Genomes and Genes
Summary: 12-Carbon saturated monocarboxylic acids.
- Jung O, Brandes R, Kim I, Schweda F, Schmidt R, Hammock B, et al. Soluble epoxide hydrolase is a main effector of angiotensin II-induced hypertension. Hypertension. 2005;45:759-65 pubmed..Direct vasodilatation of resistance arteries in skeletal muscles does not appear to contribute to the antihypertensive effects of sEH inhibition in mice. ..
- Pornpattananangkul D, Fu V, Thamphiwatana S, Zhang L, Chen M, Vecchio J, et al. In vivo treatment of Propionibacterium acnes infection with liposomal lauric acids. Adv Healthc Mater. 2013;2:1322-8 pubmed publisher..Herein, the development and evaluation of liposomal lauric acids (LipoLA) is reported as a new, effective and safe therapeutic agent for the treatment of acne infection...
- Ding L, Hao F, Shi Z, Wang Y, Zhang H, Tang H, et al. Systems biological responses to chronic perfluorododecanoic acid exposure by integrated metabonomic and transcriptomic studies. J Proteome Res. 2009;8:2882-91 pubmed publisher..Several serum metabolites exhibited dose-dependences, providing thorough descriptions of changes induced by PFDoA exposure. These observations yielded novel insights regarding the toxicological mechanism of PFCAs at the systems level. ..
- Lee J, Zhao L, Youn H, Weatherill A, Tapping R, Feng L, et al. Saturated fatty acid activates but polyunsaturated fatty acid inhibits Toll-like receptor 2 dimerized with Toll-like receptor 6 or 1. J Biol Chem. 2004;279:16971-9 pubmed..These results also suggest that inflammatory responses induced by the activation of TLRs can be differentially modulated by types of dietary fatty acids. ..
- Kim I, Nishi K, Tsai H, Bradford T, Koda Y, Watanabe T, et al. Design of bioavailable derivatives of 12-(3-adamantan-1-yl-ureido)dodecanoic acid, a potent inhibitor of the soluble epoxide hydrolase. Bioorg Med Chem. 2007;15:312-23 pubmed..The esterification of 1 results in compounds that are easier to formulate in animal food and in triglycerides for gavage and other routes of administration, making it easier to study the biological effects of sEH inhibition in vivo. ..
- Yang D, Pornpattananangkul D, Nakatsuji T, Chan M, Carson D, Huang C, et al. The antimicrobial activity of liposomal lauric acids against Propionibacterium acnes. Biomaterials. 2009;30:6035-40 pubmed publisher..acnes associated diseases. ..
- Ebata H, Toshima K, Matsumura S. Lipase-catalyzed synthesis and properties of poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] directed towards novel green and sustainable elastomers. Macromol Biosci. 2008;8:38-45 pubmed..In addition, it showed an excellent biodegradability by activated sludge and chemical recyclability by lipase. ..
- Bergsson G, Arnfinnsson J, Steingrimsson O, Thormar H. Killing of Gram-positive cocci by fatty acids and monoglycerides. APMIS. 2001;109:670-8 pubmed..The highly lethal effect of monocaprin indicates that this lipid might be useful as a microbicidal agent for prevention and treatment of infections caused by these bacteria. ..
- Fischer C, Drake D, Dawson D, Blanchette D, Brogden K, Wertz P. Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria. Antimicrob Agents Chemother. 2012;56:1157-61 pubmed publisher..5 h for some lipids but took as long as 24 h for others. Hence, sphingoid bases and fatty acids have different antibacterial activities and may have potential for prophylactic or therapeutic intervention in infection. ..
- Liu Y, Wan Y, Fang Y, Yao E, Xu S, Ning Q, et al. Epoxyeicosanoid Signaling Provides Multi-target Protective Effects on Neurovascular Unit in Rats After Focal Ischemia. J Mol Neurosci. 2016;58:254-65 pubmed publisher..The results suggest that epoxyeicosanoid signaling is a promising multi-mechanism therapeutic target for the treatment of stroke. ..
