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T. Bisogno, D. Melck, L. Petrocellis, M. Bobrov, N. Gretskaya, V. Bezuglov, N. Sitachitta, W. Gerwick, V. Marzo (1998)
Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase.Biochemical and biophysical research communications, 248 3
W. Chen, J. Huang, J. Cheng, J. Tsai, A. Chiang, K. Chou, C. Liu, C. Jan (2001)
AM-404 elevates renal intracellular Ca(2+), questioning its selectivity as a pharmacological tool for investigating the anandamide transporter.Journal of pharmacological and toxicological methods, 45 3
L. Petrocellis, T. Bisogno, John Davis, R. Pertwee, V. Marzo (2000)
Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin‐like activityFEBS Letters, 483
I. Bojesen, E. Bojesen (1994)
Binding of arachidonate and oleate to bovine serum albumin.Journal of lipid research, 35 5
T. Sugiura, S. Kondo, A. Sukagawa, S. Nakane, A. Shinoda, K. Itoh, A. Yamashita, K. Waku (1995)
2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain.Biochemical and biophysical research communications, 215 1
F. Fezza, V. Gasperi, C. Mazzei, M. Maccarrone (2005)
Radiochromatographic assay of N-acyl-phosphatidylethanolamine-specific phospholipase D activity.Analytical biochemistry, 339 1
M. López-Rodríguez, A. Viso, S. Ortega‐Gutiérrez, C. Fowler, G. Tiger, Eva Lago, J. Fernández-Ruiz, J. Ramos (2003)
Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: comparison with effects on fatty acid amidohydrolase.Journal of medicinal chemistry, 46 8
W. Devane, L. Hanuš, A. Breuer, R. Pertwee, L. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, R. Mechoulam (1992)
Isolation and structure of a brain constituent that binds to the cannabinoid receptor.Science, 258 5090
S. Saario, Juha Savinainen, J. Laitinen, T. Järvinen, R. Niemi (2004)
Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes.Biochemical pharmacology, 67 7
S. Kathuria, S. Gaetani, D. Fegley, F. Valiño, A. Duranti, A. Tontini, M. Mor, G. Tarzia, G. Rana, A. Calignano, A. Giustino, M. Tattoli, M. Palmery, V. Cuomo, D. Piomelli (2003)
Modulation of anxiety through blockade of anandamide hydrolysisNature Medicine, 9
C. Harrington (1990)
Lowry protein assay containing sodium dodecyl sulfate in microtiter plates for protein determinations on fractions from brain tissue.Analytical biochemistry, 186 2
R. Mechoulam, S. Ben-Shabat, L. Hanuš, M. Ligumsky, N. Kaminski, A. Schatz, A. Gopher, S. Almog, B. Martin, D. Compton, R. Pertwee, G. Griffin, M. Bayewitch, J. Barg, Z. Vogel (1995)
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.Biochemical pharmacology, 50 1
P. Zygmunt, H. Chuang, P. Movahed, D. Julius, E. Högestätt (2000)
The anandamide transport inhibitor AM404 activates vanilloid receptors.European journal of pharmacology, 396 1
Theresa Day, F. Rakhshan, D. Deutsch, E. Barker (2001)
Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide.Molecular pharmacology, 59 6
L. Petrocellis, M. Cascio, V. Marzo (2004)
The endocannabinoid system: a general view and latest additionsBritish Journal of Pharmacology, 141
R. Omeir, S. Chin, Yang Hong, D. Ahern, D. Deutsch (1995)
Arachidonoyl ethanolamide-[1,2-14C] as a substrate for anandamide amidase.Life sciences, 56 23-24
B. Cravatt, Dan Giang, S. Mayfield, D. Boger, R. Lerner, N. Gilula (1996)
Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amidesNature, 384
M. Bifulco, C. Laezza, M. Valenti, A. Ligresti, G. Portella, V. Marzo (2004)
A new strategy to block tumor growth by inhibiting endocannabinoid inactivationThe FASEB Journal, 18
F. Fonseca, I. Arco, F. Bermúdez-Silva, A. Bilbao, A. Cippitelli, M. Navarro (2005)
The endocannabinoid system: physiology and pharmacology.Alcohol and alcoholism, 40 1
N. Ghafouri, G. Tiger, R. Razdan, A. Mahadevan, R. Pertwee, B. Martin, C. Fowler (2004)
Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2‐arachidonoylglycerolBritish Journal of Pharmacology, 143
M. Beltramo, N. Stella, A. Calignano, S. Lin, A. Makriyannis, D. Piomelli (1997)
Functional role of high-affinity anandamide transport, as revealed by selective inhibition.Science, 277 5329
S. Maurelli, T. Bisogno, L. Petrocellis, A. Luccia, G. Marino, V. Marzo (1995)
Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma ‘anandamide amidohydrolase’FEBS Letters, 377
M. McFarland, A. Porter, F. Rakhshan, D. Rawat, R. Gibbs, E. Barker (2004)
