Characterization of glutamate-induced formation of N- acylphosphatidylethanolamine and N-acylethanolamine in cultured neocortical neurons

Journal of Neurochemistry

Volumn 69, Issue 2, 1997, Pages 753-761

  Hansen, Harald S ^a   Lauritzen, Lotte ^a   Strand, Anne Mette ^a   Vinggaard, Anne Marie ^a   Frandsen, Aase ^a   Schousboe, Arne ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Anandamide; Glutamate; N Acylethanolamine; N Acylphosphatidylethanolamine; N Methyl D aspartate receptor; Neurotoxicity

Indexed keywords

ANANDAMIDE; ETHANOLAMINE DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PHOSPHATIDYLETHANOLAMINE;

ANIMAL CELL; ARTICLE; ASTROCYTE; CELL MATURATION; CONTROLLED STUDY; LEYDIG CELL; LIPOGENESIS; MOUSE; NEOCORTEX; NERVE CELL NECROSIS; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALIA;

EID: 0030838502     PISSN: 00223042     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1471-4159.1997.69020753.x     Document Type: Article

References (58)

1. Ankarcrona M., Dypbukt J. M. Bonfoco E., Zhivotovsky B., Orrenius S., Lipton S. A., and Nicotera P. (1995) Glutamate-induced neuronal death: a succession of necrosis or apoptosis depending on mitochondrial function. Neuron 15, 961-973.
2. Blank M. L., Cress E. A., Robinson M., and Snyder F. (1985) Metabolism of unique diarachidonoyl species of ethanolamine and choline phosphoglycerides in rat testis. Biochim. Biophys. Acta 833, 366-371.
3. Cadas H., Gaillet S., Beltramo M., Venance L., and Piomelli D. (1996) Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP. J. Neurosci. 16, 3934-3942.
4. Castagna M., Takai Y., Kaibuchi K., Sano K., Kikkawa U., and Nishizuka Y. (1982) Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters. J. Biol. Chem. 13, 7847-7851.
5. Chilton F. H. and Murphy R. C. (1987) Stimulated production and natural occurrence of 1,2-diarachidonoylglycerophosphocholine in human neutrophils. Biochem. Biophys. Res. Commun. 145, 1126-1133.
6. Choi D. W. (1992) Excitotoxic cell death. J. Neurobiol. 23, 1261-1276.
7. Deutsch D. G. and Chin S. A. (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 46, 791-796.
8. Devane W. A. (1994) New dawn on cannabinoid pharmacology. Trends Pharmacol. Sci. 15, 40-41.
9. Devane W. A., Hanus L., Breuer A., Pertwee R. G., Stevenson L. A., Griffin G., Gibson D., Mandelbaum A., Etinger A., and Mechoulam R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 248, 1946-1949.
10. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino G., Schwartz J.-C., and Piomelli D. (1994) Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature 372, 686-691.
11. Di Marzo V., De Petrocellis L., Bisogno T., and Maurelli S. (1995) Pharmacology and physiology of the endogenous cannabimimetic mediator anandamide. J. Drug. Dev. Clin. Pract. 7, 199-220.
12. 18 neuroblastoma cells. Biochem. J. 316, 977-984.
13. Domingo J. C., Mora M., and Africa de Madariaga M. (1994) Role of headgroup structure in the phase behaviour of N-acylethanolamine phospholipids: hydrogen-bonding ability and head group size. Chem. Phys. Lipids 69, 229-240.
14. 3H] aspartate from cultured cerebellar granule cells: the role of glutamate receptor activation coupled to reversal of the acidic amino plasma membrane carrier. Neuro-science 50, 107-115.
15. Epps D. E., Natarajan V., Schmid P. C., and Schmid H. H. O. (1980) Accumulation of N-acylethanolamine glycerophospholipids in infarcted myocardium. Biochim. Biophys. Acta 618, 420-430.
16. 2+ release from mitochondria by N-acylethanolamines, a class of lipids synthesized in ischemic heart tissue. J. Biol. Chem. 257, 1381-1391.
17. Facci L., Dal Toso R., Romanello S., Buriani A., Skaper S. D., and Leon A. (1995) Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylamide. Proc. Natl. Acad. Sci. USA 92, 3376-3380.
