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Chapter 5
References
Ahn K, Johnson DS, Fitzgerald LR, Liimatta M, Arendse A, Stevenson T, Lund ET, Nugent RA, Nomanbhoy TK, Alexander JP, Cravatt BF (2007). "Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity".Biochemistry 46 (45): 13019– 30.
Alger BE (2002). Retrograde signaling in the regulation of synaptic transmission: focus on endocannabinoids. Prog Neurobiol 68(4):247-86.
Alhouayek M and Muccioli GG (2014).COX-2 derived endocannabinoid metabolites as novel inflammatory mediators. Trends Pharmacol Sci 35(6):284-92
Anand P, Whiteside G, Fowler CJ, Hohmann AG (2009). Targeting CB2 receptors and the endocannabinoid system for the treatment of pain. Brain Res Rev. 60(1):255-66
Atwood BK and Mackie K (2010). CB2: a cannabinoid receptor with an identity crisis. Br J
Pharmacol. 160(3):467-79
Bagavandoss P and Grimshaw S (2010). Temporal and spatial distribution of the cannabinoid receptors (CB1, CB2) and fatty acid amide hydroxylase in the rat ovary. Anat
Rec (Hoboken).293(8):1425-32.
Beltramo M, Stella N, Calignano A, Lin S.Y, Makriyannis A, Piomelli D (1997). Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 277, 1094±1097.
Bertini S, Parkkari T, Savinainen JR, Arena C, Saccomanni G, Saguto S, Ligresti A, Allarà M, Bruno A, Marinelli L, Di Marzo V, Novellino E, Manera C, Macchia M (2014). Synthesis, biological activity and molecular modeling of new biphenylic carboxamides as potent and selective CB2 receptor ligands. Eur J Med Chem. 90C:526-536
Blankman J. L, Simon G. M, Cravatt B. F (2007). A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2- arachidonoylglycerol. Chem. Biol. 14, 1347-56.
Blankman JL and Cravatt BF (2013). Chemical probes of endocannabinoid metabolism.
~ 74 ~
Boger DL, Fecik RA, Patterson JE, Miyauchi H, Patricelli MP, Cravatt BF 2000. Fatty acid amide hydrolase substrate specificity. Bioorg Med Chem Lett. 10:2613
Carlisle SJ, Marciano Cabral F, Staab A, Ludwick C, Cabral GA (2002). Differential expression of the CB2 cannabinoid receptor by rodent macrophages and macrophage-like cells in relation to cell activation. Int Immunopharmacol 2(1):69-82.
Chen R, Zhang J, Wu Y, Wang D, Feng G, Tang YP, Teng Z, Chen C. (2012) Monoacylglycerol lipase is a therapeutic target for Alzheimer’s disease. Cell Rep 2: 1329– 1339.
Chicca A, Marazzi J, Nicolussi S, Gertsch J (2012-a). Evidence for bidirectional endocannabinoid transport across cell membranes. J Biol Chem 287(41):34660-82
Chicca A, Marazzi J, Gertsch J (201b). The antinociceptive triterpene β-amyrin inhibits 2-arachidonoylglycerol (2-AG) hydrolysis without directly targeting cannabinoid receptors. Br
J Pharmacol 167(8):1596-608
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(6604):83-7.
Cravatt B. F, Demarest K, Patricelli M. P, Bracey M. H, Giang D. K, Martin B. R, Lichtman A. H (2001). Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase. Proc. Natl. Acad. Sci. U.S.A. 98, 9371-6.
Day T. A, Rakhshan F, Deutsch D. G, Barker E. L (2001). Role of fatty acid amide hydrolase in the transport of the endogenous cannabinoid anandamide. Mol Pharmacol 2001 59: 1369–1375.
Devane WA, Dysarz FA 3rd, Johnson MR, Melvin LS, Howlett AC (1988). Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol 34(5):605-13.
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(5090):1946-9.
Deutsch DG, Chin SA. (1993). Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol. 46(5): 791–6.
~ 75 ~
Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z, Howlett A. (1997). Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol. 53(3): 255–60.
