Ceramide analog b and its preparation method and application

A technology for ceramides and analogs, applied in the field of medicine, can solve the problems of biological application obstacles, the activity needs to be improved, the bottleneck in the chemical synthesis of ceramides, etc., and achieves the effects of low performance measurement, inhibition of tumor cell proliferation, and easy control.

Active Publication Date: 2021-03-23
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is a bottleneck in the chemical synthesis of C6-ceramide, and the activity needs to be improved, which hinders its biological application

Method used

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  • Ceramide analog b and its preparation method and application
  • Ceramide analog b and its preparation method and application
  • Ceramide analog b and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of New Ceramide Analog B

[0045] 1) 1 g of (2S,3R,4R)-2-amino-1,3,4-octadecanetriol (for the preparation of sphingosine B, see APPLIED ANDENVIRONMENTAL MICROBIOLOGY, 2003, 69(2): 812–819) dissolved in Dissolve in 60 ml of chloroform at 40°C. After cooling down to room temperature, add 0.432 g of isocyanate-2-chloroethyl ester dropwise, stir at room temperature, track the reaction by thin layer chromatography, and end the experiment after the reaction raw material sphingosine disappears. , concentrated by rotary evaporation, and subjected to silica gel column chromatography with a mobile phase of chloroform / methanol=20:1 to obtain 0.959 g of a new ceramide analogue (B2), a white solid, with a yield of 72.3%. The structure was identified by NMR and mass spectrometry. 1 H NMR (400 MHz, C 5 D. 5 N) δ 4.94 (s, 1H), 4.47 (d, J = 20.9 Hz, 2H), 4.28 (s,2H), 3.77 (s, 3H), 2.16 (s, 1H), 1.89 (s, 1H), 1.67 (s, 1H), 1.33 (d, J =65.1 Hz, 20H), 0.87 (t, 3H). 13 ...

Embodiment 2

[0057] The new ceramide analogue B inhibits the proliferation of human pancreatic cancer cells and human intestinal cancer cells.

[0058] All human cancer cells used in the biological experiments are colorectal cancer cells LS174T, colon cancer cells SW480, and colon cancer cells SW620; pancreatic cancer cells in situ BxPC-3, pancreatic cancer cells PANC-1, and pancreatic cancer cells SW1990. The culture system was DMEM medium containing 10% fetal bovine serum, and then placed at 37°C, 5% CO 2 , cultured under saturated humidity. Containing new ceramide analogues B (B1, B2, B3, B4) and control C6 (purchased) were prepared with DMSO into 5μM, 10μM, 15μM, 20μM stock solutions, all samples need to be fully dissolved.

[0059] (1) Select tumor cells in the logarithmic growth phase to make a single cell suspension, inoculate them in different 96-well flat culture plates, adjust the number of cells to be consistent, the number of cells in each well is 3000, and the suspension is 2...

Embodiment 3

[0068]The new ceramide analogue B2 inhibits the proliferation of human chronic myelogenous leukemia cell K562 and human monocytic leukemia cell SHI-1.

[0069] Culture of leukemia cell lines

[0070] K562 and SHI-1 leukemia cells were inoculated in IMDM medium containing 10% and 15% newborn bovine serum and 100 U / L of penicillin and streptomycin, respectively, and placed at 37°C and 5% CO 2 Suspension culture in an incubator with saturated humidity, the medium was changed every 2-3 days, and the cells in the logarithmic growth phase were taken during the experiment.

[0071] Treating Leukemia Cells

[0072] Take the K562 and SHI-1 leukemia cells in the logarithmic growth phase respectively, and adjust the cell concentration to 10 5 / ml, the final concentrations of B2 and C6 were 10mg / L, and they were inoculated in culture flasks respectively. The above culture system was placed at 37°C, 5% CO 2 and saturated humidity incubator, and change the liquid every other day. Take ...

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Abstract

The invention discloses a novel ceramide analogue B, and a preparation method and application thereof, and belongs to the technical field of medicines. On one hand, the invention further provides thenovel ceramide analogue B, and on the other hand, the invention provides the preparation method and application of the novel ceramide analogue B. The synthetic condition of the novel ceramide analogueB disclosed by the invention is mild and is easy to control, the yield is moderate, and industrialization is easy. The novel ceramide analogue B provided by the method is more easily combined with enzymes, can inhibit proliferation of tumor cells, and also has obviously influence on differentiation and period of leukemia tumor cells, and multi-way tumor resistance can be facilitated.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a new ceramide analogue B and its preparation method and application. Background technique [0002] At present, chemotherapy is still the main method for cancer. Although this method can achieve a certain effect, the side effects are obvious, which leads to the death of most patients due to ineffective chemotherapy. Recently, searching for low-toxic and effective anti-cancer lead molecules has become a hot spot. The role of biologically active sphingolipids in regulating and influencing many important biological processes is increasingly clear, and these lipids are closely related to the pathogenesis and treatment of cancer. More and more studies have shown that the abnormality of ceramide content and the expression of some enzymes in the process of sphingolipid metabolism are related to the occurrence, development, proliferation, invasion and metastasis of cancer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C275/10C07C275/24C07C273/18A61P35/00A61P35/02
Inventor 崔艳丽尹利明毛旸易牟晓洲毛建卫
Owner ZHEJIANG UNIV
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