Endogenous molecules stimulating N-acylethanolamine-hydrolyzing acid amidase (NAAA)

ACS Chemical Neuroscience

Volumn 3, Issue 5, 2012, Pages 379-385

  Tai, Tatsuya ^a,b   Tsuboi, Kazuhito ^a   Uyama, Toru ^a   Masuda, Kim ^c   Cravatt, Benjamin F ^c   Houchi, Hitoshi ^b   Ueda, Natsuo ^a  

^a KAGAWA UNIVERSITY   (Japan)

^b KAGAWA UNIVERSITY HOSPITAL   (Japan)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

dihydrolipoic acid; fatty acid amide hydrolase; N Acylethanolamine hydrolyzing acid amidase; NAAA; palmitoylethanolamide; phospholipids

Indexed keywords

CHOLINE; DIHYDROLIPOATE; ETHANOLAMINE; FATTY ACID AMIDASE; LYSOSOME ENZYME; MESSENGER RNA; N ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE; PALMIDROL; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; BRAIN; CONFERENCE PAPER; CONTROLLED STUDY; ENZYME ACTIVITY; HYDROLYSIS; LYSOSOME; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STIMULATION; WILD TYPE;

DIHYDROLIPOIC ACID; FATTY ACID AMIDE HYDROLASE; N-ACYLETHANOLAMINE-HYDROLYZING ACID AMIDASE; NAAA; PALMITOYLETHANOLAMIDE; PHOSPHOLIPID;

AMIDOHYDROLASES; ANIMALS; BRAIN; ENZYME INDUCTION; HEK293 CELLS; HUMANS; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; PHOSPHOLIPIDS; RATS;

MUS;

EID: 84862095833     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn300007s     Document Type: Conference Paper

References (45)

