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Tri-indole compound and preparation method and application thereof

An indole compound, indole technology, applied in the field of triindole compound and its preparation, to achieve the effect of unique activity, strong anti-tumor activity and novel structure

Inactive Publication Date: 2012-04-18
XIAMEN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional microbial culture methods can only obtain about 1% of microorganisms from the environment (3, Venter JC, Remington K, Heidelberg JF et al. Environmental genome shotgun sequencing of the Sargasso Sea [J]. Science2004, 304: 66-74), And metagenomics is a technical method that does not depend on pure culture (4, Amann, R.I., Ludwig, W., Schleifer, K.H., Phylogenetic identification and in situ detection of individual microbial cells without cultivation[J].Microbiol. Rev.1995, 59, 143-169)

Method used

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  • Tri-indole compound and preparation method and application thereof
  • Tri-indole compound and preparation method and application thereof
  • Tri-indole compound and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Screening of embodiment 1 clones

[0020] 1) Enrichment of deep-sea sediment samples: 10 g of sediment samples collected at 2,783 m deep in the Southwest Indian Ocean and stored at 4°C were taken out, and enriched in artificial seawater actinomycete enrichment medium;

[0021] 2) DNA extraction of deep-sea sediment enrichment samples: adding DNA extraction buffer to deep-sea sediment enrichment samples to lyse cells, extract DNA and purify;

[0022] 3) Construction of metagenomic library of deep-sea sediment enrichment samples: the plasmid vector used was Fosmid, the insert fragment was 30-40kb, and the host was Escherichia coli. A total of about 4000 clones were obtained, among which the clone numbered 19C6 The seeds appear blue on the LB plate, and the ethyl acetate crude extract of the LB fermentation broth has good cytotoxic activity against HT1080, CNE2, and BEL7402 tumor cells at a concentration of 100ug / ml, which are 94.35%, 92.52%, and 90.56%, respectively. %. ...

Embodiment 2

[0024] The preparation of embodiment 2TIE

[0025] 1. Fermentation of Escherichia coli EPI300 19C6 containing clone 19C6

[0026] Escherichia coli EPI300 19C6 containing clone 19C6 was inoculated into 3 ml of LB medium, and cultured at 37° C. and 200 rpm for 10 h. Then take 1ml of the primary culture and inoculate it into 500ml medium, cultivate it at 37°C and 200rpm for 20h, then inoculate it into a 100L fermenter, feed air at 37°C, 60L / min, ferment at 200rpm, pH7.0 for 36h, and use a continuous flow centrifuge Bacteria and bacteria fluid were collected separately.

[0027] 2. Fermentation broth extraction

[0028] 80L fermentation broth was adsorbed by macroporous adsorption resin (AB-8, 11L), washed with 33L of water to remove impurities, then eluted with 33L of ethanol, collected the eluted part of ethanol, and recovered ethanol to obtain 112.9g of extract.

[0029] 3. Separation and purification of TIE

[0030] 1) Take the extract obtained in step 2) and carry out sil...

Embodiment 3TI

[0038] Embodiment 3TIE inhibits tumor cell growth

[0039] The tumor cells in the logarithmic growth phase, including nasopharyngeal carcinoma CNE2 cells, human fibrosarcoma HT1080 cells and human liver cancer Bel-7402 cells, were digested with 0.25% trypsin and inoculated into 96-well plates with an inoculation volume of 10,000 cells / well. 37°C, 5% CO 2 After culturing overnight under conditions, add the compound to be tested TIE, take 6 concentration gradients, respectively 100μg / ml, 50μg / ml, 25μg / ml, 12.5μg / ml, 6.25μg / ml, 3.125μg / ml, with paclitaxel As a positive control, dimethyl sulfoxide (DMSO) was used as a negative control, and three replicate holes were made for each sample concentration. Cultivate for 48 hours, add 10 μg of CCK-8 reagent (purchased from Beyond Biotechnology Research Institute), cultivate for 2 hours, measure the absorbance at 450 nm, the reference wavelength is 600 nm, and calculate the half inhibitory rate (IC 50 ).

[0040] The experimental resu...

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Abstract

The invention relates to a tri-indole compound and a preparation method and application thereof. The invention belongs to the pharmaceutical chemistry field and provides the tri-indole compound and the preparation method. The chemical name of the compound is 1,2,2-tri-1H-indole-3-yl-ethanone (TIE), the molecular formula is C26H19N3O and the relative molecular mass is 388. The preparation method comprises the following steps: inoculating Escherichia coli EPI300 19C6 in culture medium to ferment, collecting the fermented fermentation liquor, separating the fermentation liquor and purifying to obtain the compound TIE. The TIE has novel structure and high antitumor activity, can obviously inhibit the growths of nasopharyngeal carcinoma CNE2 cells, human fibrosarcoma HT1080 and human liver cancer Bel-7402 cells, have the potential to be developed to antitumor drugs and wide applications in preparation of antitumor drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a triindole compound, a preparation method and application thereof. Background technique [0002] Tumor has become the second killer that threatens human life. Although there are many types of anti-tumor drugs in use today, there are problems such as drug toxicity, difference in action, and cross-drug resistance. The focus of current new drug research. For half a century, terrestrial microorganisms have become the source of biologically active substances such as antibiotics and enzyme inhibitors, and marine microorganisms will also become the source of developing new anti-tumor drugs in the 21st century. Because deep-sea microorganisms live in a special environment of high salt, high pressure and oligotrophy, they have unique metabolic methods, so they can produce many secondary metabolites with novel structures and unique activities (1, Kosta S, Jain R, and Tiwari A. Marine Fu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C12P17/16A61P35/00
Inventor 吴振肖湘丘鹰昆汤熙翔陈琳易志伟赵虎义赵敏
Owner XIAMEN UNIV
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