Deutsch D. G, Kunz J. S, Abumrad N, Hillard C. C (1999). Cellular uptake of anandamide is inhibited by blocking its degradation with FAAH inhibitors. 1999 Symposium on the
Cannabinoids,; p. 12.
De Petrocellis L, Melck D, Ueda N, Maurelli S, Kurahashi Y, Yamamoto S, Marino G, Di Marzo V (1997). "Novel inhibitors of brain, neuronal, and basophilic anandamide amidohydrolase". Biocehm Biophys Res Commun 231 (1): 82–8.
De Petrocellis L, Cascio MG, Di Marzo V (2004). The endocannabinoid system: a general view and latest additions. Br J Pharmacol 141(5):765-74.
De Petrocellis L, Di Marzo V (2009). Role of endocannabinoids and endovanilloids in Ca2+ signalling. Cell Calcium 45(6):611-24.
Di Marzo V, Fontana A, Cadas H, Schinelli S, Cimino G, Schwartz JC, Piomelli D (1994). Formation and inactivation of endogenous cannabinoid anandamide in central neurons.
Nature 15;372(6507):686-91.
Di Marzo V, Bisogno T, Melck D, Ross R, Brockie H, Stevenson L, Pertwee R.G, De Petrocellis L (1998-a). Interaction between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett. 436, 449±454.
Di Marzo V, Bisogno T, Sugiura T, Melck D, De Petrocellis L (1998-b). The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide. Biochem. J. 331, 15±19.
Di Marzo V, Bisogno T, De Petrocellis L, Melck D, Orlando P, Wagner J.A, Kunos G (1999). Biosynthesis and inactivation of the endocannabinoid 2-arachidonoylglycerol in circulating and tumoral macrophages. Eur. J. Biochem. 264, 258±267.
Di Marzo V, Bisogno T, De Petrocellis L (2000). Endocannabinoids: new targets for drug development. Curr. Pharm. Design 6, 1361±1380
Di Marzo V, Bifulco M, De Petrocellis L (2004). The endocannabinoid system and its therapeutic exploitation. Nat Rev Drug Discov 3(9):771-84
Dinh TP, Freund TF, Piomelli D (200a). A role for monoglyceride lipase in 2-arachidonoylglycerol inactivation. Chem Phys Lipids 121(1-2):149-58.
~ 76 ~
Dinh T. P, Carpenter D, Leslie F. M, Freund T. F, Katona I, Sensi S. L, Kathuria S, Piomelli D, (2002-b). Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc.
Natl. Acad. Sci. U. S. A 99, 10819-24.
Facci L, Dal Toso R, Romanello S, Buriani A, Skaper SD, Leon A (1995). Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc Natl Acad Sci U S A 92(8):3376-80.
Ferrarini PL, Calderone V, Cavallini T, Manera C, Saccomanni G, Pani L, Ruiu S, Gessa GL (2004). Synthesis and biological evaluation of 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives as new ligands of cannabinoid receptors. Bioorg Med Chem. 12(8):1921-33.
Fezza F, Bisogno T, Minassi A, Appendino G, Mechoulam R, Di Marzo V (2002). Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues. FEBS Lett 513(2-3):294-8.
Filppula S, Yaddanapudi S, Mercier R, Xu W, Pavlopoulos S, Makriyannis A (2004). Purification and mass spectro scopic analysis of human CB2 cannabinoid receptor expressed in the baculovirus system. J Pept Res 64(6): 225-36.
Fiskerstrand T, H’mida-Ben Brahim D, Johansson S, M’zahem A, Haukanes B.I, Drouot N, Zimmermann J, Cole A.J, Vedeler C, Bredrup C, Assoum M, Tazir M,Klockgether T, Hamri A, Steen VM, Boman H, Bindoff LA, Koenig M, Knappskog PM. (2010). Mutations in ABHD12 cause the neurodegenerative disease PHARC: an inborn error of endocannabinoid metabolism. Am J Hum Genet 87, 410–417.
