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Second infrared window excitation/emission fluorescent dye and preparation method and application thereof

A fluorescent dye, near-infrared technology

Inactive Publication Date: 2018-08-24
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, it has not been reported that the excitation and emission of heptamethine dyes in the second near-infrared window region can be achieved, and the imaging of mouse legs, abdomen and brain blood vessels has been realized.

Method used

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  • Second infrared window excitation/emission fluorescent dye and preparation method and application thereof
  • Second infrared window excitation/emission fluorescent dye and preparation method and application thereof
  • Second infrared window excitation/emission fluorescent dye and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of heptamethine fluorescent probe FD-1080. Specific steps are as follows:

[0034] (1) Synthesis of compound 1

[0035] Weigh 1,8-naphtholactam (0.85g, 5mmol) and potassium hydroxide (0.56g, 10mmol) and dissolve in 10mL N-methyl-2-pyrrolidone solution, stir at room temperature for 30min, then add 1,4 -Butane sultone (0.75g, 5.5mmol), the temperature was raised to 90°C, reacted for 10h, cooled to room temperature and then added acetone to obtain a precipitate, which was filtered to obtain compound 1 (1.65g, 96%).

[0036] (2) Synthesis of compound 2

[0037] Weigh compound 1 (1.50g, 5mmol) and tetrabutylammonium chloride (1.51g, 5.5mmol) and dissolve in 8mL acetic acid, react at 90°C for 0.5h, cool to room temperature, add ethyl acetate, filter, spin dry A yellow oily liquid, Compound 2 (2.5 g, 94%) was obtained.

[0038] (3) Synthesis of compound 3

[0039] Weigh compound 2 (2.73g, 5mmol) and dissolve it in 20mL anhydrous tetrahydrofuran (THF), under th...

Embodiment 2

[0043] The method for preparing the complex of heptamethine fluorescent probe FD-1080 and plasma protein, taking fetal bovine serum as an example. Specific steps are as follows:

[0044] Prepare the dimethyl sulfoxide solution of dye FD-1080 so that its concentration is 10 -3mol / L, 40 μL was added to 500 μL fetal bovine serum (FBS) solution, and incubated at 40° C. for 110 min.

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Abstract

The invention belongs to the technical field of biological materials, and in particular relates to a second infrared window excitation / emission organic small molecule fluorescent dye and a preparationmethod and application thereof. The application of the fluorescent dye comprises a synthetic process of an organic small molecule heptamethine cyanine dye fluorescent dye and formation of a complex of the organic small molecule heptamethine cyanine dye fluorescent dye with fetal bovine serum (FBS). Under heating conditions, such small molecules can easily enter the hydrophobic cavities of the FBSto form the complex. The proportion of monomers increases, meanwhile the molecular rigid structure enlarges, so that the fluorescence quantum yield is greatly increased. The complex enables imaging of blood vessels in legs, abdomens and brains of mice.

Description

technical field [0001] The invention belongs to the technical field of biomaterials, and in particular relates to a heptamethine fluorescent dye and a synthesis method thereof, and the application of the dye as a probe in vascular contrast agents. Background technique [0002] Currently common molecular imaging techniques such as X-ray, tomographic imaging (CT), magnetic resonance imaging (MRI) and ultrasound imaging (US) are used for medical diagnosis of diseases, etc., but these methods have poor spatial resolution And its shortcomings such as the inability to realize dynamic real-time monitoring. Due to the advantages of real-time, non-invasive, small amount of sample required, and high resolution, fluorescence imaging has been widely used in the fields of life science and biotechnology, especially the fluorescence imaging of biological tissues. In the past few years, researchers have devoted themselves to the study of fluorescence imaging in the first near-infrared wind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C07D209/80C09K11/06A61K49/00
CPCA61K49/0032A61K49/0056C07D209/80C09B23/08C09B23/107C09K11/06C09K2211/1029
Inventor 张凡李本浩陆凌飞赵梦瑶
Owner FUDAN UNIV
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