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Near-infrared fluorescent probe and preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of fluorescent materials, can solve the problem of inability to achieve synergistic tumor therapy, and achieve the effect of enhancing photothermal conversion effect, promoting therapeutic effect, and improving uniform distribution.

Active Publication Date: 2020-10-16
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the technical problem to be solved by the present invention is to overcome the defect that BODIPY materials in the prior art cannot realize the synergistic treatment of tumors, thereby providing a near-infrared fluorescent probe and its preparation method and application

Method used

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  • Near-infrared fluorescent probe and preparation method and application thereof
  • Near-infrared fluorescent probe and preparation method and application thereof
  • Near-infrared fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
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Embodiment

[0061] This embodiment provides the preparation method of near-infrared fluorescent probe (compound A and compound A-1), and the synthesis route of compound A and compound A-1 is as follows:

[0062]

[0063] The synthetic route of compound 4' and compound 4-1' is as follows:

[0064]

[0065] The preparation method of compound A and compound A-1 specifically comprises the following steps:

[0066] (1) Synthesis of compound 3'

[0067] In the mixed solution of 2.68g p-methoxybenzaldehyde (20mmol, compound 2'), 3.26g p-ethylaminoacetophenone (20mmol, compound 1') and 30mL absolute ethanol, slowly add 10mL sodium hydroxide solution (10wt%), reacted at room temperature for 12 hours, and filtered to obtain a yellow solid, washed with cold absolute ethanol, and dried in vacuo to obtain 3.56 g of compound 3' (63% yield).

[0068] 1 H NMR (400MHz, CDCl 3 )δ (ppm) = 7.95 (d, J = 8.4Hz, 2H), 7.75 (d, J = 15.2Hz, 1H), 7.58 (d, J = 8.4Hz, 2H), 7.45 (d, J = 15.6Hz ,1H),6.91(d,J...

experiment example 1

[0091] Adopt the following methods to detect the absorption spectra of compound 6', compound 6-1', compound A, compound A-1 respectively:

[0092] Test compound in 2mL DMSO solution (10 -6 Absorption spectra in M).

[0093] The absorption spectra of compound 6' and compound A are as Figure 5 As shown, it can be seen that the spectrum of compound 6' is red-shifted compared with that of compound A, wherein the maximum absorption wavelength of compound 6' is 768nm, and the maximum absorption wavelength of compound A is 703nm; compound 6-1' and compound A- The absorption spectrum of 1 is as Image 6 As shown, it can be seen that the spectrum of compound 6-1' is red-shifted compared with that of compound A-1, wherein the maximum absorption wavelength of compound 6-1' is 820nm, and the maximum absorption wavelength of compound A-1 is 703nm. It can be seen that compound A and compound A-1 can be used as near-infrared fluorescent probes, and can be used to prepare contrast agents ...

experiment example 2

[0095] The following methods were used to investigate the NO production of compound A and compound A-1 before and after near-infrared light irradiation:

[0096] DAF-FM DA (NO fluorescent probe) exhibits weak fluorescence, and it exhibits strong fluorescence emission after being combined with NO. 700nm laser irradiation compound A (or A-1) (10 -6 M) and DAF-FM (5 mM) in DMSO solution for 5 min, and use a fluorescence spectrometer to test the emission spectra of the mixed solution before and after irradiation.

[0097] The fluorescence spectra of the NO probe of compound A before and after near-infrared light irradiation are as follows: Figure 7 As shown, the fluorescence spectra of the NO probe of compound A-1 before and after near-infrared light irradiation are as follows: Figure 8 shown. Depend on Figure 7 and Figure 8 It can be seen that near-infrared light irradiation can also promote compound A and compound A-1 to release NO gas, and the amount of NO gas released...

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Abstract

The invention provides a near-infrared fluorescent probe and a preparation method and application thereof. According to the near-infrared fluorescent probe provided by the invention, a functional group capable of releasing nitric oxide (NO) gas is introduced into a boron difluoride-dipyrromethene (BODIPY) fluorophore skeleton, and the near-infrared fluorescent probe can release NO under the irradiation of near-infrared light. According to the near-infrared fluorescent probe provided by the invention, the synergistic effect of gas therapy, photothermal therapy and immunotherapy on tumors is realized, the near-infrared fluorescent probe has photoacoustic imaging, photo-thermal imaging and fluorescence imaging effects, the material after releasing NO gas can improve the signal-to-noise ratioof photoacoustic imaging, photo-thermal imaging and fluorescence imaging, so that the material can be used for providing reference and guidance for tumor treatment based on the imaging effect, and tumor cooperative treatment under the guidance of photoacoustic imaging, photo-thermal imaging and fluorescence imaging is realized.

Description

technical field [0001] The invention relates to the field of fluorescent materials, in particular to a near-infrared fluorescent probe and its preparation method and application. Background technique [0002] Malignant tumor, that is, cancer, is a disease that seriously threatens human health. At present, the main methods for clinical treatment of tumors are surgical resection, chemotherapy, and radiation therapy. Organs cause damage, and there are relatively large limitations. Therefore, new tumor treatment methods have been extensively studied. Light-regulated tumor therapy mainly includes photothermal therapy, chemotherapy, photodynamic therapy, etc. Due to its non-invasiveness, high selectivity and controllability, it has become a tumor treatment method that has attracted much attention in recent years. [0003] At present, there are many studies on photodynamic therapy that relies on oxygen to generate singlet oxygen. Photodynamic therapy is an oxygen-dependent photo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02A61K41/00A61K33/00A61P35/00A61K49/22A61K49/00
CPCC09K11/06C07F5/022A61K41/0052A61K33/00A61P35/00A61K49/22A61K49/0021C09K2211/107Y02P20/55
Inventor 徐云剑屈军乐刘丽炜胡睿陈振江
Owner SHENZHEN UNIV
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