Metabolism of endocannabinoids and related N-acylethanolamines: Canonical and alternative pathways

FEBS Journal

Volumn 280, Issue 9, 2013, Pages 1874-1894

  Ueda, Natsuo ^a   Tsuboi, Kazuhito ^a   Uyama, Toru ^a  

^a KAGAWA UNIVERSITY   (Japan)

Author keywords

2 arachidonoylglycerol; anandamide; HRASLS family; N acyl phosphatidylethanolamine; phospholipid

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 7 PHENYL 1 [5 (2 PYRIDINYL) 2 OXAZOLYL] 1 HEPTANONE; ACYLTRANSFERASE; AMIDASE; ANALGESIC AGENT; ANANDAMIDE; ANTIINFLAMMATORY AGENT; CALCIUM ION; CYCLOHEXYLCARBAMIC ACID 3' CARBAMOYLBIPHENYL 3 YL ESTER; ENDOCANNABINOID; ETHANOLAMINE; ETHANOLAMINE DERIVATIVE; FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; JZL 184; JZL 195; LACTONE DERIVATIVE; LYSOPHOSPHOLIPID; MESSENGER RNA; N ACYLETHANOLAMINE DERIVATIVE; N ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE; N ACYLPHOSPHATIDYLETHANOLAMINE HYDROLYZING PHOSPHOLIPASE D; PF 04457845; PF 3845; PHOSPHOLIPASE A; PHOSPHOLIPASE D; UNCLASSIFIED DRUG;

BIOSYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE; FATTY ACID METABOLISM; HUMAN; LIPID DEGRADATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; PROTEIN LIPID INTERACTION; REVIEW;

AMINO ACID SEQUENCE; ANIMALS; ARACHIDONIC ACIDS; BIOSYNTHETIC PATHWAYS; ENDOCANNABINOIDS; ETHANOLAMINES; GLYCERIDES; HUMANS; HYDROLASES; LYSOPHOSPHOLIPIDS; MOLECULAR SEQUENCE DATA; MONOACYLGLYCEROL LIPASES; PHOSPHORIC DIESTER HYDROLASES;

MAMMALIA;

EID: 84876951107     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/febs.12152     Document Type: Review

References (174)

1. Pacher P, Bátkai S, &, Kunos G, (2006) The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev 58, 389-462. (Pubitemid 44394908)
2. Pertwee RG, Howlett AC, Abood ME, Alexander SP, Di Marzo V, Elphick MR, Greasley PJ, Hansen HS, Kunos G, Mackie K, et al,. (2010) International union of basic and clinical pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2. Pharmacol Rev 62, 588-631.
3. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, &, Mechoulam R, (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949. (Pubitemid 23026736)
4. Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, Gopher A, Almog S, Martin BR, Compton DR, et al,. (1995) Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol 50, 83-90.
5. Sugiura T, Kondo S, Sukagawa A, Nakane S, Shinoda A, Itoh K, Yamashita A, &, Waku K, (1995) 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun 215, 89-97.
6. Hansen HS, &, Diep TA, (2009) N-Acylethanolamines, anandamide and food intake. Biochem Pharmacol 78, 553-560.
7. LoVerme J, La Rana G, Russo R, Calignano A, &, Piomelli D, (2005) The search for the palmitoylethanolamide receptor. Life Sci 77, 1685-1698. (Pubitemid 41073662)
8. Pavõn FJ, Serrano A, Romero-Cuevas M, Alonso M, &, Rodríguez de Fonseca F, (2010) Oleoylethanolamide: a new player in peripheral control of energy metabolism. Therapeutic implications. Drug Discov Today Dis Mech 7, e175-e183.
9. Hansen KB, Rosenkilde MM, Knop FK, Wellner N, Diep TA, Rehfeld JF, Andersen UB, Holst JJ, &, Hansen HS, (2011) 2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans. J Clin Endocrinol Metab 96, E1409-1417.
10. Ueda N, Tsuboi K, &, Uyama T, (2010a) Enzymological studies on the biosynthesis of N-acylethanolamines. Biochim Biophys Acta 1801, 1274-1285.
11. Ueda N, Tsuboi K, Uyama T, &, Ohnishi T, (2011) Biosynthesis and degradation of the endocannabinoid 2-arachidonoylglycerol. BioFactors 37, 1-7.
12. Ueda N, &, Tsuboi K, (2012) Discrimination between two endocannabinoids. Chem Biol 19, 545-547.
13. Petrosino S, &, Di Marzo V, (2010) FAAH and MAGL inhibitors: therapeutic opportunities from regulating endocannabinoid levels. Curr Opin Investig Drugs 11, 51-62.
14. Elphick MR, &, Egertová M, (2001) The neurobiology and evolution of cannabinoid signalling. Philos Trans R Soc Lond B Biol Sci 356, 381-408. (Pubitemid 32324674)
15. McPartland JM, Matias I, Di Marzo V, &, Glass M, (2006) Evolutionary origins of the endocannabinoid system. Gene 370, 64-74. (Pubitemid 43375901)
16. Kilaru A, Blancaflor EB, Venables BJ, Tripathy S, Mysore KS, &, Chapman KD, (2007) The N-acylethanolamine-mediated regulatory pathway in plants. Chem Biodivers 4, 1933-1955. (Pubitemid 47377211)
17. Lucanic M, Held JM, Vantipalli MC, Klang IM, Graham JB, Gibson BW, Lithgow GJ, &, Gill MS, (2011) N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature 473, 226-229.
18. Coulon D, Faure L, Salmon M, Wattelet V, &, Bessoule JJ, (2012a) N-Acylethanolamines and related compounds: aspects of metabolism and functions. Plant Sci 184, 129-140.
