Implication of the anti-inflammatory bioactive lipid prostaglandin D2-glycerol ester in the control of macrophage activation and inflammation by ABHD6

Proceedings of the National Academy of Sciences of the United States of America

Volumn 110, Issue 43, 2013, Pages 17558-17563

  Alhouayek, Mireille ^a   Masquelier, Julien ^a   Cani, Patrice D ^a   Lambert, Didier M ^a   Muccioli, Giulio G ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Anandamide; COX 2; FAAH; Glyceryl prostaglandin; Prostaglandin synthase

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; ACYLGLYCEROL LIPASE; ALPHA BETA HYDROLASE DOMAIN 6; ANTIINFLAMMATORY AGENT; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CYCLOOXYGENASE 2; FATTY ACID AMIDASE; FLURBIPROFEN; HYDROLASE; IBIPINABANT; INTERLEUKIN 1BETA; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MESSENGER RNA; PROSTAGLANDIN D2; PROSTAGLANDIN D2 GLYCEROL ESTER; PROSTAGLANDIN SYNTHASE; RIMONABANT; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL WALL; CEREBELLUM; CONTROLLED STUDY; HYDROLYSIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; LOCOMOTION; MACROPHAGE ACTIVATION; MICROGLIA; MOUSE; NONHUMAN; OXYGENATION; PERITONEUM MACROPHAGE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; SPLEEN WEIGHT;

ANANDAMIDE; COX-2; FAAH; GLYCERYL PROSTAGLANDIN; PROSTAGLANDIN SYNTHASE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ARACHIDONIC ACIDS; BIPHENYL COMPOUNDS; CARBAMATES; CELL LINE; CELLS, CULTURED; CYCLOOXYGENASE 2; ENDOCANNABINOIDS; ENZYME INHIBITORS; ENZYME-LINKED IMMUNOSORBENT ASSAY; ESTERS; FEMALE; GENE EXPRESSION; GLYCERIDES; GLYCEROL; INFLAMMATION; INTERLEUKIN-1BETA; INTRAMOLECULAR OXIDOREDUCTASES; LIPOCALINS; LIPOPOLYSACCHARIDES; MACROPHAGE ACTIVATION; MACROPHAGES; MALE; MICE; MICE, INBRED C57BL; MONOACYLGLYCEROL LIPASES; PROSTAGLANDIN D2; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

EID: 84886389627     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1314017110     Document Type: Article

References (47)

