Mass spectrometric characterization of human N -acylethanolamine- hydrolyzing acid amidase

Journal of Proteome Research

Volumn 11, Issue 2, 2012, Pages 972-981

  West, Jay M ^a   Zvonok, Nikolai ^a   Whitten, Kyle M ^a   Wood, Jodianne T ^a   Makriyannis, Alexandros ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

endocannabinoid; glycosylation; lysosomal enzyme; mannose 6 phosphate; N acylethanolamine; N acylethanolaminehydrolyzing acid amidase (NAAA); N terminal nucleophile hydrolase; palmitoylethanolamine (PEA)

Indexed keywords

CYSTEINE; ENZYME PRECURSOR; GLYCOPEPTIDASE; HETERODIMER; N ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE; UNCLASSIFIED DRUG;

ALKYLATION; AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; EMBRYO; ENZYME ACTIVITY; GEL PERMEATION CHROMATOGRAPHY; GLYCOSYLATION; HUMAN; HUMAN CELL; HYDROLYSIS; KINETICS; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN MODIFICATION;

AMIDOHYDROLASES; AMINO ACID SEQUENCE; CHROMATOGRAPHY, GEL; ENZYME PRECURSORS; GLYCOSYLATION; HEK293 CELLS; HUMANS; KINETICS; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; PALMITIC ACIDS; PEPTIDE-N4-(N-ACETYL-BETA-GLUCOSAMINYL) ASPARAGINE AMIDASE; PROTEIN SUBUNITS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84856669721     PISSN: 15353893     EISSN: 15353907     Source Type: Journal    
DOI: 10.1021/pr200735a     Document Type: Article

References (29)