19. Schmid HHO, Schmid PC, &, Natarajan V, (1990) N-Acylated glycerophospholipids and their derivatives. Prog Lipid Res 29, 1-43. (Pubitemid 120036504)
20. Schmid HHO, (2000) Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively? Chem Phys Lipids 108, 71-87.
21. Wellner N, Diep TA, Janfelt C, &, Hansen HS, (2013) N-Acylation of phosphatidylethanolamine and its biological functions in mammals. Biochim Biophys Acta 1831, 652-662.
22. Coulon D, Faure L, Salmon M, Wattelet V, &, Bessoule JJ, (2012b) Occurrence, biosynthesis and functions of N-acylphosphatidylethanolamines (NAPE): not just precursors of N-acylethanolamines (NAE). Biochimie 94, 75-85.
23. Gillum MP, Zhang D, Zhang X-M, Erion DM, Jamison RA, Choi C, Dong J, Shanabrough M, Duenas HR, Frederick DW, et al,. (2008) N- Acylphosphatidylethanolamine, a gut-derived circulating factor induced by fat ingestion, inhibits food intake. Cell 135, 813-824.
24. Wellner N, Tsuboi K, Madsen AN, Holst B, Diep TA, Nakao M, Tokumura A, Burns MP, Deutsch DG, Ueda N, et al,. (2011) Studies on the anorectic effect of N-acylphosphatidylethanolamine and phosphatidylethanolamine in mice. Biochim Biophys Acta 1811, 508-512.
25. Deutsch DG, Ueda N, &, Yamamoto S, (2002) The fatty acid amide hydrolase (FAAH). Prostaglandins Leukot Essent Fatty Acids 66, 201-210 (erratum appears in Prostaglandins Leukot Essent Fatty Acids 68, 69). (Pubitemid 34743595)
26. McKinney MK, &, Cravatt BF, (2005) Structure and function of fatty acid amide hydrolase. Annu Rev Biochem 74, 411-432. (Pubitemid 40995513)
27. Vandevoorde S, &, Lambert DM, (2007) The multiple pathways of endocannabinoid metabolism: a zoom out. Chem Biodivers 4, 1858-1881. (Pubitemid 47381194)
28. Fowler CJ, (2007) The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action. Br J Pharmacol 152, 594-601. (Pubitemid 350034968)
29. Hansen HS, Moesgaard B, Hansen HH, &, Petersen G, (2000) N-Acylethanolamines and precursor phospholipids-relation to cell injury. Chem Phys Lipids 108, 135-150.
30. Cadas H, di Tomaso E, &, Piomelli D, (1997) Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonoyl phosphatidylethanolamine, in rat brain. J Neurosci 17, 1226-1242. (Pubitemid 27073726)
31. 2+-independent phosphatidylethanolamine N-acyltransferase generating the anandamide precursor and its congeners. J Biol Chem 282, 3614-3623. (Pubitemid 47084458)
32. Schmid HHO, Schmid PC, &, Berdyshev EV, (2002) Cell signaling by endocannabinoids and their congeners: questions of selectivity and other challenges. Chem Phys Lipids 121, 111-134. (Pubitemid 36044547)
33. Janfelt C, Wellner N, Leger PL, Kokesch-Himmelreich J, Hansen SH, Charriaut-Marlangue C, &, Hansen HS, (2012) Visualization by mass spectrometry of 2-dimensional changes in rat brain lipids, including N-acylphosphatidylethanolamines, during neonatal brain ischemia. FASEB J 26, 2667-2673.
34. Okamoto Y, Wang J, Morishita J, &, Ueda N, (2007) Biosynthetic pathways of the endocannabinoid anandamide. Chem Biodivers 4, 1842-1857. (Pubitemid 47377206)
35. Okamoto Y, Morishita J, Tsuboi K, Tonai T, &, Ueda N, (2004) Molecular characterization of a phospholipase D generating anandamide and its congeners. J Biol Chem 279, 5298-5305. (Pubitemid 38220550)
36. Wang J, Okamoto Y, Morishita J, Tsuboi K, Miyatake A, &, Ueda N, (2006) Functional analysis of the purified anandamide-generating phospholipase D as a member of the metallo-β-lactamase family. J Biol Chem 281, 12325-12335. (Pubitemid 43855317)
37. Ueda N, Liu Q, &, Yamanaka K, (2001a) Marked activation of the N-acylphosphatidylethanolamine-hydrolyzing phosphodiesterase by divalent cations. Biochim Biophys Acta 1532, 121-127. (Pubitemid 32553955)
38. Wang J, Okamoto Y, Tsuboi K, &, Ueda N, (2008a) The stimulatory effect of phosphatidylethanolamine on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D (NAPE-PLD). Neuropharmacology 54, 8-15. (Pubitemid 350299397)
39. Liu J, Wang L, Harvey-White J, Osei-Hyiaman D, Razdan R, Gong Q, Chan AC, Zhou Z, Huang BX, Kim HY, et al,. (2006) A biosynthetic pathway for anandamide. Proc Natl Acad Sci USA 103, 13345-13350. (Pubitemid 44380110)
40. Zhu C, Solorzano C, Sahar S, Realini N, Fung E, Sassone-Corsi P, &, Piomelli D, (2011) Proinflammatory stimuli control N- acylphosphatidylethanolamine-specific phospholipase D expression in macrophages. Mol Pharmacol 79, 786-792.
41. Morishita J, Okamoto Y, Tsuboi K, Ueno M, Sakamoto H, Maekawa N, &, Ueda N, (2005) Regional distribution and age-dependent expression of N-acylphosphatidylethanolamine-hydrolyzing phospholipase D in rat brain. J Neurochem 94, 753-762. (Pubitemid 41098507)
42. 31P NMR and enzyme activity study. J Lipid Res 41, 985-990. (Pubitemid 30434330)
43. Leung D, Saghatelian A, Simon GM, &, Cravatt BF, (2006) Inactivation of N-acyl phosphatidylethanolamine phospholipase D reveals multiple mechanisms for the biosynthesis of endocannabinoids. Biochemistry 45, 4720-4726.
