Disease relevance of tetradecanoic acid

• Treatment of human adenocarcinoma MKN-7 cells with epidermal growth factor (EGF) or phorbol tetradecanoate acetate (TPA) stimulated phosphorylation of the c-erbB-2 gene product [1].
• Heterologous expression of P. aeruginosa pagL in Salmonella enterica serovar Typhimurium and Escherichia coli resulted in removal of the 3-OH C14 fatty acid from lipid A, indicating that P. aeruginosa PagL recognizes either 3-OH C10 or 3-OH C14 [2].
• These results may indicate that formation of (E)-11-tetradecenoic acid from tetradecanoic acid does not occur in the pheromone gland by dehydration of an intermediate hydroxyacid [3].
• Toxicity studies of tetradecanoic acid, 2-sulfo-, 1-methylester, sodium salt (C14-MES) [4].

High impact information on tetradecanoic acid

• The unusual NH2-terminal blocking group of the catalytic subunit of bovine cardiac muscle cyclic AMP-dependent protein was found to be amide-linked n-tetradecanoic acid by gas chromatographic-, direct chemical ionization-, and fast atom bombardment-mass spectrometry [5].
• We have found that the luminescence of some (but not all) of such aldehyde mutants is also stimulated by long chain aliphatic fatty acids, with a marked specificity for myristic (tetradecanoic) acid [6].
• An enzyme which catalyzes the following esterase reaction was isolated from mouse serum: 12-O-tetradecanoyl phorbol 13-acetate (TPA) + H2O----phorbol 13-acetate + tetradecanoic acid [7].
• Formation of the tosylhydrazone of the oxo-ester followed by reduction with sodium cyanoborohydride gave the labeled methyl tetradecanoate which, upon hydrolysis, yielded the desired tetradecanoic acid [8].
• The presence of two main molecular species as seen by thin-layer chromatography was confirmed by plasma desorption mass spectrometry, in which the larger signal was attributable to a molecular ion containing two glucosamine, two phosphate, one tetradecanoic acid, one hydroxydecanoic acid, and three hydroxytetradecanoic acid residues [9].

Biological context of tetradecanoic acid

• The acylation pattern at the 'reducing' GlcN I was identical to that of compound 406 in having two primary (R)-3-hydroxy tetradecanoic acid residues [14:0(3-OH)] attached to positions 3 (ester-linked) and 2 (amide-linked), respectively [10].

Anatomical context of tetradecanoic acid

• Among the major fatty acids, there were increased concentrations of tetradecanoic acid (C14:0), hexadecanoic acid (C16:0), 9-hexadecenoic acid (C16: 1,Delta 9), and 9-octadecanoic acid (C18:1,Delta 9) and a concomitant decrease in 9,12-octadecadienoic acid (C18:2,Delta 9,12) in less-pigmented compared with pigmented cell walls [11].
• Bovine heart submitochondrial particles were incubated for 2-6 h at 37 degrees C with various concentrations of tetradecanoic acid, and the effects on the activities, the total acid-labile sulphide content and EPR spectra of the electron transfer system were studied [12].

Associations of tetradecanoic acid with other chemical compounds

• A diterpene of the ingenane-type parent alcohol with tetradecanoic acid as the acid substituent was isolated by chromatographic methods from the latex of Euphorbia matabelensis [13].
• The purified product, methyl-3-0-(9-carboxy-anthracenyl) tetradecanoate (M/Z 462), was highly responsive to a fluorescence spectrophotometer, showing maximum emission with excitation wavelength at 257 nm and emission wavelength at 458 nm in dichloromethane, the limit of detection being as little as 10 f mol [14].
• Comparison of the amount of [3H]aldehyde produced with the bioluminescence responses of luciferase to the aldehyde product and standard aldehydes, both with respect to maximum light intensity and luminescent decay, established that tetradecanoic acid has been converted to tetradecanal, the aldehyde of the same chain length [15].

Gene context of tetradecanoic acid

• Highly lipidated C14 HSA (C14, fatty acid side-chains with 14 carbon atoms) was not itself mitogenic: unlike HSA it localized heavily to the red pulp as well as to cells of dendritic form in the splenic white pulp [16].
• In a subclone missing the lux E gene, the 42 kDa polypeptide was missing and the 54 kDa polypeptide could not be acylated in vitro with tetradecanoic acid (+ATP) and only to a low level in vivo indicating that the synthetase enzyme, responsible for fatty acid activation, is coded by the lux E gene [17].

References