1. Solorzano, C.; Antonietti, F.; Duranti, A.; Tontini, A.; Rivara, S.; Lodola, A.; Vacondio, F.; Tarzia, G.; Piomelli, D.; Mor, M. Synthesis and structure-activity relationships of N-(2-oxo-3-oxetanyl)amides as N-acylethanolamine-hydrolyzing acid amidase inhibitors J. Med. Chem. 2010, 53 (15) 5770-81
2. 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.; Piomelli, D. Selective N-acylethanolamine- hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation Proc. Natl. Acad. Sci. U.S.A. 2009, 106 (49) 20966-71
3. Ueda, N.; Tsuboi, K.; Uyama, T. N-acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase (NAAA) Prog. Lipid Res. 2010, 49 (4) 299-315
4. Calignano, A.; La Rana, G.; Giuffrida, A.; Piomelli, D. Control of pain initiation by endogenous cannabinoids Nature 1998, 394 (6690) 277-81
5. Calignano, A.; La Rana, G.; Piomelli, D. Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide Eur. J. Pharmacol. 2001, 419 (2-3) 191-8
6. Lambert, D. M.; Vandevoorde, S.; Jonsson, K. O.; Fowler, C. J. The palmitoylethanolamide family: a new class of anti-inflammatory agents? Curr. Med. Chem. 2002, 9 (6) 663-74
7. Lo Verme, J.; Fu, J.; Astarita, G.; La Rana, G.; Russo, R.; Calignano, A.; Piomelli, D. The nuclear receptor peroxisome proliferator-activated receptor-alpha mediates the anti-inflammatory actions of palmitoylethanolamide Mol. Pharmacol. 2005, 67 (1) 15-9
8. O'Sullivan, S. E. Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors Br. J. Pharmacol. 2007, 152 (5) 576-82
9. Jhaveri, M. D.; Richardson, D.; Chapman, V. Endocannabinoid metabolism and uptake: novel targets for neuropathic and inflammatory pain Br. J. Pharmacol. 2007, 152, 624-32
10. Schulze, H.; Schepers, U.; Sandhoff, K. Overexpression and mass spectrometry analysis of mature human acid ceramidase Biol. Chem. 2007, 388 (12) 1333-43
11. Shtraizent, N.; Eliyahu, E.; Park, J. H.; He, X.; Shalgi, R.; Schuchman, E. H. Autoproteolytic cleavage and activation of human acid ceramidase J. Biol. Chem. 2008, 283 (17) 11253-9
12. Zhao, L. Y.; Tsuboi, K.; Okamoto, Y.; Nagahata, S.; Ueda, N. Proteolytic activation and glycosylation of N-acylethanolamine-hydrolyzing acid amidase, a lysosomal enzyme involved in the endocannabinoid metabolism Biochim. Biophys. Acta 2007, 1771 (11) 1397-405
13. Wang, J.; Zhao, L. Y.; Uyama, T.; Tsuboi, K.; Tonai, T.; Ueda, N. Amino acid residues crucial in pH regulation and proteolytic activation of N-acylethanolamine-hydrolyzing acid amidase Biochim. Biophys. Acta 2008, 1781 (11-12) 710-7
14. Pei, Y.; Mercier, R. W.; Anday, J. K.; Thakur, G. A.; Zvonok, A. M.; Hurst, D.; Reggio, P. H.; Janero, D. R.; Makriyannis, A. Ligand-Binding Architecture of Human CB2 Cannabinoid Receptor: Evidence for Receptor Subtype-Specific Binding Motif and Modeling GPCR Activation Chem. Biol. 2008, 15 (11) 1207-19
15. Andrews, P. Estimation of the molecular weights of proteins by Sephadex gel-filtration Biochem. J. 1964, 91 (2) 222-33
16. Saturnino, C.; Petrosino, S.; Ligresti, A.; Palladino, C.; De Martino, G.; Bisogno, T.; Di Marzo, V. Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase Bioorg. Med. Chem. Lett. 2010, 20 (3) 1210-3
17. Tsuboi, K.; Sun, Y. X.; Okamoto, Y.; Araki, N.; Tonai, T.; Ueda, N. 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. 2005, 280 (12) 11082-92
18. Williams, J.; Wood, J.; Pandarinathan, L.; Karanian, D. A.; Bahr, B. A.; Vouros, P.; Makriyannis, A. Quantitative method for the profiling of the endocannabinoid metabolome by LC-atmospheric pressure chemical ionization-MS Anal. Chem. 2007, 79 (15) 5582-93
19. Wood, J. T.; Williams, J. S.; Pandarinathan, L.; Courville, A.; Keplinger, M. R.; Janero, D. R.; Vouros, P.; Makriyannis, A.; Lammi-Keefe, C. J. Comprehensive profiling of the human circulating endocannabinoid metabolome: clinical sampling and sample storage parameters Clin. Chem. Lab. Med. 2008, 46 (9) 1289-95
20. Wood, J. T.; Williams, J. S.; Pandarinathan, L.; Janero, D. R.; Lammi-Keefe, C. J.; Makriyannis, A. Dietary docosahexaenoic acid supplementation alters select physiological endocannabinoid-system metabolites in brain and plasma J. Lipid Res. 2010, 51 (6) 1416-23
21. Zvonok, N.; Williams, J.; Johnston, M.; Pandarinathan, L.; Janero, D. R.; Li, J.; Krishnan, S. C.; Makriyannis, A. Full mass spectrometric characterization of human monoacylglycerol lipase generated by large-scale expression and single-step purification J. Proteome Res. 2008, 7 (5) 2158-64
22. Ueda, N.; Yamanaka, K.; Yamamoto, S. Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance J. Biol. Chem. 2001, 276 (38) 35552-7
23. Ramarao, M. K.; Murphy, E. A.; Shen, M. W.; Wang, Y.; Bushell, K. N.; Huang, N.; Pan, N.; Williams, C.; Clark, J. D. A fluorescence-based assay for fatty acid amide hydrolase compatible with high-throughput screening Anal. Biochem. 2005, 343 (1) 143-51
24. Edge, A. S. Deglycosylation of glycoproteins with trifluoromethanesulphonic acid: elucidation of molecular structure and function Biochem. J. 2003, 376 (Pt 2) 339-50
25. Arakawa, T.; Prestrelski, S. J.; Kenney, W. C.; Carpenter, J. F. Factors affecting short-term and long-term stabilities of proteins Adv. Drug Deliv. Rev. 2001, 46 (1-3) 307-26
26. Baker, H. M.; Day, C. L.; Norris, G. E.; Baker, E. N. Enzymatic deglycosylation as a tool for crystallization of mammalian binding proteins Acta Crystallogr., D: Biol. Crystallogr. 1994, 50 (Pt 4) 380-4
27. Sola, R. J.; Griebenow, K. Effects of glycosylation on the stability of protein pharmaceuticals J. Pharm. Sci. 2009, 98 (4) 1223-45
28. Varki, A.; Kornfeld, S. Structural studies of phosphorylated high mannose-type oligosaccharides J. Biol. Chem. 1980, 255 (22) 10847-58
29. Marino, K.; Bones, J.; Kattla, J. J.; Rudd, P. M. A systematic approach to protein glycosylation analysis: a path through the maze Nat. Chem. Biol. 2010, 6 (10) 713-23