Disease relevance of lauric acid

• Protein antigens covalently conjugated with lipid groups (dodecanoic acid) have previously been shown to stimulate strong delayed-type hypersensitivity (DTH) without the aid of adjuvants [1].
• Dodecanoic acid conjugated Salmonella typhi organisms could be used in place of the BCG cell walls to produce effective adjuvant preparations [2].
• Furan species without indoles indicated Clostridium difficile, ethyl dodecanoate indicated rotavirus, ammonia without ethyl dodecanoate suggested other enteric viruses, and the absence of hydrocarbons and terpenes indicated Campylobacter infection [3].
• Steady-state turnover with YkuN or YkuP, fatty acid-bound P450 BioI, and E. coli NADPH-flavodoxin reductase indicated that both flavodoxins supported lipid hydroxylation by P450 BioI with turnover rates of up to approximately 100 min(-1) with lauric acid as substrate [4].
• In vitro and in vivo evaluations of the activities of lauric acid monoester formulations against Staphylococcus aureus [5].

High impact information on lauric acid

• Spectra of albumin complexes with the 12-carbon saturated fatty acid, lauric acid, had several narrow laurate carboxyl peaks at 35 degrees C, indicating longer lifetimes (tau much greater than 66 msec) in the different binding sites [6].
• Similarly, DCs treated with lauric acid show increased T cell activation capacity, whereas docosahexaenoic acid inhibits T cell activation induced by LPS-treated DCs [7].
• Together, these results demonstrate that lauric acid activates TLR2 dimers as well as TLR4 for which respective bacterial agonists require acylated fatty acids, whereas DHA inhibits the activation of all TLRs tested [8].
• However, neither lauric acid nor DHA affected the heterodimerization of TLR2 with TLR6 as well as the homodimerization of TLR4 as determined by co-immunoprecipitation assays in 293T cells in which these TLRs were transiently overexpressed [8].
• Using D-erythro-sphingosine and lauric acid as substrates, the reaction followed normal Michaelis-Menten kinetics [9].

Chemical compound and disease context of lauric acid

• 0. Most mycobacteria other than potential pathogens (Mycobacterium fortuitum and Mycobacterium chelonei) were resistant to saturated fatty acids, except for lauric acid (C12:0) (MIC, 6.25 to 25 micrograms/ml) and capric acid (C10:0) (MIC, 50 to 100 micrograms#ml) [10].
• (1) The Morris 7800 C1 hepatoma cells exhibited a low omega-hydroxylation activity of the 3-thia acid (and lauric acid) [11].
• Equivalence of lauric acid and glycerol monolaurate as inhibitors of signal transduction in Staphylococcus aureus [12].
• Campylobacter jejuni and most Campylobacter coli were distinguished from other campylobacteria by the presence of a C19 cyclopropane acid, and Campylobacter sputorum subsp. mucosalis differed from other species by the presence of lauric acid [13].
• Salmonella minnesota R 595 (Re) and other Salmonella strains incorporate cis-delta 9-16:1 (palmitoleic acid) at the expense of mainly dodecanoic acid into the lipid-A portion of lipopolysaccharides, when the cells are grown at low temperature (12 degrees C) [14].

Biological context of lauric acid

• Mutations of Glu(318) in CYP4A3 decrease the apparent k(cat) values for lauric acid hydroxylation [15].
• Dodecanoic acid appears to occupy an intermediate position between medium and long chain fatty acids with respect to its availability as substrate for the esterification sites concerned [16].
• In RBC suspensions with oleic, linoleic, and lauric acid, ASA hydrolysis increased as fatty acid:HSA ratios increased [17].
• Substitutions of amino acids from 107 to 110 and from 116 to 119 resulted in mutant enzymes that retained substantial lauric acid hydroxylase activity suggesting that these residues are not critical determinants of substrate specificity [18].
• Hen egg albumin (HEA), heavily conjugated with dodecanoic acid (D-HEA), stimulated sustained delayed type hypersensitivity (DTH) specific for HEA without detectable antibody formation in guinea pigs [2].

