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N-methyl-medermycin compound, and preparation method and application thereof

A technology for metamycin and its compounds, applied in the field of N-methyl-metamycin compounds and their preparation, can solve the problem of tumor cells affecting normal cell proliferation and division, high toxicity, and no specificity of metamycin, etc. problems, to achieve good application prospects, strong inhibitory effect

Active Publication Date: 2018-04-13
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have found that metamycin has no specificity, and while it acts on tumor cells, it also affects the proliferation and division of normal cells. It is too toxic for clinical development and application, so it cannot be made into a drug.

Method used

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  • N-methyl-medermycin compound, and preparation method and application thereof
  • N-methyl-medermycin compound, and preparation method and application thereof
  • N-methyl-medermycin compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1. Seed solution

[0037] Streptomyces cavourensis strain NRRL 2740 was inoculated into a 500mL Erlenmeyer flask containing 250mL of Gao's No. 1 liquid medium, and cultured in a shaker at 28°C at 180rpm for 3 days to obtain a seed solution.

[0038] 2. Fermentation

[0039] Inoculate the above-mentioned seed liquid into the culture medium with the amount of inoculating 12mL in each bottle (the culture medium in each bottle is 250mL Gao Shi No. 1 liquid medium, add 25g sea salt, then obtain through autoclaving and humid heat sterilization), in a shaker for 28 Cultivate with shaking at 180 rpm for 7 days at °C and terminate the fermentation.

[0040] 3. Rough extraction

[0041] Soak each bottle of solid fermented product with about 200 mL of EA (ethyl acetate) overnight, filter through three layers of gauze to remove mycelia, collect the filtrate, and concentrate under reduced pressure to obtain a crude extract (oily extract).

[0042] 4. Compound separation

[0043]...

Embodiment 2

[0048] The structure of the compound isolated and purified in Example 1 was identified.

[0049] The NMR data of this compound are shown in Table 1, and the NMR parameters are 1H 500MHz and 13C 125.7MHz.

[0050] Table 1

[0051]

[0052]

[0053] Combined with mass spectrometry data ( figure 1 and figure 2 ), and the molecular formula of the compound is C 23 h 25 NO 8 ([M+H] + 444.1659), the structural formula is as image 3 As shown, the compound was identified and named 3'-N-methyl-metamycin.

Embodiment 3

[0055] The SBR method was used to detect the inhibitory effect of the compound purified in Example 1 on the proliferation of human prostate cancer cell line PC3 cells.

[0056] Cells in the logarithmic growth phase were taken and configured as 5×10 4 cells / mL, spread in 96-well culture plate at 100 μL / well, CO 2 Cultivate in the incubator for 24 hours, take out the culture plate, add different concentrations of samples to be tested in each well, set 3 duplicate holes for each concentration, and place in CO 2 After continuing to cultivate in the incubator for 72 hours, take out the culture plate, discard the culture medium, add 100 μL of 10% trichloroacetic acid (TCA) pre-cooled in a refrigerator at 4°C to each well to fix it, let it stand for 5 minutes, and then move the culture plate to 4 °C refrigerator overnight. Pour off the fixative, wash each well 5 times with deionized water, spin dry, and air dry. Add 70 μL of SRB solution to each well, place at room temperature for...

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Abstract

The invention discloses an N-methyl-medermycin compound, and a preparation method and application thereof. The N-methyl-medermycin compound is named as 3'-N-methyl-medermycin. The N-methyl-medermycincompound is separated and purified from an actinomyces and is specifically named as 3'-N-methyl-medermycin. Experimental results prove that the compound has strong inhibitory effect on human prostatecancer cells and has an IC50 value of 0.51255 [mu]M. The compound has good application prospects in preparation of drugs used for treating cancers.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to an N-methyl-metamycin compound and its preparation method and application. Background technique [0002] Marine actinomycetes and fungi have attracted much attention due to their production of natural active products with novel structures and diverse functions. The special and diverse marine ecological environment has endowed marine actinomycetes and fungi with complex and unique metabolic pathways, and their secondary metabolites have different characteristics and diversity from terrestrial actinomycetes and fungi in terms of structure type and biological activity. It is an important source for discovering natural active products and new drug lead compounds. [0003] At the same time, among the secondary metabolites of Streptomyces, aromatic polyketide antibiotics are a class of compounds with diverse structures and functions. In the biosynthetic pathway of Streptomyces, this kind...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/365A61P35/00C12P17/18C12R1/465
Inventor 马忠俊黄昀陈芋宏姜庆张大杉丁婉婧
Owner ZHEJIANG UNIV
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