Determination of the endocannabinoid anandamide in human plasma by high-performance liquid chromatography

Biomedical Chromatography

Volumn 20, Issue 4, 2006, Pages 336-342

  Schmidt, Andreas ^a   Brune, Kay ^a   Hinz, Burkhard ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Anandamide; Cannabinoid receptor ligand; Fatty acid amide hydrolase; Flourescence detection; HPLC; Phenylmethylsulfonyl fluoride

Indexed keywords

AMIDES; FATTY ACIDS; FLUORINE COMPOUNDS; HYDROLASES; LIGANDS; PLASMA (HUMAN);

ANANDAMIDE; ANANDAMIDE LEVELS; CANNABINOID RECEPTOR LIGAND; CANNABINOID RECEPTORS; FATTY ACID AMIDE HYDROLASE; FLOURESCENCE DETECTION; HPLC; HUMAN PLASMAS; PHENYLMETHYLSULFONYL FLUORIDE; RECEPTOR LIGANDS;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ACETONITRILE; ANANDAMIDE; BENZYLSULFONYL FLUORIDE; DIMETHYLAMINE; ENDOCANNABINOID; FATTY ACID AMIDASE; METHANANDAMIDE; WATER;

ANALYTIC METHOD; ARTICLE; CONTROLLED STUDY; DERIVATIZATION; FLOW RATE; FLUOROMETRY; HUMAN; INCUBATION TEMPERATURE; INCUBATION TIME; LIQUID LIQUID EXTRACTION; PLASMA; QUANTITATIVE ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPECTROPHOTOMETRY; VALIDATION PROCESS;

EID: 33646066829     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.568     Document Type: Article

References (29)