44. Tsuboi K, Okamoto Y, Ikematsu N, Inoue M, Shimizu Y, Uyama T, Wang J, Deutsch DG, Burns MP, Ulloa NM, et al,. (2011) Enzymatic formation of N-acylethanolamines from N-acylethanolamine plasmalogen through N-acylphosphatidylethanolamine-hydrolyzing phospholipase D-dependent and -independent pathways. Biochim Biophys Acta 1811, 565-577.
45. Wangensteen T, Akselsen H, Holmen J, Undlien D, &, Retterstøl L, (2011) A common haplotype in NAPEPLD is associated with severe obesity in a Norwegian population-based cohort (the HUNT study). Obesity 19, 612-617.
46. Sugiura T, Kondo S, Sukagawa A, Tonegawa T, Nakane S, Yamashita A, Ishima Y, &, Waku K, (1996) Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine. Eur J Biochem 240, 53-62.
47. Arreaza G, Devane WA, Omeir RL, Sajnani G, Kunz J, Cravatt BF, &, Deutsch DG, (1997) The cloned rat hydrolytic enzyme responsible for the breakdown of anandamide also catalyzes its formation via the condensation of arachidonic acid and ethanolamine. Neurosci Lett 234, 59-62. (Pubitemid 27435969)
48. Kurahashi Y, Ueda N, Suzuki H, Suzuki M, &, Yamamoto S, (1997) Reversible hydrolysis and synthesis of anandamide demonstrated by recombinant rat fatty-acid amide hydrolase. Biochem Biophys Res Commun 237, 512-515. (Pubitemid 27434715)
49. Katayama K, Ueda N, Katoh I, &, Yamamoto S, (1999) Equilibrium in the hydrolysis and synthesis of cannabimimetic anandamide demonstrated by a purified enzyme. Biochim Biophys Acta 1440, 205-214. (Pubitemid 29424185)
50. Mukhopadhyay B, Cinar R, Yin S, Liu J, Tam J, Godlewski G, Harvey-White J, Mordi I, Cravatt BF, Lotersztajn S, et al,. (2011) Hyperactivation of anandamide synthesis and regulation of cell-cycle progression via cannabinoid type 1 (CB1) receptors in the regenerating liver. Proc Natl Acad Sci USA 108, 6323-6328.
51. McCue JM, Driscoll WJ, &, Mueller GP, (2009) In vitro synthesis of arachidonoyl amino acids by cytochrome c. Prostaglandins Other Lipid Mediat 90, 42-48.
52. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA, &, Gilula NB, (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 384, 83-87. (Pubitemid 26374593)
53. McKinney MK, &, Cravatt BF, (2003) Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad of fatty acid amide hydrolase. J Biol Chem 278, 37393-37399. (Pubitemid 37175258)
54. Cravatt BF, Demarest K, Patricelli M, Bracey MH, Giang DK, Martin BR, &, Lichtman AH, (2001) Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc Natl Acad Sci USA 98, 9371-9376. (Pubitemid 32743923)
55. Clement AB, Hawkins EG, Lichtman AH, &, Cravatt BF, (2003) Increased seizure susceptibility and proconvulsant activity of anandamide in mice lacking fatty acid amide hydrolase. J Neurosci 23, 3916-3923. (Pubitemid 36958497)
56. Saghatelian A, Trauger SA, Want EJ, Hawkins EG, Siuzdak G, &, Cravatt BF, (2004) Assignment of endogenous substrates to enzymes by global metabolite profiling. Biochemistry 43, 14332-14339. (Pubitemid 39491967)
57. Goparaju SK, Ueda N, Yamaguchi H, &, Yamamoto S, (1998) Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett 422, 69-73. (Pubitemid 28052868)
58. Goparaju SK, Ueda N, Taniguchi K, &, Yamamoto S, (1999) Enzymes of porcine brain hydrolyzing 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors. Biochem Pharmacol 57, 417-423. (Pubitemid 29065290)
59. Blankman JL, Simon GM, &, Cravatt BF, (2007) A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem Biol 14, 1347-1356. (Pubitemid 350257008)
60. Sipe JC, Chiang K, Gerber AL, Beutler E, &, Cravatt BF, (2002) A missense mutation in human fatty acid amide hydrolase associated with problem drug use. Proc Natl Acad Sci USA 99, 8394-8399. (Pubitemid 34651063)
61. Kathuria S, Gaetani S, Fegley D, Valiño F, Duranti A, Tontini A, Mor M, Tarzia G, La Rana G, Calignano A, et al,. (2003) Modulation of anxiety through blockade of anandamide hydrolysis. Nat Med 9, 76-81. (Pubitemid 36098263)
62. Lichtman AH, Leung D, Shelton CC, Saghatelian A, Hardouin C, Boger DL, &, Cravatt BF, (2004) Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity. J Pharmacol Exp Ther 311, 441-448. (Pubitemid 39391527)
63. Ahn K, Johnson DS, Mileni M, Beidler D, Long JZ, McKinney MK, Weerapana E, Sadagopan N, Liimatta M, Smith SE, et al,. (2009) Discovery and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain. Chem Biol 16, 411-420.
64. Ahn K, Smith SE, Liimatta MB, Beidler D, Sadagopan N, Dudley DT, Young T, Wren P, Zhang Y, Swaney S, et al,. (2011) Mechanistic and pharmacological characterization of PF-04457845: a highly potent and selective fatty acid amide hydrolase inhibitor that reduces inflammatory and noninflammatory pain. J Pharmacol Exp Ther 338, 114-124.
