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Sulfur-substituted podophyllin derivatives and their biotransformation and separation and purification methods

A biotransformation, separation and purification technology is applied in the fields of preparation of antitumor drugs, content detection, podophyllotoxins and their preparation, sulfur-substituted podophyllotoxins and their biotransformation, separation and purification, and can solve the problem of high price, production High cost, small scale and other problems, to achieve the effect of simple operation, easy cultivation and low cost

Inactive Publication Date: 2014-10-29
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the increasing demand of human beings, the chemical synthesis method has shown great disadvantages: first, the scale is small and the output is low; second, the chemical residues are difficult to remove; third, the production cost is high
These above-mentioned factors will inevitably lead to the high price of five kinds of sulfur-substituted podophyllotoxins such as 4-(1,2,4-triazole-3)-4-deoxy-podophyllotoxin, so looking for a suitable large-scale The method of industrial production of 4-(1,2,4-triazole-3)-4-deoxy-podophyllotoxin and other sulfur-substituted podophyllotoxins has become the top priority of research and development

Method used

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  • Sulfur-substituted podophyllin derivatives and their biotransformation and separation and purification methods
  • Sulfur-substituted podophyllin derivatives and their biotransformation and separation and purification methods
  • Sulfur-substituted podophyllin derivatives and their biotransformation and separation and purification methods

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Experimental program
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Effect test

Embodiment 1

[0084] 1. Podophyllotoxin is converted into 4-(1,2,4-triazole-3)-4-deoxy-podophyllotoxin and 4-S-(1,3,4-thiadiazole-2)-4 - Deoxypodophyllotoxin

[0085] 1), slant strain cultivation: the formula of the slant strain culture medium adopted in the present embodiment is (nutritional PDA slant): glucose 30 grams / liter, magnesium sulfate 0.5 grams / liter, potassium dihydrogen phosphate 1.5 grams / liter, Thiamine hydrochloride 0.1 g / L, agar 20 g / L, potato extract 1.0 L; the preparation method of potato dipping juice: 200g fresh potatoes are peeled and cut into cubes with a side length of about 1cm, add 1L of deionized water, Boil for 15 minutes, filter with eight layers of gauze, take the filtrate and dilute it to 1L again, and the obtained solution is used to prepare PDA medium.

[0086] Penicillium purpurogenum Y.J.Tang was inoculated on the PDA slant by the two-point method with an inoculation needle. The culture conditions: the culture temperature was 30°C. Sterilization conditio...

Embodiment 2

[0102] 1, 4'-desmethyl epipodophyllotoxin is converted into 4-S-(1,2,4-triazole-3)-4-deoxy-4'-desmethyl epipodophyllotoxin and 4-S -(1,3,4-Thiadiazole-2)-4-deoxy-4′-desmethylepipodophyllotoxin

[0103] 1), slant strain cultivation: the formula of the slant strain culture medium adopted in the present embodiment is (nutritional PDA slant): glucose 30 grams / liter, magnesium sulfate 0.5 grams / liter, potassium dihydrogen phosphate 1.5 grams / liter, Thiamine hydrochloride 0.1 g / L, agar 20 g / L, potato extract 1.0 L; the preparation method of potato dipping juice: 200g fresh potatoes are peeled and cut into cubes with a side length of about 1cm, add 1L of deionized water, Boil for 15 minutes, filter with eight layers of gauze, take the filtrate and dilute it to 1L again, and the obtained solution is used to prepare PDA medium.

[0104] Penicillium violet-producing Y.J.Tang was inoculated on the PDA slant by the two-point method with an inoculation needle. The culture conditions: the ...

Embodiment 3

[0121] 1. 4-S-(1,2,4-triazole-3)-4-deoxy-4'-demethyl epipodophyllotoxin is converted into 4-S-(1,2,4-triazole -3)-4-Deoxy-4'-desmethyl epipodophyllic acid (compound (5))

[0122]1), slant strain cultivation: the formula of the slant strain culture medium adopted in the present embodiment is (nutritional PDA slant): glucose 30 grams / liter, magnesium sulfate 0.5 grams / liter, potassium dihydrogen phosphate 1.5 grams / liter, Thiamine hydrochloride 0.1 g / L, agar 20 g / L, potato extract 1.0 L; the preparation method of potato dipping juice: 200g fresh potatoes are peeled and cut into cubes with a side length of about 1cm, add 1L of deionized water, Boil for 15 minutes, filter with eight layers of gauze, take the filtrate and dilute it to 1L again, and the obtained solution is used to prepare PDA medium.

[0123] Gibberella Fujikura SH-f13 was inoculated on the PDA slant by the two-point method with an inoculation needle, and the culture conditions were as follows: the culture tempera...

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Abstract

The invention discloses a sulfur-substituted podophyllum derivative and a bioconversion, separation and purification method thereof. The sulfur-substituted podophyllum derivative with antitumor activity, shown as Formula (I) or (II), is obtained by modifying the molecular structure of podophyllotoxin or 4'-demethylepipodophyllotoxin through a bioconversion method. Preliminary study on in-vitro tumor cytotoxicity shows that the sulfur-substituted podophyllum derivative disclosed by the invention has stronger inhabitation action on the growth of tumor cells such as BGC823, HepG2, A549 and the like, and thus can be used as an antitumor compound to achieve a potential drug development value. According to the invention, the podophyllotoxin and the 4'-demethylepipodophyllotoxin are converted into the sulfur-substituted podophyllum derivative by using a bioconversion method, and therefore, the sulfur-substituted podophyllum derivative has the advantages of low cost and E-factor, simplicity in operation, easiness for culturing, controllable quality, capability of effectively preventing chemical residuals and the like.

Description

technical field [0001] The present invention relates to podophyllum compounds and preparation methods thereof, in particular to sulfur-substituted podophyllum derivatives and methods for their biotransformation, separation and purification, and content detection. The application in the invention belongs to the field of podophyllum compounds and their biotransformation. Background technique [0002] Sulfur-substituted podophyllin derivatives are a class of podophyllin compounds, the structural formulas of which are shown in Figures (I) and (II). For the 4-position of the C ring of podophyllotoxin, the derivatives obtained by substituting the β carbon-sulfur bond aromatic ring as the modification direction generally have good antitumor activity and bioavailability. [0003] At present, the research on the structural modification of podophyllin derivatives is mainly based on chemical synthesis methods. However, with the increasing demand of human beings, the chemical synthesi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07D405/12C12P17/18C12P17/16A61K31/4196A61K31/433A61P35/00C12R1/80C12R1/645
Inventor 汤亚杰白佳珂
Owner HUBEI UNIV OF TECH
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