Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Sialic acid lipid derivative and preparation method and application thereof

A technology of lipid derivatives and sialic acid, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems that carboxyl groups cannot be exposed and are unfavorable, so as to improve placement stability, activity and selection sexual effect

Active Publication Date: 2019-12-17
SHENYANG PHARMA UNIVERSITY +1
View PDF12 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After amidating the carboxyl group of SA, the carboxyl group cannot be exposed, which is not conducive to its biological function in vivo

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Sialic acid lipid derivative and preparation method and application thereof
  • Sialic acid lipid derivative and preparation method and application thereof
  • Sialic acid lipid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] The synthesis of embodiment 1 methyl sialate (MT)

[0104] Add SA (20g, 0.064mol), methanol 250mL, and 3.68N methanolic HCl solution 1.7mL (0.0064mol) into a 500mL three-necked flask, and stir the reaction in an oil bath at 50°C for 2.5h. After suction filtration, the filtrate was evaporated to dryness to obtain 19.3 g of white solid, which was recrystallized by adding 80 mL of methanol, cooled and crystallized, and 17.90 g of white solid was obtained after suction filtration, with a yield of 86.5%.

[0105] The structural formula is as follows:

[0106]

[0107] Melting point: 182-183°C.

[0108] Mass Spectrum: m / z 346.1, MT[M+Na] + peak; no SA peak.

[0109] The SAs in the examples all take Neu5Ac as an example. Under the same reaction conditions, the corresponding products can be obtained by using Neu5Gc and KDN in the same molar ratio instead of Neu5Ac.

Embodiment 2 18

[0110] The synthesis of embodiment 2 octadecanoyl chloride

[0111] Add octadecanoic acid (8.53 g, 0.03 mol) and thionyl chloride (28.56 g, 0.24 mol) into a 100 mL eggplant-shaped bottle, and react under reflux in an oil bath at 80° C. for 1 h. The remaining thionyl chloride was distilled off under reduced pressure at 65°C to obtain 8.9 g of orange liquid with a yield of 98.2%. The acid chlorides used in the remaining examples were all synthesized under the same reaction conditions and the same molar ratio.

[0112] The structural formula is as follows:

[0113]

Embodiment 3

[0114] Synthesis of embodiment 3 MT-18 (compound 3)

[0115] Add MT (5g, 15mmol) and 4-dimethylaminopyridine (0.19g, 1.5mmol) to a 250mL three-necked flask, dissolve it with 50mL of pyridine, and add octadecanoyl chloride (7.1g, 23mmol) dropwise under an ice bath. THF solution 40mL, control the temperature at about 5°C, move to room temperature after 20min to continue the reaction, add 50mL of water after 10h of reaction, extract with 40mL of dichloromethane*3, wash with 30mL of saturated saline, dry with anhydrous MgSO4, pump Filtration, spin-drying, sample mixing, column packing, separation by silica gel column chromatography to obtain 2.82 g of white solid, yield: 55.6%.

[0116] The structural formula is as follows:

[0117]

[0118] Melting point: 140-142°C.

[0119] Mass Spectrum: m / z:612.4, MT-18[M+Na] + peak. Spectrum see attached figure 1 .

[0120] Proton nuclear magnetic resonance spectrum: 1H-NMR (600MHz, DMSO-d6): δ8.12 (d, J = 8.4Hz, 1H), 6.38 (s, 1H), 4...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention belongs to the technical field of medicines, and provides a sialic acid lipid derivative which can be used for modifying a particle preparation and a preparation method and application thereof. The structural general formula of the sialic acid lipid derivative is as shown in the specification, wherein R1 is an H atom or C1-C6 alkyl; R2 is H, (CH2) m or C2-C6 alkenyl, and m =1-17; when X is an H atom or an O atom, R3 is (CH2) n or cholesteryl, and n = 1-17; when X is a carbonyl group, R3 is a C12-C24 alkoxy group, a C12-C24 alkyl substituted amino group or cholesteryl; and R4 is -OH, -NHCOCH3 or -NHCOCH2OH. The sialic acid lipid derivative disclosed by the invention can be used for modifying a particle preparation and realizing different treatment or diagnosis purposes according to the properties of the medicine. Especially in the anti-tumor aspect, the sialic acid lipid derivative can endow a particle preparation with excellent tumor targeting ability to improve the tumorinhibition effect.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, in particular to a sialic acid lipid derivative and its preparation method and application, especially the application in the preparation and modification of microparticle preparations. Background technique [0002] Sialic acid (Sialic acid, SA) is a general term for a class of acidic amino sugars containing nine carbon atoms and a pyranose structure, and its system name is 5-amino-3,5-dideoxy-D-glycerol-D-semi Lactonulose, according to the group connected to the carbon atom at the 5th position, different SA derivatives are divided. N-acetylneuraminic acid (Neu5Gc), N-acetylneuraminic acid (Neu5Ac) and 3-deoxy-D-glycerol-D-galactononulose (KDN) are the three most common in the SA family, of which Neu5Ac is the most common. In terms of physical properties, SA is a white solid powder, easily soluble in water, slightly soluble in methanol, insoluble in ether and light petroleum, stable i...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H1/00C07H7/02C07J41/00A61K47/55A61P35/00
CPCC07H1/00C07H7/02C07J41/0055A61K47/554A61K47/55A61P35/00
Inventor 邓意辉陈国良梁凯帆高勋傅凭平冯瑞宋艳志刘欣荣胡雅维王硕
Owner SHENYANG PHARMA UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com