Oleic acid derived metabolites in mouse neuroblastoma N18TG 2 cells

Biochemistry

Volumn 43, Issue 39, 2004, Pages 12667-12674

  Merkler, David J ^a   Chew, Geoffrey H ^a,c   Gee, Andrew J ^b,d   Merkler, Kathleen A ^a   Sorondo, Jean Paul O ^a   Johnson, Mitchell E ^b  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b DUQUESNE UNIVERSITY   (United States)

^c BROWN UNIVERSITY   (United States)

^d ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CATALYSIS; CELLS; FATTY ACIDS;

ACID AMIDES; AMIDATED PEPTIDE BYOSYNTHESIS; OLEAMIDE; OLEIC ACID (OA);

ORGANIC ACIDS;

ALPHA AMIDATING ENZYME; FATTY ACID; LONG CHAIN FATTY ACID COENZYME A LIGASE; N OLEOYLGLYCINE; OLEAMIDE; OLEIC ACID; OLEOYL COENZYME A; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CATALYSIS; CELL GROWTH; CEREBROSPINAL FLUID; MOUSE; NEUROBLASTOMA CELL; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; CELL DIFFERENTIATION; CELL LINE, TUMOR; CULTURE MEDIA; ENZYME INHIBITORS; FATTY ACIDS, MONOUNSATURATED; GLYCINE; MICE; MIXED FUNCTION OXYGENASES; MULTIENZYME COMPLEXES; NEUROBLASTOMA; OLEIC ACID; OLEIC ACIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTRATE SPECIFICITY;

ANIMALIA; MAMMALIA;

EID: 4744337839     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049529p     Document Type: Article

References (48)

