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Chemical Compound Review

Myristamide     tetradecanamide

Synonyms: MYRISTICAMIDE, Myristic amide, CHEMBL88158, AG-G-37932, NSC-66436, ...
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Disease relevance of Myristate


Psychiatry related information on Myristate


High impact information on Myristate


Chemical compound and disease context of Myristate


Biological context of Myristate


Anatomical context of Myristate

  • The synthesis and secretion of plasminogen activator by cultured macrophages can be induced and stimulated by concanavalin A and by phorbol myristate acetate, and inhibited by such agents as glucocorticoids, mitotic inhibitors and compounds affecting cAMP metabolism [20].
  • This suggests that a looser subunit interaction in transducin which is due to an abundance of N-linked fatty acids other than myristate would favour the rapid turnover and catalysis essential for the visual excitation in photoreceptor cells [21].
  • In p44 MAPK-/- thymocytes, proliferation in response to activation with a monoclonal antibody to the T cell receptor in the presence of phorbol myristate acetate was severely reduced even though activation of p42 MAPK was more sustained in these cells [22].
  • The proteins were purified from serum-free culture medium taken from rabbit synovial fibroblasts stimulated with phorbol myristate acetate [23].
  • DNA strand breakage in human leukocytes exposed to a tumor promoter, phorbol myristate acetate [24].

Associations of Myristate with other chemical compounds

  • The myristate label was resistant to mild alkaline methanolysis and was found in fatty acid and sphingosine, indicating an unusual form of lipid attachment to CD45 [25].
  • Plasmids carrying either a wild-type or mutant c-fos SRE were transfected into fibroblasts and tested for their response to whole serum, purified recombinant c-sis protein, the protein kinase C activator phorbol myristate acetate, and activators of the cyclic AMP (cAMP) second messenger system [26].
  • Tolerant cells did not proliferate in response to ionomycin and phorbol myristate acetate, failing to mobilize calcium to produce IL-2 or express IL-2R, but survived for long time periods in vivo and secreted IL-10 [27].
  • FMLP-induced release of the IL-1 decoy RII was unaffected by protein synthesis inhibitors, was blocked by certain protease inhibitors, and was mimicked by agents (the Ca++ ionophore A23187 and phorbol myristate acetate) that recapitulate elements in the signal transduction pathway of chemoattractant receptors [28].
  • Thus, after triggering with phorbol myristate acetate or phagocytosis of zymosan or promastigotes, 90% of the J774G8 cells failed to reduce nitroblue tetrazolium, and released 5-10-fold less O2- and H2O2 than BALB/c macrophages [29].

Gene context of Myristate


Analytical, diagnostic and therapeutic context of Myristate

  • The production of superoxide anion by the lavage PMN in response to phorbol myristate acetate was similar to that of peripheral blood PMN [35].
  • Lamina propria mononuclear cells from inflamed and control tissues were incubated with phorbol myristate acetate, and the amount of the lymphokine in the supernatants was quantitated in a biological assay using cloned, interleukin 2-dependent, cytotoxic mouse T-cell lines [36].
  • Approximately 95% of the 3H labeled material released from [3H]myristate-43K protein by acid methanolysis was extractable in organic solvents and eluted from a C18 reverse-phase HPLC column exclusively at the position of the methyl myristate internal standard [37].
  • Using chimeric src proteins, peptides identical or related to the NH2 terminus of src, and site-directed mutagenesis, we demonstrate that NH2-terminal lysines in conjunction with myristate are essential for membrane localization [38].
  • Calcium movement and membrane potential changes in the early phase of neutrophil activation by phorbol myristate acetate: a study with ion-selective electrodes [39].


