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Preparation method and application of pentacyclic triterpene derivatives

A compound and derivative technology, which is applied in the preparation and application field of pentacyclic triterpenoid structure derivatives, can solve the problems of poor targeting and high production cost of psoriasis drugs

Active Publication Date: 2017-12-19
SHANGHAI JIAOTONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In general, the existing drugs for the treatment of psoriasis have high production costs and poor targeting, and 11 carbonyl-β-acetyl boswellic acid has great potential and excellent uses. The applicant improved the original biological efficacy of boswellic acid through chemical modification. Dramatically improves compound's ability to inhibit psoriasis and tumors in mice

Method used

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  • Preparation method and application of pentacyclic triterpene derivatives
  • Preparation method and application of pentacyclic triterpene derivatives
  • Preparation method and application of pentacyclic triterpene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of gels with compounds of formula (II-VII)

[0028] Get a certain amount of any one of the compounds with molecular formula (II-VII) to make a gel according to the following formula:

[0029] Any one of the compounds of formula (II-VII) 100 mg

[0030] Carbomer 400 mg

[0031] Glycerin 550mg

[0032] Propylene glycol 650mg

[0033] Parabens 100 mg

[0034] Triethanolamine 200 mg

[0035] Add water to 5ml.

[0036] Preparation:

[0037] Weigh any one of the compounds with molecular formula (II-VII) in the prescribed amount into the beaker, add the prescribed amount of carbomer into it, let it fully swell overnight, and then add glycerin, propylene glycol, antiseptic agent, water and triethanolamine, and stir evenly to make the pH value of the composition 5.8.

Embodiment 2

[0038] Embodiment 2: The compound of molecular formula (II-VII) inhibits the test of NF-kappa B pathway in vivo ( figure 1 )

[0039] Luciferase (luciferase) transgenic mice of NF-kappa B, 6 mice in each group, totally 8 groups Control (Ctr, blank gel group), M1 treatment group, M2 treatment group, M3 treatment group, M4 treatment group, M5 treatment group group, M6 treatment group and AKBA treatment group. Mice were first induced with imiquimod for 7 days. After treatment of "psoriatic" mice with 0.5% M1-M6 and 0.5% AKBA gel 4 times (once a day) starting from day 8, they were imaged with a small animal intravital imaging system. Through analysis, it is found that 0.5% of the compound with molecular formula (II-VII) inhibits the activation of NF-kappa B more effectively than 0.5% of AKBA.

Embodiment 3

[0040] Embodiment 3: The test that the compound with molecular formula (II-VII) inhibits the growth of keratinocytes in vitro ( figure 2 )

[0041] Take the primary mouse cells in the logarithmic growth phase in a 96-well plate, 2×10 per well 4 AKBA derivatives and AKBA in gradient concentrations were added to each cell, with a total volume of 100 μl, DMSO with a final concentration of 0.25% was added to the control group, and only 100 μl medium was added to the blank control wells, and three replicate wells were set up in each group. After 24 hours of culture in the cell incubator, add 10 μl of CCK-8 solution to each well, and place the culture plate in the incubator (37°C, 5% CO 2 conditions) and incubate for 4 hours in the dark. The O.D. value at the wavelength of 450nm was measured by a microplate reader. Calculation of inhibition rate: inhibition rate = [1-(O.D. value of experimental group / O.D. value of control group)]×100%. Among them, the compound with the molecula...

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Abstract

The invention relates to six new compounds for treating psoriasis, a preparation method and an application thereof. The six new compounds belong to a series of derivatives from a mother compound: acetyl-11-keto-[beta]-boswellic acid (AKBA) through modification of a hydrolysis reaction and an esterification reaction. Compared with the mother compound AKBA before chemical modification, the six compound, of which the structure are represented as the formulas (II-VII), can inhibit division and cell proliferation of keratinocyte in in-vitro experiments and can treat the psoriasis on mice more effectively in a live animal test. The new compounds can be used for preparing the medicine for treating the psoriasis.

Description

technical field [0001] The present invention relates to a new compound useful for treating psoriasis, specifically a new derivative obtained through chemical modification of acetyl-11-keto-β-boswellic acid (AKBA). Background technique [0002] Psoriasis is a common chronic, relapsing, inflammatory skin disease characterized by recurrent multilayered silvery white dry scales on erythema. In ancient Chinese medicine, it was called "white phlegm", and in ancient medical books, it was also called tinea pine. Western medicine is called psoriasis, commonly known as psoriasis, which is characterized by pimples and erythema of various sizes, covered with silvery white scales on the surface, with clear boundaries, and occurs on the scalp, extremities and back. It is easy to recur or aggravate in spring and winter, and it is more relieved in summer and autumn. According to investigations, the incidence of psoriasis accounts for 0.1%-3% of the world's population, the incidence of yel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P17/06
CPCC07J63/008
Inventor 王宏林白晶
Owner SHANGHAI JIAOTONG UNIV SCHOOL OF MEDICINE
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