A sensitive endocannabinoid assay. The simultaneous analysis of N- acylethanolamines and 2-monoacylglycerols

Chemistry and Physics of Lipids

Volumn 104, Issue 2, 2000, Pages 185-191

  Schmid, Patricia C ^a   Schwartz, Keith D ^a   Smith, Candice N ^a   Krebsbach, Randy J ^a   Berdyshev, Evgueni V ^a   Schmid, Harald H O ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

2 Arachidonoylglycerol; 2 Monoacylglycerol; Anandamide; JB6 P+ cells; Mass spectrometry; N Acylethanolamine; Rat organs

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; ARACHIDONIC ACID DERIVATIVE; CANNABINOID DERIVATIVE; CANNABINOID RECEPTOR; DEUTERIUM; ETHANOLAMINE DERIVATIVE; GLYCEROL DERIVATIVE; LIPID; SILANE DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; EPIDERMIS CELL; GAS CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; SOLID PHASE EXTRACTION;

ANIMALS; ARACHIDONIC ACIDS; CANNABINOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENDOCANNABINOIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLYCERIDES; INDICATORS AND REAGENTS; KIDNEY; LIVER; MALE; MYOCARDIUM; NEUROTRANSMITTER AGENTS; POLYUNSATURATED ALKAMIDES; RATS; RATS, ZUCKER; SENSITIVITY AND SPECIFICITY; SPLEEN; TESTIS;

EID: 0033989891     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(99)00124-3     Document Type: Article

References (22)

1. Bisogno T., Sepe N., Melck D., Maurelli S., De Petrocellis L., Di Marzo V. Biosynthesis, release and degradation of the novel endogenous cannabimimetic metabolite 2-arachidonoylglycerol in mouse neuroblastoma cells. Biochem. J. 322:1997;671-677.
2. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mecheulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 258:1992;1946-1949.
3. Dong Z., Ma W.-Y., Huang C., Yang C.S. Inhibition of tumor promoter-induced activator protein 1 activation and cell transformation by tea polyphenols, (-)-epigallocatechin gallate, and theaflavins. Cancer Res. 57:1997;4414-4419.
4. Felder C.C., Briley E.M., Axelrod J., Simpson J.T., Mackie K., Devane W.A. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA. 90:1993;7656-7660.
5. Folch J., Lees M., Sloane Stanley G.M. A simple method for the isolation and purification of lipids from animal tissue. J. Biol. Chem. 226:1957;497-507.
6. Giuffrida A., Piomelli D. Isotope dilution GC/MS determination of anandamide and other fatty acylethanolamides in rat blood plasma. FEBS Lett. 422:1998;373-376.
7. Hanus L., Gopher A., Almog S., Mechoulam R. Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J. Med. Chem. 36:1993;3032-3034.
8. Kempe K., Hsu F.F., Bohrer A., Turk J. 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. 271:1996;17287-17295.
9. Koga D., Santa T., Hagiwara K., Imai K., Takizawa H., Nagans T., Hirobe M., Ogawa M., Sato T., Inoue K., Kudo J. High-performance liquid chromatography and fluorometric detection of arachidonoylethanolamine (anandamide) and its analogues, derivatized with 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulphonyl-2,1,3- benzoxadiazole (DBD-COCI). Biomed. Chromatogr. 9:1995;56-57.
10. 2+-dependent and -independent mechanisms. FEBS Lett. 429:1998;152-1566.
11. Mechoulam R., Ben-Shabat S., Hanus L., Ligumski M., Kaminski N.E., Schatz A.R., Gopher A., Almeg S., Martin B.R., Compton D.R., Petwer R.G., Griffin G., Bayewitch M., Barg T., Vogel Z. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem. Pharmacol. 50:1995;83-90.
12. Schmid P.C., Schmid H.H.O. Lipase hydrolysis of mammalian long-chain 1,2-alkanediol diesters. Nonrandom distribution of fatty acids. J. Lipid. Res. 19:1978;894-898.
13. Schmid, P.C., Krebsbach, R.J., Perry, S.T., Dettmer, T.M., Maasson, J.L., Schmid, H.H.O., 1995. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 375, 117-120; Corrigendum 385, 125-126 (1996).
14. Schmid, P.C., Krebsbach, R.J., Perry, S.T., Dettmer, T.M., Maasson, J.L., Schmid, H.H.O., 1995. Occurrence and postmortem generation of anandamide and other long-chain N-acylethanolamines in mammalian brain. FEBS Lett. 375, 117-120; Corrigendum 385, 125-126 (1996).
15. Schmid P.C., Kuwae T., Krebsbach R.J., Schmid H.H.O. Anandamide and other N-acylethanolamines in mouse peritoneal macrophages. Chem. Phys. Lipids. 87:1997;103-110.
16. Schmid P.C., Paria B.C., Krebsbach R.J., Schmid H.H.O., Dey S.K. Changes in anandamide levels in mouse uterus are associated with uterine receptivity for embryo implantation. Proc. Natl. Acad. Sci. USA. 94:1997;4188-4192.
17. Schmid P.C., Schwindenhammer D., Krebsbach R.J., Schmid H.H.O. Alternative pathways of anandamide biosynthesis in rat testes. Chem. Phys. Lipids. 92:1998;27-35.
18. Stella N., Schweitzer P., Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation. Nature. 388:1997;773-778.
19. Sugiura T., Kodaka T., Nakane S., Miyashita T., Kondo S., Suhura Y., Takayama H., Waku K., Seki C., Baba N., Ishima Y. Evidence that the cannabinoid CB1 receptor is a 2-arachidonylglycerol receptor. Structure-activity relationship of 2-arachidonylglycerol, ether-linked analogues, and related compounds. J. Biol. Chem. 274:1999;2794-2801.
20. Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 215:1995;89-97.
21. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218:1996;113-117.
22. Yang H.-Y.T., Karoum F., Felder C., Badger H., Wang T.-C.L., Markey S.P. GC/MS analysis of anandamide and quantification of N-arachidonoyl-phosphatidylethanolamides in various brain regions, spinal cord, testis, and spleen of the rat. J. Neurochem. 72:1999;1959-1968.