65. Nomura DK, Blankman JL, Simon GM, Fujioka K, Issa RS, Ward AM, Cravatt BF, &, Casida JE, (2008) Activation of the endocannabinoid system by organophosphorus nerve agents. Nat Chem Biol 4, 373-378. (Pubitemid 351693991)
66. Long JZ, Nomura DK, Vann RE, Walentiny DM, Booker L, Jin X, Burston JJ, Sim-Selley LJ, Lichtman AH, Wiley JL, et al,. (2009a) Dual blockade of FAAH and MAGL identifies behavioral processes regulated by endocannabinoid crosstalk in vivo. Proc Natl Acad Sci USA 106, 20270-20275.
67. Wei BQ, Mikkelsen TS, McKinney MK, Lander ES, &, Cravatt BF, (2006) A second fatty acid amide hydrolase with variable distribution among placental mammals. J Biol Chem 281, 36569-36578. (Pubitemid 46049797)
68. Kaczocha M, Glaser ST, Chae J, Brown DA, &, Deutsch DG, (2010) Lipid droplets are novel sites of N-acylethanolamine inactivation by fatty acid amide hydrolase-2. J Biol Chem 285, 2796-2806.
69. Fu J, Bottegoni G, Sasso O, Bertorelli R, Rocchia W, Masetti M, Guijarro A, Lodola A, Armirotti A, Garau G, et al,. (2011) A catalytically silent FAAH-1 variant drives anandamide transport in neurons. Nat Neurosci 15, 64-69.
70. Leung K, Vivieca S, Sun J, Glaser ST, Deutsch DG, &, Kaczocha M, (2012) FLAT is not an intracellular anandamide transporter. 22nd Annual Symposium on the Cannabinoids, International Cannabinoid Research Society, Research Triangle Park, NC, USA, pp. 59.
71. Bornheim LM, Kim KY, Chen B, &, Correia MA, (1993) The effect of cannabidiol on mouse hepatic microsomal cytochrome P450-dependent anandamide metabolism. Biochem Biophys Res Commun 197, 740-746. (Pubitemid 24034632)
72. Ueda N, Yamamoto K, Yamamoto S, Tokunaga T, Shirakawa E, Shinkai H, Ogawa M, Sato T, Kudo I, Inoue K, et al,. (1995) Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist. Biochim Biophys Acta 1254, 127-134.
73. Hampson AJ, Hill WAG, Zan-Phillips M, Makriyannis A, Leung E, Eglen RM, &, Bornheim LM, (1995) Anandamide hydroxylation by brain lipoxygenase: metabolite structures and potencies at the cannabinoid receptor. Biochim Biophys Acta 1259, 173-179.
74. 2 ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272, 21181-21186. (Pubitemid 27373979)
75. Kozak KR, Crews BC, Morrow JD, Wang LH, Ma YH, Weinander R, Jakobsson PJ, &, Marnett LJ, (2002) Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277, 44877-44885. (Pubitemid 36159083)
76. Anantharaman V, &, Aravind L, (2003) Evolutionary history, structural features and biochemical diversity of the NlpC/P60 superfamily of enzymes. Genome Biol 4, R11.
77. Shinohara N, Uyama T, Jin X-H, Tsuboi K, Tonai T, Houchi H, &, Ueda N, (2011) Enzymological analysis of the tumor suppressor A-C1 reveals a novel group of phospholipid-metabolizing enzymes. J Lipid Res 52, 1927-1935.
78. Hajnal A, Klemenz R, &, Schäfer R, (1994) Subtraction cloning of H-rev107, a gene specifically expressed in H-ras resistant fibroblasts. Oncogene 9, 479-490. (Pubitemid 24041527)
79. Akiyama H, Hiraki Y, Noda M, Shigeno C, Ito H, &, Nakamura T, (1999) Molecular cloning and biological activity of a novel Ha-Ras suppressor gene predominantly expressed in skeletal muscle, heart, brain, and bone marrow by differential display using clonal mouse EC cells, ATDC5. J Biol Chem 274, 32192-32197.
80. Shyu R-Y, Hsieh Y-C, Tsai F-M, Wu C-C, &, Jiang S-Y, (2009) Cloning and functional characterization of the HRASLS2 gene. Amino Acids 35, 129-137.
81. Disepio D, Ghosn C, Eckert RL, Deucher A, Robinson N, Duvic M, Chandraratna RA, &, Nagpal S, (1998) Identification and characterization of a retinoid-induced class II tumor suppressor/growth regulatory gene. Proc Natl Acad Sci USA 95, 14811-14815. (Pubitemid 29003712)
82. 2+-independent phosphatidylethanolamine N-acyltransferases. Biochim Biophys Acta 1791, 32-38.
83. 1/2 of the thiol hydrolase-type. J Lipid Res 50, 685-693.
84. Uyama T, Jin X-H, Tsuboi K, Tonai T, &, Ueda N, (2009b) Characterization of the human tumor suppressors TIG3 and HRASLS2 as phospholipid-metabolizing enzymes. Biochim Biophys Acta 1791, 1114-1124.
85. Golczak M, Kiser PD, Sears AE, Lodowski DT, Blaner WS, &, Palczewski K, (2012) Structural basis for the acyltransferase activity of lecithin:retinol acyltransferase-like proteins. J Biol Chem 287, 23790-23807.
86. Uyama T, Ikematsu N, Inoue M, Shinohara N, Jin X-H, Tsuboi K, Tonai T, Tokumura A, &, Ueda N, (2012a) Generation of N-acylphosphatidylethanolamine by members of the phospholipase A/acyltransferase (PLA/AT) family. J Biol Chem 287, 31905-31919.
