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Novel near-infrared high-quantum-yield dye as well as preparation and application thereof

A near-infrared, high-quantum technology, applied in the direction of benzoxanthene dyes, analytical materials, luminescent materials, etc., can solve problems such as long emission and difficulty in fluorescent quantum yield

Active Publication Date: 2017-09-08
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is very difficult to obtain structures with longer emission and high fluorescence quantum yield.

Method used

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  • Novel near-infrared high-quantum-yield dye as well as preparation and application thereof
  • Novel near-infrared high-quantum-yield dye as well as preparation and application thereof
  • Novel near-infrared high-quantum-yield dye as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103]

[0104] 0.193 g (0.001 mol) of compound II-1 and 0.161 g (0.001 mol) of compound III-1 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.343g of compound I-1, with a yield of 82%. ESI MS: theoretical calculation m / z: 319.18, actual test m / z: 319.20. lambda abs. max / nm=615nm,λ em max / nm=638nm,Ф f = 0.80.

[0105] 0.418g (0.001mol) of compound I-1, 0.202g (0.001mol) of di-tert-butyl dicarbonate and 0.101g (0.001mol) of triethylamine were added to 10 ml of anhydrous dichloromethane respectively, After stirring for 24 hours at room temperature, the solvent was removed under vacuum, dried and purified...

Embodiment 2

[0108]

[0109] Compound III-11 was prepared from commercial compound III-1 and ethyl iodide according to literature (Org. Lett., 2011, 13, 6488-6491), with a yield of 50%.

[0110] 0.217 g (0.001 mol) of compound II-2 and 0.189 g (0.001 mol) of compound III-2 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.399 g of compound I-4, with a yield of 85%. ESI MS: Theoretical calculation m / z: 371.21, actual test m / z: 371.24. lambda abs. max / nm=635nm,λ em max / nm=658nm,Ф f = 0.73.

[0111] Dissolve 0.470 g (0.001 mmol) of compound I-4 in 5 ml of anhydrous THF, and add dropwise to 3 ml of CH containing 1 mmol u...

Embodiment 3

[0113]

[0114]Compound II-3 was prepared from 7-hydroxy-1-methyl-1,2,3,4-tetrahydroquinoline according to the literature (J.Am.Chem.Soc., 2007,129,9986-9998), the yield 76%. Compound III-3 was prepared from commercial compound III-1 and methyl iodide according to literature (Org. Lett., 2011, 13, 6488-6491), with a yield of 42%.

[0115] 0.191 g (0.001 mol) of compound II-3 and 0.189 g (0.001 mol) of compound III-3 were added to 5 ml of concentrated sulfuric acid, and then heated and stirred at 100° C. for 2 h. After cooling, the reaction solution was slowly poured into 200 ml of ice water, then 1 ml of perchloric acid (70%) was added dropwise under stirring, and a large amount of distilled water was added, and solids were precipitated after standing, filtered, and vacuum-dried , purified by column chromatography to obtain 0.391 g of compound I-6, with a yield of 88%. ESI MS: Theoretical calculation m / z: 345.20, actual test m / z: 345.26. lambda abs. max / nm=633nm,λ em...

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Abstract

The invention discloses a novel near-infrared high-quantum-yield dye which has the following structural formula I shown as the original specification, wherein R1, R2, R6 and R7 are hydrogen, a low-level alkyl, an ether group and a substituted alkyl or acyl that are independent respectively; R3, R4, R5, R8, R9 and R10 are hydrogen, a low-level alkyl or halogen that are independent respectively; R11 is hydrogen, methyl, a cyano group or trifluoromethyl; X<theta> is a negative ion. The invention discloses a preparation method of the dye. The dye has good biocompatibility, low toxicity, longer fluorescence-emission and high fluorescence quantum yield, the autofluorescence of a background is avoided, a fluorescence image with high signal-to-noise ratio can be obtained, and the dye is used for fluorescence labeling for nucleolar RNA in a biological system and plays an important pole in a study process of physiology related to the nucleolar RNA.

Description

technical field [0001] The invention relates to a near-infrared nucleolus RNA dye, and provides a novel near-infrared dye with high quantum yield, preparation and application. Background technique [0002] Owing to its high spatiotemporal resolution and fast and non-invasive operation, small molecule fluorescent dye-based fluorescence imaging has become a powerful tool for visual observation of biological phenomena (such as biomolecular detection, labeling, cancer diagnosis and treatment, etc.) in living systems. . RNA is a particularly important biomolecule in living systems, and RNA in the nucleus is located in the nucleolus, where they play crucial roles in gene coding, transcription, and expression. Many physiological processes in biochemical processes, including cell proliferation and differentiation, are closely related to the function of RNA. Therefore, real-time imaging of RNA is of great significance in biochemical research. Many fluorescent imaging techniques (R...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/14C07D311/78C09K11/06G01N21/64
CPCC07D311/78C09B57/14C09K11/06C09K2211/1029C09K2211/1059C09K2211/1092G01N21/6486
Inventor 汪鹏飞牛广乐刘卫敏张洪艳
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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