1. Arai Y, Fukushima T, Shirao M, Yang X and Imai K. Sensitive determination of anandamide in rat brain utilizing a coupled-column HPLC with fluorimetric detection. Biomedical Chromatography 2000; 14: 118-124.
2. Beltramo M, Stella N, Calignano A, Lin SY, Makriyannis A and Piomelli D. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 1997; 277: 1094-1097.
3. Bifulco M, Laezza C, Valenti M, Ligresti A, Portella G and Di Marzo V. A new strategy to block tumor growth by inhibiting endocannabinoid inactivation. FASEB Journal 2004; 18: 1606-1608.
4. Bisogno T, Maurelli S, Melck D, De Petrocellis L and Di Marzo V. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. Journal of Biological Chemistry 1997; 272: 3315-3323.
5. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA and Gilula NB. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996; 384: 83-87.
6. De Marchi N, De Petrocellis L, Orlando P, Daniele F, Fezza F and Di Marzo V. Endocannabinoid signalling in the blood of patients with schizophrenia. Lipids in Health and Disease 2003; 2: 5.
7. Deutsch DG and Chin SA. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochemical Pharmacology 1993; 46: 791-796.
8. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A and Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992; 258: 1946-1949.
9. Felder CC, Veluz JS, Williams HL, Briley EM and Matsuda LA. Cannabinoid agonists stimulate both receptor- and non-receptor-mediated signal transduction pathways in cells transfected with and expressing cannabinoid receptor clones. Molecular Pharmacology 1992; 42: 838-845.
10. Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM and Becker GW. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Letters 1996; 393: 231-235.
11. Fernandez-Rodriguez CM, Romero J, Petros TJ, Bradshaw H, Gasalla JM, Gutierrez ML, Lledo JL, Santander C, Fernandez TP, Tomas E, Cacho G and Walker JM. Circulating endogenous cannabinoid anandamide and portal, systemic and renal hemodynamics in cirrhosis. Liver International 2004; 24: 477-483.
12. Fontana A, Di Marzo V, Cadas H and Piomelli D. Analysis of anandamide, an endogenous cannabinoid substance, and of other natural N-acylethanolamines. Prostaglandins Leukocytes and Essential Fatty Acids 1995; 53: 301-308.
13. Fowler CJ, Tiger G and Stenstrom A. Ibuprofen inhibits rat brain deamidation of anandamide at pharmacologically relevant concentrations. Mode of inhibition and structure-activity relationship. Journal of Pharmacology and Experimental Therapeutics 1997; 283: 729-734.
14. Fride E and Mechoulam R. Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent. European Journal of Pharmacology 1993; 231: 313-314.
15. Habayeb OM, Taylor AH, Evans MD, Cooke MS, Taylor DJ, Bell SC and Konje JC. Plasma levels of the endocannabinoid anandamide in women - a potential role in pregnancy maintenance and labor? Journal of Clinical Endocrinology and Metabolism 2004; 89: 5482-5487.
16. Hillard CJ and Jarrahian A. Cellular accumulation of anandamide: consensus and controversy. British Journal of Pharmacology 2003; 140: 802-808.
17. Hinz B, Ramer R, Eichele K, Weinzierl U and Brune K. Up-regulation of cyclooxygenase-2 expression is involved in R(+)-methanandamide-induced apoptotic death of human neuroglioma cells. Molecular Pharmacology 2004; 66: 1643-1651.
18. Imai K, Fukushima T and Yokosu H. A novel electrophilic reagent, 4-(N-chloroformylmethyl-N-methyl)amino-7 -N,N-dimethylaminosulphonyl- 2,1,3-benzoxadiazole (DBD-COC1) for fluorometric detection of alcohols, phenols, amines and thiols. Biomedical Chromatography 1994; 8: 107-113.
19. Koga D, Santa T, Hagiwara K, Imai K, Takizawa H, Nagano T, Hirobe M, Ogawa M, Sato T, Inoue K and Kudo I. High-performance liquid chromatography and fluorometric detection of arachidonylethanolamide (anandamide) and its analogues, derivatized with 4-(N-chloroformylmethyl-N-methyl)amino-7 -N,N-dimethylaminosulphonyl-2,1,3 benzoxadiazole (DBD-COC1). Biomedical Chromatography 1995; 9: 56-57.
20. Ligresti A, Morera E, Van Der Stelt M, Monory K, Lutz B, Ortar G and Di Marzo V. Further evidence for the existence of a specific process for the membrane transport of anandamide. Biochemical Journal 2004; 380: 265-272.
21. Mechoulam R, Fride E and Di Marzo V. Endocannabinoids. European Journal of Pharmacology 1998; 359: 1-18.
22. Patel S, Wohlfeil ER, Rademacher DJ, Carrier EJ, Perry LJ, Kundu A, Falck JR, Nithipatikom K, Campbell WB and Hillard CJ. The general anesthetic propofol increases brain N-arachidonylethanolamine (anandamide) content and inhibits fatty acid amide hydrolase. British Journal of Pharmacology 2003; 139: 1005-1013.
23. Randall MD, Kendall DA and O'Sullivan S. The complexities of the cardiovascular actions of cannabinoids. British Journal of Pharmacology 2004; 142: 20-26.
24. Schmid HH. Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively? Chemistry and Physics of Lipids 2000; 108: 71-87.
25. Shah VP, Midha KK, Findlay JW, Hill HM, Hulse JD, McGilveray IJ, McKay G, Miller KJ, Patnaik RN, Powell ML, Tonelli A, Viswanathan CT and Yacobi A. Bioanalytical method validation - a revisit with a decade of progress. Pharmaceutical Research 2000; 17: 1551-1557.
26. Smith PB, Compton DR, Welch SP, Razdan RK, Mechoulam R and Martin BR. The pharmacological activity of anandamide, a putative endogenous cannabinoid, in mice. Journal of Pharmacology and Experimental Therapeutics 1994; 270: 219-227.
27. Sparling PB, Giuffrida A, Piomelli D, Rosskopf L and Dietrich A. Exercise activates the endocannabinoid system. Neuroreport 2003; 14: 2209-2211.
28. Steffens M, Feuerstein TJ, van Velthoven V, Schnierle P and Knorle R. Quantitative measurement of depolarization-induced anandamide release in human and rat neocortex. Naunyn-Schmiedeberg's Archives of Pharmacology 2003; 368: 432-436.
29. Yagen B and Burstein S. Novel and sensitive method for the detection of anandamide by the use of its dansyl derivative. Journal of Chromatography B Biomedical Science Applications 2000; 740: 93-99.