87. 2 (AdPLA). J Biol Chem 283, 25428-25436.
88. 2 containing a Cys-His-His catalytic triad. J Biol Chem 287, 35260-35274.
89. Hummasti S, Hong C, Bensinger SJ, &, Tontonoz P, (2008) HRASLS3 is a PPARγ-selective target gene that promotes adipocyte differentiation. J Lipid Res 49, 2535-2544.
90. Jaworski K, Ahmadian M, Duncan RE, Sarkadi-Nagy E, Varady KA, Hellerstein MK, Lee HY, Samuel VT, Shulman GI, Kim KH, et al,. (2009) AdPLA ablation increases lipolysis and prevents obesity induced by high-fat feeding or leptin deficiency. Nat Med 15, 159-168.
91. Uyama T, Ichi I, Kono N, Inoue A, Tsuboi K, Jin X-H, Araki N, Aoki J, Arai H, &, Ueda N, (2012b) Regulation of peroxisomal lipid metabolism by catalytic activity of tumor suppressor H-rev107. J Biol Chem 287, 2706-2718.
92. Ren X, Lin J, Jin C, &, Xia B, (2010) Solution structure of the N-terminal catalytic domain of human H-REV107-a novel circular permutated NlpC/P60 domain. FEBS Lett 584, 4222-4226.
93. Natarajan V, Schmid PC, Reddy PV, &, Schmid HHO, (1984) Catabolism of N-acylethanolamine phospholipids by dog brain preparations. J Neurochem 42, 1613-1619. (Pubitemid 14085647)
94. 2 and lysophospholipase D. Biochem J 380, 749-756. (Pubitemid 38850516)
95. Simon GM, &, Cravatt BF, (2006) Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for α/β-hydrolase 4 in this pathway. J Biol Chem 281, 26465-26472. (Pubitemid 44401855)
96. Simon GM, &, Cravatt BF, (2008) Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. J Biol Chem 283, 9341-9349.
97. Simpson CD, Hurren R, Kasimer D, MacLean N, Eberhard Y, Ketela T, Moffat J, &, Schimmer AD, (2012) A genome wide shRNA screen identifies α/β hydrolase domain containing 4 (ABHD4) as a novel regulator of anoikis resistance. Apoptosis 17, 666-678.
98. Zheng B, Chen D, &, Farquhar MG, (2000) MIR16, a putative membrane glycerophosphodiester phosphodiesterase, interacts with RGS16. Proc Natl Acad Sci USA 97, 3999-4004. (Pubitemid 30226076)
99. Zheng B, Berrie CP, Corda D, &, Farquhar MG, (2003) GDE1/MIR16 is a glycerophosphoinositol phosphodiesterase regulated by stimulation of G protein-coupled receptors. Proc Natl Acad Sci USA 100, 1745-1750. (Pubitemid 36254519)
100. Simon GM, &, Cravatt BF, (2010) Characterization of mice lacking candidate N-acyl ethanolamine biosynthetic enzymes provides evidence for multiple pathways that contribute to endocannabinoid production in vivo. Mol BioSyst 6, 1411-1418.
101. Kopp F, Komatsu T, Nomura DK, Trauger SA, Thomas JR, Siuzdak G, Simon GM, &, Cravatt BF, (2010) The glycerophospho metabolome and its influence on amino acid homeostasis revealed by brain metabolomics of GDE1(-/-) mice. Chem Biol 17, 831-840.
102. Tsuboi K, Ikematsu N, Uyama T, Deutsch DG, Tokumura A, &, Ueda N, (2013) Biosynthetic pathways of bioactive N-acylethanolamines in brain. CNS Neurol Disord Drug Targets, Epub-20130204-9.
103. Astarita G, Ahmed F, &, Piomelli D, (2008) Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain. J Lipid Res 49, 48-57.
104. Schmid PC, Reddy PV, Natarajan V, &, Schmid HHO, (1983) Metabolism of N-acylethanolamine phospholipids by a mammalian phosphodiesterase of the phospholipase D type. J Biol Chem 258, 9302-9306.
105. Liu J, Bátkai S, Pacher P, Harvey-White J, Wagner JA, Cravatt BF, Gao B, &, Kunos G, (2003) Lipopolysaccharide induces anandamide synthesis in macrophages via CD14/MAPK/phosphoinositide 3-kinase/NF-κB independently of platelet-activating factor. J Biol Chem 278, 45034-45039. (Pubitemid 37377264)
106. Liu J, Wang L, Harvey-White J, Huang BX, Kim HY, Luquet S, Palmiter RD, Krystal G, Rai R, Mahadevan A, et al,. (2008) Multiple pathways involved in the biosynthesis of anandamide. Neuropharmacology 54, 1-7. (Pubitemid 350299395)
107. Ueda N, Yamanaka K, Terasawa Y, &, Yamamoto S, (1999) An acid amidase hydrolyzing anandamide as an endogenous ligand for cannabinoid receptors. FEBS Lett 454, 267-270. (Pubitemid 29304613)
108. Ueda N, Yamanaka K, &, Yamamoto S, (2001b) Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance. J Biol Chem 276, 35552-35557.
109. Tsuboi K, Sun Y-X, Okamoto Y, Araki N, Tonai T, &, Ueda N, (2005) Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase. J Biol Chem 280, 11082-11092. (Pubitemid 40418412)
110. Tsuboi K, Takezaki N, &, Ueda N, (2007a) The N-acylethanolamine- hydrolyzing acid amidase (NAAA). Chem Biodivers 4, 1914-1925. (Pubitemid 47377209)
111. Ueda N, Tsuboi K, &, Uyama T, (2010b) N-Acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA). Prog Lipid Res 49, 299-315.
