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Compound of antitumor antibiotic of new carbon framework as well as preparation method and application

A compound and anti-tumor technology, applied in the field of medicine, can solve problems such as undiscovered patents or literature reports

Inactive Publication Date: 2005-06-15
INST OF OCEANOLOGY - CHINESE ACAD OF SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The novel carbon skeleton structure of the compound chinikomycin involved in the present invention has not been found in patents or literature reports so far

Method used

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  • Compound of antitumor antibiotic of new carbon framework as well as preparation method and application
  • Compound of antitumor antibiotic of new carbon framework as well as preparation method and application
  • Compound of antitumor antibiotic of new carbon framework as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of new carbon-skeleton anti-tumor antibiotics chinikomycin A and B (for the preparation flow chart, see image 3 ):

[0037] (1) Sample collection: sea mud samples were collected from the coastal waters of Qingdao, and Gaoshi No. 1 medium was used in the laboratory (20 g of soluble starch, 1 g of potassium nitrate, 0.5 g of potassium dihydrogen phosphate, 0.5 g of magnesium sulfate, and 0.5 g of sodium chloride) g, ferrous sulfate 0.01g, potassium dichromate 0.1g, agar powder 18g, natural seawater 500ml, tap water 500ml, adjust pH to be 7.2) carry out gradient dilution streak culture, purify and obtain a strain of marine Streptomyces sp.;

[0038] (2) Solid culture: the marine Streptomyces sp. was inoculated on M 2+ Solid medium (barley extract 10g, yeast powder 4g, glucose 4g, natural seawater 500ml, tap water 500ml, agar powder 14g, adjust pH to 7.4), culture at 28°C for 3 days until white spores grow;

[0039] (3) shaker culture: from the M 2+ Pick whi...

Embodiment 2

[0100] Oxidation from chinikomycin A to chinikomycin B:

[0101] Get the product chinikomycin A of 20mg, join in the reaction bottle, dissolve with 50ml dichloromethane (this embodiment just dissolves), slowly add about 1g of silver oxide (it is excessive with respect to the chinikomycin A in the solution), stir , reacted for about 3 hours, the color of the solution changed from yellow to red completely, and was spun to dryness, dissolved with 6ml of dichloromethane (this embodiment was fully dissolved), discarded the precipitated insoluble matter, and the dissolved part was subjected to preparative thin-layer chromatography ( PTLC), with 95% dichloromethane / 5% methanol as developing solvent, reclaim R f = 7 mg of the red compound at 0.58, the chemical structure of the compound was determined as chinikomycin B through proton nuclear magnetic resonance, carbon nuclear magnetic resonance, mass spectrometry, infrared and ultraviolet spectrometry.

Embodiment 3

[0103] Reduction of chinikomycin B to chinikomycin A:

[0104] In the test tube, add 0.5mg of chinikomycin B, dissolve it with 2ml of dichloromethane, then slowly add 1ml of 0.1N sodium dithionite solution, shake until the color of the solution changes from red to yellow, and analyze it by thin layer chromatography (TLC). R f The yellow compound at =0.34 is chinikomycinA.

[0105] Two-dimensional NMR analysis of compounds chinikomycin A and chinikomycin B further verified the structures of compounds chinikomycin A and chinikomycin B. The HMBC (→) and NOESY () effects of the hydrocarbon amide side chains can be found in figure 1 , HMBC(→) and H, H COZY() effects of the carbon skeleton see figure 2 .

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Abstract

A kind of antineoplastic antibiotic compound, chinikornycin A and B, for suppressing the cells of lung cancer, breast cancer, melanoma, renal cancer and uterine cancer is prepared from Streptomyces sp. through fermenting and chromatography by silica gel column.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a new carbon skeleton antitumor antibiotic compound and its preparation method and application. Background technique [0002] Since the discovery of penicillin in the 1930s, microorganisms have become an important source of active lead compounds. However, in recent years, the probability of isolating new structurally active compounds from soil microorganisms has dropped significantly. For example, currently, only one strain capable of producing new structurally active compounds can be screened from more than 20,000 strains of soil microorganisms. For another example, among all known microbial secondary metabolites, most of them come from Actinomycetes in soil, especially Streptomyces among them; In Streptomyces, it is difficult for people to find new compounds, especially new framework compounds, and this possibility is still plummeting (document 1: Fencial, W., Chemical Studie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/165A61P31/04A61P31/12A61P35/00C07C237/22C12P13/02
Inventor 秦松李富超阿甄达·皮·马斯克哈特马特·拉赤
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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