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Volumn 157, Issue 6, 2009, Pages 974-983

A critical cysteine residue in monoacylglycerol lipase is targeted by a new class of isothiazolinone-based enzyme inhibitors

Author keywords

2 arachidonoylglycerol; Endocannabinoids; Monoacylglycerol lipase

Indexed keywords

2 METHYL 4 ISOTHIAZOLIN 3 ONE; 2 OLEOYL 4 ISOTHIAZOLINE 3 ONE; ACYLGLYCEROL LIPASE; CYSTEINE; ENZYME INHIBITOR; GLYCINE; MALEIMIDE DERIVATIVE; N ARACHIDONYLMALEIMIDE; OCTHILINONE; UNCLASSIFIED DRUG;

EID: 70350339817     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2009.00276.x     Document Type: Article
Times cited : (80)

References (28)
  • 1
    • 40949095655 scopus 로고    scopus 로고
    • Guide to receptors and channels (GRAC)
    • 3rd edn
    • Alexander SPH, Mathie A, Peters JA (2008). Guide to receptors and channels (GRAC), 3rd edn. Br J Pharmacol 153 (Suppl. 2): S1-S209.
    • (2008) Br J Pharmacol , vol.153 , Issue.SUPPL. 2
    • Alexander, S.P.H.1    Mathie, A.2    Peters, J.A.3
  • 2
    • 0037568064 scopus 로고    scopus 로고
    • Studies of chemical electivity of hapten, reactivity, and skin sensitization potency. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3- one (MCI) and 2-methylisothiazol-3-one (MI)
    • Alvarez-Sanchez R, Basketter D, Pease C, Lepoittevin JP (2002). Studies of chemical electivity of hapten, reactivity, and skin sensitization potency. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI). Chem Res Toxicol 16: 627-636.
    • (2002) Chem Res Toxicol , vol.16 , pp. 627-636
    • Alvarez-Sanchez, R.1    Basketter, D.2    Pease, C.3    Lepoittevin, J.P.4
  • 3
    • 36348940009 scopus 로고    scopus 로고
    • Intestinal monoacylg-lycerol metabolism: Developmental and nutritional regulation of monoacylglycerol lipase and monoacylglycerol acyltransferase
    • Chon SH, Zhou YX, Dixon JL, Storch J (2007). Intestinal monoacylg-lycerol metabolism: developmental and nutritional regulation of monoacylglycerol lipase and monoacylglycerol acyltransferase. J Biol Chem 282: 33346-33357.
    • (2007) J Biol Chem , vol.282 , pp. 33346-33357
    • Chon, S.H.1    Zhou, Y.X.2    Dixon, J.L.3    Storch, J.4
  • 4
    • 35648973242 scopus 로고    scopus 로고
    • The inhibition of monoacylglycerol lipase by URB602 showed an anti-inflammatory and anti-nociceptive effect in a murine model of acute inflammation
    • Comelli F, Giagnoni G, Bettoni I, Colleoni M, Costa B (2007). The inhibition of monoacylglycerol lipase by URB602 showed an anti-inflammatory and anti-nociceptive effect in a murine model of acute inflammation. Br J Pharmacol 152: 787-794.
    • (2007) Br J Pharmacol , vol.152 , pp. 787-794
    • Comelli, F.1    Giagnoni, G.2    Bettoni, I.3    Colleoni, M.4    Costa, B.5
  • 5
    • 70350323519 scopus 로고    scopus 로고
    • Lead optimization and SAR for reversible inhibitors
    • In: Copeland RA (ed.) John Wiley and Sons Inc.: Hoboken, NJ
    • Copeland RA (2005). Lead optimization and SAR for reversible inhibitors. In: Copeland RA (ed.). Evaluation of Enzyme Inhibitors in Drug Discovery. John Wiley and Sons Inc.: Hoboken, NJ, pp. 125-128.
    • (2005) Evaluation of Enzyme Inhibitors in Drug Discovery , pp. 125-128
    • Copeland, R.A.1
  • 6
    • 57349137829 scopus 로고    scopus 로고
    • Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model
    • Desroches J, Guindon J, Lambert C, Beaulieu P (2008). Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model. Br J Pharmacol 155: 913-924.
    • (2008) Br J Pharmacol , vol.155 , pp. 913-924
    • Desroches, J.1    Guindon, J.2    Lambert, C.3    Beaulieu, P.4
  • 8
