- Light-Controlled Lipid Interaction and Membrane Organization in Photolipid Bilayer Vesicles
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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.
- Urban, Patrick,Pritzl, Stefanie D.,Konrad, David B.,Frank, James A.,Pernpeintner, Carla,Roeske, Christian R.,Trauner, Dirk,Lohmüller, Theobald
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- Production method for lysophosphatidyl choline
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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.
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Paragraph 0014-0016
(2017/08/29)
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- Phosphatidylcholine with cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid Isomers: Synthesis and Cytotoxic Studies
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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.
- Niezgoda, Natalia,Gliszczyńska, Anna,G?adkowski, Witold,Kempińska, Katarzyna,Wietrzyk, Joanna,Wawrzeńczyk, Czes?aw
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p. 1065 - 1075
(2016/01/15)
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- Process for preparing lysophoshatidylcholine
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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.
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Page/Page column 7
(2010/11/08)
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- Tin-mediated synthesis of lyso-phospholipids
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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.
- Fasoli, Ezio,Arnone, Alberto,Caligiuri, Antonio,D'Arrigo, Paola,De Ferra, Lorenzo,Servi, Stefano
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p. 2974 - 2978
(2008/02/11)
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- γ-Ray irradiation of liposomes of polymerizable phospholipids containing octadeca-2,4-dienoyl groups and characterization of the irradiated liposomes
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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.
- Akama, Kazuhiro,Yano, Yoshihiro,Tokuyama, Satoru,Hosoi, Fumio,Omichi, Hideki
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p. 1047 - 1059
(2007/10/03)
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- Effects of molecular structures on the olfactory responses of phospholipid membranes to four alcohols
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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.
- Zhou, Qingzhong,Yang, Yanan,Chen, Zhikuan,Sun, Anna
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- The stereospecific synthesis of mixed-acid phospholipids with polyunsaturated fatty acid from D-mannitol
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The polyunsaturated mixed-acid phosphatidylcholine, 1-palimoyl-2-linolenoyl-sn-glycerophosphocholine 1a and 1-stearoyl-2-linolenoyl-sn-glycerophosph 1b prepared from D-mannitol as an optically active starting material is described.
- Xia, Jie,Hui, Yong-Zheng
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p. 451 - 458
(2007/10/03)
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- Asymmetric synthesis of diacylglycerophosphocholine hydroperoxide VIa, lipoxygenase-catalyzed hydroperoxidation of linoleic acid and lipase-catalyzed enantioselective stearoylation of 2-O-benzoyl-1,3-propanediol
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Phosphatidylcholine hydroperoxide (11) bearing (S)-13-hydroperoxy-9Z,11E-octadecadienoic acid has been synthesized for the first time using lipoxygenase and lipase in addition to conventional chemical methods.As an extension of the study, lipase-catalyzed
- Baba, N,Yoneda, K,Iwasa, J,Tahara, S,Kaneko, T,Matsuo, M
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p. 824 - 827
(2007/10/02)
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- A Regioselective, Stereoselective Synthesis of a Diacylglycerophosphocholine Hydroperoxide by use of Lipoxygenase and Lipase
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1-Stearoyl-2--sn-glycero-3-phosphocholine (11) was synthesized without contamination by any regio- and stereo-chemical isomers by a combination of lipoxygenase-catalysed peroxidation, lipase-catalysed stearo
- Baba, Naomichi,Yoneda, Kenji,Tahara, Shoich,Iwasa, Junkichi,Kaneko, Takao,Matsuo, Mitsuyoshi
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p. 1281 - 1282
(2007/10/02)
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- NMR Studies of Micellar Aggregates in 1-Acyl-sn-glycerophosphocholine Systems. The Formation of a Cubic Liquid Crystalline Phase
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Measurements of the amphiphile diffusion coefficient, using the NMR pulsed-field gradient technique, have been performed on micellar solutions and cubic liquid crystalline phases of the following lysophosphatidylcholines: 1-lauroyl-sn-glycero-3-phosphocholine (LaLPC), 1-myristoyl-sn-glycero-3-phosphocholine (MyLPC), 1-palmitoyl-sn-glycero-3-phosphocholine (PaLPC), 1-stearoyl-sn-glycero-3-phosphocholine (StLPC), 1-oleoyl-sn-glycero-3-phosphocholine (OlLPC), and 1-linoleoyl-sn-glycero-3-phosphocholine (LiLPC).The 2H spin relaxation rates at two magnetic fields have been measured in micellar solutions of PaLPC.The phase equilibria at 25 and 35 deg C in the aqueous binary systems of LaLPC and MyLPC have been studied by 31P NMR and by optical techniques for lipid concentrations up to 50percent (w/w) 2H2O. 2H and 14N quadrupole splittings have been measured in anisotropic phases of PaLPC, OlLPC, and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC).A cubic liquid crystalline phase, I1, located between the micellar and hexagonal phase regions, is formed by LaLPC and MyLPC between approximately 40percent and 45percent (w/w) lipid in 2H2O.As previously shown the I1 phase is also formed by PaLPC while not by StLPC, OlLPC, and LiLPC for which a concentrated micellar solution is in equilibrium with the hexagonal phase (Arvidson et al.Eur.J.Biochem. 1985, 152, 753).For LaLPC, amphiphile diffusion measurements show that the cubic phase I1 consists of closed micellar aggregates.Amphiphile diffusion and 2H spin relaxation studies of the micellar phases show that the aggregates formed by LaLPC, MyLPC, PaLPC, and StLPC remain small and globular over the whole micellar phase region, while the micelles of OlLPC and LiLPC are large and polydispersed.Micelle diffusion measurements provide information about aggregate interactions, which is shown to be compatible with magnitudes of the hydration force and the van der Waals interactions previously obtained for corresponding bilayers.The formation of the cubic face I1 is discussed in terms of the packing of interacting micellar aggregates in a newly proposed structure for the cubic phase.
- Eriksson, Per-Olof,Lindblom, Goeran,Arvidson, Goesta
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p. 846 - 853
(2007/10/02)
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