Fowler CJ, Jonsson KD, Tiger G (2001). Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide. Biochem Pharmacol 62:517
Fowler C. J (2013). Transport of endocannabinoids across the plasma membrane and within the cell. FEBS J. 280(9):1895-904
Freund TF, Katona I, Piomelli D (2003). Role of endogenous cannabinoids in synaptic signaling. Physiol Rev 83(3):1017-66.
Galiegue S, Mary S, Marchand J, Dussossoy D, Carriere D, Carayon P, Bouaboula M, Shire D, Le Fur G, Casellas P (1995). Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem 232(1):54-61.
Gatta L, Piscitelli F, Giordano C, Boccella S, Lichtman A, Maione S, Di Marzo V (2007). Discovery of prostamide F2α and its role in inflammatory pain and dorsal horn nociceptive neuron hyperexcitability. PLoS One. 7(2):e31111
~ 77 ~
Gerard CM, Mollereau C, Vassart G, Parmentier M (1991). Molecular cloning of a human cannabinoid receptor which is also expressed in testis. Biochem J 279 ( Pt 1):129-34.
Ghafouri N, Tiger G, Razdan R. K, Mahadevan A, Pertwee R. G, Martin B. R, Fowler C. J (2004). Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2- arachidonoylglycerol. Br. J. Pharmacol 143, 774-84.
Gonsiorek W, Lunn C, Fan X, Narula S, Lundell D, Hipkin RW (2000). Endocannabinoid 2-arachidonyl glycerol is a full agonist through human type 2 cannabinoid receptor: antagonism by anandamide. Mol Pharmacol 57(5): 1045-50.
Guindon J, Hohmann AG (2008). Cannabinoid CB2 receptors: a therapeutic target for the treatment of inflammatory and neuropathic pain. Br J Pharmacol 153(2):319-34
Hanus L, Abu-Lafi S, Fride E, Breuer A, Vogel Z, Shalev DE, Kustanovich I, Mechoulam R (2001). 2-arachidonylglyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc Natl Acad Sci U S A 98(7):3662-5.
Hashimotodani Y, Ohno-Shosaku T, Tsubokawa H, Ogata H, Emoto K, Maejima T, Araishi K, Shin HS, Kano M (2005). Phospholipase Cbeta serves as a coincidence detector through its Ca2+ dependency for triggering retrograde endocannabinoid signal. Neuron 45(2):257-68.
DJ Hermanson, ND Hartley, J Gamble-George, N Brown, BC Shonesy, PJ Kingsley, RJ Colbran, J Reese, LJ Marnett, S Patel (2013). Substrate-selective COX-2 inhibition decreases anxiety via endocannabinoid activation. Nat. Neurosci. 1291–1298.
Hillard C. J, Wilkison D. M, Edgemond W. S, Campbell W. B. (1995) Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain. Biochim Biophys Acta 1257: 249–256.
Hillard CJ, Edgemond WS, Jarrahian A, Campbell WB (1997). Accumulation of N-arachidonoylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion. J. Neurochem. 69, 631–638
Hillard C.J, Jarrahian A (2000). The movement of N-arachidonoylethanolamine (anandamide) across cellular membranes. Chem. Phys. Lipids 108, 123±134.
Howlett AC, Barth F, Bonner TI, Cabral G, Casellas P, Devane WA, Felder CC, Herkenham M, Mackie K, Martin BR, Mechoulam R, Pertwee RG (2002). International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev 54(2):161-202.
Huang SM, Walker JM (2006). Enhancement of spontaneous and heat-evoked activity in spinal nociceptive neurons by the endovanilloid/endocannabinoidN-arachidonoyldopamine (NADA). J Neurophysiol 95(2): 1207-12.
~ 78 ~
Hungund BL, Vinod KY, Kassir SA, Basavarajappa BS, Yalamanchili R, Cooper TB, Mann JJ, Arango V (2004). Upregulation of CB1 receptors and agonist-stimulated [35S]GTPgammaS binding in the prefrontal cortex of depressed suicide victims. Mol
Psychiatry 9(2):184-90.
Kano M, Ohno-Shosaku T, Hashimotodani Y, Uchigashima M, Watanabe M (2009). Endocannabinoid mediated control of synaptic transmission. Physiol Rev 89(1):309-80.
