Ceramide analog a 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, bottlenecks in the chemical synthesis of ceramides, and the activity needs to be improved, and achieves the effects of improving solubility, inhibiting tumor cell proliferation, and being easy to 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 a and its preparation method and application
  • Ceramide analog a and its preparation method and application
  • Ceramide analog a and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Neuronamide analog A synthesis

[0034] 1) 4,5 - Construction of cis spanner

[0035] The raw material uses a contained galactose as a chiral source. The first step is a 4,6-bit hydroxyl group of galactose; the second step is oxidized, and the aldehyde group is generated at a 3-gyroxyl group, and the sugar 1, 2 bits of carbon; the third step is used with wittg reaction, and Pre-synthesized fourteen carbon phosphorid reacted, 4,5-cisole olefin, which is a relatively key step; the fourth step is supernatified in carbon on the original 5-position hydroxyl group, in this position and carbon-structured Turning to obtain the desired structure; fifth step descending ketone reaction; the sixth stepped nitrogen is converted to an amino group, obtained (2S, 3R, 4Z) -2-amino-1,3-octadecyl diol (4, 5-cis spanner B). (4,5-cis sphingol A) See CN201410678188.5)

[0036] 2) 1 grams of 4,5-cis sphingol A is dissolved in 30 ml of chloroform, 40 ° C is dissolved, after lowering to room temper...

Embodiment 2

[0050] Neuronamide analog A inhibits human colorectal cancer cells, human pancreatic cancer cell proliferation.

[0051] Biological experiments are employed in human cancer cells, respectively, colorect cancer cells LS174T, colon cancer cell SW480, colon cancer cell SW620; in situ pancreatic adenocarcinoma cell BXPC-3, pancreatic cancer cells PANC-1, pancreatic cancer cells SW1990. The culture system is DMEM culture solution, which contains 10% fetal bovine serum, then placed at 37 ° C, 5% CO 2 , Cultured under saturation humidity. The new neuramide analogs A (A1, A2, A3) and the control C6 (purchase) were formulated into a culture system, and 10% fetal bovine serum was included, and then placed at 37 ° C, 5% CO. 2 , Cultured under saturation humidity. The new neural amide analog A and the control C6 (purchase) were formulated into 5 μm, 10 μm, 15 μm, 20 μm, and all samples were fully dissolved.

[0052] (1) Select the tumor cells in which the long-term long-term tumor cells are m...

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Abstract

The invention discloses a novel ceramide analogue A and a preparation method and application thereof, and belongs to the technical field of medicaments. The novel ceramide analogue structure introduces two amino groups to improve the carbonyl electronegativity between the two amino groups, and halogen is introduced at the tail end, so that the novel ceramide analogue is easier to combine with enzyme; the novel ceramide analogue has cis-double bonds, the solubility of molecules is improved, and the space trend of long chain connected with the double bonds is changed; the novel ceramide analoguecan not only inhibit the proliferation of tumor cells, but also have obvious influence on the differentiation and cycle of leukemia tumor cells, thereby being beneficial to multi-way tumor prevention; the novel ceramide analogue shows better performance in inhibiting human colorectal adenocarcinoma cell LS174T than positive control C6, shows a leader molecule with antitumor application potentialand has certain proliferation promoting effect on cancer cells.

Description

Technical field [0001] The present invention belongs to the art of the drug, and in particular, the present invention relates to neuronamide analogs A and its preparation method, application. Background technique [0002] Current cancer is still chemotherapy as the main means. Although this method can achieve a certain effect, it is obvious, which in turn leads to most of the patient deaths due to chemotherapy. Recently looking for low toxic, effective anti-cancer pilot elements have become the current hotspot. It is increasingly clear that there is more and more effective in regulation and affecting many important biological processes, and these lipids and cancer pathogenesis are closely linked. More and more studies have shown that there is a certain relationship between abnormalities in neuroin content and expression of enzymes in some sheath fat metabolism, and a certain relationship between the production, development, value added, invasive and metastasis of cancer, thereby ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C275/20C07C273/18C07C275/24A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07C275/20C07C275/24
Inventor 崔艳丽尹利明毛旸易牟晓洲张勇民毛建卫
Owner ZHEJIANG UNIV
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