Abstract：
:The recently discovered marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid was synthesized for the first time in six steps (26% overall yield) starting from commercially available methyl 12-methyltridecanoate. The synthetic approach provided enough material to corroborate the structure of the acid, which was recently identified in the sponge Amphimedon complanata from Aguadilla, Puerto Rico, and to test its cytotoxicity to three leukemia cell lines. The key step in the synthesis was the addition of trimethylsilyl cyanide to 12-methyltridecanal under triethylamine catalysis. Nuclear magnetic resonance data are provided for the first time for this methoxylated fatty acid and the synthetic approach utilized is of general applicability since it can be used in the synthesis of other methyl-branched 2-methoxylated fatty acids. We also report that the acid (+/-)-2-methoxy-13-methyltetradecanoic acid is cytotoxic to human chronic myelogenous leukemia K-562 (EC50=238 microM), histiocytic lymphoma U-937 (EC50=250 microM), and promielocytic leukemia HL-60 (EC50=476 microM) in RPMI 1640 medium.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Carballeira NM,Cruz H,Orellano EA,González FAdoi
10.1016/s0009-3084(03)00110-5subject
Has Abstractpub_date
2003-12-01 00:00:00pages
149-53issue
2eissn
0009-3084issn
1873-2941pii
S0009308403001105journal_volume
126pub_type
杂志文章abstract：:A myriad of health benefits including the prevention of cancer and heart disease accompanies consumption of polyunsaturated fatty acids (PUFA). Of special importance is the omega-3-PUFA docosahexaenoic acid (DHA), with 22 carbons and six double bonds that constitute the most highly unsaturated fatty acid naturally occ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.09.007
更新日期：2004-11-01 00:00:00
abstract：:In liotropic lipid systems phase transitions can be induced isothermally by changing the solvent concentration or composition; alternatively, lipid composition can be modified by (bio)chemical means. The probability for isothermal phase transitions increases with the decreasing transition entropy; it is proportional t...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(91)90082-m
更新日期：1991-03-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(89)90047-9
更新日期：1989-10-01 00:00:00
abstract：:20-hydroxycholesterol is a signaling oxysterol with immunomodulating functions and, thus, structural analogues with reporter capabilities could be useful for studying and modulating the cellular processes concerned. We have synthesized three new 20-hydroxycholesterol-like pregn-5-en-3β-ol derivatives with fluorescent ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2019.104850
更新日期：2020-03-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(91)90039-e
更新日期：1991-12-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(02)00014-2
更新日期：2002-05-01 00:00:00
abstract：:Binary membranes composed of dimyristoylphosphatidylcholine (DMPC) and natural ceramide (up to a mole fraction Xcer = 0.25) were investigated by measuring the excimer:monomer fluorescence emission intensity ratio IE:IM for the pyrene labeled phospholipid probe 1-palmitoyl-2[(pyren-1-yl)]decanoyl-sn-glycero-3-phosphoch...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(97)00040-6
更新日期：1997-08-08 00:00:00
abstract：:We performed differential scanning calorimetric (DSC) and Fourier transform infrared (FTIR) spectroscopic studies of the effects of cholesterol (CHOL), 7-dehydrocholeterol (7DHC) and desmosterol (DES) on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine (DPPC) bilayer membranes. 7DHC a...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2015.09.002
更新日期：2015-10-01 00:00:00
abstract：:A polymorphic variation of sialic acid species of sialosyllactosylceramide was found in dog erythrocytes. The analysis of the glycolipids in the erythrocytes of the individual dogs in a family of a Japanese breed of dog, Shiba-Inu, showed that the expression of sialosyllactosylceramide containing N-glycolylneuraminic ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(86)90044-7
更新日期：1986-12-15 00:00:00
abstract：:The ionic transport properties, capacitance and breakdown voltage of bilayer macrovesicles made from lecithin, dodecaprenol and their mixtures have been studied. The electrical measurements showed that polyprenol in lipid bilayers increases membrane permeability and elasticity, and decreases membrane thickness. Some p...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90116-7
更新日期：1986-03-01 00:00:00
abstract：:Structural analysis, a purification scheme and stability information on a fluorescent cholesterol analogue, which has been used as a probe in several model and biological systems, are presented. The proposed structure for the fluorophore, cholestatrien-3 beta-ol, closely resembles that of cholesterol. However, problem...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(84)90086-0
更新日期：1984-11-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2003.09.007
更新日期：2004-01-01 00:00:00
abstract：:This work is focused on the study of the dynamic surface properties of spread monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), which is the main component of the pulmonary surfactant (PS), in the region of high surface pressures and at different temperatures. The increase of temperature from 25 to 35 ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2019.104812
更新日期：2019-12-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.05.003
更新日期：2004-09-01 00:00:00
abstract：:Non-coding RNAs (ncRNAs) like microRNAs (miRNAs) or small interference RNAs (siRNAs) with their power to selectively silence any gene of interest enable the targeting of so far 'undruggable' proteins and diseases. Such RNA molecules have gained much attention from biotech and pharmaceutical companies, which led to the...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2019.104837
更新日期：2020-01-01 00:00:00
