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Perylene bisimide derivative and application thereof

A technology of perylene imide and derivatives, which is applied in the field of perylene imide derivatives and its application, and can solve the problems of perylene imide derivatives to be studied

Active Publication Date: 2021-03-19
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, researchers have prepared a variety of peryleneimide derivative molecules to realize photothermal or photodynamic therapy of tumors guided by photoacoustic imaging, but the application of peryleneimide derivatives in tumor chemotherapy remains to be studied

Method used

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  • Perylene bisimide derivative and application thereof
  • Perylene bisimide derivative and application thereof
  • Perylene bisimide derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation and characterization of embodiment 1 perylene imide derivatives

[0020] PDIC-NC preparation and characterization. Dissolve N,N'-dimethylethylenediamine (2.5 mmol) in N-methylpyrrolidone (50 mL), then add 1,6,7,12-tetrachloro-3,4,9,10-perylenetetra Carboxylic acid dianhydride (1 mmol), under argon protection, react at 80 °C for 24 h, cool to room temperature, add 100 mL of acetone, stir at room temperature for 2 h, filter with suction, wash with water until neutral, add 2 M HCl at room temperature (20 mL ) reacted for 24 h, cooled and stood still, suction filtered, dried, dissolved in water and dialyzed for 24 h (dialysis bag specification: 500-1000Da), and the dialysate was freeze-dried (-62 °C, 24 h) to obtain PDIC-NC. 1 H NMR (CF 3 COOD, 400 MHz) δ 3.29 (d, J = 6.2 Hz, 12 H), 3.87 (s, 4 H), 4.88 (t, J = 5.0 Hz, 13 C NMR (100 MHz, CF 3 COOD): δ 167.32, 138.74, 136.30, 133.28,132.43, 125.30, 123.84, 123.83, 59.78, 46.10, 38.35; HRMS (MALDI-TOF): m / z:[M...

Embodiment 2

[0023] Embodiment 2 organ distribution of perylene imide derivatives

[0024] Normal mice were divided into groups (n = 3), and the above-mentioned peryleneimide derivatives PDI-NC and PDIC-NC aqueous solution were injected through the tail vein, and the main organs (heart, liver, spleen, lung, kidney) were collected by:

[0025] (1) Organ fluorescence imaging detection. In vivo imaging fluorescence imaging system was used to collect fluorescence images of major organs, quantify the fluorescence intensity, and analyze the distribution of compounds in major organs (n ​​= 3);

[0026] (2) Quantitative analysis of organ fluorescence intensity. Take 50-70 mg of heart, liver, spleen, lung, and kidney, add tissue lysate, extract tissue fluid, carry out fluorescence spectrum detection, and quantitatively analyze the distribution of compounds in heart, liver, spleen, lung, and kidney according to the compound standard curve (n = 3);

[0027] (3) Organ tissue frozen section detectio...

Embodiment 3

[0029] Example 3 The ability of peryleneimide derivatives to inhibit the proliferation of lung cancer cells

[0030] Non-small cell lung adenocarcinoma cell A549 and small cell lung cancer cell H446 were used as tumor cell models, and normal bronchial epithelial cells BESA-2B and human normal lung fibroblast HFL-1 were selected as cell comparison models. All cells were purchased from the ATCC cell bank in the United States. After the cells reached about 80% confluence, they were digested and subcultured with 0.25% trypsin, and the cells in the logarithmic growth phase were used for in vitro cell viability experiments.

[0031] (1) CCK-8 assay to determine the ability of peryleneimide derivatives to inhibit tumor cell proliferation

[0032] Cells were digested and inoculated in 96-well plates, each well containing 100 μL cell suspension (cell concentration per mL 5×10 4 ), placed in a cell culture incubator (5% CO 2 , 37°C) and cultured for 12 h, the blank control group, PBS...

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Abstract

The invention provides a perylene bisimide derivative and an application thereof, and belongs to the technical field of biological medicines, the perylene bisimide derivative is a compound with a structural formula shown in the specification, and the derivative can be used for detecting the distribution of the compound in organs and organelles by utilizing fluorescence imaging, and has lung and mitochondria advantage distribution characteristics. Compared with a first-line anti-lung cancer drug cis-platinum, the compound can improve the lung cancer tumor cell proliferation inhibition capability, the half inhibition concentration is about 16-48% of cis-platinum, and in-vivo tumor proliferation can be efficiently inhibited.

Description

technical field [0001] The invention belongs to the field of biomedicine, and specifically relates to a perylene imide derivative and its application. Background technique [0002] The etiology and pathogenesis of lung cancer are complex. Most of the clinically diagnosed patients are middle-advanced lung cancer patients. The main treatment plan is platinum-based chemotherapy. However, platinum-based compounds are non-dominantly distributed drugs for lung cancer, and patients are prone to drug resistance during treatment. And liver, kidney toxicity and other side effects, damage to normal tissues and organs is greater. In order to improve the effect of chemotherapy for lung cancer, the drug can be prepared with predominant distribution in the lung and organelles. On the one hand, it enhances the enrichment of drugs in the lungs and increases the uptake of drugs in the lungs; on the other hand, it damages organelles with drugs, effectively kills tumor cells, and improves the ...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06A61K49/00A61P11/00A61P35/00
CPCC07D471/06C09K11/06A61P35/00A61P11/00A61K49/0021C09K2211/1044
Inventor 黄永伟刘中华王颖哲马翡雁高一剑
Owner HENAN UNIVERSITY
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