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Novel D-A-D organic near-infrared tumor therapy reagent based on diketopyrrolopyrrole and preparation method thereof

A technology for diketopyrrolopyrrole, tumor treatment, applied in diketopyrrolopyrrole dyes, organic chemistry, antitumor drugs, etc., can solve the problems of difficult modification, restricted material development, poor photostability, etc. Small side effects, excellent photothermal conversion ability and singlet oxygen generation ability, and clear reagent structure

Inactive Publication Date: 2018-02-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Small molecule organic compounds, such as indocyanine green (ICG), have good in vivo biocompatibility and low toxicity, but due to their poor photostability, difficult modification and poor targeting, It also restricts the further development of this kind of materials

Method used

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  • Novel D-A-D organic near-infrared tumor therapy reagent based on diketopyrrolopyrrole and preparation method thereof
  • Novel D-A-D organic near-infrared tumor therapy reagent based on diketopyrrolopyrrole and preparation method thereof
  • Novel D-A-D organic near-infrared tumor therapy reagent based on diketopyrrolopyrrole and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The preparation of embodiment 1PD-Br

[0053] In a two-neck flask (250mL), dissolve 10-(4-bromophenyl)-10H-phenothiazine (3.540g, 10mmol) in 30mL of chloroform, replace nitrogen three times, add N,N-dimethyl Add formamide (7mL, 88.00mmol), add phosphorus oxychloride (7.8mL, 80.00mmol), heat to 90°C, and stir for 12 hours. Pour into ice water, adjust the pH to 6-7 with sodium hydroxide, extract with dichloromethane, dry, concentrate, and separate by column chromatography to obtain yellow powder 10-(4-bromophenyl)-10H-phenothiazine-3- Formaldehyde 2.9g, yield 75%. 1 H NMR (400MHz, CDCl 3 ): δppm7.70 (d, J=8.4Hz, 2H), 7.26 (d, J=8.4Hz, 2H), 7.04 (dd, J 1 =7.4,J 2 =1.8Hz, 2H), 6.88(m, 4H), 6.24(dd, J 1 =8.0,J 2 = 1.4Hz, 2H).

[0054] In a two-necked flask (250 mL), 1,8-diazabicycloundecene-7-ene (2 mL, 6.24 mmol) and lithium chloride (0.308 g, 7.28 mmol) were dissolved in tetrahydrofuran (50 mL), Replace nitrogen three times, cool down to 0°C, add ethyl 2-(diethoxyp...

Embodiment 2

[0058] Embodiment 2PD-Br NPs preparation

[0059] Dissolve PD-Br (0.002g) in 100 μL THF, slowly add dropwise (drop rate: 15-20 drops / min) into 10 mL PBS with rapid stirring (1000 rpm), stir for 5 minutes, blow nitrogen to remove THF , to obtain organic nanoparticles PD-Br NPs. figure 1 It is the dynamic light scattering (DLS) result and the transmission electron microscope (TEM) picture of the organic nanoparticle PD-Br NPs test. The particle size of the obtained nanoparticles is about 100nm.

Embodiment 3

[0060] Embodiment 3PD-Br NPs spectrum test:

[0061] Select a 1 cm wide quartz cuvette, add 3 mL of PD-Br NPs PBS (50 μg / mL) solution, and test its ultraviolet absorption spectrum and fluorescence emission spectrum. Such as figure 2 As shown, in the ultraviolet-visible light absorption spectrum of PD-Br NPs, there are absorption peaks in the range of 600-1000nm, the maximum absorption peak is at 675nm, and the spectral range reaches the near-infrared region. image 3 It is the fluorescence emission spectrum of PD-Br NPs, and its emission spectrum ranges from 600-900nm, reaching the near-infrared region.

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Abstract

The invention discloses design synthesis and application performance of a novel D-A-D organic near-infrared tumor therapy reagent based on diketopyrrolopyrrole. The reagent provided by the invention is mainly obtained by Suzuki coupling reaction of 3, 6-bis(thieno[3, 2-c]thiophene)-2, 5-dihydropyrrolo[3, 4-c]pyrrole-1, 4-dione derivative and phenothiazine borate. By means of a reprecipitation method, the reagent can acquire a nano material with absorption wavelength in a near-infrared area, the nano material has high singlet oxygen yield, good photothermal conversion efficiency, excellent water dispersibility and tumor tissue targeting properties, can be applied to tumor cell and living body treatment, can effectively inhibit tumor cell migration while effectively killing tumor cells, thereby achieving the photothermal and photodynamic synergistic treatment effect. Therefore, the reagent can have enormous application prospects in tumor therapy.

Description

technical field [0001] The invention belongs to the field of materials and biomedicine, and specifically relates to a novel D-A-D organic near-infrared tumor treatment reagent based on diketopyrrolopyrrole, a preparation method thereof and its application in photothermal / photodynamic tumor synergistic treatment. Background technique [0002] Malignant tumor, namely cancer, is one of the major diseases threatening the whole world in the 21st century. Currently, the clinically applied cancer therapies include radiotherapy, chemotherapy and surgery. These methods will cause side effects to the organism to a certain extent, such as killing tumor cells while killing normal cells, destroying the human immune system, increasing the incidence of second cancers, and the resistance of chemotherapy drugs also greatly limits its use. application. Therefore, the development of more effective cancer therapeutic agents has become a key issue at present. [0003] At present, organic near...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K11/06C09B57/00A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057C09K11/06C07D519/00C09B57/004C09K2211/1029C09K2211/1092C09K2211/1037
Inventor 邵进军董晓臣黄维张琪杨雪张幸林
Owner NANJING UNIV OF TECH
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