- Synthesis of alkyl-glycerolipids standards for gas chromatography analysis: Application for chimera and shark liver oils
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Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood plasma, and bone marrow. Only a few AEL are commercially available, while many others with saturated or mono-unsaturated alkyl chains of variable length are not available. These compounds are, however, necessary as standards for analytical methods. Here, we investigated different reported procedures and we adapted some of them to prepare a series of 1-O-alkyl-glycerols featuring mainly saturated alkyl chains of various lengths (14:0, 16:0, 17:0, 19:0, 20:0, 22:0) and two monounsaturated chains (16:1, 18:1). All of these standards were fully characterized by NMR and GC-MS. Finally, we used these standards to identify the AEL subtypes in shark and chimera liver oils. The distribution of the identified AEL were: 14:0 (20–24%), 16:0 (42–54%) and 18:1 (6–16%) and, to a lesser extent, (0.2–2%) for each of the following: 16:1, 17:0, 18:0, and 20:0. These standards open the possibilities to identify AEL subtypes in tumours and compare their composition to those of non-tumour tissues.
- Pinault, Michelle,Guimaraes, Cyrille,Couthon, Hélène,Thibonnet, Jér?me,Fontaine, Delphine,Chant?me, Aurélie,Chevalier, Stephan,Besson, Pierre,Jaffrès, Paul-Alain,Vandier, Christophe
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- METHOD FOR PREPARING GLYCEROL ETHER AND GLYCOL ETHER
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The present invention concerns a method for preparing glycerol ether or glycol ether comprising the reaction of a compound of formula (II) with a compound of formula (III) in the presence of a heterogeneous acid catalyst of formulas (II) and (III).
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Paragraph 0079
(2015/03/28)
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- PROCESS FOR PREPARING A POLYOL ETHER
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The present invention relates to a process for preparing a polyol ether of formula (I), comprising a step of reductive alkylation involving a compound of general formula (II) and a compound of general formula (III): in which R1, R2, R3 and R4 are as defined in claim 1.
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Paragraph 0127
(2014/02/16)
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- Selective synthesis of 1-O-Alkyl(poly)glycerol ethers by catalytic reductive alkylation of carboxylic acids with a recyclable catalytic system
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(Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio-sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion-exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism is proposed for this transformation.
- Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
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p. 2397 - 2409
(2013/02/23)
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- Synthesis of lipid-oligonucleotide conjugates for RNA interference studies
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The synthesis of RNA molecules carrying lipids at their 3′-termini and 5′-termini is reported. These conjugates were fully characterized by MALDI-TOF mass spectrometry and HPLC chromatography. The ability of these conjugates to silence gene expression was
- Grijalvo, Santiago,Ocampo, Sandra M.,Perales, Jose C.,Eritja, Ramon
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experimental part
p. 287 - 299
(2011/10/03)
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- Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties
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We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37°C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.
- Huang, Zhaohua,Szoka Jr., Francis C.
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supporting information; experimental part
p. 15702 - 15712
(2009/03/12)
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- Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof
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The invention provides anti-apoptotic compositions lysophosphatidic acids and methods for making and using the compositions. Such compositions can also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.
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Page/Page column 36
(2008/06/13)
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- Compositions containing lysophosphotidic acids which inhibit apoptosis and uses thereof
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The present invention provides therapeutic compositions containing lysophosphotidic acids, methods for making the compositions, and methods of using the compositions in the preservation and treatment of organs.
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- Nucleoside Conjugates. 14. Synthesis and Antitumor Activity of 1-β-D-Arabinofuranosylcytosine Conjugates of Ether Lipids with Improved Water Solubility
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A series of ara-CDP-rac-1-O-alkyl-2-O-acylglycerols (9a-f), analogues of highly active ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (1) and Cytoros (2), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated.Conjugates 9a-f containing sn-1 alkyl (C16) and the sn-2 fatty acyl (>C16) such as conjugate 1 were sparingly soluble.Conjugates 9a-c,e were almost completely solubilized in water by shaking.However, a large portion of conjugates 9d and 9f in water by shaking exist in micelles with mean diameters ranging 7.0-55.2 nm.The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 9-18 times greater than that of ara-C.A single dose (300 mg/kg) of conjugates 9d and 9f produced a significant increase in life span (ILS 206 to >543percent) with 17-67percent long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia.These results were comparable to those of the previous conjugate 1 and Cytoros (2).In contrast,conjugates 9a-c,e at single doses were less effective (ILS 69-178percent with no long-term survivors).However, two (qd, 1, 7) or three (qd 1, 5, 9) divided doses of these conjugates were found to be as effective as a single dose of the previous conjugates.The three divided doses (150 mg/kg per day) of conjugates 9d, 9e, and 9f produced a remarkable antitumor activity in L1210 leukemic mice (ILS >350percent with >50percent long-term servivors).Because of the convenient formulation and the significant antitumor activities, the water-soluble conjugates 9d, 9e, and 9f warrant further investigation.
- Hong, Chung Il,Nechaev, Alexander,Kirisits, Alan J.,Vig, Rakesh,Hui, Sek-Wen,West, Charles R.
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p. 1629 - 1634
(2007/10/02)
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- A comparative study of the liquid-crystalline behavior of three homologous series of 1,2-propanediol derivatives
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Homologous series (R = n-hexyl to n-tetradecyl) of 3-(alkylamino)-, 3-(alkylthio)- and 3-alkoxy-1,2-propanediols have been synthesized and their thermal behavior studied by thermomicroscopy and differential-scanning calorimetry.The occurence of liquid-crystalline behavior was found to be strongly dependent on both the alkyl-chain length and the hetero-atom that links the alkyl chain to the 1,2-propanediol moiety. No thermotropic liquid-crystalline behavior could be observed for 3-alkoxy-1,2-propanediols; 3-(heptylamino)- through 3-(nonylamino)-1,2-propanediol exhibit a transient smectic A phase on supercooling of the isotropic liquid, whereas 3-(hexylthio)-1,2-propanediol through 3-(nonylthio)-1,2-propanediol form smectic phases that are quite stable.Although the thermal behavior in the pure form differs considerably, all three classes of compounds are capable of lyotropic mesophase formation in the presence of water.
- Doren, Henk A. van,Geest, Ralph van der,Kellogg, Richard M.,Wynberg, Hans
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p. 197 - 203
(2007/10/02)
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- PROPOSAL FOR MODULABLE PHOTOAFFINITY LABELLING
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The synthesis of various glyceric derivatives unsymmetrically 1,3-disubstituted or 1,2,3-trisubstituted is described.Corresponding molecular probes, photosensitive and functionalized are proposed for photolabelling studies.
- Aranda, G.,Lallemand, J. Y.
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