Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: CAS:638-53-9 (tridecanoic acid)
 65 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The aim of the investigations was to develop a long-acting depot contraceptive on the basis of norethisterone or levonorgestrel. Disappointing results with levonorgestrel nonanoate and levonorgestrel undecylate showed that elongation of the fatty acid, esterified with the steroid, decreased the bioavailability of the latter due to incomplete hydrolysis of the ester. Therefore, several new compounds were synthesized which contained a bifunctional molecule between the steroid and the fatty acid. In vivo studies showed an increase in hydrolysis when glycolic acid was taken as the "bridge", compared to the hitherto known esters. Due to the new principle of the steroid-fatty acid connection, in the case of norethisterone, it was possible to introduce tridecanoic acid as lipophilic release controlling substituent without a loss of bioavailability in the baboon. This compound (called: "norethisterone glycotridecanoate") and the corresponding levonorgestral derivative were chosen for a pharmacokinetic-clinical study in women.
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PMID:A new principle of injectable depot contraceptives. I Drug selection and studies in monkeys. 11 May 13

Omega-Cyclohexyl undecanoic acid and omega-cyclohexyl tridecanoic acid were found in 10 strains of acido-thermophilic bacteria isolated from different Japanese hot springs. These unusual fatty acids were found in the esterified form in glyceride type complex lipids and constituted 74 to 93% of the total fatty acids in the bacteria. The fatty acids other than omega-cyclohexyl fatty acids found were 14-methyl hexadecanoic acid (3 to 15%) and 15-methyl hexadecanoic acid (1 to 6%), and trace amounts of straight chain and methyl-branched tetra- and penta-decanoic acids. Biosynthesis of omega-cyclohexyl fatty acids increased with increase in the concentration of glucose in the culture medium. The metabolism of omega-cyclohexyl fatty acids was studied using deuterium-labeled precursors by mass fragmentation analysis. The deuterium of [2-D]glucose was specifically incorporated into position 2 of the cyclohexyl ring of the fatty acids, indicating that the ring was synthesized from the glucose molecule. Radioactivity was efficiently incorporated into the omega-cyclohexyl fatty acids from labeled glucose, shikimate, and cyclohexyl carboxylate. These findings indicate that omega-cyclohexyl fatty acids are synthesized with glucose through shikimic acid and probably cyclohexyl carboxylyl-CoA derivative as the intermediates.
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PMID:Omega-cyclohexyl fatty acids in acidophilic thermophilic bacteria. Studies on their presence, structure, and biosynthesis using precursors labeled with stable isotopes and radioisotopes. 115 90

Structures of the fatty acid residues characterizing the various components of A40926 were determined by gas chromatography/mass spectrometry on the methyl esters obtained by methanolysis of the complex. The results confirm the residues previously assigned to Factor A (n-undecanoic acid) and B (10-methyl-undecanoic acid) and establish the residues of Factor A1 (9-methyl-decanoic acid), B1 (n-dodecanoic acid), RS1 (8-methyl-nonanoic acid), RS2 (n-decanoic acid), and RS3 (n-tridecanoic acid). As the Actinomadura species contain in their mycelia large quantities of C15-C17 fatty acid residues as membrane phospholipids, these mycelia were saponified and the fatty acids obtained were analyzed as above. There is a close correlation between the fatty acid content of A40926 complex and that of the longer homologues in the producer mycelia.
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PMID:Determination of the acyl moieties of the antibiotic complex A40926 and their relation with the membrane lipids of the producer strain. 150 39

A total of 108 pectolytic, soft-rotting Erwinia strains were collected from 11 types of cacti growing in Arizona, Texas, northern Mexico, and Australia between 1958 and 1989. Four strains were collected from soils beneath or close to naturally rotting saguaro cacti. Collectively, these strains caused soft rots of saguaro, organ pipe, and senita cacti, Opuntia (cactus) fruits and pads, tomato fruits, and potato slices, but only occasionally caused soft rots of slices of carrot roots. A numerical cluster analysis showed that 98 of the 112 strains formed a uniform group (cluster 1A) that was distinguished from other pectolytic erwinias by an API 20E code of 1205131, by negative reactions in API 50CHE tests for L-arabinose, myo-inositol, D-cellobiose, melibiose, and D-raffinose, and, in supplemental tests, by positive reactions for malonate and growth at 43 degrees C. The average levels of DNA relatedness of 22 cluster 1A strains to the proposed type strain (strain 1-12) as determined by the hydroxyapatite method were 88% in 60 degrees C reactions (with 1% divergence within related sequences) and 87% in 75 degrees C reactions. The levels of relatedness to the type strains of other Erwinia spp. were less than or equal to 38% in 75 degrees C reactions. Cluster 1A strains also had a characteristic cellular fatty acid profile containing cyclo-(11,12)-nonadecanoic acid (C19:0 Cyclo C11-12) and missing tridecanoic acid (C13:0), heptadecanoic acid (C17:0), and cis-9-heptadecenoic acid (C17:1 CIS 9), which separated them from other pectolytic erwinias. Collectively, these data indicate that the members of cluster 1A are members of a new species, which we name Erwinia cacticida. Three cactus strains in cluster 1B appear to represent a second new species that is closely related to E. cacticida; these strains are designated E. cacticida-like pending the availability of additional strains for testing. The remaining cactus strains (in cluster 4) have the physiological, DNA, and fatty acid profiles of Erwinia carotovora.
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PMID:Taxonomy and pathogenicity of Erwinia cacticida sp. nov. 185 34