  1. Rous sarcoma virus transforming protein lacking myristic acid phosphorylates known polypeptide substrates without inducing transformation. Kamps, M.P., Buss, J.E., Sefton, B.M. Cell (1986) [Pubmed]
  2. Local and systemic effects of intradermal recombinant interferon-gamma in patients with lepromatous leprosy. Nathan, C.F., Kaplan, G., Levis, W.R., Nusrat, A., Witmer, M.D., Sherwin, S.A., Job, C.K., Horowitz, C.R., Steinman, R.M., Cohn, Z.A. N. Engl. J. Med. (1986) [Pubmed]
  3. Myristylation of picornavirus capsid protein VP4 and its structural significance. Chow, M., Newman, J.F., Filman, D., Hogle, J.M., Rowlands, D.J., Brown, F. Nature (1987) [Pubmed]
  4. Myristic acid is coupled to a structural protein of polyoma virus and SV40. Streuli, C.H., Griffin, B.E. Nature (1987) [Pubmed]
  5. Squalene in hair--a natural reference substance for the improved interpretation of fatty acid ethyl ester concentrations with respect to alcohol misuse. Auwärter, V., Kiessling, B., Pragst, F. Forensic Sci. Int. (2004) [Pubmed]
  6. Fatty acid synthesis by elongases in trypanosomes. Lee, S.H., Stephens, J.L., Paul, K.S., Englund, P.T. Cell (2006) [Pubmed]
  7. A novel protein kinase homolog essential for protein sorting to the yeast lysosome-like vacuole. Herman, P.K., Stack, J.H., DeModena, J.A., Emr, S.D. Cell (1991) [Pubmed]
  8. Fatty acid remodeling: a novel reaction sequence in the biosynthesis of trypanosome glycosyl phosphatidylinositol membrane anchors. Masterson, W.J., Raper, J., Doering, T.L., Hart, G.W., Englund, P.T. Cell (1990) [Pubmed]
  9. B lymphocyte receptors and polyphosphoinositide degradation. Bijsterbosch, M.K., Meade, C.J., Turner, G.A., Klaus, G.G. Cell (1985) [Pubmed]
  10. EGF receptor affinity is regulated by intracellular calcium and protein kinase C. Fearn, J.C., King, A.C. Cell (1985) [Pubmed]
  11. Immunostimulators induce granulocyte/macrophage colony-stimulating activity and block proliferation in a monocyte tumor cell line. Ralph, P., Broxmeyer, H.E., Nakoinz, I. J. Exp. Med. (1977) [Pubmed]
  12. Bone resorption in organ culture: inhibition by the divalent cation ionophores A23187 and X-537A. Ivey, J.L., Wright, D.R., Tashjian, A.H. J. Clin. Invest. (1976) [Pubmed]
  13. Myristylation site in Pr65gag is essential for virus particle formation by Moloney murine leukemia virus. Rein, A., McClure, M.R., Rice, N.R., Luftig, R.B., Schultz, A.M. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  14. Covalently bound myristate in a lymphoma tyrosine protein kinase. Marchildon, G.A., Casnellie, J.E., Walsh, K.A., Krebs, E.G. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  15. Modification of the substrate specificity of an acyl-acyl carrier protein thioesterase by protein engineering. Yuan, L., Voelker, T.A., Hawkins, D.J. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  16. Alteration of the chemotactic response of NIH/3T3 cells to PDGF by growth factors, transformation, and tumor promoters. Grotendorst, G.R. Cell (1984) [Pubmed]
  17. Stimulated neutrophils from patients with autosomal recessive chronic granulomatous disease fail to phosphorylate a Mr-44,000 protein. Segal, A.W., Heyworth, P.G., Cockcroft, S., Barrowman, M.M. Nature (1985) [Pubmed]
  18. Acylation of proteins with myristic acid occurs cotranslationally. Wilcox, C., Hu, J.S., Olson, E.N. Science (1987) [Pubmed]
  19. Functionally distinct NF-kappa B binding sites in the immunoglobulin kappa and IL-2 receptor alpha chain genes. Cross, S.L., Halden, N.F., Lenardo, M.J., Leonard, W.J. Science (1989) [Pubmed]
  20. Macrophage plasminogen activator: induction by concanavalin A and phorbol myristate acetate. Vassalli, J.D., Hamilton, J., Reich, E. Cell (1977) [Pubmed]