Koutek B, Prestwich GD, Howlett AC, Chin SA, Salehani D, Akhavan N, Deutsch DG (1994). Inhibitors of arachidonoyl ethanolamide hydrolysis.. J Biol Chem. 269 (37): 22937– 40
Kozłowska H, Baranowska M, Schlicker E, Kozłowski M, Laudanski J, Malinowska B (2008). Virodhamine relaxes the human pulmonary artery through the endothelial cannabinoid receptor and indirectly through a COX product. Br J Pharmacol 155(7):1034-42.
Jarrahian A, Manna S, Edgemond W.S, Campbell W.B, Hillard C.J (2000). Structure-activity relationships among anandamide head group analogs for the anandamide transporter. J.
Neurochem. 74, 2597±2606.
Idris AI, Sophocleous A, Landao-Bassonga E, van't Hof RJ, Ralston SH (2008). Regulation of bone mass, osteoclast function, and ovariectomy-induced bone loss by the type 2 cannabinoid receptor. Endocrinology. 149(11):5619-26
Labar G, Bauvois C, Muccioli G. G, Wouters J, Lambert D. M (2007). Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling. Chembiochem. 8, 1293-7.
Labari G, Wouters J, Lambert D.M (2010). A Review on the Monoacylglycerol Lipase: At the Interface Between Fat and Endocannabinoid Signalling. Curr. Med. Chem 17, 2588-2607
La Rana G, Russo R, Campolongo P, Bortolato M, Mangieri RA, Cuomo V, Iacono A, Raso GM, Meli R, Piomelli D, Calignano A (2006). Modulation of neuropathic and inflammatory pain by the endocannabinoid transport inhibitor AM404 [N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide]. J Pharmacol Exp Ther 317(3):1365-71
Leggett JD, Aspley S, Beckett SR, D'Antona AM, Kendall DA (2004). Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors. Br J Pharmacol 141(2):253-62.
Li F, Fei X, Xu J, Ji C (2009). An unannotated alpha/beta hydrolase superfamily member, ABHD6 differentially expressed among cancer cell lines. Mol Biol Rep 36, 691–696.
~ 79 ~
Liu J, Wang L, Harvey-White J, Huang B. X, Kim H. Y, Luquet S, Palmiter R. D, Krystal G, Rai R, Mahadevan A, Razdan R. K, Kunos G, (2008). Multiple pathways involved in the biosynthesis of anandamide. Neuropharmacology 54, 1-7.
Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavón FJ, Serrano AM, Selley DE, Parsons LH, Lichtman AH, Cravatt BF. (2009-a). Selective blockade of 2- arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol 5: 37–44.
Long J. Z, Nomura D. K, Cravatt B. F (2009-b). Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism. Chem.
Biol. 16, 744-53.
Lucchesi V, Parkkari T, Savinainen JR, Malfitano AM, Allarà M, Bertini S, Castelli F, Del Carlo S, Laezza C, Ligresti A, Saccomanni G, Bifulco M, Di Marzo V, Macchia M, Manera C (2014). 1,2-Dihydro-2-oxopyridine-3-carboxamides: the C-5 substituent is responsible for functionality switch at CB2 cannabinoid receptor. Eur J Med Chem. 3;74:524-32
Lynn AB, Herkenham M (1994). Localization of cannabinoid receptors and nonsaturable high-density cannabinoid binding sites in peripheral tissues of the rat: implications for receptor-mediated immune modulation by cannabinoids. J Pharmacol Exp Ther. 268(3):1612-23.
Maccarrone M, Bari M, Lorenzon T, Bisogno T, Di Marzo V, Finazzi-AgroÁ A (2000). Anandamide uptake by human endothelial cells and its regulation by nitric oxide. J. Biol.
Chem. 275, 13484±13492.