A Role for Caveolae/Lipid Rafts in the Uptake and Recycling of the Endogenous Cannabinoid Anandamide*Journal of Biological Chemistry, 279
C. Hillard, W. Edgemond, A. Jarrahian, W. Campbell (1997)
Accumulation of N‐Arachidonoylethanolamine (Anandamide) into Cerebellar Granule Cells Occurs via Facilitated DiffusionJournal of Neurochemistry, 69
Fowler Inhibition of FAAH and MAGL by VDM11
D. Fegley, S. Kathuria, R. Mercier, C. Li, A. Goutopoulos, A. Makriyannis, D. Piomelli (2004)
Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172.Proceedings of the National Academy of Sciences of the United States of America, 101 23
M. Melis, S. Perra, A. Muntoni, G. Pillolla, B. Lutz, G. Marsicano, V. Marzo, G. Gessa, M. Pistis (2004)
Prefrontal Cortex Stimulation Induces 2-Arachidonoyl-Glycerol-Mediated Suppression of Excitation in Dopamine NeuronsThe Journal of Neuroscience, 24
C. Fowler, G. Tiger, A. Ligresti, M. López-Rodríguez, V. Marzo (2004)
Selective inhibition of anandamide cellular uptake versus enzymatic hydrolysis--a difficult issue to handle.European journal of pharmacology, 492 1
A. Jarrahian, S. Manna, W. Edgemond, W. Campbell, C. Hillard (2000)
Structure—Activity Relationships Among N‐Arachidonylethanolamine (Anandamide) Head Group Analogues for the Anandamide TransporterJournal of Neurochemistry, 74
M. Karlsson, Charlotta Påhlsson, C. Fowler (2004)
Reversible, temperature-dependent, and AM404-inhibitable adsorption of anandamide to cell culture wells as a confounding factor in release experiments.European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 22 2-3
K. Jonsson, A. Andersson, S. Jacobsson, S. Vandevoorde, D. Lambert, C. Fowler (2003)
AM404 and VDM 11 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamideArchives of Toxicology, 77
N. Hájos, S. Kathuria, Thien Dinh, D. Piomelli, T. Freund (2004)
Endocannabinoid transport tightly controls 2‐arachidonoyl glycerol actions in the hippocampus: effects of low temperature and the transport inhibitor AM404European Journal of Neuroscience, 19
A. Ligresti, E. Morera, Mario Stelt, K. Monory, B. Lutz, G. Ortar, V. Marzo (2004)
Further evidence for the existence of a specific process for the membrane transport of anandamide.The Biochemical journal, 380 Pt 1
S. Goparaju, N. Ueda, H. Yamaguchi, S. Yamamoto (1998)
Anandamide amidohydrolase reacting with 2‐arachidonoylglycerol, another cannabinoid receptor ligandFEBS Letters, 422
D. Deutsch, S. Chin (1993)
Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist.Biochemical pharmacology, 46 5
G. Ortar, A. Ligresti, L. Petrocellis, E. Morera, V. Marzo (2003)
Novel selective and metabolically stable inhibitors of anandamide cellular uptake.Biochemical pharmacology, 65 9
C. Hillard, A. Jarrahian (2003)
Cellular accumulation of anandamide: consensus and controversyBritish Journal of Pharmacology, 140
K. Eggenreich, S. Golouch, B. Töscher, H. Beck, Doris Kuehnelt, Reinhold Wintersteiger (2004)
Determination of 4-amino-m-cresol and 5-amino-o-cresol and metabolites in human keratinocytes (HaCaT) by high-performance liquid chromatography with DAD and MS detection.Journal of biochemical and biophysical methods, 61 1-2
S. Ortega‐Gutiérrez, E. Hawkins, A. Viso, M. López-Rodríguez, B. Cravatt (2004)
Comparison of anandamide transport in FAAH wild-type and knockout neurons: evidence for contributions by both FAAH and the CB1 receptor to anandamide uptake.Biochemistry, 43 25
I. Bojesen, H. Hansen (2003)
Binding of anandamide to bovine serum albumin
Eva Lago, A. Ligresti, G. Ortar, E. Morera, A. Cabranes, G. Pryce, M. Bifulco, D. Baker, J. Fernández-Ruiz, V. Marzo (2004)
In vivo pharmacological actions of two novel inhibitors of anandamide cellular uptake.European journal of pharmacology, 484 2-3
D. Deutsch, S. Glaser, J. Howell, Jeffrey Kunz, R. Puffenbarger, C. Hillard, N. Abumrad (2001)
The Cellular Uptake of Anandamide Is Coupled to Its Breakdown by Fatty-acid Amide Hydrolase*The Journal of Biological Chemistry, 276
H. Bradshaw, J. Walker (2005)
The expanding field of cannabimimetic and related lipid mediatorsBritish Journal of Pharmacology, 144
S. Glaser, N. Abumrad, Folayan Fatade, M. Kaczocha, K. Studholme, D. Deutsch (2003)
Evidence against the presence of an anandamide transporterProceedings of the National Academy of Sciences of the United States of America, 100
