 0.54mmol of anhydrous sodium acetate under the protection of argon, react at 30°C for 10h, and the reaction is completed. The reaction solution was poured into 100mL of methyl tert-butyl ether, and a green solid was precipitated, separated and purified by 200-300 mesh silica gel column chromatography, and the eluent was a mixture of dichloromethane and methanol at a volume ratio of 4:1 to obtain 55mg The green metallic color crystal is a near-infrared fl...

Embodiment 2

[0049] Add 0.25mmol of compound 5 into a 100mL reaction flask, add 50mL of anhydrous tetrahydrofuran (THF) and stir to dissolve, under the protection of argon, add 0.60mmol of compound 4 dropwise at 0°C, stir at 0°C for 3h, and the reaction ends. The product precipitated from the system, was filtered and dried to obtain 0.10 g of white powdery solid. . Mp=247-248°C.

[0050] Take 0.54mmol of compound 3 into a 50mL reaction flask, add 20mL of acetic anhydride and stir to dissolve, add 0.27mmol of compound 2 and 0.54mmol of anhydrous sodium acetate under the protection of argon, react at 20°C for 10h, and the reaction is completed. The reaction solution was poured into 100mL ether, and a green solid was precipitated, which was separated and purified by 200-300 mesh silica gel column chromatography. The eluent was a mixture of dichloromethane and methanol at a volume ratio of 8:1, and 53 mg of green metallic color crystals were obtained. Near-infrared fluorescent molecular prob...

Embodiment 3

[0052] Add 0.25mmol of compound 5 into a 100mL reaction flask, add 50mL of anhydrous tetrahydrofuran (THF) and stir to dissolve, under the protection of argon, add 0.90mmol of compound 4 dropwise at 0°C, stir at 0°C for 2h, and the reaction ends. The product precipitated from the system, was filtered and dried to obtain 0.105 g of white powdery solid.

[0053] Take 0.54mmol of compound 3 into a 50mL reaction flask, add 20mL of acetic anhydride and stir to dissolve, add 0.27mmol of compound 2 and 0.54mmol of anhydrous sodium acetate under the protection of argon, react at 30°C for 12h, and the reaction is completed. The reaction solution was poured into 100mL ether, and a green solid was precipitated, which was separated and purified by 200-300 mesh silica gel column chromatography. The eluent was a mixture of ethyl acetate and methanol at a volume ratio of 3:1, and 53.5 mg of green metallic color crystals were obtained. It is a near-infrared fluorescent molecular probe.

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Abstract

The invention provides a near infrared fluorescence molecular probe which has a structural formula as described in the specification. The invention further provides a preparation method for the near infrared fluorescence molecular probe. The invention also provides application of the near infrared fluorescence molecular probe in imaging in MCF-7 cells. The near infrared fluorescence molecular probe provided by the invention has a novel structure, is easy to prepare, can effectively shun from interference by biological autofluorescence and endogenous substances of cells, has high sensitivity, good optical stability and good cytomembrane permeability and is applicable as a near infrared fluorescence probe for detection of bioimaging.

Description

technical field [0001] The invention belongs to the field of biochemical detection, and in particular relates to a new near-infrared fluorescent molecular probe, and also relates to a preparation method of the molecular probe and its application in cell imaging. Background technique [0002] With the development of biological imaging related technologies, medical imaging has become a key science at the intersection of medical applications and life sciences. At present, medical imaging technology presents a trend of multi-polarization development, mainly including: magnetic resonance imaging, computed tomography, single photon emission computed tomography, positron emission tomography, ultrasound imaging, etc. [Deng Dawei, Liu et al. Fei, Cao Jie, etc. China Laser, 2010, 37(11) 2735-2742.]. Although these techniques have many advantages, they also have many disadvantages, such as complex operation, low spatial and temporal resolution, and expensive equipment. Therefore, how...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/08G01N21/64C12Q1/02
Inventor 吉民孙春龙蔡进宗玺
Owner SOUTHEAST UNIV
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