Maione S, Morera E, Marabese I, Ligresti A, Luongo L, Ortar G, Di Marzo V (2008) Antinociceptive effects of tetrazole inhibitors of endocannabinoid inactivation: cannabinoid and non-cannabinoidreceptor-mediated mechanisms. Br J Pharmacol. 155(5):775-82
Manera C, Tuccinardi T, Martinelli A (2008). Indoles and related compounds as cannabinoid ligands. Mini Rev Med Chem 8(4):370-87
Manera C, Saccomanni G, Adinolfi B, Benetti V, Ligresti A, Cascio MG, Tuccinardi T, Lucchesi V, Martinelli A, Nieri P, Masini E, Di Marzo V, Ferrarini PL (2009). Rational design, synthesis, and pharmacological properties of new 1,8-naphthyridin-2(1H)-on-3-carboxamide derivatives as highly selective cannabinoid-2 receptor agonists. J Med Chem 52(12):3644-51
Manera C, Saccomanni G, Malfitano AM, Bertini S, Castelli F, Laezza C, Ligresti A, Lucchesi V, Tuccinardi T, Rizzolio F, Bifulco M, Di Marzo V, Giordano A, Macchia M,
~ 80 ~
Martinelli A (2012). Rational design, synthesis and anti-proliferative properties of new CB2 selective cannabinoid receptor ligands: an investigation of the 1,8-naphthyridin-2(1H)-one scaffold. Eur J Med Chem. 52:284-94
Marrs W.R, Blankman J.L, Horne E.A, Thomazeau A, Lin Y.H, Coy J, Bodor A.L, Muccioli G.G, Hu S.S, Woodruff G, Fung S, Lafourcade M, Alexander JP, Long JZ,Li W, Xu C, Möller T, Mackie K, Manzoni OJ, Cravatt BF, Stella N (2010). The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nat
Neurosci 13, 951–957.
Martin RS, Luong LA, Welsh NJ, Eglen RM, Martin GR, MacLennan SJ (2000). Effects of cannabinoid receptor agonists on neuronally-evoked contractions of urinary bladder tissues isolated from rat, mouse, pig, dog, monkey and human. Br J Pharmacol 129(8):1707-15.
Martinez-Gonzalez D, Bonilla-Jaime H, Morales-Otal A, Henriksen SJ, Velazquez-Moctezuma J, Prospero-Garcia O (2004). Oleamide and anandamide effects on food intake and sexual behavior of rats. Neurosci Lett 364(1): 1-6.
Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI (1990). Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346(6284):561-4.
Max D, Hesse M, Volkmer I, Staege M.S (2009). High expression of the evolutionarily conserved alpha/beta hydrolase domain containing 6 (ABHD6) in Ewing tumors. Cancer Sci 100, 2383–2389.
McKinney MK and 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
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(1):83-90.
Munro S, Thomas KL, Abu-Shaar M (1993). Molecular characterization of a peripheral receptor for cannabinoids. Nature 365(6441):61-5.
Murillo-Rodriguez E, Poot-Ake A, Arias-Carrion O, Pacheco-Pantoja E, Fuente-Ortegon Ade L, Arankowsky-Sand oval G (2011). The emerging role of the endocannabinoid system in the sleep-wake cycle modulation. Cent Nerv Syst Agents Med Chem 11(3):189-96.
Naccarato M, Pizzuti D, Petrosino S, Simonetto M, Ferigo L, Grandi FC, Pizzolato G, Di Marzo V (2010). Possible Anandamide and Palmitoylethanolamide involvement in human stroke. Lipids Health Dis 9:47.
~ 81 ~
Nicolussi S, Chicca A, Rau M, Rihs S, Soeberdt M, Abels C, Gertsch J (2014). Correlating FAAH and anandamide cellular uptake inhibition using N-alkylcarbamate inhibitors: From ultrapotent to hyperpotent. Biochem Pharmacol. 15;92(4):669-89
Nomura DK, Morrison BE, Blankman JL, Long JZ, Kinsey SG, Marcondes MC, Ward AM, Hahn YK, Lichtman AH, Conti B, Cravatt BF (2011). Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation. Science 334: 809–813.
Ohno-Shosaku T, Maejima T, Kano M (2001). Endogenous cannabinoids mediate retrograde signals from depolarized postsynaptic neurons to presynaptic terminals. Neuron 29(3):729-38.