112. Hong S-B, Li C-M, Rhee H-J, Park J-H, He X, Levy B, Yoo OJ, &, Schuchman EH, (1999) Molecular cloning and characterization of a human cDNA and gene encoding a novel acid ceramidase-like protein. Genomics 62, 232-241. (Pubitemid 30053939)
113. Zhao L-Y, Tsuboi K, Okamoto Y, Nagahata S, &, Ueda N, (2007) Proteolytic activation and glycosylation of N-acylethanolamine-hydrolyzing acid amidase, a lysosomal enzyme involved in the endocannabinoid metabolism. Biochim Biophys Acta 1771, 1397-1405. (Pubitemid 350217097)
114. West JM, Zvonok N, Whitten KM, Wood JT, &, Makriyannis A, (2012a) Mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase. J Proteome Res 11, 972-981.
115. Shtraizent N, Eliyahu E, Park J-H, He X, Shalgi R, &, Schuchman EH, (2008) Autoproteolytic cleavage and activation of human acid ceramidase. J Biol Chem 283, 11253-11259.
116. Armirotti A, Romeo E, Ponzano S, Mengatto L, Dionisi M, Karacsonyi C, Bertozzi F, Garau G, Tarozzo G, Reggiani A, et al,. (2012) β-Lactones inhibit N-acylethanolamine acid amidase by S-acylation of the catalytic N-terminal cysteine. ACS Med Chem Lett 3, 422-426.
117. West JM, Zvonok N, Whitten KM, Vadivel SK, Bowman AL, &, Makriyannis A, (2012b) Biochemical and mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase inhibition. PLoS One 7, e43877.
118. Sun Y-X, Tsuboi K, Zhao L-Y, Okamoto Y, Lambert DM, &, Ueda N, (2005) Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages. Biochim Biophys Acta 1736, 211-220. (Pubitemid 41423705)
119. Tsuboi K, Zhao L-Y, Okamoto Y, Araki N, Ueno M, Sakamoto H, &, Ueda N, (2007b) Predominant expression of lysosomal N-acylethanolamine-hydrolyzing acid amidase in macrophages revealed by immunochemical studies. Biochim Biophys Acta 1771, 623-632. (Pubitemid 46670796)
120. Wang J, Zhao L-Y, Uyama T, Tsuboi K, Wu X-X, Kakehi Y, &, Ueda N, (2008b) Expression and secretion of N-acylethanolamine-hydrolysing acid amidase in human prostate cancer cells. J Biochem 144, 685-690.
121. Tai T, Tsuboi K, Uyama T, Masuda K, Cravatt BF, Houchi H, &, Ueda N, (2012) Endogenous molecules stimulating N-acylethanolamine-hydrolyzing acid amidase (NAAA). ACS Chem Neurosci 3, 379-385.
122. Petrosino S, Iuvone T, &, Di Marzo V, (2010) N-Palmitoyl- ethanolamine: biochemistry and new therapeutic opportunities. Biochimie 92, 724-727.
123. Vandevoorde S, Tsuboi K, Ueda N, Jonsson K-O, Fowler CJ, &, Lambert DM, (2003) Esters, retroesters and retroamide of palmitic acid: pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase. J Med Chem 46, 4373-4376. (Pubitemid 37238741)
124. Tsuboi K, Hilligsmann C, Vandevoorde S, Lambert DM, &, Ueda N, (2004) N-Cyclohexanecarbonylpentadecylamine: a selective inhibitor of the acid amidase hydrolysing N-acylethanolamines, as a tool to distinguish acid amidase from fatty acid amide hydrolase. Biochem J 379, 99-106. (Pubitemid 38491364)
125. Solorzano C, Zhu C, Battista N, Astarita G, Lodola A, Rivara S, Mor M, Russo R, Maccarrone M, Antonietti F, et al,. (2009) Selective N-acylethanolamine-hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation. Proc Natl Acad Sci USA 106, 20966-20971.
126. Solorzano C, Antonietti F, Duranti A, Tontini A, Rivara S, Lodola A, Vacondio F, Tarzia G, Piomelli D, &, Mor M, (2010) Synthesis and structure-activity relationships of N-(2-oxo-3-oxetanyl)amides as N-acylethanolamine-hydrolyzing acid amidase inhibitors. J Med Chem 53, 5770-5781.
127. Saturnino C, Petrosino S, Ligresti A, Palladino C, De Martino G, Bisogno T, &, Di Marzo V, (2010) Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase. Bioorg Med Chem Lett 20, 1210-1213.
128. Duranti A, Tontini A, Antonietti F, Vacondio F, Fioni A, Silva C, Lodola A, Rivara S, Solorzano C, Piomelli D, et al,. (2012) N-(2-Oxo-3-oxetanyl) carbamic acid esters as N-acylethanolamine acid amidase inhibitors: synthesis and structure-activity and structure-property relationships. J Med Chem 55, 4824-4836.
129. Yamano Y, Tsuboi K, Hozaki Y, Takahashi K, Jin X-H, Ueda N, &, Wada A, (2012) Lipophilic amines as potent inhibitors of N-acylethanolamine- hydrolyzing acid amidase. Bioorg Med Chem 20, 3658-3665.
130. Li Y, Yang L, Chen L, Zhu C, Huang R, Zheng X, Qiu Y, &, Fu J, (2012) Design and synthesis of potent N-acylethanolamine-hydrolyzing acid amidase (NAAA) inhibitor as anti-inflammatory compounds. PLoS One 7, e43023.
131. Prescott SM, &, Majerus PW, (1983) Characterization of 1,2-diacylglycerol hydrolysis in human platelets. Demonstration of an arachidonoyl-monoacylglycerol intermediate. J Biol Chem 258, 764-769. (Pubitemid 13139323)
132. Sugiura T, Kishimoto S, Oka S, &, Gokoh M, (2006) Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Prog Lipid Res 45, 405-446.
