Pillararene type compound as well as preparation method, pharmaceutical composition and application thereof

A technology of complexes and pillar aromatics, applied in the field of medicine

Inactive Publication Date: 2017-09-29
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, no work has been reported on the inclusion of drug molecules based on pillararene derivatives to improve drug bioavailability, stability or solubility.

Method used

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  • Pillararene type compound as well as preparation method, pharmaceutical composition and application thereof
  • Pillararene type compound as well as preparation method, pharmaceutical composition and application thereof
  • Pillararene type compound as well as preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Example 1: Preparation and characterization of CP6A / nitrogen mustard complex

[0097] Preparation and characterization of CP6A / nitrogen mustard complex:

[0098] Accurately weigh 20mg nitrogen mustard (purchased from Beijing Yinuokai Co., Ltd.) (0.105mmol) and 171mg CP6A (M is ammonium ion, the preparation method can refer to J.Am.Chem.SOC.2012,134,13248-13251) (0.105mmol) was mixed and dissolved in 5mL water until it was fully and uniformly mixed, and then the solution of the mixture was vacuum freeze-dried within 10 minutes to obtain a nitrogen mustard / CP6A complex. Composite 1 H-NMR and CP6A alone and nitrogen mustard alone in D 2 O's 1 H-NMR such as Figure 4 , the chemical shift values ​​of the nitrogen mustard in the complex are shown in Table 1 below:

[0099] Table 1

[0100]

[0101] From Table 1, Figure 4 It can be clearly seen that when the nitrogen mustard drug is included by CP6A, its chemical shift value changes significantly, and the H a 、H ...

Embodiment 2

[0102] Example 2: Preparation and Characterization of CP6A / Oxaliplatin Complex

[0103] Accurately weigh 20mg of oxaliplatin (0.05mmol) (purchased from Beijing Yinuokai Co., Ltd.) and 82mg of CP6A (0.05mmol) and mix them in 10mL of water. The drug is completely dissolved and uniformly mixed, and the mixed solution is freeze-dried under vacuum to obtain the CP6A / oxaliplatin complex. Composite 1 H-NMR and individual subject CP6A and individual oxaliplatin drug in D 2 O's 1 H-NMR such as Figure 5 , the chemical shift values ​​of oxaliplatin in the complex are shown in Table 2 below:

[0104] Table 2

[0105]

[0106]

[0107] From Table 2, Figure 5 It can be clearly seen that after oxaliplatin and CP6A form a complex, the chemical shift value changes significantly, and the H a，a’ 、H b,b’ and H c The proton peak broadens significantly, nearly disappears, and moves to high fields. The change value of its chemical shift is shown in Table 2, which shows that the c...

Embodiment 3

[0109] Example 3: Evaluation of the inhibitory effect of CP6A / nitrogen mustard complex on tumor cells

[0110] 1. Experimental samples

[0111] CP6A / nitrogen mustard complex: prepared in Example 1.

[0112] Human breast cancer cell MCF-7 and liver cancer cell HepG2: both provided by Peking Union Medical College Cell Bank.

[0113] 2. Experimental method

[0114]MTT method was used to evaluate the inhibitory effect of CP6A / nitrogen mustard complex on human breast cancer cell MCF-7 and liver cancer cell HepG2. Nitrogen mustard alone was used as the control group, and its toxicity was measured 48 hours after administration.

[0115] For each type of cell, collect logarithmic growth cells (MCF-7, HepG-2 cells), adjust the concentration of the cell suspension, inoculate the cell suspension in a 96-well plate, and plate to adjust the density of the cells to be tested to about 10,000 / well, 100 μL cell suspension per well, in 5% CO 2 , incubate at a constant temperature of 37°C...

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Abstract

The invention belongs to the technical field of medicines and relates to a pillararene type compound as well as a preparation method, a pharmaceutical composition and application thereof. Specifically, the invention relates to a compound shown as a formula I as well as a preparation method, a pharmaceutical composition and application thereof. According to the compound provided by the invention, the stability of a medicine is improved and the inhibition effect of the medicine on tumor cells is also enhanced. The preparation method of the compound is simple and the compound has very important meaning on secondary development and utilization of the medicine. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a pillar aromatic compound, its preparation method, pharmaceutical composition and application. Specifically, the pillararene compound refers to a complex formed by a pillararene derivative and a drug. Specifically, the drug is an antineoplastic drug. Background technique [0002] With the continuous development of medicinal chemistry, more and more new drugs have been developed and marketed. However, some drugs have low bioavailability due to problems such as poor solubility, poor oral absorption, and poor biocompatibility. [0003] Nitrogen mustard is the earliest anti-tumor drug used clinically and has achieved outstanding curative effect. It is mainly used for the treatment of malignant lymphoma, and it also has certain curative effects on ovarian cancer, breast cancer, and prostate cancer. Its anti-tumor mechanism is due to the existence of highly active dual Chloroethylami...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/54A61K33/24A61K31/131A61K31/555A61P35/00
CPCA61K31/131A61K31/555A61K33/24A61K47/58
Inventor 孟庆斌李春举李斌孟昭董华进贾学顺刘克良
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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