PH sensitive near-infrared fluorescence molecular probe and preparation method and use thereof

A fluorescent molecular probe, near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as difficult application, and achieve novel structure, high sensitivity, and good cell membrane permeability.

Inactive Publication Date: 2014-02-05
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing research on fluorescent molecular probes is mainly the research on acidic near-infrared pH fluorescent probes, which are difficult to app...

Method used

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  • PH sensitive near-infrared fluorescence molecular probe and preparation method and use thereof
  • PH sensitive near-infrared fluorescence molecular probe and preparation method and use thereof
  • PH sensitive near-infrared fluorescence molecular probe and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Take 1.0g of compound IR-820 and 1.18g of methylpiperazine, mix them in 20ml of THF, heat and stir at 80°C for 5h; concentrate the solvent under reduced pressure, add 80ml of methyl tert-butyl ether, a dark blue solid precipitates out, and filter out the solid to obtain Dark blue crude product; the dark blue crude product is separated by 200-300 mesh silica gel column chromatography with dichloromethane:methanol as eluent (4:1v / v), then the solvent is concentrated under reduced pressure, and vacuum-dried to obtain near-infrared fluorescence The pure product of probe MP-Cy was 0.42g, and the yield was 38.89%.

[0030] Its hydrogen spectrum and mass spectrum are shown in figure 1 and figure 2 .

[0031] 1 H NMR (500MHz, DMSO-d 6 ):δ1.94(s,12H),1.70-1.90(m,12H),2.43-2.50(m,4H),2.51-2.69(m,6H),3.29(s,3H),3.70(m,4H ),4.18(m,4H),6.07(d,2H,J=13.2Hz),7.43(t,2H,J=7.3Hz),7.59(t,2H,J=7.3Hz)7.68(d,2H, J=8.0Hz), 7.84(d, 2H, J=8.0Hz), 8.0(d, 2H, J=13.2Hz), 8.24(d, 2H, J=13.2...

Embodiment 2

[0039] Take 5.0 g of compound IR-820 and 5.90 g of methylpiperazine, mix them in 100 ml of THF, heat and stir at 80°C for 6 h; concentrate the solvent under reduced pressure, add 400 ml of diethyl ether, a dark blue solid precipitates out, and filter the solid to obtain a dark blue crude product; The dark blue crude product was separated by chromatography on a 200-300 mesh silica gel column with dichloromethane:methanol as the eluent (6:1v / v), then the solvent was concentrated under reduced pressure and dried in vacuo to obtain the near-infrared fluorescent probe MP-Cy The pure product is 2.50g, and the yield is 46.90%.

Embodiment 3

[0041] Take 10.0g of compound IR-820 and 11.70g of methylpiperazine, mix them in 200ml of THF, heat and stir at 80°C for 6.5h; concentrate the solvent under reduced pressure, add 800ml of methyl tert-butyl ether, a dark blue solid precipitates out, and filter out the solid. The dark blue crude product was obtained; the dark blue crude product was separated by column chromatography with ethyl acetate:methanol (4:1v / v) as the eluent, and then the solvent was concentrated under reduced pressure and dried in vacuo to obtain the near-infrared fluorescent probe MP-Cy The pure product is 3.62g; the yield is 33.92%.

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Abstract

The invention provides a pH sensitive near-infrared fluorescent molecular probe MP-Cy with a structural formula shown as follows. The invention also provides a preparation method of the molecular probe and its application in pH detection. The fluorescent molecular probe has the advantages of novel structure and simple preparation process, can effectively avoid interferences of biological autofluorescence and cell endogenous substances, is high in sensitivity, good in optical stability and good in cell membrane permeability, and can accurately monitor the near-in-vivo neutral physiological pH value fluctuations.

Description

technical field [0001] The invention belongs to the field of biochemical detection, and in particular relates to a pH-sensitive near-infrared fluorescent molecular probe, and also relates to a preparation method of the molecular probe and its application in pH detection. Background technique [0002] Changes in intracellular pH affect many cellular activities, including receptor-mediated signal transduction, enzyme activity, cell growth and apoptosis, ion migration and balance, calcium regulation, endocytosis, chemotaxis and cell adhesion, etc. will have an important impact. For example, intracellular pH changes when tumors develop. [0003] The pH measurement method based on the change of optical signal can make up for the difficulty of measuring pH in vivo with glass electrodes. The fluorescence or light absorption properties of some organic compounds change with pH, ​​which can be used to indicate the change of acidity and alkalinity in the target medium. The use of flu...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/60G01N21/64
Inventor 吉民孙春龙蔡进王鹏宗玺李鲁申周高信
Owner SOUTHEAST UNIV
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