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A near-infrared second region fluorescent compound capable of targeting mitochondria, its preparation method and application

A fluorescent compound and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., to achieve the effects of high industrial production value, simple synthesis route and high yield

Active Publication Date: 2020-08-07
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report of replacing the oxygen atom in the pyrylium salt with a sulfur atom to obtain a thiopyrylium salt

Method used

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  • A near-infrared second region fluorescent compound capable of targeting mitochondria, its preparation method and application
  • A near-infrared second region fluorescent compound capable of targeting mitochondria, its preparation method and application
  • A near-infrared second region fluorescent compound capable of targeting mitochondria, its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: the preparation of compound 4a

[0057] Compound 2a (1.36 g, 10 mmol) was dissolved in 20 mL of ethanol, 20% KOH (20 mL) solution was added and reacted at room temperature for 10 minutes. Benzaldehyde 3a (1.16 g, 11 mmol) was then added to the mixture, and the reaction was stirred at room temperature overnight. After cooling to room temperature, the reaction solution was adjusted to pH=3 with 2M HCl solution. The yellow intermediate chalcone formed was collected by filtration. Add chalcone (1.12g, 5mmol), potassium carbonate (1.52g, 11mol) and acetone (10mL) into the reaction vessel, stir at room temperature for 10 minutes, then add 3-bromopropyne (0.654g, 5.5 mol) was heated to reflux and stirred for 4 hours. The mixture was then filtered and the filtrate was concentrated under reduced pressure to afford product 4a (1.27 g, 97% yield).

[0058] The structure determination data of compound 4a are as follows:

[0059] 1H NMR (400MHz, Acetone-d6) δ8.24–...

Embodiment 2

[0061] Embodiment 2: the preparation of compound 6a

[0062] Cyclopentanone (1.2 g, 14.3 mmol) and tetrahydropyrrole (1.02 g, 14.3 mmol) were dissolved in benzene (20 mL), and the solution was heated to 100° C. and stirred for 4 hours. After cooling to room temperature, the benzene was removed under reduced pressure. Then compound 4a (2.5 g, 9.53 mmol) and anhydrous 1,4-dioxane (20 mL) were added to the above reaction solution, and the solution was heated under reflux for 6 hours. After the reaction was complete, water (40 mL) was added to the mixture, and extracted with ethyl acetate (50 mL×3). After that, the organic layer was washed with saturated brine. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The solvent was then removed in vacuo and the crude product was purified by silica gel column chromatography (2.17 g, yield 66%).

[0063] The structure determination data of compound 6a are as follows:

[0064] 1H NMR (...

Embodiment 3

[0066] Embodiment 3: the preparation of compound 7a

[0067] Compound 6a (1.2g, 3.46mmol) was dissolved in diethyl ether (10mL) and stirred for 10 minutes, thioacetic acid (659mg, 8.66mmol) and boron trifluoride ether (2.46g, 17.32mmol) were added to the mixture in Heat at reflux for 3 hours. After cooling to room temperature, the reaction mixture was quenched with water, and excess diethyl ether was added to the solution. The mixture was then stirred at room temperature to precipitate a pale yellow solid (400 mg, yield 50%).

[0068] The structure determination data of compound 7a are as follows:

[0069] 1H NMR (400MHz, Acetonitrile-d3) δ8.63(s, 1H), 8.01(d, J=9.1Hz, 2H), 7.85–7.76(m, 2H), 7.76–7.63(m, 3H), 7.29( d, J=8.9Hz, 2H), 4.92(d, J=2.4Hz, 2H), 3.67(t, J=7.6Hz, 2H), 3.34(t, J=7.4Hz, 3H), 2.95(t, J=2.5Hz,1H),2.37(p,J=7.5Hz,2H).

[0070] 13C NMR (101MHz, Acetonitrile-d3) δ174.5, 165.7, 161.9, 159.4, 149.5, 137.2, 132.5, 131.7, 130.3, 129.3, 129.2, 127.3, 116.6, 77....

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Abstract

The invention discloses a near-infrared second-region fluorescent compound capable of targeting mitochondria as well as a preparation method and application thereof. According to the compound, the emission wavelength ranges from 600 nm to 1200 nm and can reach the near-infrared second-region (900-1200 nm) after the compound is modified by different functional groups. The compound can be used for the biological fields of mitochondrion imaging, photo-thermal therapy and osteosarcoma and whole-body bone imaging; and added modified sites can be used for connecting different bioactive groups, so that the water solubility, the biocompatibility and the targeting property are improved, and the compound can also be used for in-vitro detection of various disease markers and in-vivo early diagnosis of breast cancer, brain glioma, colon cancer, liver cancer and the like. The fluorescent compound has the advantages of being novel in structure, simple in synthesis steps, resistant to photobleaching,non-toxic, good in biocompatibility and excellent in industrial production value and biomedical application prospect.

Description

technical field [0001] The invention belongs to the field of fluorescent probe dyes in the second near-infrared region, in particular to a novel near-infrared fluorescent compound with a thiopyrylium structure, and its emission wavelength is located at 600-1200nm. After modification with different functional groups, its emission wavelength can reach the second near-infrared region (900-1600nm), which can be used in mitochondrial imaging and photothermal therapy, cancer detection, tumor imaging and surgical navigation in the field of biomedical materials. Background technique [0002] Cancer (also known as malignant tumor) is a serious threat to human health. Due to the limitation of medical technology level, there is currently no effective treatment for advanced cancer, so early diagnosis of cancer is particularly important for patients. Early detection and timely treatment can significantly improve the survival rate of cancer patients. The emergence of molecular imaging te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06C07D409/14C07D417/06C07D417/14C07D413/06C07D413/14C09K11/06C08G81/00
CPCC07D409/06C07D409/14C07D413/06C07D413/14C07D417/06C07D417/14C08G81/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092
Inventor 洪学传周晖肖玉玲丁兵兵段建利
Owner WUHAN UNIV
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