18. Frandsen A. and Schousboe A. (1990) Development of excitatory amino acid induced cytotoxicity in cultured neurons. Int. J. Dev. Neurosci. 8, 209-216.
19. Frandsen A. and Schousboe A. (1993) Excitatory amino-acid mediated cytotoxicity and calcium homeostasis in cultured neurons. J. Neurochem. 60, 1202-1211.
20. Garthwaite J., Garthwaite G., Palmer R. M. J., and Moncada S. (1989) NMDA receptor activation induces nitric oxide synthesis from arginine in rat brain slices. Eur. J. Pharmacol. 172, 413-416.
21. Gulaya N. M., Volkov G. L., Klimashevsky V. M., Goseeva N. N., and Melnik A. A. (1989) Changes in lipid composition of neuroblastoma C1300 N18 cell during differentiation. Neuroscience 30, 153-164.
22. Hannun Y. A. and Obeid L. M. (1995) Ceramide: an intracellular signal for apoptosis. Trends Biochem. Sci. 20, 73-77.
23. Hansen H. S., Lauritzen L., Strand A. M., Moesgaard B., and Frandsen A. (1995) Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta 1258, 303-308.
24. Herbert J. M., Augereau J. M., Gleye J., and Maffrand J. P. (1990) Chelerythrine is a potent and specific inhibitor of protein kinase C. Biochem. Biophys. Res. Commun. 172, 993-999.
25. Hertz E., Yu C. H., Hertz L., Juurlink B. H. J., and Schousboe A. (1989) Preparation of primary cultures of mouse cortical neurons, in A Dissection and Tissue Culture Manual for the Nervous System (Shahar A., de Vellis J., Vernadakis A., and Haber B., eds), pp. 183-186. Alan R. Liss, New York.
26. Hertz L., Juurlink B. H. J., Fosmark H., and Schousboe A. (1982) Astrocytes in primary culture, in Neurosciences Approached Through Cell Culture, Vol I (Pfeiffer S. E., ed), pp. 175-186. CRC Press, Boca Raton, Florida.
27. Kempe K., Hsu F.-F., Bohrer A., and Turk J. (1996) Isotope dilution mass spectrometric measurements indicate that arachidonylethanolamide, the proposed endogenous ligand of the cannabinoid receptor, accumulates in rat brain tissue post mortem but is contained at low levels in or is absent from fresh tissue. J. Biol. Chem. 271, 17287-17295.
28. 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 anti-inflammatory agent. J. Am. Chem. Soc. 79, 5577-5578.
29. Larsson O. M., Drejer J., Kvamme E., Svenneby G., Hertz L., and Schousboe A. (1985) Ontogenetic development of glutamate and GABA metabolizing enzymes. Int. J. Dev. Neurosci. 3, 177-185.
30. Lauritzen L., Nielsen L.-L. A., Vinggaard A. M., and Hansen H. S. (1994) Agents that increase phosphatidic acid inhibit the LH-induced testosterone production. Mol. Cell. Endocrinol. 104, 229-235.
31. Mazzari S., Canella R., Petrelli L., Marcolongo G., and Leon A. (1996) N-(2-Hydroxyethyl)hexadecanamide is orally active in reducing edema formation and inflammatory hyperalgesia by down-modulating mast cell activation. Eur. J. Pharmacol. 300, 227-236.
32. Mikkelsen L., Hansen H. S., Grunnet N., and Dich J. (1994) Cytoprotective effect of tocopherols in hepatocytes cultured with polyunsaturated fatty acids. Lipids 29, 369-372.
33. Mossmann T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63.
34. Natarajan V., Schmid P. C., Reddy P. V., Zuzarte-Augustin M. L., and Schmid H. H. O. (1983) Biosynthesis of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 41, 1303-1312.
35. Natarajan V., Schmid P. C., and Schmid H. H. O. (1986) N-Acylethanolamine phospholipid metabolism in normal and ischemic rat brain. Biochim. Biophys. Acta 878, 32-41.
36. Newman J. L., Stiers D. L., Anderson W. H., and Schmid H. H. O. (1986) Phase behaviour of synthetic N-acylethanolamine phospholipids. Chem. Phys. Lipids 42, 249-260.
37. Nicholls D. and Attwell D. (1990) The release and uptake of excitatory amino acids. Trends Pharmacol. Sci. 11, 462-468.
