5655-17-4Relevant articles and documents
Method for synthesizing platelet activating factor (PAF) analog
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Paragraph 0095-0097, (2019/11/28)
The invention discloses a method for synthesizing a platelet activating factor (PAF) analog which is of a formula shown in the specification from glyceryl phosphoryl choline as a raw material according to scheme of the following three steps of reactions: 1, enabling glyceryl phosphoryl choline, a hydroxyl activator and an aliphatic hydrocarbon carbonyl compound to react to generate an intermediate1; 2, enabling the intermediate 1 to react with cyclic anhydride to generate an intermediate 2; and 3, enabling the intermediate 2 to react with nitrophenol and a condensing agent to generate a product, namely the PAF analog. In the step 1, the glyceryl phosphoryl choline is adopted as a reaction initializing raw material, and a series of PAF analogs can be derived; in the step 2, a catalyst is additionally used, so that the yield can be increased; and in the step 3, a condensing agent which is gentle in reaction condition is selected, so that reaction steps can be reduced, an acyl chloride intermediate which is good in corrosiveness and easy to dehydrate is not generated, and equipment consumption can be reduced.
A high-purity dissolved blood phosphatidyl choline and its preparation method (by machine translation)
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Paragraph 0060-0061, (2019/01/15)
The present invention provides a high purity dissolved blood phosphatidyl choline and its preparation, wherein the preparation method at least comprises the following steps: synthetic phosphatidyl choline, 1st mixed solvent and inorganic alkali; hydrolytic reaction, to be synthetic phosphatidyl choline reaction is complete; through the column chromatography purification, to obtain high-purity hemolyzed phosphatidyl choline. The present invention provides a high purity of chancing of the preparation method, the method for preparing the chancing high purity, and the fatty acid purity is greater than 99%, mild reaction conditions and the production cycle is comparatively short, low production cost, simple process, easy to industrial production. (by machine translation)
Light-Controlled Lipid Interaction and Membrane Organization in Photolipid Bilayer Vesicles
Urban, Patrick,Pritzl, Stefanie D.,Konrad, David B.,Frank, James A.,Pernpeintner, Carla,Roeske, Christian R.,Trauner, Dirk,Lohmüller, Theobald
, p. 13368 - 13374 (2018/11/23)
Controlling lateral interactions between lipid molecules in a bilayer membrane to guide membrane organization and domain formation is a key factor for studying and emulating membrane functionality in synthetic biological systems. Here, we demonstrate an approach to reversibly control lipid organization, domain formation, and membrane stiffness of phospholipid bilayer membranes using the photoswitchable phospholipid azo-PC. azo-PC contains an azobenzene group in the sn2 acyl chain that undergoes reversible photoisomerization on illumination with UV-A and visible light. We demonstrate that the concentration of the photolipid molecules and also the assembly and disassembly of photolipids into lipid domains can be monitored by UV-vis spectroscopy because of a blue shift induced by photolipid aggregation.
Production method for lysophosphatidyl choline
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Paragraph 0014-0016, (2017/08/29)
The invention provides a production method for lysophosphatidyl choline. By taking glycerol phosphocholine as a raw material, the lysophosphatidyl choline containing single ester group can be obtained by tin complexing and o-acylation; therefore, the production cost is low. The production method for the lysophosphatidyl choline, provided by the invention, has the advantages of short process route, simple treatment method and easy product purification.
Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies
Niezgoda, Natalia,Gliszczyńska, Anna,G?adkowski, Witold,Kempińska, Katarzyna,Wietrzyk, Joanna,Wawrzeńczyk, Czes?aw
, p. 1065 - 1075 (2016/01/15)
Novel phosphatidylcholines and lysophosphatidylcholines with cis-9,trans-11 and trans-10,cis-12 conjugated linoleic acid (CLA) were synthesized in high yields (75-99%). The in vitro cytotoxic activities of these compounds against three human cancer cell lines (HL-60, MCF-7, and HT-29) were evaluated. The results revealed that there are differences in the activity between phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 CLA acyl groups. 1,2-Di(9Z,11E)-octadecadienoyl-sn-glycero-3-phosphocholine was the most potent cytotoxic agent among all tested CLA derivatives and its IC50 (concentration of a compound that inhibits the proliferation of 50% of the cancer cell population) was 29.4M against HL-60. Moreover, phosphatidylcholines with CLA acyls exhibited much lower cytotoxicity against non-cancer cells (Balb/3T3) than free CLA isomers.
