Naphthoquinone dimer and preparation method and applications thereof

A naphthoquinone dimer and carrier technology, applied in the field of medicine, can solve problems such as no naphthoquinone dimer, and achieve the effects of good controllability and reproducibility, low cost and convenient operation

Active Publication Date: 2017-11-07
CHINA PHARM UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there is no report of Rubiaceae plant-derived naphthoquinone dimer Rubioncolin C(1) as an inhibitor of NF-κB signaling pathway and an antitumor drug

Method used

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  • Naphthoquinone dimer and preparation method and applications thereof
  • Naphthoquinone dimer and preparation method and applications thereof
  • Naphthoquinone dimer and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of naphthoquinone dimer Rubioncolin C (1) (flow process sees figure 1 ), including the following steps:

[0031] Take 10kg of roots and rhizomes of Rubia petioli, after drying and crushing, extract 3 times under methanol reflux (20L×3), the time is 4h, 3h and 3h, and the total methanol extract after the extract is concentrated under reduced pressure is 1.42kg. The total extract was chromatographed on a silica gel column and eluted with a gradient of chloroform / methanol (100:0, 9:1, 8:2, 7:3, 1:1, 0:100) to obtain six components Fr.1 -Fr.6; wherein the low polar part Fr.1 (53g) was subjected to silica gel column chromatography and eluted with petroleum ether / acetone (30:1, 15:1, 5:1, 1:1) gradient to obtain 4 subfractions Fr.1-1-Fr.1-4; Fr.1-3 (17g) subfractions were subjected to Sephadex LH-20 gel column chromatography, 1:1 chloroform / methanol as eluent , to obtain 3 subcomponents Fr.1-3-1-Fr.1-3-3; Fr.1-3-2 (5.2g) was repeatedly subjected to si...

Embodiment 2

[0033] The naphthoquinone dimer Rubioncolin C (1) of the present invention utilizes SRB colorimetry to evaluate its effect on human non-small cell lung cancer cell line (A549), human liver cancer cell line (BEL-7402, HepG2 and SMMC-7721), human gastric adenocarcinoma Cell lines (BGC-823 and SGC-7901), human prostate cancer cell lines (DU145), human cervical cancer cell lines (HeLa), human breast cancer cell lines (MDA-MB-231 and MCF-7) and human glia The cytotoxic activity of 11 kinds of tumor cell lines (all cells come from Shanghai Cell Bank, Chinese Academy of Sciences) including plasmoma cell line (U251) was found to have cytotoxic activity of naphthoquinone dimer. The experimental principles, methods and results are as follows:

[0034] Experimental principle: SRB (sulfonylrhodamine B), a water-soluble protein dye, has a sulfonic acid group anion in the molecule, and can combine with basic amino acids of intracellular proteins under weakly acidic conditions. The base dis...

Embodiment 3

[0040] The naphthoquinone dimer Rubioncolin C(1) of the present invention is evaluated for its anti-tumor activity in vivo by using the human liver cancer HepG2 nude mouse xenograft model, and the results show that the naphthoquinone dimer has better anti-tumor activity in vivo. The experimental methods and results are as follows:

[0041] Human liver cancer cells HepG2 (from Shanghai Cell Bank, Chinese Academy of Sciences) were prepared with serum-free DMEM medium to a concentration of 1×10 5 cells / mL cell suspension, which was inoculated subcutaneously in the left armpit of BABL / c nude mice, and after 7 days of growth, a tumor-bearing mouse model was formed. The well-inoculated tumor-bearing mice were randomly divided into groups, and injected intraperitoneally with naphthoquinone dimer Rubioncolin C (1) (40 mg / kg, 20 mg / kg and 10 mg / kg), administered once every other day, and sacrificed 14 days after administration All animals were stripped and weighed, the tumor inhibitio...

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Abstract

The invention discloses a naphthoquinone dimer separated from Rubia plant, a pharmaceutical composition taking the naphthoquinone dimer as an active ingredient, an Nf-kB signal pathway inhibitor taking the naphthoquinone dimer as an active ingredient, a preparation method, and applications of the naphthoquinone dimer in drugs for treatment and prevention of related inflammatory diseases and cancers activated by abnormality of an Nf-kB signal pathway, belonging to the technical field of pharmaceuticals. The Rubioncolin C (1) is a naphthoquinone dimer separated from Rubiapodantha D., and has in vitro and vivo anti-tumor and Nf-kB signal pathway inhibition activity. The naphthoquinone dimer can be applied in preparation of anti-tumor pharmaceutical preparation and precursor drugs, and has the advantages of being low in preparation cost, low in toxicity, good in anti-tumor effect, and the like.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a class of naphthoquinone dimers, their application as NF-κB signaling pathway inhibitors or antitumor drugs, and pharmaceutical compositions using them as active ingredients, their preparation methods and their use in Application in preparation of medicines for treating and preventing inflammatory diseases and cancers related to NF-κB signaling pathway. Background technique [0002] In 1986, Sen and Baltimore first discovered the nuclear transcription factor NF-κB in mature B cells, which is a protein factor that can specifically bind to the sequence of the enhancer κB of the immunoglobulin κ light chain gene. NF-κB is widely involved in a variety of biological effects, including important physiological and pathological processes such as cell proliferation, apoptosis, inflammatory response, immune response, and tumor development. It is one of the most important sig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/94C07C67/48C07C67/56A61K31/235A61P35/00
CPCA61K36/74C07C67/48C07C67/56C07C69/94
Inventor 谭宁华汪哲赵思蒙宋立华陈小强
Owner CHINA PHARM UNIV
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