133. Kano M, Ohno-Shosaku T, Hashimotodani Y, Uchigashima M, &, Watanabe M, (2009) Endocannabinoid-mediated control of synaptic transmission. Physiol Rev 89, 309-380.
134. Fukami K, Inanobe S, Kanemaru K, &, Nakamura Y, (2010) Phospholipase C is a key enzyme regulating intracellular calcium and modulating the phosphoinositide balance. Prog Lipid Res 49, 429-437.
135. Bisogno T, Melck D, De Petrocellis L, &, Di Marzo V, (1999) Phosphatidic acid as the biosynthetic precursor of the endocannabinoid 2-arachidonoylglycerol in intact mouse neuroblastoma cells stimulated with ionomycin. J Neurochem 72, 2113-2119. (Pubitemid 29186018)
136. Oka S, Yanagimoto S, Ikeda S, Gokoh M, Kishimoto S, Waku K, Ishima Y, &, Sugiura T, (2005) Evidence for the involvement of the cannabinoid CB2 receptor and its endogenous ligand 2-arachidonoylglycerol in 12-O-tetradecanoylphorbol-13-acetate-induced acute inflammation in mouse ear. J Biol Chem 280, 18488-18497. (Pubitemid 41389098)
137. 1 followed by lysophosphoinositide-specific phospholipase C in rat brain. J Neurochem 61, 1874-1881. (Pubitemid 23317215)
138. Tsutsumi T, Kobayashi T, Ueda H, Yamauchi E, Watanabe S, &, Okuyama H, (1994) Lysophosphoinositide-specific phospholipase C in rat brain synaptic plasma membranes. Neurochem Res 19, 399-406. (Pubitemid 24286606)
139. Nakane S, Oka S, Arai S, Waku K, Ishima Y, Tokumura A, &, Sugiura T, (2002) 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch Biochem Biophys 402, 51-58. (Pubitemid 34848294)
140. Okazaki T, Sagawa N, Okita JR, Bleasdale JE, MacDonald PC, &, Johnston JM, (1981) Diacylglycerol metabolism and arachidonic acid release in human fetal membranes and decidua vera. J Biol Chem 256, 7316-7321. (Pubitemid 11021809)
141. Chau LY, &, Tai HH, (1981) Release of arachidonate from diglyceride in human platelets requires the sequential action of a diglyceride lipase and a monoglyceride lipase. Biochem Biophys Res Commun 100, 1688-1695. (Pubitemid 11026067)
142. Bisogno T, Howell F, Williams G, Minassi A, Cascio MG, Ligresti A, Matias I, Schiano-Moriello A, Paul P, Williams EJ, et al,. (2003) Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol 163, 463-468. (Pubitemid 37429860)
143. Jung KM, Astarita G, Zhu C, Wallace M, Mackie K, &, Piomelli D, (2007) A key role for diacylglycerol lipase-alpha in metabotropic glutamate receptor-dependent endocannabinoid mobilization. Mol Pharmacol 72, 612-621. (Pubitemid 47347296)
144. Tanimura A, Yamazaki M, Hashimotodani Y, Uchigashima M, Kawata S, Abe M, Kita Y, Hashimoto K, Shimizu T, Watanabe M, et al,. (2010) The endocannabinoid 2-arachidonoylglycerol produced by diacylglycerol lipase α mediates retrograde suppression of synaptic transmission. Neuron 65, 320-327.
145. Gao Y, Vasilyev DV, Goncalves MB, Howell FV, Hobbs C, Reisenberg M, Shen R, Zhang MY, Strassle BW, Lu P, et al,. (2010) Loss of retrograde endocannabinoid signaling and reduced adult neurogenesis in diacylglycerol lipase knock-out mice. J Neurosci 30, 2017-2024.
146. Hoover HS, Blankman JL, Niessen S, &, Cravatt BF, (2008) Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling. Bioorg Med Chem Lett 18, 5838-5841.
147. Bisogno T, Cascio MG, Saha B, Mahadevan A, Urbani P, Minassi A, Appendino G, Saturnino C, Martin B, Razdan R, et al,. (2006) Development of the first potent and specific inhibitors of endocannabinoid biosynthesis. Biochim Biophys Acta 1761, 205-212.
148. Bisogno T, Burston JJ, Rai R, Allarà M, Saha B, Mahadevan A, Razdan RK, Wiley JL, &, Di Marzo V, (2009) Synthesis and pharmacological activity of a potent inhibitor of the biosynthesis of the endocannabinoid 2-arachidonoylglycerol. ChemMedChem 4, 946-950.
149. Min R, Testa-Silva G, Heistek TS, Canto CB, Lodder JC, Bisogno T, Di Marzo V, Brussaard AB, Burnashev N, &, Mansvelder HD, (2010) Diacylglycerol lipase is not involved in depolarization-induced suppression of inhibition at unitary inhibitory connections in mouse hippocampus. J Neurosci 30, 2710-2715.
150. Fowler CJ, (2012) Monoacylglycerol lipase-a target for drug development? Br J Pharmacol 166, 1568-1585.
151. Tornqvist H, &, Belfrage P, (1976) Purification and some properties of a monoacylglycerol-hydrolyzing enzyme of rat adipose tissue. J Biol Chem 251, 813-819.
152. Karlsson M, Contreras JA, Hellman U, Tornqvist H, &, Holm C, (1997) cDNA cloning, tissue distribution, and identification of the catalytic triad of monoglyceride lipase. Evolutionary relationship to esterases, lysophospholipases, and haloperoxidases. J Biol Chem 272, 27218-27223. (Pubitemid 27452682)
153. Labar G, Wouters J, &, Lambert DM, (2010a) A review on the monoacylglycerol lipase: at the interface between fat and endocannabinoid signalling. Curr Med Chem 17, 2588-2607.