- Schäfer S, Hansen B, Volkl A, Fahimi H, Pill J. Biochemical and morphological effects of K-111, a peroxisome proliferator-activated receptor (PPAR)alpha activator, in non-human primates. Biochem Pharmacol. 2004;68:239-51 pubmed..This pharmacological profile makes K-111 a highly promising drug candidate for clinical applications in the treatment of type 2 diabetes, dyslipidaemia, obesity and the metabolic syndrome. ..
- Kolesnikov Y, Sõritsa D. Analgesic synergy between topical opioids and topical non-steroidal anti-inflammatory drugs in the mouse model of thermal pain. Eur J Pharmacol. 2008;579:126-33 pubmed..001) and this analgesic effect lasted for 120 min. Our current findings support the supra-additive interaction of topical mu opioids, S-ibuprofen and diclofenac in a model of moderate to severe pain, radiant heat tail-flick assay. ..
- Merabet N, Bellien J, Glevarec E, Nicol L, Lucas D, Remy Jouet I, et al. Soluble epoxide hydrolase inhibition improves myocardial perfusion and function in experimental heart failure. J Mol Cell Cardiol. 2012;52:660-6 pubmed publisher..This notably results from short-term processes, i.e. increased LV perfusion, reduced LV oxidative stress and peripheral vasodilatation, but also from long-term effects, i.e. reduced LV remodeling. ..
- Aasum E, Cooper M, Severson D, Larsen T. Effect of BM 17.0744, a PPARalpha ligand, on the metabolism of perfused hearts from control and diabetic mice. Can J Physiol Pharmacol. 2005;83:183-90 pubmed..Despite normalization of cardiac metabolism, PPARalpha treatment did not improve cardiac function in diabetic hearts. ..
- Kizhakkedathu J, Nisha C, Manorama S, Maiti S. Water-soluble nanoparticles from random copolymer and oppositely charged surfactant, 3a. Nanoparticles of poly(ethylene glycol)-based cationic random copolymer and fatty acid salts. Macromol Biosci. 2005;5:549-58 pubmed..The formation of water-soluble nanoparticles by the self-assembly of fatty acid salts upon interacting with oppositely charged poly(ethylene glycol)-based polyions. ..
- Zemaitis M, Poloyac S, Frye R. Identification of omega hydroxy fatty acids in biological samples as their pentafluoropropyl derivatives by gas chromatography/mass spectrometry with positive and negative ion detection. Rapid Commun Mass Spectrom. 2002;16:1411-5 pubmed..The reaction appears to be specific, since derivatives of subterminal fatty acids (secondary alcohols) could not be detected. ..
- Girvan H, Levy C, Williams P, Fisher K, Cheesman M, Rigby S, et al. Glutamate-haem ester bond formation is disfavoured in flavocytochrome P450 BM3: characterization of glutamate substitution mutants at the haem site of P450 BM3. Biochem J. 2010;427:455-66 pubmed publisher..Our data point strongly to a likelihood that glutamate-haem linkages are disfavoured in this most catalytically efficient P450, possibly due to the absence of a methylene radical species during catalysis. ..
- Diani Moore S, Ma Y, Gross S, Rifkind A. Increases in levels of epoxyeicosatrienoic and dihydroxyeicosatrienoic acids (EETs and DHETs) in liver and heart in vivo by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and in hepatic EET:DHET ratios by cotreatment with TCDD and the soluble epoxide hyd. Drug Metab Dispos. 2014;42:294-300 pubmed publisher..Cotreatment with AUDA increased hepatic EET-to-DHET ratios, indicating that the in vivo profile of P450-arachidonic acid metabolites can be modified for potential therapeutic intervention. ..
- Yang J, Liu Y, Wang H, Liu L, Wang W, Wang C, et al. The biocompatibility of fatty acid modified dextran-agmatine bioconjugate gene delivery vector. Biomaterials. 2012;33:604-13 pubmed publisher..Importantly, cells cultured with the degraded products of Dex-Agm and Dex-L-Agm retained more than 80% viability, suggest their potential application as a gene delivery vector. ..
