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Benzo-pyronine near-infrared fluorescent dye as well as preparation method and application thereof

A benzene ring and alkyl technology, applied in the field of near-infrared fluorescent dyes based on benzopyronine and its preparation, can solve the problems of small Stokes shift, limited application, detection error, etc.

Active Publication Date: 2020-10-20
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still some problems in the research and development of xanthene dyes: the Stokes shift of xanthene dyes is generally relatively small, resulting in serious fluorescence self-quenching and detection errors due to Rayleigh scattering
However, due to the short emission wavelength and small Stokes shift of pyronin, its application in the field of fluorescence imaging is limited.

Method used

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  • Benzo-pyronine near-infrared fluorescent dye as well as preparation method and application thereof
  • Benzo-pyronine near-infrared fluorescent dye as well as preparation method and application thereof
  • Benzo-pyronine near-infrared fluorescent dye as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0064]

[0065] Compound II-1 was prepared from m-N,N-diethyl-aminophenol according to the literature (Imaging Science and Photochemistry, 2015, 33(2), 154–160), with a total yield of 40%.

[0066] Dissolve 0.26g (0.001mol) of compound II-1 and 0.27g (0.002mol) of compound III-1 in 5 ml of acetic acid, add 0.1 ml of perchloric acid (mass percentage concentration is 70%), and heat to 150°C, react for 2h. After cooling, add 1 milliliter of perchloric acid (mass percentage concentration is 70%), then slowly add distilled water dropwise, precipitate solid, filter, vacuum dry, column chromatography purification and separation to obtain 0.13g compound I-1, yield 29.3% . ESI MS: m / z, 346.2 (M+H). lambda ab. max / nm=624nm,λ em max / nm=688nm,Ф f = 0.66. Compound I-1 in dichloromethane, compared with Pyronin B, has a red-shift of 68nm in absorption, a red-shift of 92nm in fluorescence, a 1-fold increase in Stokes shift, and a 1.5-fold increase in fluorescence quantum yield. ...

Embodiment 2

[0068]

[0069] Dissolve 0.26g (0.001mol) of compound II-1 and 0.16g (0.001mol) of compound III-2 in 10ml of ethanol, add 2ml of concentrated sulfuric acid, heat to 80°C, and react for 3h. After cooling, 0.5 ml of perchloric acid (mass percent concentration: 70%) was added, and distilled water was slowly added dropwise to precipitate a solid, which was filtered, vacuum-dried, and purified by column chromatography to obtain 0.16 g of compound I-2 with a yield of 34.0%. ESI MS: m / z, 371.2. lambda ab. max / nm=625nm,λ em max / nm=686nm,Ф f = 0.65.

Embodiment 3

[0071]

[0072] Dissolve 0.23g (0.001mol) of compound II-2 and 0.19g (0.001mol) of compound III-3 in 5ml of acetic acid, add 1ml of concentrated sulfuric acid, heat to 100°C, and react for 2h. After cooling, add 2 milliliters of perchloric acid (mass percentage concentration is 70%), then slowly add distilled water dropwise, precipitate solid, filter, vacuum dry, column chromatography purification and separation give 0.13g compound I-3, yield 27.7% . ESI MS: m / z, 369.2. lambda ab. max / nm=625nm,λ em max / nm=689nm,Ф f = 0.68.

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Abstract

The invention discloses a benzo-pyronine near-infrared fluorescent dye. The benzo-pyronine near-infrared fluorescent dye has the following structural formula I. The invention also discloses a preparation method of the dye. The dye has good biocompatibility and light stability, near-infrared fluorescence emission and high fluorescence quantum yield, and is used for covalent or non-covalent fluorescence labeling of fluorophore and biomacromolecules of fluorescent probes.

Description

technical field [0001] The invention relates to a class of near-infrared fluorescent dyes and their preparation methods and applications, in particular to a class of benzopyronine-based near-infrared fluorescent dyes and their preparation methods and applications. Background technique [0002] In recent years, due to the advantages of good selectivity, high spatio-temporal resolution, non-destructive and fast operation, fluorescence imaging has attracted more and more researches in real-time monitoring of important biomolecules in vivo and tracking various physiological processes in cells. interest. Fluorescent dyes play a vital role in fluorescence imaging technology. Therefore, the research and development of new fluorescent dyes with excellent optical properties, high detection sensitivity, high stability, and biological and environmental friendliness are of great importance to promote the practical application of fluorescence technology. development is of great signific...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C07D491/052C07D491/16C09B57/00C09K11/06C12Q1/68G01N21/64
CPCC09B57/00C09K11/06C12Q1/68G01N21/6428C09K2211/1088C09K2211/1029G01N2021/6439C12Q2563/107Y02P20/55
Inventor 刘卫敏王秀萍汪鹏飞吴加胜任昊慧
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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