Near-infrared fluorescent compound for detecting viscosity as well as preparation and application thereof

A fluorescent compound and near-infrared technology, applied in luminescent materials, organic chemistry, measuring devices, etc., can solve problems such as the inability to detect cell viscosity, and achieve the effects of small light damage, low background interference, and high viscosity sensitivity

Active Publication Date: 2021-09-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the traditional method for detecting viscosity is mainly based on in vitro viscosity and cannot detect viscosity at the cellular level, so it is urgent to develop a new method for detecting intracellular viscosity

Method used

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  • Near-infrared fluorescent compound for detecting viscosity as well as preparation and application thereof
  • Near-infrared fluorescent compound for detecting viscosity as well as preparation and application thereof
  • Near-infrared fluorescent compound for detecting viscosity as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]Embodiment 1: the preparation of compound (I)

[0040] Add 1mmol of compound (II), 1.2mmol of compound (III) and 0.2mmol of piperidine into a sufficient amount of ethanol solvent (5ml), stir at 85°C for 12h; concentrate the reactant under reduced pressure at 45°C to 500uL, oily liquid, Purified by silica column chromatography, eluted with dichloromethane / methanol (v / v, 1:10), collected the eluent, and dried to obtain compound (I) (53% yield), which H NMR spectrum see figure 1 , C NMR see figure 2 . 1 H NMR (500MHz, CDCl 3 ).

[0041]

Embodiment 2

[0042] Embodiment 2: the fluorescence absorption spectrum figure (excitation wavelength is 480nm, emission wavelength is 670nm) of compound (I) (5 μ M) in PBS and the glycerol that volume fraction is 90%

[0043] Accurately weigh a certain amount of compound (I) prepared in Example 1, prepare a probe mother solution with a concentration of 0.1mM with dimethyl sulfoxide, pipette 2 μL and add it to 0.398mL glycerol / PBS buffer solution (glycerol / PBS , v:v, 1:9), and then added to a 96-well plate, and then measure the fluorescence emission spectrum of compound (I).

[0044] Fluorescence spectrum see image 3 , the calculated Stokes shift is 190nm. Experimental result shows, when excited with 480nm wavelength, in PBS buffer solution, the absorption of compound (I) at 480nm place is weaker; When buffer solution viscosity is higher, the absorption of compound (I) at 480nm place is stronger, illustrates The probe is sensitive to viscosity.

Embodiment 3

[0045] Embodiment 3: compound (I), in DMSO / PBS buffer solution (v / v=1 / 99), under the condition of pH=7.4, the fluorescence intensity of probe changes with viscosity

[0046] Accurately weigh a certain amount of compound (I) prepared in Example 1, prepare a probe mother solution with a concentration of 1 mM with dimethyl sulfoxide, and pipette 2 μL of PBS buffer solution that is added to 0.398 mL of different viscosity values ​​(final viscosity Values ​​of 100cp, 200cp, 300cp, 400cp, 500cp, 600cp, 700cp, 800cp, 950cp) were added to a 96-well plate at 37°C, then the fluorescence spectrum of compound (I) was measured, and a correlation linear curve was made.

[0047] Fluorescence spectrum see Figure 4 and Figure 5 . The data showed that the fluorescence intensity of compound (I) increased significantly with the increase of buffer viscosity. When the viscosity value is 950cp, the fluorescence intensity is increased by nearly 130 times, and it has a good linear relationship (R...

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Abstract

The invention provides a high-sensitivity near-infrared fluorescent compound capable of being used for detecting viscosity as well as a preparation method and application thereof. The structure of the near-infrared fluorescent compound is represented by a formula (I). The compound disclosed by the invention has the main beneficial effects that the compound (I) can be used as a fluorescent probe for detecting viscosity, the fluorescence property excitation of the compound is that ex is equal to 480 nm and em is equal to 670 nm, and the compound has relatively large Stokes shift, has the advantages of low background interference, small light damage to a biological sample and the like and is high in viscosity sensitivity; and an effective research tool is provided for researching the physiological action of viscosity in cells.

Description

[0001] (1) Technical field [0002] The invention relates to a near-infrared fluorescent compound for detecting viscosity, a preparation method thereof and an application in preparing a fluorescent probe for viscosity detection. [0003] (2) Background technology [0004] A stable intracellular microenvironment is an important condition for maintaining the normal operation of a series of cell life activities (such as: proliferation, differentiation, metabolism, etc.). Among them, intracellular viscosity plays a particularly important role in processes such as material exchange, interaction between biomolecules, chemical signaling and metabolic transmission. Abnormal viscosity is related to many diseases and cellular dysfunctions, such as atherosclerosis, diabetes, Alzheimer's disease, malignant tumors, etc. Therefore, early diagnosis of these diseases can be made by monitoring viscosity. Therefore, viscosity can be used as a reference index to measure the state of living cells...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C09K11/06G01N11/00
CPCC07D409/06C09K11/06G01N11/00G01N2011/008C09K2211/1029C09K2211/1092
Inventor 朱勍孙悦付曼琳卢奇曾伟
Owner ZHEJIANG UNIV OF TECH
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