- Pons N, Pipino S, De Matteis F. Interaction of polyhalogenated compounds of appropriate configuration with mammalian or bacterial CYP enzymes. Increased bilirubin and uroporphyrinogen oxidation in vitro. Biochem Pharmacol. 2003;66:405-14 pubmed..A role of the ferryl-oxygen intermediate is suggested in the oxidation of biologically important molecules, with possible implications for the therapy of jaundice and for toxic oxidative reactions, such as uroporphyria and cancer. ..
- Holmes V, Bruce M, Shaw P, Bell D, Qi F, Barrett D. A gas chromatography-mass spectrometry method for the measurement of fatty acid omega and omega(-1) hydroxylation kinetics by CYP4A1 using an artificial membrane system. Anal Biochem. 2004;325:354-63 pubmed..Using this method, the kinetics of omega and omega(-1) oxidation of lauric, myristic, and palmitic acids by CYP4A enzymes were measured and compared in rat liver microsomes and an artificial membrane system. ..
- Yi M, Shin J, Lee S. Expression of CYP4V2 in human THP1 macrophages and its transcriptional regulation by peroxisome proliferator-activated receptor gamma. Toxicol Appl Pharmacol. 2017;330:100-106 pubmed publisher..Further study is required to understand the role of CYP4V2 with regard to fat accumulation in the activated macrophage and atherosclerotic plaque development. ..
- van Zijderveld S, Fonken B, Dijkstra J, Gerrits W, Perdok H, Fokkink W, et al. Effects of a combination of feed additives on methane production, diet digestibility, and animal performance in lactating dairy cows. J Dairy Sci. 2011;94:1445-54 pubmed publisher..Total volatile fatty acid concentrations were lower for ADD, whereas molar proportions of propionate increased at the expense of acetate and butyrate. ..
- Brummund J, Meyer F, Liese A, Eggers R, Hilterhaus L. Dissolving carbon dioxide in high viscous substrates to accelerate biocatalytic reactions. Biotechnol Bioeng. 2011;108:2765-9 pubmed publisher..Thus the reaction rate was increased by a factor of 4 while working at a pressure of 280 bar and 60°C. ..
- Jiang M, Mezentsev A, Kemp R, Byun K, Falck J, Miano J, et al. Smooth muscle--specific expression of CYP4A1 induces endothelial sprouting in renal arterial microvessels. Circ Res. 2004;94:167-74 pubmed..We conclude that Ad-SM22-4A1 drives a smooth muscle-specific functional expression of CYP4A1 and demonstrates increased angiogenesis, presumably via increased production of 20-HETE. ..
- Helvig C, Tijet N, Feyereisen R, Walker F, Restifo L. Drosophila melanogaster CYP6A8, an insect P450 that catalyzes lauric acid (omega-1)-hydroxylation. Biochem Biophys Res Commun. 2004;325:1495-502 pubmed..Our data open new prospects for the CYP6 P450 enzymes, which could be involved in important physiological functions through fatty acid metabolism. ..
- Fernandes R, Beserra B, Cunha R, Hillesheim E, Camargo C, Pequito D, et al. Relationship between acute phase proteins and serum fatty acid composition in morbidly obese patients. Dis Markers. 2013;35:105-12 pubmed publisher..027) and margaric acid (P = 0.008). Other correlations were not statistically significant. Our findings suggest that serum fatty acids are linked to acute phase proteins in morbidly obese patients. ..
- Soliva C, Hindrichsen I, Meile L, Kreuzer M, Machmuller A. Effects of mixtures of lauric and myristic acid on rumen methanogens and methanogenesis in vitro. Lett Appl Microbiol. 2003;37:35-9 pubmed..The results support strategies for an environment-friendly ruminant nutrition as it was demonstrated that part of the less palatable C12 could be replaced by C14 without losing its methane-suppressing potential. ..
- Wang Y, Fan Q, Song Y, Michniak B. Effects of fatty acids and iontophoresis on the delivery of midodrine hydrochloride and the structure of human skin. Pharm Res. 2003;20:1612-8 pubmed..1 mA/cm2, the daily delivery of midodrine hydrochloride can provide an adequate clinical application. The enhancement of passive and iontophoretic delivery by fatty acids may be occurring through the same mechanism. ..
