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Near-infrared fluorescent molecular probe, preparation method thereof and application of near-infrared fluorescent molecular probe in cell imaging

A fluorescent molecular probe and near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, to achieve the effect of novel structure, simple preparation process, and avoid interference

Active Publication Date: 2021-07-23
BINZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, how to realize the organic combination of highly sensitive and high-resolution tumor imaging diagnosis and effective treatment, and provide effective information for tumor diagnosis and treatment is still a major problem in the integration of cancer diagnosis and treatment.
Currently there is no research report on the integration of diagnosis and treatment of EML4-ALK positive non-small cell lung cancer

Method used

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  • Near-infrared fluorescent molecular probe, preparation method thereof and application of near-infrared fluorescent molecular probe in cell imaging
  • Near-infrared fluorescent molecular probe, preparation method thereof and application of near-infrared fluorescent molecular probe in cell imaging
  • Near-infrared fluorescent molecular probe, preparation method thereof and application of near-infrared fluorescent molecular probe in cell imaging

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 0.15mmol of compound 3 to a 50mL reaction flask, add 3mL of anhydrous N,N-dimethylformamide (DMF), stir, heat to 25°C, dissolve, and add 0.6mmol of compound 2 under argon protection, at 25°C Stirring for 2h, the reaction ended. The reaction solution was poured into 25 mL of methyl tert-butyl ether, a green solid was precipitated, filtered through filter paper, and the upper layer of solid matter was collected. 200-300 mesh silica gel column chromatography separation and purification, the eluent is a mixture of dichloromethane and methanol at a volume ratio of 30:1, and 11 mg of green metallic color crystals are obtained as near-infrared fluorescent probes.

[0035] Its mass spectrogram see figure 1 , see the hydrogen spectrum figure 2 .

[0036] ESI-MS m / z: 1060.56[M+H-I] + .

[0037] 1 H-NMR (500MHz, DMSO-d 6 )δ(ppm)=8.18(s,1H), 7.95(d,1H), 7.93(s,1H), 7.88-7.76(d,1H), 7.73-7.70(m,3H), 7.70(d,1H ), 7.41-7.32(m,4H), 7.14-7.11(m,3H), 6.95(s,1H), 5.99(d,1H), 4....

Embodiment 2

[0040] Add 0.15mmol of compound 3 to a 50mL reaction flask, add 3mL of anhydrous dimethyl sulfoxide (DMSO) and stir, heat to 25°C, dissolve, under the protection of argon, add 0.6mmol of compound 2, stir at 25°C for 2h, react Finish. The reaction solution was poured into 25 mL of diethyl ether, and a green solid was precipitated, filtered through filter paper, and the solid substance in the upper layer was collected. 200-300 mesh silica gel column chromatography separation and purification, the eluent is a mixture of dichloromethane and methanol at a volume ratio of 30:1, and 10 mg of green metallic color crystals are obtained as near-infrared fluorescent probes.

Embodiment 3

[0042] Add 0.15mmol of compound 3 to a 50mL reaction flask, add 3mL of anhydrous dimethyl sulfoxide (DMSO) and stir, heat to 25°C, dissolve, under the protection of argon, add 0.6mmol of compound 2, stir at 25°C for 2h, react Finish. The reaction solution was poured into 25 mL of diethyl ether, and a green solid was precipitated, filtered through filter paper, and the solid substance in the upper layer was collected. 200-300 mesh silica gel column chromatography separation and purification, the eluent is a mixture of dichloromethane and methanol at a volume ratio of 35:1, and 8 mg of green metallic color crystals are obtained as near-infrared fluorescent probes.

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Abstract

The invention provides a near-infrared fluorescent molecular probe, which has the following structural formula. The invention also provides a preparation method of the near-infrared fluorescent molecular probe. The invention also provides an application of the near infrared fluorescent molecular probe in targeted imaging in EML4-ALK positive non-small cell lung cancer cells (NCIH3122 cells). The near-infrared fluorescent molecular probe provided by the invention is novel in structure, simple in preparation process, capable of effectively avoiding interference of biological autofluorescence and cell endogenous substances, high in sensitivity, good in optical stability and good in cell membrane permeability, and can be used as a near-infrared fluorescent probe for EML4-ALK positive non-small cell lung cancer (NCIH3122 cells) fluorescence imaging.

Description

technical field [0001] The invention belongs to the technical field of fluorescent molecular probes, and in particular relates to a near-infrared fluorescent molecular probe, a preparation method thereof and an application in cell imaging. Background technique [0002] The near-infrared light system refers to the light waves in the range of 650-900nm. The light in this range has strong anti-interference ability, and can generate light signals in deep tissues without affecting the body tissues. Near-infrared imaging technology has been widely used in bioscience fields such as tumor tissue positioning imaging, imaging of metal ions or other trace bioactive components in vivo, and drug modification. , in-situ detection and other advantages have become a hot spot in the field of imaging detection [Maxwell D, Chang Q, Zhang X, et al. Bioconjug Chem, 2009, 20(4): 702-709. Yi X, Wang F, Qin W, et al. al.International Journal of Nanomedicine,2014,9:1347–1365.Chen H,Lin W,Cui H,et a...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/14G01N21/64
CPCC09K11/06C07D401/14G01N21/6428G01N21/6456G01N21/6458G01N21/6402C09K2211/1007C09K2211/1044C09K2211/1029
Inventor 孙春龙
Owner BINZHOU UNIV
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