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Application of icetexane type abietane diterpene in the preparation of colorectal cancer therapeutic drug

A kind of technology of abietane diterpene and therapeutic drug, which is applied in the application field of preparation of colorectal cancer therapeutic drug, achieves strong anti-colorectal cancer activity and expands the effect of application range

Active Publication Date: 2022-04-01
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the application of Icetexane-type abietane diterpenes in the field of antitumor only focuses on its cytotoxic activity, and there is no report on its mechanism of action

Method used

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  • Application of icetexane type abietane diterpene in the preparation of colorectal cancer therapeutic drug
  • Application of icetexane type abietane diterpene in the preparation of colorectal cancer therapeutic drug
  • Application of icetexane type abietane diterpene in the preparation of colorectal cancer therapeutic drug

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Experimental program
Comparison scheme
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Embodiment 1

[0061] Embodiment 1 of the present invention is: the preparation method of Icetexane type abietane diterpene and its derivatives, comprising the following steps:

[0062] S1, the preparation of compound 2:

[0063]

[0064] Weigh 1.0g (3mmol) of compound 1 (carnosic acid) into a 100mL round bottom flask, add 12.5mL of toluene and 2.5mL of methanol to dissolve, slowly add 3mL of trimethylsilyldiazomethane in n-hexane dropwise at 0°C solution (2.0mol / L, 6mmol). TLC monitoring, after the reaction is complete, add 1 mL of glacial acetic acid dropwise to the reaction solution, remove the reaction solvent by rotary evaporation, add 50 mL of saturated brine, extract with ethyl acetate (3 × 30 mL), and dry the ethyl acetate layer with anhydrous sodium sulfate. Silica gel column chromatography (volume ratio of PE (petroleum ether) to EA (ethyl acrylate) was 10:1) obtained 945 mg of intermediate (yellow solid, yield 91%).

[0065] 1 H NMR (400MHz, CDCl 3 )δ7.52(s,1H),6.59(s,1H),5...

Embodiment 5

[0120] Embodiment 5 of the present invention is: flow cytometry determination (+)-Grandione influence on HCT-116 cell BiP protein translocation

[0121] HCT116 cells in the logarithmic growth phase were digested with 0.25% trypsin and blown into single cells, 5*10 cells per well 5 Cells were seeded in 6-well plates and cultured overnight in an oven. Add 20 μM, 10 μM, 5 μM, 0 μM (blank control) (+)-Grandione respectively, and incubate for 24 hours. Cells were collected, centrifuged at 1000 rpm at 4°C for 10 min, and the supernatant was discarded. Wash the cells three times with cold PBS, add 200 μL of binding buffer working solution (1×Annexin V binding buffer) to resuspend the cells, add 10 μL of Annex in V-FITC to the cell suspension, mix gently, and react at room temperature in the dark for 15 minute. Add 300 μL of binding buffer and 5 μL of PI (propidium iodide), and detect with a flow cytometer.

Embodiment 6

[0122] Embodiment 6 of the present invention is: the influence of (+)-Grandione on HCT-116 cell BiP protein translocation is determined by immunofluorescence method

[0123] HCT116 cells in the logarithmic growth phase were digested with 0.25% trypsin and blown into single cells, 5*10 cells per well 5 Cells were seeded in a 6-well plate (including cell slides), cultured overnight in an oven to adhere to the wall, and 20 μM, 10 μM, 5 μM and 0 μM (blank control) (+)-Grandione were added and incubated for 24 hours. After washing with PBS for 3 times, fix with fixative solution (PBS solution with mass fraction of 4% paraformaldehyde) at 4°C for 12h, then wash with PBS for 3 times, and permeabilize with Triton-X100 (Triton) in PBS solution for 10min Finally, wash with PBS 3 times, 5% BSA in PBS solution blocked for 60min, add BiP antibody, wet box 4 overnight. The next day, wash 3 times with PBS, 5min each time, then add AlexaFluor 488goat anti-rabbit IgG secondary antibody, incub...

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Abstract

The invention discloses the application of Icetexane-type abietane diterpene in the preparation of colorectal cancer therapeutic drugs, and its action mechanism is to up-regulate the level of chaperone protein BiP (Binding immunoglobulin protein) in endoplasmic reticulum, and promote the transfer of BiP protein from cytoplasm to nuclei, thereby inducing apoptosis. The invention further expands the application range of the Icetexane type abietane diterpene and its derivatives.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to the application of an Icetexane type abietane diterpene in the preparation of medicines for treating colorectal cancer. Background technique [0002] Icetexane-type abietane diterpenoids are B-ring-expanded abietane diterpenoids. There are more than 70 natural products of this type that have been reported so far. They are widely distributed and found in many families of plants. [0003] The dimeric Icetexane-type abietane diterpene biperovskatone and the Icetexane-type C18 norabietane diterpene Norperovskatone isolated from the plants of the genus Aphrodisiac possess anti-HBV activity. A dimer of C23 terpenoids and Icetexane diterpenoids isolated from Salvia gansifolia, gancy sagerenone A has the effect on a variety of tumor cell lines HL-60, SMMC-7721, A-549, MCF -7, SW480, Beas-2B have significant cytotoxic activity. Dimeric Icetexane type diterpene Premnalatifolin A has si...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/192A61K31/05A61K31/122A61K31/336A61K31/343A61K31/357A61P1/00A61P35/00
CPCA61K31/192A61K31/05A61K31/122A61K31/336A61K31/343A61K31/357A61P1/00A61P35/00
Inventor 邓旭周应军曹伟刘婷婷杨舒婷曾光尧
Owner CENT SOUTH UNIV
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