38. Pomés A., Frandsen A., Sunol C., Rodriguez-Farre E., and Schousboe A. (1994) Lindane cytotoxicity in cultured neocortical neurons is ameliorated by GABA and flunitrazepam. J. Neurosci. Res. 39, 663-668.
39. Robinson M., Blank M. L., and Snyder F. (1986) Highly unsaturated phospholipid molecular species of rat erythrocyte membranes: selective incorporation of arachidonic acid into phosphoglycerides containing polyunsaturation in both acyl chains. Arch. Biochem. Biophys. 250, 271-279.
40. Schinder A. F., Olson E. C., Spitzer N. C., and Montai M. (1996) Mitochondrial dysfunction is a primary event in glutamate neurotoxicity. J. Neurosci. 16, 6125-6133.
41. Schmid H. H. O., Schmid P. C., and Natarajan V. (1990) N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29, 1-43.
42. Schmid H. H. O., Schmid P. C., and Natarajan V. (1996) The N-acylation-phosphodiesterase pathway and cell signalling. Chem. Phys. Lipids 80, 133-142.
43. Schmid P. C., Reddy P. V., Natarajan V., and Schmid H. H. O. (1983) Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J. Biol. Chem. 258, 9302-9306.
44. Schmid P. C., Kresbach R. J., Perry S. R., Dettmer T. M., Maasson J. L., and Schmid H. H. O. (1995a) Occurrence and post mortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 375, 117-120.
45. Schmid P. C., Spimrova I., and Schmid H. H. O. (1995b) Incorporation of exogenous fatty acids into molecular species of rat hepatocyte phosphatidylcholine. Arch. Biochem. Biophys. 322, 306-312.
46. Shen M., Piser T. M., Seybold V. S., and Thayer S. A. (1996) Cannabinoid receptor agonists inhibit glutamatergic synaptic transmission in rat hippocampal cultures. J. Neurosci. 16, 4322-4334.
47. Skaper S. D., Facci L., Romanello S., and Leon A. (1996a) Mast cell activation causes delayed neurodegeneration in mixed hippocampal cultures via the nitric oxide pathway. J. Neurochem. 66, 1157-1166.
48. Skaper S. D., Buriani A., Dal Toso R., Petrelli L., Romanello S., Facci L., and Leon A. (1996b) The ALIAmide palmitoylethanolamine and cannabinoids, but not anandamide, are protective in a delayed postglutamate paradigm of excitotoxic death in cerebellar granule neurons. Proc. Natl. Acad. Sci. USA 93, 3984-3989.
49. Sugita M., Williams M., Dulaney J., and Moser H. (1975) Ceramidase and ceramide synthesis in human kidney and cerebellum. Description of a new alkaline ceramidase. Biochim. Biophys. Acta 398, 125-131.
50. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218, 113-117.
51. Sugiura T., Kondo S., Sukagawa A., Tonegawa T., Nakane S., Yamashita A., Ishima Y., and Waku K. (1996b) Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine. Biochem. J. 240, 53-62.
52. Vigers G. A. and Ziegler F. D. (1968) Azide inhibition of mitochondrial ATPase. Biochem. Biophys. Res. Commun. 30, 83-88.
53. Vinggaard A. M. and Hansen H. S. (1991) Phorbol ester and vasopressin activate phospholipase D in Leydig cells. Mol. Cell. Endocrinol. 79, 157-165.
54. 2+ in cerebral cortex neurons is transient in immature cells but permanent in mature cells. J. Neurochem. 53, 1316-1319.
55. Wallén-Öhman M. and Borrebaeck C. A. K. (1994) A cell surface antigen (BAL) defined by a mouse monoclonal antibody inducing apoptosis in a human lymphocytic leukaemia cell line. Int. J. Cancer 57, 544-552.
56. Watkins J. C., Krogsgaard-Larsen P., and Honoré T. (1990) Structure-activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol. Sci. 11, 25-33.
57. Wiesner D. A. and Dawson G. (1996) Staurosporine induces programmed cell death in embryonic neurons and activation of the ceramide pathway. J. Neurochem. 66, 1418-1425.
58. Ziegler-Heitbrock H. W. L., Thiel E., Füttere A., Herzog V., Wirtz A., and Rietmuller G. (1988) Establishment of a human cell line (Mono Mac 6) with characteristics of mature monocytes. Int. J. Cancer 41, 456-461.