abstract：:The synthesis and self-assembling properties of a model compound in a new class of cationic phospholipids with a highly unsaturated conjugated fatty acid are described. In addition, the potential of this new lipid as a nucleic acid carrier was evaluated through lipoplex formulations employing 1,2-dioleoyl-sn-glycero-3...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.03.002
更新日期：2013-05-01 00:00:00
abstract：:The reasons for lipid diversity in membranes are not understood. Here we review evidence supporting the proposal that factors related to the polymorphic capabilities of lipids provide a rationale for lipid diversity. In particular, the ability of lipids to adopt different polymorphic phases appears to be related to a ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90067-8
更新日期：1986-06-01 00:00:00
abstract：:For the design of new synthetic substrates for the assay of pancreatic lipases activity, acyl dialkylglycerols of variable chain length were prepared. Titrimetric assay of these substrates showed the highest lipolytic activity of porcine pancreas lipase (pPL) with butanoyl dibutylglycerol. The activity is lower but co...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(01)00143-8
更新日期：2001-06-01 00:00:00
abstract：:The transformation between a gel and a fluid phase in dipalmitoyl-phosphatidylcholine (DPPC) bilayers has been simulated using a coarse grained (CG) model by cooling bilayer patches composed of up to 8000 lipids. The critical step in the transformation process is the nucleation of a gel cluster consisting of 20-80 lip...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2005.03.001
更新日期：2005-06-01 00:00:00
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journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(02)00004-x
更新日期：2002-02-01 00:00:00
abstract：:Oxysterols are oxidized products of cholesterol that play several roles in various pathophysiological processes, including the control of lipid metabolism, immunological processes, and cytotoxicity. Mesenchymal stem cells are multipotent cells with properties of self-renewal and the ability to differentiate into other...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2017.06.009
更新日期：2017-10-01 00:00:00
abstract：:The structural polymorphism of two selected disaccharide glycolipids with a maltose (DMMA) and a melibiose (DMME) carbohydrate headgroup linked to dimyristyl alkyl chains were investigated by FTIR-spectroscopy, differential scanning calorimetry (DSC), small-angle X-ray scattering (SAXS) and film-balance measurements. ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2007.09.004
更新日期：2008-01-01 00:00:00
abstract：:The indolic plant hormone, indole-3-acetic acid (IAA), mediated the transport of Mn2+ and other ions into small unilamellar vesicles prepared from soybean phosphatidylinositol (PI) and this process has been studied using 31P nuclear magnetic resonance spectroscopy (NMR). The rate of Mn2+ movement into PI vesicles is d...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(92)90010-m
更新日期：1992-04-01 00:00:00
abstract：:Under condition of ROS formation in lipid membranes, free radical reactions can proceed in both hydrophobic (peroxidation of lipids, POL) and polar (free radical fragmentation) parts of the bilayer. Free-radical fragmentation is typical for the lipids containing a hydroxyl group in β-position with respect to an ester ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.10.010
更新日期：2014-01-01 00:00:00
abstract：:Three novel polymerizable ether lipids, 1,2-O-bis[10(2',4'-hexadienoyloxy)decyl]-rac, 1,2-O-bis(10,12-tricosadiynyl)-rac, and (-)-2,3-O-bis(10,12-tricosadiynyl)-sn-glycero-1-phosphocholine, were synthesized from 3-O-benzyl-rac, 3-O-trityl-rac and (-)-1-O-trityl-sn-glycerol as starting materials, respectively. All the ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(92)90100-4
更新日期：1992-05-01 00:00:00
abstract：:Isoprostanes (IsoPs) are a complex family of compounds produced, in vivo, from peroxidation of polyunsaturated fatty acids (AA, DHA, EPA, alpha-linolenic) via a free-radical-catalyzed mechanism. Carbocyclic annulations are extremely important reactions and the stereocontrolled intramolecular free-radical cyclization h...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2003.10.008
更新日期：2004-03-01 00:00:00
abstract：:Reduction of 3beta-benzoyloxy-14alpha,15alpha-epoxy-5alpha-cholest-7-ene with either lithium triethylboro-hydride or lithium aluminum hydride (4 molar excess) gave 5-alpha-cholest-8(14)-en-3beta,15alpha-diol in high yield. Reduction of the epoxy ester with lithium triethylborodeuteride or lithium aluminum deuteride (4...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(77)90013-5
更新日期：1977-04-01 00:00:00
abstract：:The development of "molecular rulers" would allow one to quantitatively locate the penetration depth of intercalants within lipid bilayers. To this end, an attempt was made to correlate the (13)C NMR chemical shift of polarizable "reporter" carbons (e.g., carbonyls) of intercalants within DMPC liposomal bilayers - wit...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2014.07.007
更新日期：2014-12-01 00:00:00
abstract：:Melatonin and its structural analogues display antioxidant activity in vivo but their activity in model membranes is not very well known. In this study, we have investigated the antioxidant capacity of melatonin and structural analogues on Fe(2+)-initiated peroxidation of sonicated liposomes made of retinal lipids. Th...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2011.07.004
更新日期：2011-10-01 00:00:00
abstract：:A simplified procedure for lipid digestion, well suited for handling a large number of samples, was used to analyze a variety of common phospholipids. This procedure involves digestion of phospholipids in perchloric acid at 130 degrees C with minimal sample manipulation. For all lipids tested, complete destruction, ne...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90111-8
更新日期：1986-01-01 00:00:00