Thien Dinh, D. Carpenter, F. Leslie, T. Freund, I. Katona, S. Sensi, S. Kathuria, D. Piomelli (2002)
Brain monoglyceride lipase participating in endocannabinoid inactivationProceedings of the National Academy of Sciences of the United States of America, 99
D. Boger, Haruhiko Sato, Aaron Lerner, Michael Hedrick, R. Fecik, H. Miyauchi, Gordon Wilkie, B. Austin, M. Patricelli, B. Cravatt (2000)
Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide.Proceedings of the National Academy of Sciences of the United States of America, 97 10
K. Jonsson, S. Vandevoorde, D. Lambert, G. Tiger, C. Fowler (2001)
Effects of homologues and analogues of palmitoylethanolamide upon the inactivation of the endocannabinoid anandamideBritish Journal of Pharmacology, 133
V. Marzo, A. Fontana, H. Cadas, S. Schinelli, G. Cimino, J. Schwartz, D. Piomelli (1994)
Formation and inactivation of endogenous cannabinoid anandamide in central neuronsNature, 372
Brooke Kelley, S. Thayer (2004)
Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors.European journal of pharmacology, 496 1-3
C. Fowler, S. Holt, O. Nilsson, K. Jonsson, G. Tiger, S. Jacobsson (2005)
The endocannabinoid signaling system: Pharmacological and therapeutic aspectsPharmacology Biochemistry and Behavior, 81
D. Piomelli (2004)
The endogenous cannabinoid system and the treatment of marijuana dependenceNeuropharmacology, 47
A. Lichtman, D. Leung, C. Shelton, A. Saghatelian, C. Hardouin, D. Boger, B. Cravatt (2004)
Reversible Inhibitors of Fatty Acid Amide Hydrolase That Promote Analgesia: Evidence for an Unprecedented Combination of Potency and SelectivityJournal of Pharmacology and Experimental Therapeutics, 311
Eva Lago, J. Fernández-Ruiz, S. Ortega‐Gutiérrez, A. Viso, M. López-Rodríguez, J. Ramos (2002)
UCM707, a potent and selective inhibitor of endocannabinoid uptake, potentiates hypokinetic and antinociceptive effects of anandamide.European journal of pharmacology, 449 1-2
1 There is some dispute concerning the extent to which the uptake inhibitor VDM11 (N‐(4‐hydroxy‐2‐methylphenyl) arachidonoyl amide) is capable of inhibiting the metabolism of the endocannabinoid anandamide (AEA) by fatty acid amide hydrolase (FAAH). In view of a recent study demonstrating that the closely related compound AM404 (N‐(4‐hydroxyphenyl)arachidonylamide) is a substrate for FAAH, we re‐examined the interaction of VDM11 with FAAH. 2 In the presence of fatty acid‐free bovine serum albumin (BSA, 0.125% w v−1), both AM404 and VDM11 inhibited the metabolism of AEA by rat brain FAAH with similar potencies (IC50 values of 2.1 and 2.6 μM, respectively). The compounds were about 10‐fold less potent as inhibitors of the metabolism of 2‐oleoylglycerol (2‐OG) by cytosolic monoacylglycerol lipase (MAGL). 3 The potency of VDM11 towards FAAH was dependent upon the assay concentration of fatty acid‐free bovine serum albumin (BSA). Thus, in the absence of fatty acid‐free BSA, the IC50 value for inhibition of FAAH was reduced by a factor of about two (from 2.9 to 1.6 μM). A similar reduction in the IC50 value for the inhibition of membrane bound MAGL by both this compound (from 14 to 6 μM) and by arachidonoyl serinol (from 24 to 13 μM) was seen. 4 An HPLC assay was set up to measure 4‐amino‐m‐cresol, the hypothesised product of FAAH‐catalysed VDM11 hydrolysis. 4‐Amino‐m‐cresol was eluted with a retention time of ∼2.4 min, but showed a time‐dependent degradation to compounds eluting at peaks of ∼5.6 and ∼8 min. Peaks with the same retention times were also found following incubation of the membranes with VDM11, but were not seen when the membranes were preincubated with the FAAH inhibitors URB597 (3′‐carbamoyl‐biphenyl‐3‐yl‐cyclohexylcarbamate) and CAY10401 (1‐oxazolo(4,5‐b)pyridin‐2‐yl‐9‐octadecyn‐1‐one) prior to addition of VDM11. The rate of metabolism of VDM11 was estimated to be roughly 15–20% of that for anandamide. 5 It is concluded that VDM11 is an inhibitor of FAAH under the assay conditions used here, and that the inhibition may at least in part be a consequence of the compound acting as an alternative substrate. British Journal of Pharmacology (2005) 145, 885–893. doi:10.1038/sj.bjp.0706253
British Journal of Pharmacology – Wiley
Published: Aug 1, 2005
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