1. Schmid, H. H. O., Schmid, P. C., and Natarajan, V. (1990) N-Acylated glycerophospholipids and their derivatives Prog. Lipid Res. 29, 1-43 (Pubitemid 120036504)
2. Devane, W. A., Hanuš, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258, 1946-1949 (Pubitemid 23026736)
3. Zygmunt, P. M., Petersson, J., Andersson, D. A., Chuang, H., Sørgård, M., Di Marzo, V., Julius, D., and Högestätt, E. D. (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide Nature 400, 452-457 (Pubitemid 29361798)
4. 2 Pharmacol. Rev. 62, 588-631
5. Calignano, A., La Rana, G., Giuffrida, A., and Piomelli, D. (1998) Control of pain initiation by endogenous cannabinoids Nature 394, 277-281 (Pubitemid 28335039)
6. Lambert, D. M., Vandevoorde, S., Jonsson, K.-O., and Fowler, C. J. (2002) The palmitoylethanolamide family: a new class of anti-inflammatory agents? Curr. Med. Chem. 9, 663-674 (Pubitemid 34296196)
7. LoVerme, J., Russo, R., La Rana, G., Fu, J., Farthing, J., Mattace-Raso, G., Meli, R., Hohmann, A., Calignano, A., and Piomelli, D. (2006) Rapid broad-spectrum analgesia through activation of peroxisome proliferator-activated receptor-α J. Pharmacol. Exp. Ther. 319, 1051-1061
8. Rodríguez de Fonseca, F., Navarro, M., Gómez, R., Escuredo, L., Nava, F., Fu, J., Murillo-Rodríguez, E., Giuffrida, A., LoVerme, J., Gaetani, S., Kathuria, S., Gall, C., and Piomelli, D. (2001) An anorexic lipid mediator regulated by feeding Nature 414, 209-212 (Pubitemid 33051235)
9. Pavón, F. J., Serrano, A., Romero-Cuevas, M., Alonso, M., and Rodríguez de Fonseca, F. (2010) Oleoylethanolamide: A new player in peripheral control of energy metabolism. Therapeutic implications Drug Discovery Today: Dis. Mech. 7, e175-e183
10. Fu, J., Gaetani, S., Oveisi, F., Lo Verme, J., Serrano, A., Fonseca, R. D., Rosengarth, A., Luecke, H., Di Giacomo, B., Tarzia, G., and Piomelli, D. (2003) Oleylethanolamide regulates feeding and body weight through activation of the nuclear receptor PPAR-α Nature 425, 90-93 (Pubitemid 37101723)
11. Ahern, G. P. (2003) Activation of TRPV1 by the satiety factor oleoylethanolamide J. Biol. Chem. 278, 30429-30434 (Pubitemid 36994545)
12. Overton, H. A., Babbs, A. J., Doel, S. M., Fyfe, M. C. T., Gardner, L. S., Griffin, G., Jackson, H. C., Procter, M. J., Rasamison, C. M., Tang-Christensen, M., Widdowson, P. S., Williams, G. M., and Reynet, C. (2006) Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents Cell Metab. 167-175
13. Garg, P., Duncan, R. S., Kaja, S., Zabaneh, A., Chapman, K. D., and Koulen, P. (2011) Lauroylethanolamide and linoleoylethanolamide improve functional outcome in a rodent model for stroke Neurosci. Lett. 492, 134-138
14. Ueda, N., Tsuboi, K., and Uyama, T. (2010) Enzymological studies on the biosynthesis of N-acylethanolamines Biochim. Biophys. Acta 1801, 1274-1285
15. Okamoto, Y., Morishita, J., Tsuboi, K., Tonai, T., and Ueda, N. (2004) Molecular characterization of a phospholipase D generating anandamide and its congeners J. Biol. Chem. 279, 5298-5305 (Pubitemid 38220550)
16. 2and lysophospholipase D Biochem. J. 380, 749-756 (Pubitemid 38850516)
17. Simon, G. M. and Cravatt, B. F. (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)
18. Cravatt, B. F., Giang, D. K., Mayfield, S. P., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides Nature 384, 83-87 (Pubitemid 26374593)
19. McKinney, M. K. and Cravatt, B. F. (2005) Structure and function of fatty acid amide hydrolase Annu. Rev. Biochem. 74, 411-432 (Pubitemid 40995513)
20. Cravatt, B. F., Demarest, K., Patricelli, M. P., Bracey, M. H., Giang, D. K., Martin, B. R., and 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, 9371-9376 (Pubitemid 32743923)
21. Clement, A. B., Hawkins, E. G., Lichtman, A. H., and Cravatt, B. F. (2003) Increased seizure susceptibility and proconvulsant activity of anandamide in mice lacking fatty acid amide hydrolase J. Neurosci. 23, 3916-3923 (Pubitemid 36958497)
22. Lichtman, A. H., Leung, D., Shelton, C. C., Saghatelian, A., Hardouin, C., Boger, D. L., and Cravatt, B. F. (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)
23. Fegley, D., Gaetani, S., Duranti, A., Tontini, A., Mor, M., Tarzia, G., and Piomelli, D. (2005) Characterization of the fatty acid amide hydrolase inhibitor cyclohexyl carbamic acid 3′-carbamoyl-biphenyl-3-yl ester (URB597): effects on anandamide and oleoylethanolamide deactivation J. Pharmacol. Exp. Ther. 313, 352-358 (Pubitemid 40411361)