  21. Lipid modification at the N terminus of photoreceptor G-protein alpha-subunit. Kokame, K., Fukada, Y., Yoshizawa, T., Takao, T., Shimonishi, Y. Nature (1992) [Pubmed]
  22. Defective thymocyte maturation in p44 MAP kinase (Erk 1) knockout mice. Pagès, G., Guérin, S., Grall, D., Bonino, F., Smith, A., Anjuere, F., Auberger, P., Pouysségur, J. Science (1999) [Pubmed]
  23. Autocrine induction of collagenase by serum amyloid A-like and beta 2-microglobulin-like proteins. Brinckerhoff, C.E., Mitchell, T.I., Karmilowicz, M.J., Kluve-Beckerman, B., Benson, M.D. Science (1989) [Pubmed]
  24. DNA strand breakage in human leukocytes exposed to a tumor promoter, phorbol myristate acetate. Birnboim, H.C. Science (1982) [Pubmed]
  25. An unusual form of lipid linkage to the CD45 peptide. Takeda, A., Maizel, A.L. Science (1990) [Pubmed]
  26. The c-fos serum response element responds to protein kinase C-dependent and -independent signals but not to cyclic AMP. Gilman, M.Z. Genes Dev. (1988) [Pubmed]
  27. Modifications of CD8+ T cell function during in vivo memory or tolerance induction. Tanchot, C., Guillaume, S., Delon, J., Bourgeois, C., Franzke, A., Sarukhan, A., Trautmann, A., Rocha, B. Immunity (1998) [Pubmed]
  28. Chemoattractants induce rapid release of the interleukin 1 type II decoy receptor in human polymorphonuclear cells. Colotta, F., Orlando, S., Fadlon, E.J., Sozzani, S., Matteucci, C., Mantovani, A. J. Exp. Med. (1995) [Pubmed]
  29. Interaction of Leishmania with a macrophage cell line. Correlation between intracellular killing and the generation of oxygen intermediates. Murray, H.W. J. Exp. Med. (1981) [Pubmed]
  30. Production of tumor necrosis factor/cachectin by human T cell lines and peripheral blood T lymphocytes stimulated by phorbol myristate acetate and anti-CD3 antibody. Sung, S.S., Bjorndahl, J.M., Wang, C.Y., Kao, H.T., Fu, S.M. J. Exp. Med. (1988) [Pubmed]
  31. Interleukin-10 induces a long-term antigen-specific anergic state in human CD4+ T cells. Groux, H., Bigler, M., de Vries, J.E., Roncarolo, M.G. J. Exp. Med. (1996) [Pubmed]
  32. Interleukin 2 receptors on human B cells. Implications for the role of interleukin 2 in human B cell function. Muraguchi, A., Kehrl, J.H., Longo, D.L., Volkman, D.J., Smith, K.A., Fauci, A.S. J. Exp. Med. (1985) [Pubmed]
  33. Interleukin-2 and interleukin-2 receptor expression in human corticotrophic adenoma and murine pituitary cell cultures. Arzt, E., Stelzer, G., Renner, U., Lange, M., Müller, O.A., Stalla, G.K. J. Clin. Invest. (1992) [Pubmed]
  34. Regulation of interleukin-8 production in a human colon epithelial cell line (HT-29). Gross, V., Andus, T., Daig, R., Aschenbrenner, E., Schölmerich, J., Falk, W. Gastroenterology (1995) [Pubmed]
  35. Effects of leukotriene B4 in the human lung. Recruitment of neutrophils into the alveolar spaces without a change in protein permeability. Martin, T.R., Pistorese, B.P., Chi, E.Y., Goodman, R.B., Matthay, M.A. J. Clin. Invest. (1989) [Pubmed]
  36. Interleukin 2 activity of human intestinal mucosa mononuclear cells. Decreased levels in inflammatory bowel disease. Fiocchi, C., Hilfiker, M.L., Youngman, K.R., Doerder, N.C., Finke, J.H. Gastroenterology (1984) [Pubmed]
  37. Acetylcholine receptor-associated 43K protein contains covalently bound myristate. Musil, L.S., Carr, C., Cohen, J.B., Merlie, J.P. J. Cell Biol. (1988) [Pubmed]
  38. Lysine residues form an integral component of a novel NH2-terminal membrane targeting motif for myristylated pp60v-src. Silverman, L., Resh, M.D. J. Cell Biol. (1992) [Pubmed]
  39. Calcium movement and membrane potential changes in the early phase of neutrophil activation by phorbol myristate acetate: a study with ion-selective electrodes. Mottola, C., Romeo, D. J. Cell Biol. (1982) [Pubmed]
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