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Near-infrared fluorescent compounds using cyanine dyes as skeleton, and preparation and application thereof

A technology of fluorescent compounds and cyanine dyes, applied in the directions of methine/polymethine dyes, organic dyes, fluorescence/phosphorescence, etc., can solve the problems of interfering with the fluorescence detection and imaging of biological samples, and achieve the effect of high selectivity and high sensitivity

Inactive Publication Date: 2015-11-11
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many organisms and their tissues emit fluorescence when excited by visible light, which interferes with the fluorescence detection and imaging of biological samples.

Method used

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  • Near-infrared fluorescent compounds using cyanine dyes as skeleton, and preparation and application thereof
  • Near-infrared fluorescent compounds using cyanine dyes as skeleton, and preparation and application thereof
  • Near-infrared fluorescent compounds using cyanine dyes as skeleton, and preparation and application thereof

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Embodiment 1

[0019] Embodiment 1: the synthesis of compound I

[0020] The synthetic route is as follows:

[0021]

[0022] Concrete synthetic steps are as follows:

[0023] 1) Under inert and oxygen-free conditions, add IR-780 iodide (0.5mmol), piperazine (2mmol) and dry dehydrated N,N-dimethylformamide into a two-necked flask, react at 85°C for 4 hours, After the reaction, use CH 2 Cl 2 Extraction, the organic layer was washed with anhydrous Na 2 SO 4 Dry, remove the solvent by rotary evaporation, and separate by column chromatography to obtain a blue solid piperazine-substituted cyanine dye intermediate. Yield: 85%; 1 HNMR (400MHz, CDCl 3 )δ7.66(d, J=15.0Hz, 2H), 7.26-7.32(m, 4H), 7.09(t, J=6.0Hz, 2H), 6.97(d, J=6.0Hz, 2H), 5.80( d, J=15.0Hz, 2H), 3.88(m, 8H), 3.26(t, J=6.0Hz, 4H), 2.44(t, J=6.0Hz, 4H), 1.84(m, 6H), 1.68( s,12H),1.02(t,J=6.0Hz,6H); ESIMSm / z589.6[M-I - ] + , calcdexactmass716.3.

[0024] 2) Under inert and anaerobic conditions, add the blue solid (0.5 mmol...

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Abstract

The invention relates to near-infrared fluorescent compounds using cyanine dyes as a skeleton, and preparation and application thereof. The near-infrared fluorescent compounds have the structure disclosed as the following general formula (I). The preparation method comprises the following steps: 1) under inert oxygen-free conditions, reacting IR-780 iodide (cyanine dye intermediate) with piperazine in an organic solvent, and carrying out after-treatment to obtain a piperazino substituted cyanine dye intermediate; and 2) under inert oxygen-free conditions, reacting the piperazino substituted cyanine dye intermediate compound obtained in the step 1) with 4-chloro-7-nitro-2,1,3-benzooxa-oxadiazole in an organic solvent in the presence of alkali, and carrying out after-treatment to obtain the compounds disclosed as Formula I. The compounds can be used for near-infrared fluorescent identification of hydrogen sulfide molecules.

Description

technical field [0001] The invention relates to a near-infrared fluorescent compound based on a cyanine dye as a skeleton, its preparation and application. Background technique [0002] There are many modern chemical detection methods, such as ultraviolet absorptiometry, infrared analysis, electrochemical method and so on. In recent years, fluorescent probe detection methods have attracted more and more attention. Fluorescent probe detection is a method to study structural changes in organisms at the molecular level by means of the sensitivity of the photophysical and photochemical properties of probe molecules to changes in the microenvironment. This change is accompanied by a change in fluorescence color or fluorescence intensity. Qualitative or quantitative analysis of the detected substance is realized by detecting the fluorescence change generated. Fluorescent probes are widely used in environmental detection, biomolecular imaging, and medical diagnosis due to their ...

Claims

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Application Information

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IPC IPC(8): C09B23/10C09K11/06C07D413/14G01N21/64
Inventor 尹军张宇峰刘盛华
Owner HUAZHONG NORMAL UNIV