myristic acids

Summary

Summary: 14-carbon saturated monocarboxylic acids.

Top Publications

  1. Zhou W, Parent L, Wills J, Resh M. Identification of a membrane-binding domain within the amino-terminal region of human immunodeficiency virus type 1 Gag protein which interacts with acidic phospholipids. J Virol. 1994;68:2556-69 pubmed
    ..We propose that the N-terminal Gag sequence functions as a targeting signal to direct interaction with acidic phospholipids on the cytoplasmic leaflet of the plasma membrane. ..
  2. Linder M, Middleton P, Hepler J, Taussig R, Gilman A, Mumby S. Lipid modifications of G proteins: alpha subunits are palmitoylated. Proc Natl Acad Sci U S A. 1993;90:3675-9 pubmed
    ..These data are consistent with palmitoylation of the proteins near their amino termini, most likely on Cys-3. Reversible acylation of G-protein alpha subunits may provide an additional mechanism for regulation of signal transduction. ..
  3. Tanaka T, Ames J, Harvey T, Stryer L, Ikura M. Sequestration of the membrane-targeting myristoyl group of recoverin in the calcium-free state. Nature. 1995;376:444-7 pubmed
    ..The myristoyl group is sequestered in a deep hydrophobic pocket formed by many aromatic and other hydrophobic residues from five flanking helices. ..
  4. Alland L, Peseckis S, Atherton R, Berthiaume L, Resh M. Dual myristylation and palmitylation of Src family member p59fyn affects subcellular localization. J Biol Chem. 1994;269:16701-5 pubmed
    ..These results serve to delineate sequence elements important for dual acylation of proteins, and further illustrate the utility of radioiodinated fatty acid analogs for studies of protein fatty acid acylation. ..
  5. Wongtangtintharn S, Oku H, Iwasaki H, Toda T. Effect of branched-chain fatty acids on fatty acid biosynthesis of human breast cancer cells. J Nutr Sci Vitaminol (Tokyo). 2004;50:137-43 pubmed
    ..The present study thus suggests that BCFA synthetically lowers the fatty acid biosynthesis by reducing the precursors, in addition to its direct inhibitory effect on fatty acid synthetase. ..
  6. Gerlach H, Laumann V, Martens S, Becker C, Goody R, Geyer M. HIV-1 Nef membrane association depends on charge, curvature, composition and sequence. Nat Chem Biol. 2010;6:46-53 pubmed publisher
    ..Moreover, Nef binding to membranes requires negatively charged liposomes, and mutations of basic and hydrophobic residues strongly diminished the association and changed the binding kinetics differently. ..
  7. Parenti M, Vigano M, Newman C, Milligan G, Magee A. A novel N-terminal motif for palmitoylation of G-protein alpha subunits. Biochem J. 1993;291 ( Pt 2):349-53 pubmed
    ..The non-palmitoylated alpha o mutant is still myristoylated but shows reduced membrane binding, suggesting that reversible palmitoylation may regulate G alpha localization and function. ..
  8. Voon P, Ng T, Lee V, Nesaretnam K. Diets high in palmitic acid (16:0), lauric and myristic acids (12:0 + 14:0), or oleic acid (18:1) do not alter postprandial or fasting plasma homocysteine and inflammatory markers in healthy Malaysian adults. Am J Clin Nutr. 2011;94:1451-7 pubmed publisher
    ..This trial was registered at clinicaltrials.gov as NCT00941837. ..
  9. Lin T, Yin X, Cai Q, Fan X, Xu K, Huang L, et al. 13-Methyltetradecanoic acid induces mitochondrial-mediated apoptosis in human bladder cancer cells. Urol Oncol. 2012;30:339-45 pubmed publisher
    ..Taken together, these data indicate that 13-MTD induces mitochondrial-mediated apoptosis through regulation of the AKT and MAPK pathways, suggesting 13-MTD is a potential candidate for treatment of human bladder cancer. ..

