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Aromatic reductive derivative of geldanamycin benzoquinone, preparation method and use thereof

A technique for geldanamycin and aromatization, which is applied in the fields of aromatized reduction derivatives of geldanamycin-like benzoquinones and their preparation and application, and can solve problems such as the reduction of benzoquinones that have not yet been seen

Inactive Publication Date: 2007-03-14
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of structure type, in all the geldanamycin compounds that have been recorded in the literature so far, it has not been seen that the benzoquinone of this type of compound is reduced to an aromatic ring and there is an oxygen heterocycle derivatization on the aromatic ring. thing

Method used

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  • Aromatic reductive derivative of geldanamycin benzoquinone, preparation method and use thereof
  • Aromatic reductive derivative of geldanamycin benzoquinone, preparation method and use thereof
  • Aromatic reductive derivative of geldanamycin benzoquinone, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Fermentative production and separation and purification of embodiment 1 compound 1

[0087] Fermentation production

[0088] Toxin-producing bacteria The toxin-producing bacteria used to ferment and produce Compound 1 in this example was isolated from soil samples collected from Xishuangbanna and identified as Streptomyces pseudoverticillus strain YN17707 CGMCC No.1452 through taxonomic studies.

[0089] Fermentative culture of toxin-producing bacteria According to the conventional method of cultivating microorganisms, take an appropriate amount of Streptomyces pseudoverticillus YN17707 CGMCC No.1452 strain, inoculate it into an eggplant-shaped bottle on Gaoshi Synthetic No. 1 agar solid slant medium, and cultivate it at 28 degrees Celsius Activation culture in the box for 7 days. Get the eggplant-shaped bottle slope that has been activated and cultivated for 7 days, add 15 milliliters of sterile water, scrape off the spores with an inoculation needle, make a spore sus...

Embodiment 2

[0097] The separation and purification of embodiment 2 compound 2

[0098] Get 30 grams of the chloroform extract obtained in the above-mentioned Example 1, dissolve it with an appropriate amount of chloroform, add 50 grams of silica gel G (200-300 mesh) produced by Qingdao Ocean Chemical Factory to mix the sample, add to the silica gel that is equipped with 300 grams of thin-layer chromatography. 60H (Qingdao Haiyang Chemical Factory) glass decompression column, carry out decompression column chromatography, use chloroform-methanol system (100:0→80:20) gradient elution, every 500ml is a fraction, and several fractions are obtained. share. According to the results of TLC detection and activity test, the corresponding fractions were combined to obtain the active component Fr-4 containing compound 2 (the elution fraction of chloroform-methanol 80:20). Dissolve the active component Fr-4 in an appropriate amount of chloroform, add an appropriate amount of silica gel G (200-300 me...

Embodiment 3

[0104] Example 3 Cell Cycle Inhibitory Activity Test of Compound 1 and Compound 2

[0105] Experimental samples and experimental methods

[0106] Preparation of test sample solution The test samples are pure compound 1 and compound 2 separated and purified in the above-mentioned examples 1 and 2. Accurately weigh an appropriate amount of sample, and use methanol to make a solution of the required concentration for testing the activity.

[0107] The subculture activity test of cell lines and cells adopts the temperature-sensitive mouse breast cancer tsFT210 cell line, and the cells are relayed in RPMI-1640 medium containing 10% FBS in a cell incubator with 5% carbon dioxide at 32 degrees Celsius subculture.

[0108] Flow Cytometry Activity Assay Method

[0109] asynchronous culture test

[0110] Take the tsFT210 cells in the logarithmic growth phase, and use fresh RPMI-1640 medium to prepare a density of 2×10 per ml 5 The cell suspension of each cell was inoculated in a 24...

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Abstract

The present invention relates to geldanamycin type aromatic reduced benzoquinone derivative and its preparation process as well as the medicine composition with the compound as active component and its use. The compound is prepared through fermentation with, say, pseudostreptoverticillium, and it is proved experimentally that the compound may be used in preparing cell period inhibitor and antitumor preparation.

Description

Technical field: [0001] The present invention relates to aromatized reduction derivatives of geldanamycin-like benzoquinones, a method for preparing such compounds by fermentation, a pharmaceutical composition containing such compounds as active ingredients, and the use of such compounds for the preparation of cell cycle inhibitors, Uses of cell proliferation inhibitors and antitumor drugs. Background technique: [0002] Geldanamycin was first discovered in 1970 from Streptomyces products [C.DeBoer, et al.; Geldanamycin, a new antibiotic: J.Antibiot., 1970, 23(9), 442-447], and later, Many similar compounds have been discovered from microbial products or artificially synthesized and found to have a variety of biological activities. Such as literature [M.Muroi, et al.; The structures of macbecin I and II: Tetrahedron, 1981, 37, pp.1123-1131], literature [R.C.Schnur, et al.; Inhibition of the oncogene product p185 erbB-2 in vitro and in vivo by geldanamycin and dihydrogelda...

Claims

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Application Information

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IPC IPC(8): C07D225/06C07D491/08C12P17/10C12P17/18C12N1/20A61K31/395A61P35/00
Inventor 崔承彬韩冰蔡兵
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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