24. Ahn, K., Smith, S. E., Liimatta, M. B., Beidler, D., Sadagopan, N., Dudley, D. T., Young, T., Wren, P., Zhang, Y., Swaney, S., Van Becelaere, K., Blankman, J. L., Nomura, D. K., Bhattachar, S. N., Stiff, C., Nomanbhoy, T. K., Weerapana, E., Johnson, D. S., and Cravatt, B. F. (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
25. Ueda, N., Yamanaka, K., Terasawa, Y., and Yamamoto, S. (1999) An acid amidase hydrolyzing anandamide as an endogenous ligand for cannabinoid receptors FEBS Lett. 454, 267-270 (Pubitemid 29304613)
26. Ueda, N., Yamanaka, K., and Yamamoto, S. (2001) Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance J. Biol. Chem. 276, 35552-35557
27. Tsuboi, K., Sun, Y.-X., Okamoto, Y., Araki, N., Tonai, T., and 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)
28. Ueda, N., Tsuboi, K., and Uyama, T. (2010) N-acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA) Prog. Lipid Res. 49, 299-315
29. Zhao, L.-Y., Tsuboi, K., Okamoto, Y., Nagahata, S., and 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)
30. West, J. M., Zvonok, N., Whitten, K. M., Wood, J. T., and Makriyannis, A. (2012) Mass spectrometric characterization of human N-acylethanolamine- hydrolyzing acid amidase J. Proteome Res. 11, 972-981
31. Sun, Y.-X., Tsuboi, K., Zhao, L.-Y., Okamoto, Y., Lambert, D. M., and 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)
32. Tsuboi, K., Zhao, L.-Y., Okamoto, Y., Araki, N., Ueno, M., Sakamoto, H., and Ueda, N. (2007) Predominant expression of lysosomal N-acylethanolamine- hydrolyzing acid amidase in macrophages revealed by immunochemical studies Biochim. Biophys. Acta 1771, 623-632 (Pubitemid 46670796)
33. Wang, J., Zhao, L.-Y., Uyama, T., Tsuboi, K., Wu, X.-X., Kakehi, Y., and Ueda, N. (2008) Expression and secretion of N-acylethanolamine-hydrolysing acid amidase in human prostate cancer cells J. Biochem. 144, 685-690
34. Tsuboi, K., Hilligsmann, C., Vandevoorde, S., Lambert, D. M., and 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)
35. Solorzano, C., Zhu, C., Battista, N., Astarita, G., Lodola, A., Rivara, S., Mor, M., Russo, R., Maccarrone, M., Antonietti, F., Duranti, A., Tontini, A., Cuzzocrea, S., Tarzia, G., and Piomelli, D. (2009) Selective N-acylethanolamine-hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation Proc. Natl. Acad. Sci. U.S.A. 106, 20966-20971
36. Saturnino, C., Petrosino, S., Ligresti, A., Palladino, C., De Martino, G., Bisogno, T., and 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
37. Solorzano, C., Antonietti, F., Duranti, A., Tontini, A., Rivara, S., Lodola, A., Vacondio, F., Tarzia, G., Piomelli, D., and 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
38. Wang, J., Okamoto, Y., Tsuboi, K., and Ueda, N. (2008) The stimulatory effect of phosphatidylethanolamine on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D (NAPE-PLD) Neuropharmacology 54, 8-15 (Pubitemid 350299397)
39. Petersen, G., Pedersen, A. H., Pickering, D. S., Begtrup, M., and Hansen, H. S. (2009) Effect of synthetic and natural phospholipids on N-acylphosphatidylethanolamine-hydrolyzing phospholipase D activity Chem. Phys. Lipids 162, 53-61
40. Bustamante, J., Lodge, J. K., Marcocci, L., Tritschler, H. J., Packer, L., and Rihn, B. H. (1998) α-Lipoic acid in liver metabolism and disease Free Radical Biol. Med. 24, 1023-1039 (Pubitemid 28186244)
41. 110Cys in active site of membrane-associated prostaglandin E synthase-2 Biochem. Biophys. Res. Commun. 306, 577-581 (Pubitemid 36683114)
42. Lübke, T., Lobel, P., and Sleat, D. E. (2009) Proteomics of the lysosome Biochim. Biophys. Acta 1793, 625-635
43. Wang, J., Zhao, L.-Y., Uyama, T., Tsuboi, K., Tonai, T., and Ueda, N. (2008) Amino acid residues crucial in pH regulation and proteolytic activation of N-acylethanolamine-hydrolyzing acid amidase Biochim. Biophys. Acta 1781, 710-717
44. Ueda, N., Yamamoto, K., Yamamoto, S., Tokunaga, T., Shirakawa, E., Shinkai, H., Ogawa, M., Sato, T., Kudo, I., Inoue, K., Takizawa, H., Nagano, T., Hirobe, M., Matsuki, N., and Saito, H. (1995) Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist Biochim. Biophys. Acta 1254, 127-134
45. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72, 248-254