- Sivakumar R, Jebanesan A, Govindarajan M, Rajasekar P. Oviposition attractancy of dodecanoic, hexadecanoic and tetradecanoic acids against Aedes aegypti and Culex quinquefasciatus (Diptera: Culicidae). Eur Rev Med Pharmacol Sci. 2011;15:1172-5 pubmed..aegypti and Cx. quinquefasciatus. In this result it can be concluded that the three compounds possess remarkable oviposition attractancy against Ae. aegypti and Cx. quinquefasciatus. ..
- Chung A, Liu Q, Ouyang S, Wu Q, Chen G. Microbial production of 3-hydroxydodecanoic acid by pha operon and fadBA knockout mutant of Pseudomonas putida KT2442 harboring tesB gene. Appl Microbiol Biotechnol. 2009;83:513-9 pubmed publisher..27 g/l extracellular 3HA containing 96 mol% fraction of 3HDD after 28 h of growth. For the first time, it became possible to produce 3HDD-dominant 3HA monomers. ..
- Lim Y, Eun C, Park H, Han S, Han J, Cho K, et al. Regioselective oxidation of lauric acid by CYP119, an orphan cytochrome P450 from Sulfolobus acidocaldarius. J Microbiol Biotechnol. 2010;20:574-8 pubmed..In addition, regioselectivity control of CYP119 without altering its thermostability can lead to the development of novel CYP119-based catalysts through protein engineering. ..
- Amenitsch H, Bombelli C, Borocci S, Ceccacci F, Mancini G, Rappolt M. Elucidation of the isomeric domains formed by sodium N-dodecanoyl-L-prolinate. J Colloid Interface Sci. 2004;280:212-8 pubmed..SAXS experiments gave the average size and structural features of the aggregates. A NMR ROESY experiment evidenced the mosaic-like nature of the domains inside the same aggregate. ..
- Blanco E, Rodriguez Abreu C, Schulz P, Ruso J. Effect of alkyl chain asymmetry on catanionic mixtures of hydrogenated and fluorinated surfactants. J Colloid Interface Sci. 2010;341:261-6 pubmed publisher..Meanwhile, system containing just hydrogenated surfactants form hexagonal phases or they are arranged in elongated aggregates. ..
- Faciola A, Broderick G. Effects of feeding lauric acid on ruminal protozoa numbers, fermentation, and digestion and on milk production in dairy cows. J Anim Sci. 2013;91:2243-53 pubmed publisher..01); DM, OM, NDF, and CP digestibility (P < 0.01); and milk production and milk components (P < 0.01). Therefore, LA does not appear to be a feasible RP suppressant for feeding in practical diets. ..
- Pereira C, da Silva M, Langone M. Enzymatic synthesis of monolaurin. Appl Biochem Biotechnol. 2004;113-116:433-45 pubmed..0, and 3.0% (w/w) enzyme concentration. The final product, obtained after 6 h of reaction, was 45.5% monolaurin, 26.8% dilaurin, 3.1% trilaurin, and 24.6% lauric acid. The reusability of the enzyme was also studied. ..
- Kragh Hansen U, Dørge E, Pedersen A. Rate-of-dialysis technique: theoretical and practical aspects. Anal Biochem. 2005;340:145-53 pubmed..The technique is well suited for binding studies performed with high protein concentrations because it is not affected by any osmosis or Donnan effects. ..
- Liu C, Huang H. In vitro anti-propionibacterium activity by curcumin containing vesicle system. Chem Pharm Bull (Tokyo). 2013;61:419-25 pubmed..Curcumin-loaded vehicles could efficiently accumulate in the skin and inhibit P. acnes in vitro. Our results highlight the potential of using vehicles containing lauric acid and curcumin as an alternative treatment for acne vulgaris. ..