Anatomical context of lauric acid

• These data suggest the presence of at least two P-450 isozymes in rabbit lung microsomes capable of lauric acid omega-hydroxylation [19].
• Purification and properties of cytochrome P-450 obtained from liver microsomes of untreated rats by lauric acid affinity chromatography [20].
• Butyric and hexanoic acids were employed as mitochondrial substrates, 1, omega-dicarboxylic acids as predominantly peroxisomal substrates, and lauric acid as a substrate for both mitochondria and peroxisomes [21].
• To help elucidate these hypotheses, we synthesized a photoreactive analog of dodecanoic acid, 12-(4-azido-2-nitrophenylamino)dodecanoic acid (AzDA), and studied its effect on transport in mitochondria and proteoliposomes [22].
• Chinese hamster ovary (CHO) cells incorporate 12-(1'-pyrene) dodecanoic acid (P12) into membrane lipids [23].

Associations of lauric acid with other chemical compounds

• The lauric acid hydroxylase activities of all chimeras and mutant cytochromes P450 differed by 2-fold or less, demonstrating that the changes in progesterone hydroxylase activity reflected altered interactions with the substrate [24].
• In microsomes from Helianthus tuberosus tuber the omega-2, omega-3, and omega-4 hydroxylation of lauric acid is catalyzed by one or a few closely related aminopyrine- and MnCl2-inducible cytochrome P450(s) [25].
• The L131F mutant is highly uncoupled in that it slowly (omega-1)-hydroxylates lauric acid yet consumes NADPH at approximately the same rate as the wild-type enzyme [26].
• From the molecular mass (1828 Da) of the native glycopeptidolipid, determined by cesium ion liquid secondary ion mass spectrometry using the amphipathic triethylene glycol monobutyl ether matrix, it was deduced that the tetrapeptide was amidified by a dodecanoic acid [27].
• Moreover, distinct modes of regulation are observed between the isozymes involved in steroid hydroxylation and those which catalyze the 11- and 12-hydroxylations of lauric acid in mouse renal microsomes [28].

Gene context of lauric acid

• These results demonstrate that NFkappaB activation and COX-2 expression induced by lauric acid are at least partly mediated through the TLR4/PI3K/AKT signaling pathway [29].
• In contrast, COX-2 expression by TLR2 or TRL4 agonist was potentiated by lauric acid, a saturated fatty acid [30].
• Human CYP2E1 had the highest lauric acid (omega-1)-hydroxylation activity and also had catalytic properties similar to those of rat CYP2E1 [31].
• Results of docking of a common substrate, lauric acid, into the binding site of both CYP4A11 and CYP102 and molecular dynamics simulations provided additional support for this hypothesis [32].
• Drosophila melanogaster CYP6A8, an insect P450 that catalyzes lauric acid (omega-1)-hydroxylation [33].

Analytical, diagnostic and therapeutic context of lauric acid

• Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119 [34].
• Consistent with the inhibitory biochemical effects on PLD alpha in vitro, N-lauroylethanolamine, but not lauric acid, selectively inhibited abscisic acid-induced closure of stomata in epidermal peels of tobacco (Nicotiana tabacum cv Xanthi) and Commelina communis at low micromolar concentrations [35].
• Tumor necrosis factor induces necrosis of human carcinoma xenografts in the presence of tricyclodecan-9-yl-xanthogenate and lauric acid [36].
• Confocal microscopy of a fluorescent analogue of dodecanoic acid clearly demonstrated that it entered the cytosol and was not merely partitioning in the cell membrane [37].
• Decreased intestinal absorption of water, sodium, glucose, alanine, and lauric acid are present as early as the first changes in mucosal histology and are useful indices of rejection of intestinal allografts [38].

References