More Information

Publications62

  1. Wongtangtintharn S, Oku H, Iwasaki H, Inafuku M, Toda T, Yanagita T. Incorporation of branched-chain fatty acid into cellular lipids and caspase-independent apoptosis in human breast cancer cell line, SKBR-3. Lipids Health Dis. 2005;4:29 pubmed
    ..These results showed that 13-MTD disrupted the mitochondrial integrity, and induced apoptosis via caspase-independent death pathway. ..
  2. Breuer S, Gerlach H, Kolaric B, Urbanke C, Opitz N, Geyer M. Biochemical indication for myristoylation-dependent conformational changes in HIV-1 Nef. Biochemistry. 2006;45:2339-49 pubmed
    ..Taken together, our data indicated myristoylation-dependent conformational changes in Nef, suggesting a rather compact and monomeric form for the lipidated protein in solution. ..
  3. Ladant D. Calcium and membrane binding properties of bovine neurocalcin delta expressed in Escherichia coli. J Biol Chem. 1995;270:3179-85 pubmed
    ..Calcium and membrane binding properties of the mutant-myristoylated proteins suggest that binding of calcium to EF2 is critical in triggering the binding of the protein to membranes. ..
  4. Robbins S, Quintrell N, Bishop J. Myristoylation and differential palmitoylation of the HCK protein-tyrosine kinases govern their attachment to membranes and association with caveolae. Mol Cell Biol. 1995;15:3507-15 pubmed
    ..Taken together, the results suggest that HCK and several of its relatives may participate in the functions of caveolae, which apparently include the transduction of signals across the plasma membrane to the interior of the cell. ..
  5. Resh M. Myristylation and palmitylation of Src family members: the fats of the matter. Cell. 1994;76:411-3 pubmed
  6. Duronio R, Jackson Machelski E, Heuckeroth R, Olins P, Devine C, Yonemoto W, et al. Protein N-myristoylation in Escherichia coli: reconstitution of a eukaryotic protein modification in bacteria. Proc Natl Acad Sci U S A. 1990;87:1506-10 pubmed
    ..Our experimental system may prove useful for recapitulating other eukaryotic protein modifications in E. coli so that structure-activity relationships of modifying enzymes and their substrates can be more readily assessed. ..
  7. Antonny B, Beraud Dufour S, Chardin P, Chabre M. N-terminal hydrophobic residues of the G-protein ADP-ribosylation factor-1 insert into membrane phospholipids upon GDP to GTP exchange. Biochemistry. 1997;36:4675-84 pubmed
    ..This strongly suggests that, upon GDP/GTP exchange, the N-terminal helix is released from the protein core so its hydrophobic residues can interact with membrane phospholipids. ..
  8. Chen J, Lobachev K, Grindel B, Farach Carson M, Hyzy S, El Baradie K, et al. Chaperone properties of pdia3 participate in rapid membrane actions of 1?,25-dihydroxyvitamin d3. Mol Endocrinol. 2013;27:1065-77 pubmed publisher
    ..These data indicate that both the chaperone functional domains and the subcellular location of Pdia3 control rapid membrane responses to 1?,25(OH)2D3. ..
  9. Wang C, Hamamoto S, Orci L, Schekman R. Exomer: A coat complex for transport of select membrane proteins from the trans-Golgi network to the plasma membrane in yeast. J Cell Biol. 2006;174:973-83 pubmed
    ..Unlike other coats (e.g., coat protein complex I, II, and clathrin/adaptor protein complex), the exomer does not form buds or vesicles on liposomes...
  10. Kamata N, Jotte R, Holt J. Myristylation alters DNA-binding activity and transactivation of FBR (gag-fos) protein. Mol Cell Biol. 1991;11:765-72 pubmed
    ..These findings demonstrate that protein myristylation can modulate gene regulation by a DNA-binding protein...
  11. Buss J, Mumby S, Casey P, Gilman A, Sefton B. Myristoylated alpha subunits of guanine nucleotide-binding regulatory proteins. Proc Natl Acad Sci U S A. 1987;84:7493-7 pubmed
    ..Myristate may play an important role in stabilizing interactions of G proteins with phospholipid or with membrane-bound proteins. ..