Process for the production of phospholipids
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Page/Page column 16, (2008/06/13)
A new enzymatic process for preparing 1,2-diacylated phospholipids using an enzyme preparation possessing phospholipase activity towards acylation at the sn-1 and sn-2 sites in a microaqueous reaction system. More particularly, the 1,2-diacyl-phospholipids produced according to the esterification/transesterification process are obtainable in high yield and purity and carry identical desired carboxylic acid, preferably fatty acid, acyl groups at the sn-1 and sn-2 positions. The process involves esterification/transesterification (acylation) of a glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of the above mentioned appropriate enzyme preparation. The process of the invention further relates to a process for the production of 1-acyl-2-lyso-glycerophospholipid, preferably 2-lyso-PC by reacting glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of a sn-1 specific phospholipase (PLA1 or PLA1,2) and a solvent, in a microaqueous medium.
Tin-mediated synthesis of lyso-phospholipids
Fasoli, Ezio,Arnone, Alberto,Caligiuri, Antonio,D'Arrigo, Paola,De Ferra, Lorenzo,Servi, Stefano
, p. 2974 - 2978 (2008/02/11)
1-O-Acyl-sn-glycero-3-phosphocholine and 1-O-acyl-sn-glycero-3-phosphoric acid have been prepared selectively and with high yields from the corresponding diols, glycerophosphoryl choline and glycerol-3-phosphate. Starting from the diols, the activated tin ketals were prepared in 2-propanol by reaction with dialkyltin oxide. The intermediates were acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso- phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed. The Royal Society of Chemistry 2006.
Process for preparing lysophoshatidylcholine
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Page/Page column 7, (2010/11/08)
What is described is a process for preparing lysophosphatidylcholine by selective monoacylation of glycerophosphorylcholine (I), in the presence of an acylating agent and of dialkyltin derivatives, according to the following diagram: the process being particularly simple and having high overall yields.
γ-Ray irradiation of liposomes of polymerizable phospholipids containing octadeca-2,4-dienoyl groups and characterization of the irradiated liposomes
Akama, Kazuhiro,Yano, Yoshihiro,Tokuyama, Satoru,Hosoi, Fumio,Omichi, Hideki
, p. 1047 - 1059 (2007/10/03)
The synthesis of a variety of polymerizable phospholipids containing the octadeca-2,4-dienoyl moiety on 2-acyl chains and the characteristics of liposomes containing those phospholipids of the γ-irradiation are described. We synthesized three different polymerizable phosphocholines that have different 1-acyl chain lengths with the octadeca-2,4-dienoyl moiety on the 2- acyl chain: myristoyl (MODPC), palmitoyl (PODPC) and stearoyl (SODPC). The liposomes were prepared by extrusion through polycarbonate filters with a pore size of 0.2 μm, and were polymerized by γ-irradiation with various dose rates. The polymerization rate increased in the order SODPC>MODPC>PODPC. The mechanism of the polymerization of SODPC was the same as that of 1,2-bis- [(E,E)-octadeca-2,4-dienoyl]-sn-glycero-3-phosphocholine (DODPC), but differed from that of MODPC and PODPC. Freeze-thaw testing was used to evaluate the stability of the polymerizable liposomes. The MODPC liposome was more stable than other monofunctional liposomes. For similar irradiation, the polymerization behavior of the liposomes was significantly affected by the 1- acyl length.
Effects of molecular structures on the olfactory responses of phospholipid membranes to four alcohols
Zhou, Qingzhong,Yang, Yanan,Chen, Zhikuan,Sun, Anna
, p. 1 - 9 (2007/10/03)
In order to understand the relationship between phospholipid molecular structures and their olfactory responses to odorants, we designed and synthesized four phosphatidylcholine analogues with different long hydrocarbon (CH) chains and selected three natural phospholipids with different head-groups. By using interdigital electrodes (IEs) as olfactory sensors (OSs), we measured the responses of the IEs coated with these seven different lipid membranes to four alcohol vapors in a gas flow system. The IEs voltage changes were recorded and the voltage-relative saturate vapor pressure (V-P/P°) curves were also plotted. It was found that with a methyl (-CH3) placed at the C-8 position in the 18-carbon chain, the olfactory responses could be improved about ten times and with conjugated double bonds (C=C) in the long chains, the sensitivity could be increased by 3~4 orders of magnitude. As to head-groups, choline is preferred over ethanolamine and serine in phospholipid structures in terms of high olfactory sensitivity. These results are expected to be useful in further designing and manufacturing lipid-mimicking OSs. Copyright (C) 1998 Elsevier Science Ireland Ltd.