We have explored the acyl-CoA substrate specificity of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase (NMT) by synthesizing 81 fatty acid analogs and surveying their activity in a coupled in vitro assay containing Pseudomonas acyl-CoA synthetase and Escherichia coli-derived yeast NMT. Single oxygen or sulfur substitution for C-3 through C-13 is well tolerated by both enzymes. Detailed kinetic analyses suggest that the acyl-CoA and peptide-binding sites of NMT are relatively insensitive to placement of single group 6B heteroatoms. By contrast, di-oxygen-substituted analogs were very poor substrates, producing dramatic reductions in the affinity of NMTs peptide-binding site for a synthetic octapeptide substrate derived from the NH2-terminal sequence of a known N-myristoylprotein, the gag poly-protein precursor of human immunodeficiency virus 1 (HIV-1). This observation provides an example of binding site cooperativity in NMT. Replacement of one oxygen with sulfur at either the 6, 9, or 12 position of dioxatetradecanoic acids results in a general increase in peptide catalytic efficiency (Vmax/Km). An analysis of five fatty acids from octanoic to dodecanoic having terminal phenyl groups indicated that the best substrate was 10-phenyldecanoic acid even though Corey-Pauling-Koltun molecular models indicate that it has a length equivalent to that of tridecanoic acid. Six analogs having an equivalent length of 13 carbon atoms were subsequently prepared in which the phenyl group was systematically moved one methylene group closer to carboxyl. Movement of the phenyl just one carbon closer to carboxyl (producing 9-(p-methylphenyl) nonanoic acid) decreases peptide catalytic efficiency (Vmax/Km) severalfold compared to 10-phenyldecanoic acid. 10-(4-Tolyl)decanoic acid has the same relative positions of phenyl and carboxyl as 10-phenyldecanoic acid even though a methyl group is present on the phenyl ring. It produces peptide Km and Vmax values that are the same as 10-phenyldecanoic acid. Substitution of either oxygen or sulfur for a methylene group fails to override the effects noted when the phenyl group position is altered in the C-14 equivalent fatty acid series. Several fatty acids of differing chain lengths with cyclohexyl-, 2-furyl, and 2-thienyl groups at their omega termnius had activity profiles that paralleled those of the comparable phenyl-substituted compounds. Myristic acid analogs with triple bonds (beginning at positions 2 through 13), cis-double bonds (positions 3 through 13) and trans-double bond isomers (E5, E6, and E7) were also tested.(ABSTRACT TRUNCATED AT 400 WORDS)
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PMID:The substrate specificity of Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase. Analysis of myristic acid analogs containing oxygen, sulfur, double bonds, triple bonds, and/or an aromatic residue. 202 98

The structure of the lipid A from S. typhimurium harboring the derepressed plasmids Col Ib is very similar: i, 1,4'-bis-phosphorylated-beta-1',6-linked glucosamine disaccharide forms a backbone of the lipid; ii, lipid preparations contain four residues of 3-hydroxytetradecanoic acid at positions C3, C3' and the amide linked at C2, C2' and two free hydroxyl groups at positions C4 and C6'. Differences concern: i, substitution of phosphoryl groups by 4-amino-4-deoxy-L-arabinopyranose and phosphorylethanolamine in S. typhimurium with Col Ib plasmids; ii, the degree of acylation of hydroxyl groups of 3-hydroxytetradecanoic acid by myristic, lauric and palmatic acids; iii, presence of tridecanoic acid bound to hydroxyl of 3-hydroxy-tetradecanate residue in S. typhimurium with Col Ibdrd2 plasmid. Lipopolysaccharides from the plasmid mutant strains express several times higher lethal toxicity in chick embryos compared to lipopolysaccharides from the strain with the wild type Col Ib.
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PMID:Lipid a component of Salmonella typhimurium carrying the derepressed Col Ib plasmids. 210 Aug 94