Onaivi ES, Leonard CM, Ishiguro H, Zhang PW, Lin Z, Akinshola BE, Uhl GR (2002). Endocannabinoids and cannabinoid receptor genetics. Prog Neurobiol 66(5):307-44.
Onaivi ES, Ishiguro H, Gong JP, Patel S, Perchuk A, Meozzi PA, Myers L, Mora Z, Tagliaferro P, Gardner E, Brusco A, Akinshola BE, Liu QR, Hope B, Iwasaki S, Arinami T, Teasenfitz L, Uhl GR (2006). Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain. Ann N Y Acad Sci 1074:514-36
Pacher P, Bátkai S, Kunos G (2006). The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev. 58(3):389-462
Pan B, Wang W, Zhong P, Blankman JL, Cravatt BF, Liu QS. (2011) Alterations of endocannabinoid signaling, synaptic plasticity, learning, and memory in monoacylglycerol lipase knock-out mice. J Neurosci 31: 13420–13430.
Pasquini S, Botta L, Semeraro T, Mugnaini C, Ligresti A, Palazzo E, Maione S, Di Marzo V, Corelli F (2008). Investigations on the
4-quinolone-3-carboxylic acid motif. 2. Synthesis and structure-activity relationship of
potent and selective cannabinoid2 receptor agonists endowed with analgesic activity in vivo.
J Med Chem 51, 5075-5084.
Patricelli MP, Lovato MA, Cravatt BF (1999). Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolases with distinct catalytic properties. Biochemistry. 38:9804
Patricelli MP and Cravatt BF (1999). Fatty acid amide hydrolase competitively degrades bioactive amides and esters through a nonconventional catalytic mechanism. Biochemistry 38:14125.
Patricelli MP and Cravatt BF (2000). Clarifying the catalytic roles of conserved residues in the amidase signature family. J Biol Chem. 275:19177
~ 82 ~
Patricelli MP and Cravatt BF (2001). Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase. Biochemistry. 40:6107
Pertwee RG (1997). Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol Ther 74(2):129-80.
Pertwee RG (1999). Pharmacology of cannabinoid receptor ligands. Curr Med Chem 6(8):635-64
Pertwee RG (2005). Pharmacological actions of cannabinoids. Handb Exp Pharmacol. (168):1-51
Pertwee RG, Howlett AC, Abood ME, Alexander SP, Di Marzo V, Elphick MR, Greasley PJ, Hansen HS, Kunos G, Mackie K, Mechoulam R, Ross RA (2010). International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB₁ and CB₂. Pharmacol Rev 62(4):588-631.
Piomelli D, Beltramo M, Glasnapp S, Lin S.Y, Goutopoulos A, Xie X.Q, Makriyannis A (1999). Structural determinants for recognition and translocation by the anandamide transporter. Proc. Natl Acad. Sci. USA 96, 5802±5807.
Porter AC, Sauer JM, Knierman MD, Becker GW, Berna MJ, Bao J, Nomikos GG, Carter P, Bymaster FP, Leese AB, Felder CC (2002). Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J Pharmacol Exp Ther 301(3):1020-4.
Raduner S, Majewska A, Chen JZ, Xie XQ, Hamon J, Faller B, Altmann KH, Gertsch J (2006). Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects. J Biol
Chem. 281(20):14192-206
Rakhshan F, Day T.A, Blakely R.D, Barker E.L (2000). Carrier-mediated uptake of the endogenous cannabinoid anandamide in RBL-2H3 cells. J. Pharmacol. Exp. Ther. 292, 960±967.
Rodriguez de Fonseca F, Del Arco I, Bermudez-Silva FJ, Bilbao A, Cippitelli A, Navarro M (2005). The endocannabinoid system: physiology and pharmacology. Alcohol Alcohol 40(1):2-14.
Ruiz-Llorente L, Sanchez MG, Carmena MJ, Prieto JC, Sanchez-Chapado M, Izquierdo A, Diaz-Laviada I (2003). Expression of functionally active cannabinoid receptor CB1 in the human prostate gland. Prostate 54(2):95-102.