1. Kuehl, F. A., Jr., Jacob, T. A., Ganley, O. H., Ormond, R. E., and Meisinger, M. A. P. (1957) The identification of N-(2-hydroxyethyl)-palmitamide as a naturally occurring antiinflammatory agent, J. Am. Chem. Soc. 79, 5577-5578.
2. Bezuglov, V. V., Bobrov, M. Yu., and Archakov, A. V. (1998) Bioactive amides of fatty acids, Biochemistry (Moscow) 63, 22-30.
3. Di Marzo, V., Bisogno, T., De Petrocellis, L., Melck, D., and Martin, R. B. (1999) Cannabimimetic fatty acid derivatives: the anandamide family of other endocannabinoids, Curr. Med. Chem. 6, 721-744.
4. Schmid, H. H. O., and Berdyshev, E. V. (2002) Cannabinoid receptor-inactive N-acylethanolamines and other fatty acid amides: metabolism and function, Prostaglandins Leukot. Essent. Fatty Acids 66, 63-376.
5. Di Marzo, V. (1999) Biosynthesis and inactivation of endocannabinoids: relevance to their proposed role as neuromodulators, Life Sci. 65, 645-655.
6. Schmid, H. H. O. (2000) Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively? Chem. Phys. Lipids 108, 71-87.
7. Cravatt, B. F., and Patricelli, M. P. (2001) Proteins regulating the biosynthesis and inactivation of neuromodulatory fatty acid amides, Vitam. Horm. 62, 95-131.
8. Arafat, E. S., Trimble, J. W., Andersen, R. N., Dass, C., and Desiderio, D. M. (1989) Identification of fatty acid amides in human plasma, Life Sci. 45, 1679-1687.
9. Cravatt, B. F., Prospéro-García, O., Siuzdak, G., Gilula, N. B., Henriksen, S. J., Boger, D. L., and Lerner, R. A. (1995) Chemical characterization of a family of brain lipids that induce sleep, Science 268, 1506-1509.
10. Basile, A. S., Hanuš, L., and Mendelson, W. B. (1999) Characterization f the hypnotic properties of oleamide, NeuroReport 10, 947-951.
11. Stewart, J. M., Boudreau, N. M., Blakely, J. A., and Storey, K. B. (2002) A comparison of oleamide in the brains of hibernating and nonhibernating Richard's ground squirrel (Spermophilus richardonii) and its inability to bind to brain fatty acid binding protein, J. Therm. Biol. 27, 309-315.
12. Guan, X., Cravatt, B. F., Ehring, G. R., Hall, J. E., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1997) The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells, J. Cell Biol. 139, 1785-1792.
13. Boger, D. L., Patterson, J. E., Guan, X., Cravatt, B. F., Lerner, R. A., and Gilula, N. B. (1998) Chemical requirements for inhibition of gap junction communication by the biologically active lipid oleamide, Proc. Natl. Acad. Sci. U.S.A. 95, 4810-4815.
14. Murillo-Rodríguez, E., Giordano, M., Cabeza, R., Henriksen, S. J., Díaz, M. M., Navarro, L., and Prospéro-García, O. (2001) Oleamide modulates memory in rats, Neurosci. Lett. 313, 61-64.
15. Huitrón-Reséndiz, S., Gombart, L., Cravatt, B. F., and Henriksen, S. J. (2001) Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats, Exp. Neurol. 172, 235-243.
16. 2+ signaling in human bladder cancer cells, Biochem. Pharmacol. 62, 1363-1369.
17. Nicholson, R. A., Zheng, J., Ganellin, C. R., Verdon, B., and Lees, G. (2001) Anesthetic-like interaction of the sleep-inducing lipid oleamide with voltage-gated sodium channels in mammalian brain, Anesthesiology 94, 120-128.
18. + Channels in vitro: a putative endogenous ligand for depressant drug sites in CNS, Br. J. Pharmacol. 129, 283-290.
19. Yost, C. S., Hampson, A. J., Leonoudakis, D., Koblin, D. D., Bomheim, L. M., and Gray, A. T. (1998) Oleamide potentiates benzodiazepine-sensitive γ-aminobutyric acid receptor activity but does not alter minimum alveolar anesthetic concentration, Anesth. Analg. 86, 1294-1300.
20. A receptor β 3 subunit eliminates the hypnotic actions of oleamide in mice, NeuroReport 12, 4143-4147.
21. Huidobro-Toro, J. P., and Harris, R. A. (1996) Brain lipids that induce sleep are novel modulators of 5-hydroxytryptamine receptors, Proc. Natl. Acad. Sci. U.S.A. 93, 8078-8082.
22. 7 receptors, Biochem. Pharmacol. 58, 1807-1813.
23. Langstein, J., Hofstädter, F., and Schwarz, H. (1996) cis-9,10-Octadecenoamide, an endogenous sleep-inducing CNS compound, inhibits lymphocyte proliferation, Res. Immunol. 147, 389-396.
24. Bisogno, T., Katayama, K., Melck, D., Ueda, N., De Petrocellis, L., Yamamoto, S., and Di Marzo, V. (1998) Biosynthesis and degradation of bioactive fatty acid amides in human breast cancer and rat pheochromocytoma cells. Implications for cell proliferation and differentiation, Eur. J. Biochem. 254, 634-642.
25. 2+ levels in MDCK renal tubular cells, Life Sci. 68, 997-1004.
26. 3 cells, Eur. J. Pharmacol. 458, 37-47.