- Porto Fett A, Campano S, Smith J, Oser A, Shoyer B, Call J, et al. Control of Listeria monocytogenes on commercially-produced frankfurters prepared with and without potassium lactate and sodium diacetate and surface treated with lauric arginate using the Sprayed Lethality in Container (SLIC(R)) delivery method. Meat Sci. 2010;85:312-8 pubmed publisher..monocytogenes and when used in combination with reduced levels/ratio of lactate and diacetate as an ingredient for frankfurters provides inhibition throughout shelf life. ..
- Desai K, Mallery S, Schwendeman S. Effect of formulation parameters on 2-methoxyestradiol release from injectable cylindrical poly(DL-lactide-co-glycolide) implants. Eur J Pharm Biopharm. 2008;70:187-98 pubmed publisher..Hence, these formulation approaches provide several possible avenues to improve release rates of the hydrophobic drug, 2-ME, from PLGA for future application in regional anti-cancer therapy. ..
- Barboza Silva E, Castro A, Marquis R. Fluoride, triclosan and organic weak acids as modulators of the arginine deiminase system in biofilms and suspension cells of oral streptococci. Oral Microbiol Immunol. 2009;24:265-71 pubmed publisher..The weak acid indomethacin was nearly as potent at pH 4.0 as triclosan, while capric and lauric acids were less potent, especially for biofilms. The methyl ester of lauric acid was slightly stimulatory...
- Gilep A, Guryev O, Usanov S, Estabrook R. Reconstitution of the enzymatic activities of cytochrome P450s using recombinant flavocytochromes containing rat cytochrome b(5) fused to NADPH--cytochrome P450 reductase with various membrane-binding segments. Arch Biochem Biophys. 2001;390:215-21 pubmed
- Cryle M, Hayes P, De Voss J. Enzyme-substrate complementarity governs access to a cationic reaction manifold in the P450(BM3)-catalysed oxidation of cyclopropyl fatty acids. Chemistry. 2012;18:15994-9 pubmed publisher..This also aids in reconciling literature reports supporting the presence of cationic intermediates with certain cytochrome P450 enzyme/substrate pairs. ..
- Revermann M, Schloss M, Barbosa Sicard E, Mieth A, Liebner S, Morisseau C, et al. Soluble epoxide hydrolase deficiency attenuates neointima formation in the femoral cuff model of hyperlipidemic mice. Arterioscler Thromb Vasc Biol. 2010;30:909-14 pubmed publisher..These observations suggest that inhibition of sEH prevents vascular remodeling in an inflammatory model but not in a blood flow-dependent model of neointima formation. ..
- de Souza R, de Faria E, Figueiredo R, Freitas L, Iglesias M, Mattedi S, et al. Protic ionic liquid as additive on lipase immobilization using silica sol-gel. Enzyme Microb Technol. 2013;52:141-50 pubmed publisher..The physico-chemical characterization confirmed the presence of the enzyme and its immobilized derivatives obtained in this study by identifying the presence of amino groups, and profiling enthalpy changes of mass loss. ..
- Afitlhile M, Fukushige H, Hildebrand D. Labeling of major plant lipids and jasmonic acid using [1-(14C)] lauric acid. Phytochemistry. 2004;65:2679-84 pubmed..In Artemisia, [14C]JA was actively metabolized into [14C]MJ. Extracts prepared from the leaves of Artemisia, exhibited higher in vitro JA methyltransferase activity than those from Arabidopsis. ..
- Bailo E, Fruk L, Niemeyer C, Deckert V. Surface-enhanced Raman scattering as a tool to probe cytochrome P450-catalysed substrate oxidation. Anal Bioanal Chem. 2009;394:1797-801 pubmed publisher..Specific spectral changes could be assigned to changes in the heme environment only for myristic acid, indicating an occurrence of oxidation process characteristic for the enzymatic substrate. ..
- Carroll R, Severson D. Peroxisome proliferator-activated receptor-alpha ligands inhibit cardiac lipoprotein lipase activity. Am J Physiol Heart Circ Physiol. 2001;281:H888-94 pubmed..In conclusion, two different PPAR-alpha ligands (Wy-14643 and BM-17.0744) inhibited cellular LPL activity in cultured cardiomyocytes by a posttranscriptional and posttranslational mechanism. ..