Due to the inhibition of beta-oxidation, radiolabeled long-chain fatty acids with substituents in the alkyl chain often can enhance the retention of myocardial radioactivity. In this connection the synthesis and biodistribution of 12 new radioiodinated omega-(p-iodophenyl)fatty acids is described featuring a p-phenylene group as an inhibiting group. Phenyl fatty acid esters were acylated (Friedel-Crafts) with omega-(p-halophenyl)fatty acid chlorides, reduced and hydrolyzed (Wolff-Kishner) to form the omega-(p-halophenyl)-p-phenylene-fatty acid (PHIPA) derivatives. The peak heart uptake and the loss of radioactivity from the myocardium of fasted Sprague-Dawley rats depended on the alkyl-chain length and p-phenylene position. Thus, compared to radioiodinated 15-(p-iodophenyl)pentadecanoic acid (IPPA) some of the 131I labeled PHIPA derivatives with 12, 13 or 14 methylene groups proved to show an about equal initial heart uptake (about 5% inj. dose/g at 2.5 min). This was especially true for those PHIPA derivatives with a p-phenylene moiety close to the carboxylic acid group. The retention of radioactivity in the heart was also significantly prolonged when the p-phenylene group was in this position. Among the PHIPA derivatives investigated, 13-(p[131I]iodophenyl)-3-(p-phenylene)tridecanoic acid (PHIPA 3-10) and 14-(p-[131I] iodophenyl)-4-(p-phenylene)tetradecanoic acid (PHIPA 4-10) showed the most promising characteristics for potential use as new myocardial imaging agents. Both agents showed an initial heart/blood activity ratio of about 10 which increased to 15 after 10-30 min. This high value was maintained for at least 4 h.
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PMID:Radioiodinated p-phenylene bridged fatty acids as new myocardial imaging agents: syntheses and biodistribution in rats. 284 99

Renin A from the submaxillary gland of male mice has been shown by a gas chromatography/mass spectrometry method to contain near stoichiometric amounts of a fatty acid mixture. The fatty acids on mouse renin were partially exchangeable with free tridecanoic acid in solution, with the tridecanoic acid truly exchanged and not just adsorbed in addition to the fatty acids already present. A gas chromatography/mass spectrometry analysis of the composition of the free fatty acids of the submaxillary gland of male mice showed that the mixture of fatty acids extracted from the gland was significantly different from the mixture of free fatty acids extracted from renin A. The renin-extracted fatty acids were relatively richer in saturated fatty acids, like myristic and palmitic acids, and poorer in polyunsaturated fatty acids, like linoleic and arachidonic acid, than the free fatty acids of the gland. The enzymatic activity of mouse renin was markedly stimulated by saturated fatty acids in 50 mM sodium acetate, pH 5.38, in a concentration-dependent, saturable manner. Palmitic acid stimulated renin activity versus synthetic tetradecapeptide renin substrate about 7-fold in this buffer, with half-maximal stimulation at 14 microM. Stearic and myristic acids also showed good stimulation but linoleic acid and ethyl myristate were much less effective at the stimulation. A possible physiological role for the loss of renin activity at acid pH due to loss of bound fatty acids would be to protect the mouse against internalized renin.
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PMID:Mouse submaxillary gland renin contains a noncovalently attached fatty acid. 635 Feb 84

The ratio of teichoic acid to lipoteichoic acid (LTA) in a strain of Streptococcus agalactiae type III was found to be 8:1, with the total amount of LTA being 0.1% of the dry weight of the organism. Purified teichoic acid contained D-alanine and possibly a small amount of D-glucose and was approximately 22 glycerol phosphate units in length. The linkage between each of these units was 1-3. In addition, LTA contained a complex lipid, more glucose, and an unusually high content of a short-chain fatty acid, tridecanoic acid. This LTA was cytotoxic for a variety of human cell monolayers in tissue culture, including one derived from the human central nervous system. Established human cells were more sensitive than primary cell monolayers to this LTA, with as little as 12.5 micrograms of LTA per ml being cytotoxic for HeLa cells. Teichoic acid (250 micrograms/ml) was nontoxic under identical conditions. These cytotoxicity results suggest an LTA involvement in group B streptococcal pathogenesis. Also, the first model system for the study of group B streptococcal adherence to primary human embryonic amnion cells in tissue culture is detailed. This system was used to quantitate pronounced differences in tissue tropism between S. agalactiae and Streptococcus pyogenes and showed enhanced binding by this group A coccus over that of S. agalactiae for amnion cell monolayers. The adherence of both streptococcal species to only a portion (40%) of these amnion cells suggested that host cell receptor expression may vary for primary cells in vitro. Finally, this strain of S. agalactiae was shown to adhere to amnion cells by a non-LTA-mediated mechanism. The possibility of an LTA-mediated versus a protein-mediated adherence mechanism for host cells that is related to the virulence of S. agalactiae is discussed.
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PMID:Teichoic acids of Streptococcus agalactiae: chemistry, cytotoxicity, and effect on bacterial adherence to human cells in tissue culture. 636 97

The characterization of an antibiotic isolated from a strain of Bacillus subtilis revealed that this compound is a new antifungal antibiotic of the iturin group. It contains a lipid moiety which is a mixture of 3-amino 12-methyl tridecanoic acid (40%) and 3-amino 12-methyl tetradecanoic acid (60%) and a peptide moiety: L-Asp1, D-Asp1, L-Glu1, L-Pro1, D-Ser1, L-Thr1 and D-Tyr1. These two moieties are joined by a threonyl-beta-aminoacid linkage.
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PMID:Characterization of a new antibiotic of iturin group: bacillomycin D. 745 65


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