    • 6944247598 scopus 로고    scopus 로고
    • RNA interference suggests a primary role for monoacylglycerol lipase in the degradation of the endocannabinoid 2-arachidonoylglycerol
    • Dinh TP, Kathuria S, Piomelli D (2004). RNA interference suggests a primary role for monoacylglycerol lipase in the degradation of the endocannabinoid 2-arachidonoylglycerol. Mol Pharmacol 66: 1260-1264.
    • (2004) Mol Pharmacol , vol.66 , pp. 1260-1264
    • Dinh, T.P.1    Kathuria, S.2    Piomelli, D.3
  • 9
    • 0037661996 scopus 로고    scopus 로고
    • Role of endogenous cannab-inoids in synaptic signaling
    • Freund TF, Katona I, Piomelli D (2003). Role of endogenous cannab-inoids in synaptic signaling. Physiol Rev 83: 1017-1066.
    • (2003) Physiol Rev , vol.83 , pp. 1017-1066
    • Freund, T.F.1    Katona, I.2    Piomelli, D.3
  • 10
    • 0032898720 scopus 로고    scopus 로고
    • Enzymes of porcine brain hydrolyzing 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors
    • DOI 10.1016/S0006-2952(98)00314-1, PII S0006295298003141
    • 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)
    • (1999) Biochemical Pharmacology , vol.57 , Issue.4 , pp. 417-423
    • Goparaju, S.K.1    Ueda, N.2    Taniguchi, K.3    Yamamoto, S.4
  • 11
    • 3242751838 scopus 로고    scopus 로고
    • Segregation of two endocannabinoid-hydrolyzing enzymes into pre-and postsynaptic compartments in the rat hippocampus, cerebellum and amygdala
    • Gulyas AI, Cravatt BF, Bracey MH, Dinh TP, Piomelli D, Boscia F et al. (2004). Segregation of two endocannabinoid-hydrolyzing enzymes into pre-and postsynaptic compartments in the rat hippocampus, cerebellum and amygdala. Eur J Neurosci 20: 441-458.
    • (2004) Eur J Neurosci , vol.20 , pp. 441-458
    • Gulyas, A.I.1    Cravatt, B.F.2    Bracey, M.H.3    Dinh, T.P.4    Piomelli, D.5    Boscia, F.6
  • 12
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parametrization, and performance of MMFF94
    • Halgren TA (1996). Merck molecular force field. I. Basis, form, scope, parametrization, and performance of MMFF94. J Comput Chem 17: 490-519.
    • (1996) J Comput Chem , vol.17 , pp. 490-519
    • Halgren, T.A.1
  • 13
    • 5544242529 scopus 로고    scopus 로고
    • MMFF VI. MMFF94s option for energy minimization studies
    • Halgren TA (1999). MMFF VI. MMFF94s option for energy minimization studies. J Comput Chem 20: 720-729.
    • (1999) J Comput Chem , vol.20 , pp. 720-729
    • Halgren, T.A.1
  • 14
    • 33846795915 scopus 로고    scopus 로고
    • Presynaptic monoacylglycerol lipase activity determines basal endocannab-inoid tone and terminates retrograde endocannabinoid signaling in the hippocampus
    • Hashimotodani Y, Ohno-Shosaku T, Kano M (2007). Presynaptic monoacylglycerol lipase activity determines basal endocannab-inoid tone and terminates retrograde endocannabinoid signaling in the hippocampus. J Neurosci 27: 1211-1219.
    • (2007) J Neurosci , vol.27 , pp. 1211-1219
    • Hashimotodani, Y.1    Ohno-Shosaku, T.2    Kano, M.3
  • 17
    • 0030767295 scopus 로고    scopus 로고
    • CDNA cloning, tissue distribution, and identification of the catalytic triad of monoglyceride lipase. Evolutionary relationship to esterases, lysophospholipases, and haloperoxidases
    • 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.
    • (1997) J Biol Chem , vol.272 , pp. 27218-27223
    • Karlsson, M.1    Contreras, J.A.2    Hellman, U.3    Tornqvist, H.4    Holm, C.5
  • 18
    • 37149011506 scopus 로고    scopus 로고
    • URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices
    • King AR, Duranti A, Tontini A, Rivara S, Rosengarth A, Clapper JR et al. (2007). URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices. Chem Biol 14: 1357-1365.
    • (2007) Chem Biol , vol.14 , pp. 1357-1365
    • King, A.R.1    Duranti, A.2    Tontini, A.3    Rivara, S.4    Rosengarth, A.5    Clapper, J.R.6
  • 19
    • 34547483026 scopus 로고    scopus 로고
    • Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling
    • Labar G, Bauvois C, Muccioli GG, Wouters J, Lambert DM (2007). Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling. Chembiochem 8: 1293-1297.
    • (2007) Chembiochem , vol.8 , pp. 1293-1297
    • Labar, G.1    Bauvois, C.2    Muccioli, G.G.3    Wouters, J.4    Lambert, D.M.5
  • 20
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski RA, MacArthur MW, Moss DS, Thornton JM (1993). PROCHECK: a program to check the stereochemical quality of protein structures. J Appl Cryst 26: 283-291.
    • (1993) J Appl Cryst , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 21
    • 25844440525 scopus 로고    scopus 로고
    • Selective inhibition of 2-AG hydrolysis enhances end-ocannabinoid signaling in hippocampus
    • Makara JK, Mor M, Fegley D, Szabo SI, Kathuria S, Astarita G et al. (2005). Selective inhibition of 2-AG hydrolysis enhances end-ocannabinoid signaling in hippocampus. Nat Neurosci 8: 1139-1141.
    • (2005) Nat Neurosci , vol.8 , pp. 1139-1141
    • Makara, J.K.1    Mor, M.2    Fegley, D.3    Szabo, S.I.4    Kathuria, S.5    Astarita, G.6
  • 22
    • 38449086056 scopus 로고    scopus 로고
    • Endocannabinoids and traumatic brain injury
    • Mechoulam R, Shohami E (2007). Endocannabinoids and traumatic brain injury. Mol Neurobiol 36: 68-74.
    • (2007) Mol Neurobiol , vol.36 , pp. 68-74
    • Mechoulam, R.1    Shohami, E.2
  • 24
    • 0242268553 scopus 로고    scopus 로고
    • The molecular logic of endocannabinoid signalling
    • Piomelli D (2003). The molecular logic of endocannabinoid signalling. Nat Rev Neurosci 4: 873-884.
    • (2003) Nat Rev Neurosci , vol.4 , pp. 873-884
    • Piomelli, D.1
  • 25
    • 21344432777 scopus 로고    scopus 로고
    • The endocannabinoid system: A drug discovery perspective
    • Piomelli D (2005). The endocannabinoid system: a drug discovery perspective. Curr Opin Investig Drugs 6: 672-679.
    • (2005) Curr Opin Investig Drugs , vol.6 , pp. 672-679
    • Piomelli, D.1
  • 26
    • 24944508307 scopus 로고    scopus 로고
    • Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes
    • Saario SM, Salo OMH, Nevalainen T, Poso A, Laitinen JT, Järvinen T et al. (2005). Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem Biol 12: 649-656.
    • (2005) Chem Biol , vol.12 , pp. 649-656
    • Saario, S.M.1    Salo, O.M.H.2    Nevalainen, T.3    Poso, A.4    Laitinen, J.T.5    Järvinen, T.6
  • 27
    • 0027136282 scopus 로고
    • Comparative protein modelling by satisfaction of spatial restraints
    • Sali A, Blundell TL (1993). Comparative protein modelling by satisfaction of spatial restraints. J Mol Biol 234: 779-815.
    • (1993) J Mol Biol , vol.234 , pp. 779-815
    • Sali, A.1    Blundell, T.L.2
  • 28
    • 49449092396 scopus 로고    scopus 로고
    • Covalent inhibitors of human monoacylg-lycerol lipase: Ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis
    • Zvonok N, Pandarinathan L, Williams J, Johnston M, Karageorgos I, Janero DR et al. (2008). Covalent inhibitors of human monoacylg-lycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis. Chem Biol 15: 854-862.
    • (2008) Chem Biol , vol.15 , pp. 854-862
    • Zvonok, N.1    Pandarinathan, L.2    Williams, J.3    Johnston, M.4    Karageorgos, I.5    Janero, D.R.6


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