154. Labar G, Bauvois C, Borel F, Ferrer J-L, Wouters J, &, Lambert DM, (2010b) Crystal structure of the human monoacylglycerol lipase, a key actor in endocannabinoid signaling. ChemBioChem 11, 218-227.
155. Bertrand T, Augé F, Houtmann J, Rak A, Vallée F, Mikol V, Berne PF, Michot N, Cheuret D, Hoornaert C, et al,. (2010) Structural basis for human monoglyceride lipase inhibition. J Mol Biol 396, 663-673.
156. Dinh TP, Carpenter D, Leslie FM, Freund TF, Katona I, Sensi SL, Kathuria S, &, Piomelli D, (2002) Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99, 10819-10824 (erratum appears in Proc Natl Acad Sci USA 99, 13961).
157. Tanimura A, Uchigashima M, Yamazaki M, Uesaka N, Mikuni T, Abe M, Hashimoto K, Watanabe M, Sakimura K, &, Kano M, (2012) Synapse type-independent degradation of the endocannabinoid 2-arachidonoylglycerol after retrograde synaptic suppression. Proc Natl Acad Sci USA 109, 12195-12200.
158. Minkkilä A, Saario S, &, Nevalainen T, (2010) Discovery and development of endocannabinoid-hydrolyzing enzyme inhibitors. Curr Top Med Chem 10, 828-858.
159. Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavon FJ, Serrano AM, Selley DE, Parsons LH, et al,. (2009b) Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol 5, 37-44.
160. Chang JW, Niphakis MJ, Lum KM, Cognetta AB III, Wang C, Matthews ML, Niessen S, Buczynski MW, Parsons LH, &, Cravatt BF, (2012) Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates. Chem Biol 19, 579-588.
161. Schlosburg JE, Blankman JL, Long JZ, Nomura DK, Pan B, Kinsey SG, Nguyen PT, Ramesh D, Booker L, Burston JJ, et al,. (2010) Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nat Neurosci 13, 1113-1119.
162. Chanda PK, Gao Y, Mark L, Btesh J, Strassle BW, Lu P, Piesla MJ, Zhang MY, Bingham B, Uveges A, et al,. (2010) Monoacylglycerol lipase activity is a critical modulator of the tone and integrity of the endocannabinoid system. Mol Pharmacol 78, 996-1003.
163. Taschler U, Radner FP, Heier C, Schreiber R, Schweiger M, Schoiswohl G, Preiss-Landl K, Jaeger D, Reiter B, Koefeler HC, et al,. (2011) Monoglyceride lipase deficiency in mice impairs lipolysis and attenuates diet-induced insulin resistance. J Biol Chem 286, 17467-17477.
164. Nomura DK, Morrison BE, Blankman JL, Long JZ, Kinsey SG, Marcondes MC, Ward AM, Hahn YK, Lichtman AH, Conti B, et al,. (2011) Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation. Science 334, 809-813.
165. Nomura DK, Long JZ, Niessen S, Hoover HS, Ng SW, &, Cravatt BF, (2010) Monoacylglycerol lipase regulates a fatty acid network that promotes cancer pathogenesis. Cell 140, 49-61.
166. Savinainen JR, Saario SM, &, Laitinen JT, (2012) The serine hydrolases MAGL, ABHD6 and ABHD12 as guardians of 2-arachidonoylglycerol signalling through cannabinoid receptors. Acta Physiol (Oxf) 204, 267-276 [erratum appears in Acta Physiol (Oxf) 204, 460].
167. Navia-Paldanius D, Savinainen JR, &, Laitinen JT, (2012) Biochemical and pharmacological characterization of human α/β-hydrolase domain containing 6 (ABHD6) and 12 (ABHD12). J Lipid Res 53, 2413-2424.
168. Marrs WR, Blankman JL, Horne EA, Thomazeau A, Lin YH, Coy J, Bodor AL, Muccioli GG, Hu SS, Woodruff G, et al,. (2010) The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nat Neurosci 13, 951-957.
169. Marrs WR, Horne EA, Ortega-Gutierrez S, Cisneros JA, Xu C, Lin YH, Muccioli GG, Lopez-Rodriguez ML, &, Stella N, (2011) Dual inhibition of α/β-hydrolase domain 6 and fatty acid amide hydrolase increases endocannabinoid levels in neurons. J Biol Chem 286, 28723-28728.
170. Fiskerstrand T, H'mida-Ben Brahim D, Johansson S, M'zahem A, Haukanes BI, Drouot N, Zimmermann J, Cole AJ, Vedeler C, Bredrup C, et al,. (2010) Mutations in ABHD12 cause the neurodegenerative disease PHARC: an inborn error of endocannabinoid metabolism. Am J Hum Genet 87, 410-417.
171. Kozak KR, &, Marnett LJ, (2002) Oxidative metabolism of endocannabinoids. Prostaglandins Leukot Essent Fatty Acids 66, 211-220. (Pubitemid 34743596)
172. Rouzer CA, &, Marnett LJ, (2008) Non-redundant functions of cyclooxygenases: oxygenation of endocannabinoids. J Biol Chem 283, 8065-8069.
173. Duggan KC, Hermanson DJ, Musee J, Prusakiewicz JJ, Scheib JL, Carter BD, Banerjee S, Oates JA, &, Marnett LJ, (2011) (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2. Nat Chem Biol 7, 803-809.
174. Blankman JL, Long JZ, Trauger SA, Siuzdak G, &, Cravatt BF, (2013) ABHD12 controls brain lysophosphatidylserine pathways that are deregulated in a murine model of the neurodegenerative disease PHARC. Proc Natl Acad Sci USA 110, 1500-1505.