27. Wakamatsu, K., Masaki, T., Itoh, F., Kondo, K., and Sudo, K. (1990) Isolation of fatty acid amide as an angiogenic principle from bovine mesentery, Biochem. Biophys. Res. Commun. 168, 423-429.
28. Hamberger, A., and Stenhagen, G. (2003) Erucamide as a modulator of water balance: new function of a fatty acid amide, Neurochem. Res. 28, 177-185.
29. Morisseau, C., Newman, J. W., Dowdy, D. L., Goodrow, M. H., and Hammock, B. D. (2001) Inhibition of microsomal epoxide hydrolases by ureas, amides, and amines, Chem. Res. Toxicol. 14, 409-415.
30. Cravatt, B. F., Giang, D. K., Mayfield, S. P., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty acid amides, Nature 384, 83-87.
31. Merkler, D. J., Merkler, K. A., Stern, W., and Fleming, F. F. (1996) Fatty acid amide biosynthesis: a possible new role for peptidylglycine α-amidating enzyme and acyl coenzyme A:glycine N-acyltransferase, Arch. Biochem. Biophys. 330, 430-434.
32. Wilcox, B. J., Ritenour-Rodgers, K. J., Asser, A. S., Baumgart, L. E., Baumgart, M. A., Boger, D. L., DeBlassio, J. L., deLong, M. A., Glufke, U., Henz, M. E., King, L., III, Merkler, K. A., Patterson, J. E., Robleski, J. J., Vederas, J. C., and Merkler, D. J. (1999) N-Acylglycine amidation: implications for the biosynthesis of fatty acid primary amides, Biochemistry 38, 3235-3245.
33. 2 cells: a model for studying oleamide biosynthesis, Biochem. Biophys. Res. Commun. 267, 521-526.
34. Waku, K. (1991) Origins and fates of fatty acyl-CoA esters, Biochim. Biophys. Acta 1124, 101-111.
35. Mains, R. E., Park, L. P., and Eipper, E. A. (1986) Inhibition of peptide amidation by disulfiram and diethyldithiocarbamate, J. Biol. Chem. 261, 11938-11941.
36. Huang, S. M., Bisogno, T., Petros, T. J., Chang, S. Y., Zavitsanos, P. A., Zipkin, R. E., Sivakumar, R., Coop, A., Maeda, D. Y., De Petrocellis, L., Burstein, S., Di Marzo, V., and Walker, J. M. (2001) Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain, J. Biol. Chem. 276, 42639-42644.
37. O'Byrne, J., Hunt, M. C., Rai, D. K., Saeki, M., and Alexson, S. E. H. (2003) The human bile acid-CoA:amino acid N-acyltransferase functions in the conjugation of fatty acids to glycine, J. Biol. Chem. 278, 34237-34244.
38. Killenberg, P. G., and Jordan, J. T. (1978) Purification and characterization of bile acid-CoA: amino acid N-acyltransferase from rat liver, J. Biol. Chem. 253, 1005-1010.
39. Burstein, S. H., Rossetti, R. G., Yagen, B., and Zurier, R. B. (2000) Oxidative metabolism of anandamide, Prostaglandins Other Lipid Mediat. 61, 29-41.
40. Fezza, F., Dillwith, J. W., Bisogno, T., Tucker, J. S., Di Marzo, V., and Sauer, J. R. (2003) Endocannabinoids and related fatty acid amides, and their regulation, in the salivary glands of the lone star fick, Biochim. Biophys. Acta 1633, 61-67.
41. Bisogno, T., Sepe, N., De Petrocellis, L., Mechoulam, R., and Di Marzo, V. (1997) The sleep inducing factor oleamide is produced by mouse neuroblastoma cells, Biochem. Biophys. Res. Commun. 239, 473-479.
42. Gee, A. J., Groen, L. A., and Johnson, M. E. (1999) Determination of fatty acid amides as trimethylsilyl derivatives by gas chromatography with mass spectrometric detection, J. Chromatogr. A. 849, 541-552.
43. Bradbury, A. F., Mistry, J., Roos, B. A., and Smyth, D. G. (1990) 4-Phenyl-3-butenoic acid, an in vivo inhibitor of peptidylglycine hydroxylase (peptide amidating enzyme), Eur. J. Biochem. 189, 363-368.
44. Sugano, K., Aponte, G. W., and Yamada, T. (1985) Identification and characterization of glycine-extended posttranslational processing intermediates of progastrin in porcine stomach, J. Biol. Chem. 260, 11724-11729.
45. Marchand, J. E., Hershman, K., Kumar, M. S. A., Thompson, M. L., and Kream, R. M. (1990) Disulfiram administration affects substance P-like immunoreactive and monoaminergic neural systems in rodent brain, J. Biol. Chem. 265, 264-273.
46. Driscoll, W. J., König, S., Fales, H. M., Pannell, L. K., Eipper, B. A., and Mueller, G. P. (2000) Peptidylglycine-α-hydroxylating monooxygenase generates two hydroxylated products from its mechanism-based suicide substrate, 4-phenyl-3-butenoic acid, Biochemistry 39, 8007-8016.
47. Oldham, C. D., Li, C., Girard, P. R., Nerem, R. M., and May, S. W. (1992) Peptide amidating enzymes are present in cultured endothelial cells, Biochem. Biophys. Res. Commun. 184, 323-329.
48. Mueller, G. P., Driscoll, W. J., and Eipper, B. A. (1999) In vivo inhibition of peptidylglycine-α-hydroxylating monooxygenase by 4-phenyl-3-butenoic acid, J. Pharmacol. Exp. Ther. 290, 1331-1336.