  12. Mumby S, Heukeroth R, Gordon J, Gilman A. G-protein alpha-subunit expression, myristoylation, and membrane association in COS cells. Proc Natl Acad Sci U S A. 1990;87:728-32 pubmed
    ..The results are consistent with a model wherein the hydrophobic interaction of myristate with the bilayer permits continued association of the protein with the plasma membrane when G-protein alpha subunits dissociate from beta gamma. ..
  13. Varner A, De Vos M, Creaser S, Peterson B, Smith C. A fluorescence-based high performance liquid chromatographic method for the characterization of palmitoyl acyl transferase activity. Anal Biochem. 2002;308:160-7 pubmed
  14. Buck R, Cai J, Eleazer P, Staat R, Hurst H. Detoxification of endotoxin by endodontic irrigants and calcium hydroxide. J Endod. 2001;27:325-7 pubmed
    ..Long-term calcium hydroxide--as well as 30-min exposure to an alkaline mixture of chlorhexidine, ethanol, and sodium hypochlorite--did detoxify LPS molecules by hydrolysis of ester bonds in the fatty acid chains of the lipid A moiety. ..
  15. Andriotis V, Rathjen J. The Pto kinase of tomato, which regulates plant immunity, is repressed by its myristoylated N terminus. J Biol Chem. 2006;281:26578-86 pubmed publisher
  16. Dizhoor A, Ericsson L, Johnson R, Kumar S, Olshevskaya E, Zozulya S, et al. The NH2 terminus of retinal recoverin is acylated by a small family of fatty acids. J Biol Chem. 1992;267:16033-6 pubmed
    ..The NH2-terminal glycine of each retinal recoverin molecule is linked to one of four different types of acyl groups. The most abundant is myristoleate (14:1), but 14:0, 14:2, and 12:0 acyl residues are also present. ..
  17. Jones P, Moffitt M, Joseph D, Harthcock P, Boriack R, Ibdah J, et al. Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid. Clin Chem. 2001;47:1190-4 pubmed
    ..Measurement of 3-OHFA excretion from LCHAD- or MTFP-deficient cell lines can be used as a diagnostic tool. Free FAs are the predominant form of these abnormal metabolic intermediates in culture media. ..
  18. Kato L, Szejtli J, Szente L. Water soluble complexes of C14 and C16 fatty acids and alcohols in media for cultivation of leprosy-derived psychrophilic mycobacteria. Int J Lepr Other Mycobact Dis. 1994;62:75-88 pubmed
    ..Mycobacteria of this cluster do not distinguish between 14 or 16 C long chains with COOH or CH2OH as terminal bindings. Cells are quite aerophilic and grow preferentially on agar slant surfaces.(ABSTRACT TRUNCATED AT 400 WORDS) ..
  19. Wang Y, Catlett N, Weisman L. Vac8p, a vacuolar protein with armadillo repeats, functions in both vacuole inheritance and protein targeting from the cytoplasm to vacuole. J Cell Biol. 1998;140:1063-74 pubmed
    ..Vac8p is related to beta-catenin and plakoglobin, which connect a specific region of the plasma membrane to the actin cytoskeleton. In analogy, Vac8p may link the vacuole to actin during vacuole partitioning. ..
  20. Adam B, Hall E, Sternberg M, Lim T, Flores S, O BRIEN S, et al. The stability of markers in dried-blood spots for recommended newborn screening disorders in the United States. Clin Biochem. 2011;44:1445-50 pubmed publisher
    ..Minimizing both humidity and temperature in DBS transportation and storage environments is essential to maintaining sample integrity. ..
  21. Manosroi A, Chaikul P, Abe M, Manosroi W, Manosroi J. Melanogenesis of methyl myristate loaded niosomes in B16F10 melanoma cells. J Biomed Nanotechnol. 2013;9:626-38 pubmed
    ..42 and 1.70 folds of the control and 1.14 and 1.59 folds higher than theophylline, respectively. This study has suggested the potential of methyl myristate loaded cationic niosomes for canities treatment. ..
  22. Carballeira N, Ortiz D, Parang K, Sardari S. Total synthesis and in vitro-antifungal activity of (+/-)-2-methoxytetradecanoic Acid. Arch Pharm (Weinheim). 2004;337:152-5 pubmed
    ..neoformans. The antifungal activity of (+/-)-2-methoxytetradecanoic acid is explained in terms of inhibition of N-myristoyltransferase. ..
