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Near-infrared second window excitation/emission fluorescent dye and preparation method and application

A fluorescent dye, near-infrared technology, used in luminescent materials, methine/polymethine dyes, organic dyes, etc., can solve problems such as short blood half-life

Active Publication Date: 2021-04-30
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The second, the present invention is aimed at existing dyestuff, for example the problem such as indocyanine green (ICG) blood half-life is short (5min), has synthesized the fluorescent dye that can realize the position such as blood vessel to detect for a long time

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  • Near-infrared second window excitation/emission fluorescent dye and preparation method and application
  • Near-infrared second window excitation/emission fluorescent dye and preparation method and application
  • Near-infrared second window excitation/emission fluorescent dye and preparation method and application

Examples

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Embodiment 1

[0047] Example 1: Preparation of LZ dye. Specific steps are as follows.

[0048] (1) Synthesis of Compound 1

[0049] Weigh 2-phenylindole (386mg, 2.0mmol) and 60% sodium hydride (84mg, 2.1mmol) and dissolve in 10mL anhydrous THF solution, stir for 20min under ice bath, then add 1,4-butanesulfonic acid Lactone (272mg, 2.0mmol), the temperature was raised to 100°C, reacted for 2h, cooled to room temperature and then added isopropanol to obtain a white precipitate, which was filtered to obtain compound 1 (663mg, 95%).

[0050] (2) Synthesis of compound 2

[0051] Weigh 5,6-methylenedioxy-2-phenylindole (415mg, 2.0mmol) and 60% sodium hydride (84mg, 2.1mmol) and dissolve in 10mL anhydrous tetrahydrofuran solution, stir for 40min under ice bath , then added 1,4-butane sultone (272mg, 2.0mmol), the temperature rose to 100 ° C, reacted for 4h, cooled to room temperature and then added isopropanol to obtain a white precipitate, which was filtered to obtain compound 2 (782mg, 99 %...

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Abstract

The invention belongs to the technical field of biological materials, and specifically relates to a fluorescent dye excited and emitted by a second near-infrared window, a preparation method and application thereof. The fluorescent dye of the present invention is an organic small molecule heptamethine fluorescent dye having a dye structure of the general formula LZ; the present invention utilizes an indole compound, acetyl chloride and a condensing agent to efficiently synthesize the target product in one pot; the fluorescent dye has good water solubility, and Linked with active groups such as carboxyl, amino, maleimide groups, etc., it can modify proteins, polypeptides, amino acids, DNA, etc.; this fluorescent dye can be used as an angiography agent for biological vascular imaging, and has Circulatory functions, such as dynamic imaging of blood vessels in the legs, abdomen and brain of mice, and monitoring of ischemia-reperfusion in the legs of mice, arterial thrombolysis, and the opening and closing of the blood-brain barrier in the brain.

Description

technical field [0001] The invention belongs to the technical field of biomaterials, and in particular relates to a fluorescent dye excited / emitted by a second near-infrared window and a preparation method and application thereof. Background technique [0002] Currently common molecular imaging techniques such as X-ray Tomography (X-CT), Ultrasound Imaging (UI), Positron Emission Tomography (PET) and Magnetic Resonance Imaging (MRI) have been widely used in medical diagnosis of diseases. However, these current imaging technologies have their own shortcomings, such as radiation, poor spatial resolution, and inability to realize dynamic real-time monitoring. Due to the advantages of real-time, non-invasive, high resolution, and less sample required, fluorescence imaging is widely used in the field of biotechnology, especially the fluorescence imaging of biological tissues. In the past few years, chemists have mainly focused on the research of fluorescence imaging methods in t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D405/14C09B23/10C07D209/10C07D519/00C07D209/12C09K11/06A61K49/00
CPCA61K49/0021C07D209/10C07D209/12C07D519/00C09B23/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088
Inventor 张凡李本浩赵梦瑶
Owner FUDAN UNIV