Novel symmetric cytisine type alkaloid compound as well as preparation and application thereof

A technology of cytisine and alkaloids, applied in drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problems that no small molecules have been approved yet, and achieve the effect of wide application prospects

Pending Publication Date: 2022-04-12
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the drugs that act on the immune target of PD-1 approved by the US FDA are all monoclonal antibody biomacromolecules, and no small molecules have been approved yet.
In 2021, some scholars reported a biphenyl-imidazole compound, which was confirmed to have an inhibitory effect on targeting the PD-1 pathway after initial molecular docking scoring and screening. Currently, research on small molecule inhibitors of PD-1 is still in progress middle

Method used

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  • Novel symmetric cytisine type alkaloid compound as well as preparation and application thereof
  • Novel symmetric cytisine type alkaloid compound as well as preparation and application thereof
  • Novel symmetric cytisine type alkaloid compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Isolation and structural identification of novel symmetrical cytisine-type alkaloids in Sophora flavescens

[0042] 1.1 Experimental medicinal reagents:

[0043] Sophora flavescens root, purchased in Zhengzhou, Henan, was identified as the dried root of Sophora Flavescens Ait by Professor Yin Xiaoying of Shanghai University of Engineering and Technology, and was pulverized according to the Chinese Pharmacopoeia medicinal material pulverization method.

[0044] Methanol (AR, Shanghai Titan Technology Co., Ltd.); dichloromethane (AR, Shanghai Titan Technology Co., Ltd.); ammonia (AR, Sinopharm Chemical Reagent Co., Ltd.); bismuth potassium iodide (AR, Shanghai Titan Technology Co., Ltd. company); ODS (50 μm, Japan YMC Company); silica gel (200-300 mesh, Qingdao Hailang Silica Gel Desiccant Co., Ltd.);

[0045] 1.2 Extraction of total alkaloids of Sophora flavescens:

[0046] Sophora flavescens root (50kg) was crushed and then heated and extracted with 85% ethan...

Embodiment 2

[0058] Example 2: Study on tumor cytotoxicity of novel symmetrical cytisine-type alkaloids in Sophora flavescens

[0059] 2.1 Experimental reagents and cells

[0060] Fetal bovine serum (Biological Industries, product number: 04-007-1A); DMEM-H medium (Corning, product number: 10-013-CVRC); glutamine (Gino Biotechnology Co., Ltd., product number: GNM21051); acetone Sodium Acetate (Gino Biotechnology Co., Ltd., product number: GNM11444); RPMI-1640 medium (Corning, product number: 10-010-CV); PBS (Procell, product number: WH0112201 911XP); trypsin (Biosharp, product number: 143188) ; CCK8 (Invigentech, Cat. No.: IV08-100)

[0061] Cell lines A431 cells and BT474 cells were purchased from Shanghai Saibaikang Biological Co., Ltd.

[0062] 2.2 Cell culture and sample processing

[0063] For A431 cells, prepare the complete cell culture medium according to the ratio of DMEM-H medium: fetal bovine serum at 9:1, and add sodium pyruvate and glutamine at the same time.

[0064] For ...

Embodiment 3

[0077] Example 3: Study on PD-1 inhibitory effect of novel symmetrical cytisine-type alkaloids in Sophora flavescens

[0078] 3.1 Experimental operation software and database

[0079]All work of the present invention is all finished in Microsoft Windows XP Professional operating system, adopts AutoDockTools-1.5.6, AutoDock Vina software of The Scripps Research Institute institute Dr.Oleg Trott laboratory development and maintenance to carry out molecular docking, ChemBioOffice2004 of U.S. Cambridge Company The Chem 3D module in the program and the open-source software Pymol of DeLano Scientific LLC company are used for compound processing. Parameter settings are default values ​​unless otherwise specified.

[0080] RCSB PDB protein database (RCSB Protein Data Bank, PDB) is the only database in the world about the three-dimensional structure information of large biomolecules (including proteins and nucleic acids). Species covered include humans, bacteria, yeast, plants, flies...

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PUM

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Abstract

The invention relates to a novel symmetric cytisine type alkaloid compound and preparation and application thereof, the chemical structural formula of the alkaloid compound is shown as follows: compared with the prior art, the compound has the cytotoxicity of human epidermal cancer cells A431 and human breast duct cancer cells BT474, the IC50 values of the compound reach 216.1 [mu] M and 193.3 [mu] M respectively, and the compound can be used as a novel symmetric cytisine type alkaloid compound. Therefore, the compound has a cytotoxic effect on tumor cells, and can obviously inhibit the activity of the tumor cells and the like.

Description

technical field [0001] The invention belongs to the technical field of alkaloid compounds, and relates to a novel symmetrical cytisine-type alkaloid compound and its preparation and application. Background technique [0002] Sophora flavescens is a traditional Chinese medicine, which is the dried root of Sophora flavescens, also known as Sophora flavescens root, Digu, Phoenix claw, etc. Its surface is grayish-brown or brownish-yellow, with longitudinal wrinkles and horizontal long lenticel-like protrusions. The outer skin is thin, often cracked and rolled back, easy to peel off, and the peeled part is yellow and smooth. Hard, not easy to break, broken section fibers. According to the "Chinese Pharmacopoeia" in 2015, Sophora flavescens clears heat and dampness, kills insects, and diuresis. It can be used to treat dysentery, hematochezia, jaundice and anuria, leucorrhea, pruritus vulvae, eczema, eczema, itchy skin, mange and leprosy, external treatment of trichomonal vaginit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22A61P35/00
Inventor 尹小英陈圣雪
Owner SHANGHAI UNIV OF ENG SCI
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