  23. Baldanzi G, Cutrupi S, Chianale F, Gnocchi V, Rainero E, Porporato P, et al. Diacylglycerol kinase-alpha phosphorylation by Src on Y335 is required for activation, membrane recruitment and Hgf-induced cell motility. Oncogene. 2008;27:942-56 pubmed
  24. Busconi L, Michel T. Endothelial nitric oxide synthase. N-terminal myristoylation determines subcellular localization. J Biol Chem. 1993;268:8410-3 pubmed
    ..N-terminal myristoylation of the endothelial NO synthase may provide a potential point of regulation of the biological functions of endothelium-derived NO in situ. ..
  25. Song A, Jia X, Teng M, Hao J. Ca2+- and ba2+-ligand coordinated unilamellar, multilamellar, and oligovesicular vesicles. Chemistry. 2007;13:496-501 pubmed
    ..A mechanism is proposed that accounts for the formation of these new metal-ligand coordinated vesicles. ..
  26. DeLucca A, Brogden K, Catalano E, Morris N. Biophysical alteration of lung surfactant by extracts of cotton dust. Br J Ind Med. 1991;48:41-7 pubmed
    ..The data suggest that biophysical alterations to lung surfactant may play a part in the pathogenesis of byssinosis. ..
  27. Johnson D, Cok S, Feldmann H, Gordon J. Suppressors of nmtl-181, a conditional lethal allele of the Saccharomyces cerevisiae myristoyl-CoA:protein N-myristoyltransferase gene, reveal proteins involved in regulating protein N-myristoylation. Proc Natl Acad Sci U S A. 1994;91:10158-62 pubmed
    ..These observations provide a potential mechanism for coupling phosphate metabolism with the regulation of myristoyl-CoA synthesis and protein N-myristoylation. ..
  28. Solaiman D, Ashby R, Hotchkiss A, Foglia T. Biosynthesis of medium-chain-length poly(hydroxyalkanoates) from soy molasses. Biotechnol Lett. 2006;28:157-62 pubmed
    ..This work represents the first description of fermentative mcl-PHA production from the soy molasses. ..
  29. Lu W, Ness J, Xie W, Zhang X, Minshull J, Gross R. Biosynthesis of monomers for plastics from renewable oils. J Am Chem Soc. 2010;132:15451-5 pubmed publisher
    ..Biocatalysis using engineered C. tropicalis is thus a potentially attractive biocatalytic platform for producing commodity chemicals from renewable resources. ..
  30. Lystad E, Høstmark A, Jebens E. Apoptotic effects of dichloro stearic and dichloro myristic acid in human hepatoma cells (HepG2). Pharmacol Toxicol. 2001;89:85-91 pubmed
    ..Apoptosis by the chlorinated fatty acids was however less than that of docosahexaenoic acid, a known apoptosis effector. In conclusion, chlorinated fatty acids seem to possess the ability to cause apoptosis. ..
  31. Utsumi T, Nakano K, Funakoshi T, Kayano Y, Nakao S, Sakurai N, et al. Vertical-scanning mutagenesis of amino acids in a model N-myristoylation motif reveals the major amino-terminal sequence requirements for protein N-myristoylation. Eur J Biochem. 2004;271:863-74 pubmed
    ..These observations strongly indicate that the combination of amino acids at position 3, 6 and 7 is a major determinant for protein N-myristoylation. ..
  32. Kuo A, Zhong C, Lane W, Derynck R. Transmembrane transforming growth factor-alpha tethers to the PDZ domain-containing, Golgi membrane-associated protein p59/GRASP55. EMBO J. 2000;19:6427-39 pubmed
    ..Our observations suggest a role for membrane tethering of p59/GRASP55 to select transmembrane proteins, including TGF-alpha, in maturation and transport to the cell surface. ..