~ 83 ~
Saario SM, Salo OM, Nevalainen T, Poso A, Laitinen JT, Jarvinen T, Niemi R (2005). Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem Biol 12(6):649-56.
Saario SM, Palomaki V, Lehtonen M, Nevalainen T, Jarvinen T, Laitinen JT (2006). URB754 has no effect on the hydrolysis or signaling capacity of 2-AG in the rat brain. Chem
Biol 13(8):811-4.
Sagredo O, García-Arencibia M, de Lago E, Finetti S, Decio A, Fernández-Ruiz J (2007). Cannabinoids and neuroprotection in basal ganglia disorders. Mol Neurobiol. 36(1):82-91
Savinainen JR, Saario SM, Laitinen JT (2012). The serine hydrolases MAGL, ABHD6 and ABHD12 as guardians of 2-arachidonoylglycerolsignalling through cannabinoid receptors.
Acta Physiol (Oxf) 204(2):267-76.
Schuel H, Burkman LJ, Lippes J, Crickard K, Forester E, Piomelli D, Giuffrida A (2002). N-Acylethanolamines in human reproductive fluids. Chem Phys Lipids 121(1-2):211-27.
Schuehly W, Paredes JM, Kleyer J, Huefner A, Anavi-Goffer S, Raduner S, Altmann KH, Gertsch J (2011). Mechanisms of osteoclastogenesis inhibition by a novel class of biphenyl-type cannabinoid CB(2) receptor inverse agonists. Chem Biol. 26;18(8):1053-64
Shoemaker JL, Joseph BK, Ruckle MB, Mayeux PR, Prather PL (2005). The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors. J
Pharmacol Exp Ther 314(2):868-75.
Shoemaker JL, Seely KA, Reed RL, Crow JP, Prather PL (2007). The CB2 cannabinoid agonist AM-1241 prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis when initiated at symptom onset. J Neurochem. 101(1):87-98
Seltzman HH (1999). Structure and receptor activity for classical cannabinoids. Curr Med
Chem. 6(8):685-704.
Steffens M, Zentner J, Honegger J, Feuerstein TJ (2005). Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB1 receptor.
BiochemPharmacol 69(1):169-78.
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(1):89-97.
Sugiura T, Kobayashi Y, Oka S, Waku K (2002). Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological ignificance.
~ 84 ~
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(5):405-46.
Sugiura T (2009). Physiological roles of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Biofactors 35(1):88-97.
Tornqvist H and Belfrage P (1976). Purification and some properties of a monoacylglycerol-hydrolyzing enzyme of rat adipose tissue. J. Biol. Chem.251, 813-9.
Urquhart P, Nicolaou A, Woodward DF (2014). Endocannabinoids and their oxygenation by cyclo-oxygenases, lipoxygenases and other oxygenases. Biochim Biophys Acta S1388-1981(14)00267-4.
Valdeolivas S, Pazos MR, Bisogno T, Piscitelli F, Iannotti FA, Allarà M, Sagredo O, Di Marzo V, Fernández-Ruiz J (2013). The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG. Cell Death Dis. 4:e862
Xia R, Dekermendjian K, Lullau E, Dekker N (2011) . TRPV1: a therapy target that attracts the pharmaceutical interests. Adv Exp Med Biol 704:637-65.
Yiangou Y, Facer P, Durrenberger P, Chessell IP, Naylor A, Bountra C, Banati RR, Anand P (2006). COX-2, CB2 and P2X7-immunoreactivities are increased in activated microglial cells/macrophages of multiple sclerosis and amyotrophic lateral sclerosis spinal cord. BMC
Neurol. 2;6:12.
Wang, J. Ueda, N. (2009). Biology of endocannabinoid synthesis system. Prostaglandins
Other Lipid Mediat. 89, 112-9.
Whiteside GT, Lee GP, Valenzano KJ (2007). The role of the cannabinoid CB2 receptor in pain transmission and therapeutic potential of small molecule CB2 receptor agonists. Curr