1. Valledor AF, Comalada M, Santamaría-Babi LF, Lloberas J, Celada A (2010) Macrophage proinflammatory activation and deactivation: A question of balance. Adv Immunol 108:1-20.
2. Mosser DM, Edwards JP (2008) Exploring the full spectrum of macrophage activation. Nat Rev Immunol 8(12):958-969.
3. Murray PJ, Wynn TA (2011) Protective and pathogenic functions of macrophage subsets. Nat Rev Immunol 11(11):723-737.
4. Chawla A, Nguyen KD, Goh YP (2011) Macrophage-mediated inflammation in metabolic disease. Nat Rev Immunol 11(11):738-749.
5. Alhouayek M, Lambert DM, Delzenne NM, Cani PD, Muccioli GG (2011) Increasing endogenous 2-arachidonoylglycerol levels counteracts colitis and related systemic inflammation. FASEB J 25(8):2711-2721.
6. Khasabova IA, Chandiramani A, Harding-Rose C, Simone DA, Seybold VS (2011) Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain. Pharmacol Res 64(1):60-67.
7. Kinsey SG, et al. (2009) Blockade of endocannabinoid-degrading enzymes attenuates neuropathic pain. J Pharmacol Exp Ther 330(3):902-910.
8. Sciolino NR, Zhou W, Hohmann AG (2011) Enhancement of endocannabinoid signaling with JZL184, an inhibitor of the 2-arachidonoylglycerol hydrolyzing enzyme monoacylglycerol lipase, produces anxiolytic effects under conditions of high environmental aversiveness in rats. Pharmacol Res 64(3):226-234.
9. Spradley JM, Guindon J, Hohmann AG (2010) Inhibitors of monoacylglycerol lipase, fatty-acid amide hydrolase and endocannabinoid transport differentially suppress capsaicin-induced behavioral sensitization through peripheral endocannabinoid mechanisms. Pharmacol Res 62(3):249-258.
10. Chang YH, Lee ST, Lin WW (2001) Effects of cannabinoids on LPS-stimulated inflammatory mediator release from macrophages: Involvement of eicosanoids. J Cell Biochem 81(4):715-723.
11. Gallily R, Breuer A, Mechoulam R (2000) 2-Arachidonylglycerol, an endogenous cannabinoid, inhibits tumor necrosis factor-alpha production in murine macrophages, and in mice. Eur J Pharmacol 406(1):R5-R7.
12. Muccioli GG (2010) Endocannabinoid biosynthesis and inactivation, from simple to complex. Drug Discov Today 15(11-12):474-483.
13. 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(5):1260-1264.
14. Blankman JL, Simon GM, Cravatt BF (2007) A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem Biol 14(12):1347-1356.
15. Long JZ, et al. (2009) Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol 5(1):37-44.
16. Muccioli GG, et al. (2007) Identification of a novel endocannabinoid- hydrolyzing enzyme expressed by microglial cells. J Neurosci 27(11):2883-2889.
17. Marrs WR, et al. (2010) The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nat Neurosci 13(8):951-957.
18. Marrs WR, et al. (2011) Dual inhibition of alpha/beta-hydrolase domain 6 and fatty acid amide hydrolase increases endocannabinoid levels in neurons. J Biol Chem 286(33):28723-28728.
19. Alhouayek M, Masquelier J, Muccioli GG (2013) Controlling 2-arachidonoylglycerol metabolism as an anti-inflammatory strategy. Drug Discov Today, 10.1016/j.drudis. 2013.07.009.
20. Pertwee RG, et al. (2010) International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: Beyond CB1 and CB2. Pharmacol Rev 62(4):588-631.
21. Rouzer CA, Marnett LJ (2011) Endocannabinoid oxygenation by cyclooxygenases, lipoxygenases, and cytochromes P450: Cross-talk between the eicosanoid and endocannabinoid signaling pathways. Chem Rev 111(10):5899-5921.
22. Lawrence T, Natoli G (2011) Transcriptional regulation of macrophage polarization: Enabling diversity with identity. Nat Rev Immunol 11(11):750-761.
23. Li W, Blankman JL, Cravatt BF (2007) A functional proteomic strategy to discover inhibitors for uncharacterized hydrolases. J Am Chem Soc 129(31):9594-9595.
24. Straiker A, et al. (2009) Monoacylglycerol lipase limits the duration of endocannabinoid-mediated depolarization-induced suppression of excitation in autaptic hippocampal neurons. Mol Pharmacol 76(6):1220-1227.
25. Ahn K, et al. (2007) Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity. Biochemistry 46(45):13019-13030.
26. O'Sullivan SE, Kendall DA (2010) Cannabinoid activation of peroxisome proliferatoractivated receptors: potential for modulation of inflammatory disease. Immunobiology 215(8):611-616.
27. Chawla A (2010) Control of macrophage activation and function by PPARs. Circ Res 106(10):1559-1569.
28. Michalik L, et al. (2006) International Union of Pharmacology. LXI. Peroxisome proliferator-activated receptors. Pharmacol Rev 58(4):726-741.
29. Alexander SP, Mathie A, Peters JA (2008) Guide to Receptors and Channels (GRAC), 3rd edition. Br J Pharmacol 153(Suppl 2):S1-S209.
30. Duggan KC, et al. (2011) (R)-Profens are substrate-selective inhibitors of endocannabinoid oxygenation by COX-2. Nat Chem Biol 7(11):803-809.
31. Hu SS, Bradshaw HB, Chen JS, Tan B, Walker JM (2008) Prostaglandin E2 glycerol ester, an endogenous COX-2 metabolite of 2-arachidonoylglycerol, induces hyperalgesia and modulates NFkappaB activity. Br J Pharmacol 153(7):1538-1549.
32. Cani PD, et al. (2007) Metabolic endotoxemia initiates obesity and insulin resistance. Diabetes 56(7):1761-1772.
33. Maloy KJ, Powrie F (2011) Intestinal homeostasis and its breakdown in inflammatory bowel disease. Nature 474(7351):298-306.
34. Odegaard JI, Chawla A (2011) Alternative macrophage activation and metabolism. Annu Rev Pathol 6:275-297.
35. Long JZ, Nomura DK, Cravatt BF (2009) Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism. Chem Biol 16(7):744-753.
36. Nomura DK, et al. (2011) Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation. Science 334(6057):809-813.
37. Schlosburg JE, et al. (2010) Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nat Neurosci 13(9):1113-1119.
38. Piscitelli F, Di Marzo V (2012) "Redundancy" of endocannabinoid inactivation: New challenges and opportunities for pain control. ACS Chem Neurosci 3(5):356-363.
39. Rockwell CE, Snider NT, Thompson JT, Vanden Heuvel JP, Kaminski NE (2006) Interleukin-2 suppression by 2-arachidonyl glycerol is mediated through peroxisome proliferator-activated receptor gamma independently of cannabinoid receptors 1 and 2. Mol Pharmacol 70(1):101-111.
40. Keown OP, et al. (2010) 2-arachidonyl glycerol activates platelets via conversion to arachidonic acid and not by direct activation of cannabinoid receptors. Br J Clin Pharmacol 70(2):180-188.
41. Chouinard F, et al. (2011) The endocannabinoid 2-arachidonoyl-glycerol activates human neutrophils: Critical role of its hydrolysis and de novo leukotriene B4 biosynthesis. J Immunol 186(5):3188-3196.
42. Rouzer CA, et al. (2005) RAW264.7 cells lack prostaglandin-dependent autoregulation of tumor necrosis factor-alpha secretion. J Lipid Res 46(5):1027-1037.
43. Yu R, Xiao L, Zhao G, Christman JW, van Breemen RB (2011) Competitive enzymatic interactions determine the relative amounts of prostaglandins E2 and D2. J Pharmacol Exp Ther 339(2):716-725.
44. Muccioli GG, Stella N (2008) An optimized GC-MS method detects nanomolar amounts of anandamide in mouse brain. Anal Biochem 373(2):220-228.
45. Muccioli GG, et al. (2010) The endocannabinoid system links gut microbiota to adipogenesis. Mol Syst Biol 6:392.
46. Nithipatikom K, et al. (2002) Determination of cyclooxygenase and arachidonic acid metabolites in invasive human prostate cancer cells. Adv Exp Med Biol 507:269-274.
47. Zhang X, Goncalves R, Mosser DM(2008) The isolation and characterization of murine macrophages. Curr Protoc Immunol, 10.1002/0471142735.im1401s83.