Viscosity fluorescent probe with mitochondrial targeting function as well as preparation method and application thereof

A technology of fluorescent probes and mitochondria, which is applied in the field of viscosity fluorescent probes and its preparation, can solve the problems of inability to detect the viscosity of cell organelles, the inability to realize viscosity detection, short emission wavelength, etc., and achieve easy separation and purification of products and excellent anti-interference ability , The effect of simple synthesis method

Active Publication Date: 2020-05-08
BOHAI UNIV
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  • Description
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  • Application Information

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Problems solved by technology

Using fluorescent probes to detect viscosity changes in living organisms is one of the current research hotspots. It can overcome the shortcomings of traditional viscosity measurement devices that can only be used for macroscopic fluids and cannot visually monitor the viscosity changes in the microenvironment of living organisms. In recent years, it has been widely accepted. focus on
[0003] Altho...

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  • Viscosity fluorescent probe with mitochondrial targeting function as well as preparation method and application thereof
  • Viscosity fluorescent probe with mitochondrial targeting function as well as preparation method and application thereof
  • Viscosity fluorescent probe with mitochondrial targeting function as well as preparation method and application thereof

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Embodiment

[0035] (1) The reaction formula for synthesizing a viscous fluorescent probe with mitochondrial targeting function:

[0036]

[0037] (2) Concrete steps for synthesizing a viscous fluorescent probe with mitochondrial targeting function:

[0038] Dissolve 269mg of 5-methyl-3-(2′-benzothiazolyl)-4-hydroxybenzaldehyde and 260mg of 2-pyridine acetonitrile methylium salt in 10mL of absolute ethanol, add 20 microliters of piperidine, and dissolve the mixture Heating to reflux for 6 hours, wherein the heating and reflux temperature is 78° C., filtering the precipitate after cooling, and then recrystallizing the solid with ethanol to obtain a viscous fluorescent probe with mitochondrial targeting function, with a yield of 39%. Melting point: 249.3-250.7°C. NMR and high-resolution mass spectrometry results such as Figure 1-3 shown. 1 H NMR (400MHz, DMSO-d 6 )δ13.21(s,1H),9.15(d,J=6.1Hz,1H),8.72(t,J=7.8Hz,1H),8.60(s,1H),8.37(d,J=7.6Hz, 1H), 8.26(d, J=7.9Hz, 1H), 8.20(t, J=6.9Hz...

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Abstract

The invention discloses a viscosity fluorescent probe with a mitochondrial targeting function as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The preparation method comprises the following steps: dissolving 5-methyl-3-(2'-benzothiazolyl)-4-hydroxybenzaldehyde and 2-pyridylacetonitrile onium iodide into absoluteethyl alcohol, adding piperidine, heating and refluxing the mixture for 6 hours, cooling, filtering, precipitating, and recrystallizing the solid with ethanol to obtain a yellow solid, namely the probe (Z)-2-(2-(3-(2-benzothiazolyl)-4-hydroxy-5-methylphenyl)-1-cyanovinyl)-1-methylpyridine-1-iodide. The fluorescent probe has the advantages of excellent viscosity detection performance, excellent anti-interference capability and good mitochondria targeting positioning function, can be used for monitoring the viscosity change of mitochondria, cells, animal tissues and organs and mouse living bodies, and has a wide application prospect in the field of organism viscosity detection.

Description

technical field [0001] The invention relates to the field of functional materials, in particular to a viscous fluorescent probe with mitochondrial targeting function and its preparation method and application. Background technique [0002] Cellular viscosity is an important microenvironmental parameter that plays an important role in signaling as well as interactions between biomolecules. The abnormality of mitochondrial viscosity will cause the corresponding changes in physiological functions or the occurrence of diseases. Therefore, it is of great significance to accurately measure the changes of local microviscosity in the mitochondria of living cells. Using fluorescent probes to detect viscosity changes in living organisms is one of the current research hotspots. It can overcome the shortcomings of traditional viscosity measurement devices that can only be used for macroscopic fluids and cannot visually monitor the viscosity changes in the microenvironment of living orga...

Claims

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Application Information

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IPC IPC(8): C07D417/10C09K11/06G01N21/64
CPCC07D417/10C09K11/06G01N21/643G01N21/6428G01N21/6447G01N21/6486C09K2211/1007C09K2211/1029C09K2211/1037
Inventor 汤立军周磊钟克利边延江侯淑华
Owner BOHAI UNIV
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