  33. Spearman P, Horton R, Ratner L, Kuli Zade I. Membrane binding of human immunodeficiency virus type 1 matrix protein in vivo supports a conformational myristyl switch mechanism. J Virol. 1997;71:6582-92 pubmed
  34. Chan C, Zhang S, Cagatay T, Wharton K. Cell-autonomous, myristyl-independent activity of the Drosophila Wnt/Wingless antagonist Naked cuticle (Nkd). Dev Biol. 2007;311:538-53 pubmed
    ..In conjunction with our recent observation that Nkd requires nuclear localization for function, our data suggest that Nkd acts at more than one subcellular location within signal-receiving cells to attenuate Wg signaling. ..
  35. Lindström F, Thurnhofer S, Vetter W, Gröbner G. Impact on lipid membrane organization by free branched-chain fatty acids. Phys Chem Chem Phys. 2006;8:4792-7 pubmed
  36. Liang J, Kornfeld S. Comparative activity of ADP-ribosylation factor family members in the early steps of coated vesicle formation on rat liver Golgi membranes. J Biol Chem. 1997;272:4141-8 pubmed
    ..These data indicate that the specificity for ARF action on the Golgi membranes is primarily determined by the Golgi guanine nucleotide exchange factor, which has a strong preference for myristoylated mammalian ARF1...
  37. Denner E, Paukner S, Kampfer P, Moore E, Abraham W, Busse H, et al. Sphingomonas pituitosa sp. nov., an exopolysaccharide-producing bacterium that secretes an unusual type of sphingan. Int J Syst Evol Microbiol. 2001;51:827-41 pubmed
    ..Glucuronic acid, which is commonly found in sphingans, was absent. The mean molecular mass of PS-EDIV was approximately 3 x 10(6) Da. ..
  38. Islam N, Igarashi K, Tachibana T, Ooshima H, Azuma M. Synthesis and degradation of acyl peptide using enzyme from Pseudomonas aeruginosa. J Biosci Bioeng. 2008;105:282-7 pubmed publisher
    ..The optimum pH and temperature of the degradation reaction were consistent with those of the synthetic reaction. The degradation reaction was inhibited by divalent cations. ..
  39. Morowvat M, Rasoul Amini S, Ghasemi Y. Chlamydomonas as a "new" organism for biodiesel production. Bioresour Technol. 2010;101:2059-62 pubmed publisher
    ..The composition of fatty acids in the studied species of microalga was mainly docosanoic acid methyl ester, tetradecanoic acid methyl ester, hexadecanoic acid methyl ester and nonanoic acid methyl ester. ..
  40. Wang B, Kruh G. Subcellular localization of the Arg protein tyrosine kinase. Oncogene. 1996;13:193-7 pubmed
    ..In addition, Arg, like c-Abl, is expressed as myristoylated and nonmyristoylated isoforms, suggesting that it may have dual cytoplasmic subcellular localizations, and possibly participate in diverse signaling pathways. ..
  41. Shapiro A, Ross P, Gao N, Livchak S, Kern G, Yang W, et al. A high-throughput-compatible fluorescence anisotropy-based assay for competitive inhibitors of Escherichia coli UDP-N-acetylglucosamine acyltransferase (LpxA). J Biomol Screen. 2013;18:341-7 pubmed publisher
    ..The IC(50)s were not significantly affected by the presence of ACP. ..
  42. Menon A, Schwarz R, Mayor S, Cross G. Cell-free synthesis of glycosyl-phosphatidylinositol precursors for the glycolipid membrane anchor of Trypanosoma brucei variant surface glycoproteins. Structural characterization of putative biosynthetic intermediates. J Biol Chem. 1990;265:9033-42 pubmed
    ..Structural analyses of these putative biosynthetic intermediates suggest that glycolipid assembly occurs via the sequential glycosylation of phosphatidylinositol. ..
  43. Kamata N, Holt J. Inhibitory effect of myristylation on transrepression by FBR (Gag-Fos) protein. Mol Cell Biol. 1992;12:876-82 pubmed
  44. Valentine K, Mesleh M, Opella S, Ikura M, Ames J. Structure, topology, and dynamics of myristoylated recoverin bound to phospholipid bilayers. Biochemistry. 2003;42:6333-40 pubmed
    ..These results demonstrate that membrane binding by recoverin is achieved primarily by insertion of the myristoyl group inside the bilayer with apparently little rearrangement of the protein structure. ..
