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Sphingomyelin-derived lipid and method for producing same

A production method and technology of sphingomyelin, applied in the field of sphingomyelin-derived lipids and its production, can solve the problems of reducing membrane fusion promotion

Pending Publication Date: 2020-10-09
NOF CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Non-Patent Document 2 reports that ceramide analogs having no secondary hydroxyl group or double bond show significantly reduced membrane fusion-promoting effect compared to ceramide

Method used

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  • Sphingomyelin-derived lipid and method for producing same
  • Sphingomyelin-derived lipid and method for producing same
  • Sphingomyelin-derived lipid and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of sphingomyelin-derived lipids

[0067] Add egg yolk sphingomyelin (manufactured by NOF CORPORATION; COATSOME NM-10; R 1 is an alkyl group with 15 carbon atoms, R 2 Containing an acyl group having 16 carbon atoms (81%) and an acyl group having 18 carbon atoms (7%)) (40 g), palladium carbon (manufactured by N.E.CHEMCAT Corporation, palladium content is 5 wt %) (10 g), ethanol ( 200 g) and cyclohexene (manufactured by KANTO CHEMICAL CO., INC.) (60 g), and the mixture was reacted at 55° C. for 6 hours under a nitrogen atmosphere. The reaction solution was filtered, and the filtrate was concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: mixed solvent of chloroform / methanol / water) to obtain the title compound as a white solid (yield: 1.96 g, 4.9%).

[0068] 1 H-NMR (600MHz, δppm, CD 3 OD): 0.88 (6H, t), 1.2-1.4 (48H, t), 1.55 (2H, m), 1.64 (2H, m), 2.29 (2H, m), 2.58 (2H, m), 3.22 (9H , s), 3.6...

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Abstract

The purpose of the present invention is to provide a component of a liposome for a DDS carrier, said component not exhibiting a membrane fusion promoting effect on a virus. The present invention pertains to: a sphingomyelin-derived lipid represented by formula (1) (wherein, R1 represents an alkyl group having 13-17 carbon atoms, and R2 represents an acyl group having 12-24 carbon atoms); and a method for producing the same.

Description

technical field [0001] The present application relates to sphingomyelin-derived lipids useful for pharmaceutical and cosmetic use and methods for their production. Background technique [0002] In the field of drug delivery systems (DDS), research on pharmaceutical products using liposomes composed of phospholipids, sphingolipids, cholesterol, etc. has been actively conducted, and various products have been commercially available. Liposomes can suppress the side effects of encapsulated drugs, or prevent the breakdown of unstable compounds in the bulk. In addition, various functions can be endowed by modifying the surface of liposomes. For example, polyethylene glycol-modified liposomes can improve blood retention compared to unmodified liposomes. [0003] Some drugs encapsulated in liposomes require an acidic environment with a pH of 2 to 4 to maintain their chemical stability when retained in the blood. Phospholipids are the lipids most commonly used as liposome constitu...

Claims

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Application Information

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IPC IPC(8): C07F9/09
CPCC07F9/09C07F9/091C07F9/11
Inventor 太田雅己
Owner NOF CORP