  45. Vadovic P, Fodorova M, Toman R. Structural features of lipid A of Piscirickettsia salmonis, the etiological agent of the salmonid rickettsial septicemia. Acta Virol. 2007;51:249-59 pubmed
    ..The P. salmonis lipid A resembles structurally strongly endotoxic enterobacterial lipid A. This could be one of the reasons for the observed high endotoxicity of P. salmonis. ..
  46. Sivaramakrishna D, Swamy M. Synthesis, characterization and thermotropic phase behavior of a homologous series of N-acyl-L-alaninols and interaction of N-myristoyl L-alaninol with dimyristoylphosphatidylcholine. Chem Phys Lipids. 2016;196:5-12 pubmed publisher
    ..Transmission electron microscopic studies show that the NMAOH:DMPC (45:55, mol/mol) mixture forms unilamellar vesicles of about 120-150 nm in diameter. ..
  47. Gunn J, Ernst R, McCoy A, Miller S. Constitutive mutations of the Salmonella enterica serovar Typhimurium transcriptional virulence regulator phoP. Infect Immun. 2000;68:3758-62 pubmed
    ..As the first constitutive mutant of phoP identified, this allele will be invaluable to future genetic and biochemical studies of this and likely other regulatory systems. ..
  48. Odegard A, Chandran K, Zhang X, Parker J, Baker T, Nibert M. Putative autocleavage of outer capsid protein micro1, allowing release of myristoylated peptide micro1N during particle uncoating, is critical for cell entry by reovirus. J Virol. 2004;78:8732-45 pubmed
    ..The results thus suggest that hydrophobic peptide release following capsid protein autocleavage is part of a general mechanism of membrane penetration shared by several diverse nonenveloped animal viruses. ..
  49. Hristov A, Lee C, Cassidy T, Long M, Heyler K, Corl B, et al. Effects of lauric and myristic acids on ruminal fermentation, production, and milk fatty acid composition in lactating dairy cows. J Dairy Sci. 2011;94:382-95 pubmed publisher
    ..Both LA and MA modified milk FA profile significantly. ..
  50. Sanford J, Codina J, Birnbaumer L. Gamma-subunits of G proteins, but not their alpha- or beta-subunits, are polyisoprenylated. Studies on post-translational modifications using in vitro translation with rabbit reticulocyte lysates. J Biol Chem. 1991;266:9570-9 pubmed
    ..Polyisoprenylation, which increases hydrophobicity of the derivatized protein, may play a role in anchoring not only ras but also G proteins to membranes. ..
  51. Martin D, Vilas G, Prescher J, Rajaiah G, Falck J, Bertozzi C, et al. Rapid detection, discovery, and identification of post-translationally myristoylated proteins during apoptosis using a bio-orthogonal azidomyristate analog. FASEB J. 2008;22:797-806 pubmed
    ..This suggests that post-translational myristoylation of caspase-cleaved proteins represents a novel mechanism widely used to regulate cell death. ..
  52. Furuishi K, Matsuoka H, Takama M, Takahashi I, Misumi S, Shoji S. Blockage of N-myristoylation of HIV-1 gag induces the production of impotent progeny virus. Biochem Biophys Res Commun. 1997;237:504-11 pubmed
    ..Taken together, the results suggest that the myristoylation of HIV-1 gag seems to be responsible for both maturation of gag and acquisition of HIV-1 infectivity. ..
  53. Anderson M, Robertson A, Macher I, Raetz C. Biosynthesis of lipid A in Escherichia coli: identification of UDP-3-O-[(R)-3-hydroxymyristoyl]-alpha-D-glucosamine as a precursor of UDP-N2,O3-bis[(R)-3-hydroxymyristoyl]-alpha-D-glucosamine. Biochemistry. 1988;27:1908-17 pubmed
    ..Our observations provide strong evidence that UDP-3-O-[(R)-3-hydroxymyristoyl]glucosamine is a true intermediate in the biosynthesis of UDP-2,3-diacyl-GlcN and lipid A...