High-performance liquid chromatography assay with fluorescence detection for the evaluation of inhibitors against human recombinant monoacylglycerol lipase

Analytical Biochemistry

Volumn 399, Issue 2, 2010, Pages 218-224

  Holtfrerich, Angela ^a   Makharadze, Teona ^a   Lehr, Matthias ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Fluorescence detection; HPLC; Inhibitors; Monoacylglycerol lipase; Pyrene substituted 2 acylglycerol; Rearrangement

Indexed keywords

CARBOXYLATION; CORROSION INHIBITORS; FLUORESCENCE; GLYCEROL;

FLUORESCENCE DETECTION; FLUORESCENT ASSAYS; FLUOROGENIC SUBSTRATE; HPLC; MONOACYLGLYCEROL; REARRANGEMENT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC); SURFACTANT TRITON-X;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

1,3 DIHYDROXYPROPAN 2 YL 4 PYREN 1 YLBUTANOATE; 4 NITROPHENYL 4 [BIS(1,3 BENZODIOXOL 5 YL)HYDROXYMETHYL]PIPERIDINE 1 CARBOXYLATE; ACYLGLYCEROL LIPASE; BUTYRIC ACID DERIVATIVE; ENZYME INHIBITOR; METHYL ARACHIDONYLFLUOROPHOSPHONATE; RECOMBINANT ENZYME; TRITON X 100; UNCLASSIFIED DRUG; [4 (5 METHOXY 2 OXO 1,3,4 OXADIAZOL 3 YL) 2 METHYLPHENYL]CARBAMIC ACID BENZYL ESTER;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; COVALENT BOND; ENZYME SUBSTRATE; FLUORESCENCE ANALYSIS; IC 50; INCUBATION TIME; ISOMERIZATION; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 77049087509     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2009.12.015     Document Type: Article

References (38)

1. Labar G., and Michaux C. Fatty acid amide hydrolase: from characterization to therapeutics. Chem. Biodivers. 4 (2007) 1882-1902
2. Saario S.M., and Laitinen J.T. Monoglyceride lipase as an enzyme hydrolyzing 2-arachidonoylglycerol. Chem. Biodivers. 4 (2007) 1903-1913
3. Saario S.M., and Laitinen J.T. Therapeutic potential of endocannabinoid-hydrolysing enzyme inhibitors. Basic Clin. Pharmacol. Toxicol. 101 (2007) 287-293
4. Schlosburg J.E., Kinsey S.G., and Lichtman A.H. Targeting fatty acid amide hydrolase (FAAH) to treat pain and inflammation. AAPS J. 11 (2009) 39-44
5. Long J.Z., Li W., Booker L., Burston J.J., Kinsey S.G., Schlosburg J.E., Pavón F.J., Serrano A.M., Selley D.E., Parsons L.H., Lichtman A.H., and Cravatt B.F. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat. Chem. Biol. 5 (2009) 37-44
6. Vandevoorde S. Overview of the chemical families of fatty acid amide hydrolase and monoacylglycerol lipase inhibitors. Curr. Top. Med. Chem. 8 (2008) 247-267
7. Seierstad M., and Breitenbucher J.G. Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. J. Med. Chem. 51 (2008) 7327-7343
8. Viso A., Cisneros J.A., and Ortega-Gutiérrez S. The medicinal chemistry of agents targeting monoacylglycerol lipase. Curr. Top. Med. Chem. 8 (2008) 231-246
9. Dinh T.P., Carpenter D., Leslie F.M., Freund T.F., Katona I., Sensi S.L., Kathuria S., and Piomelli D. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc. Natl. Acad. Sci. USA 99 (2002) 10819-10824 (Erratum: Proc. Natl. Acad. Sci. USA 99 (2002) 13961)
10. Ortar G., Cascio M.G., Moriello A.S., Camalli M., Morera E., Nalli M., and Di Marzo V. Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: a critical revisitation. Eur. J. Med. Chem. 43 (2008) 62-72
11. Bisogno T., Ortar G., Petrosino S., Morera E., Palazzo E., Nalli M., Maione S., and Di Marzo V. Development of a potent inhibitor of 2-arachidonoylglycerol hydrolysis with antinociceptive activity in vivo. Biochim. Biophys. Acta 1791 (2009) 53-60
12. Ortar G., Bisogno T., Ligresti A., Morera E., Nalli M., and Di Marzo V. Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism. J. Med. Chem. 51 (2008) 6970-6979
13. Ghafouri N., Tiger G., Razdan R.K., Mahadevan A., Pertwee R.G., Martin B.R., and Fowler C.J. Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol. Br. J. Pharmacol. 143 (2004) 774-784
14. Makara J.K., Mor M., Fegley D., Szabó S.I., Kathuria S., Astarita G., Duranti A., Tontini A., Tarzia G., Rivara S., Freund T.F., and Piomelli D. Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus. Nat. Neurosci. 8 (2005) 1139-1141 (Erratum: Nat. Neurosci. 10 (2007) 134)
15. Vandevoorde S., Saha B., Mahadevan A., Razdan R.K., Pertwee R.G., Martin B.R., and Fowler C.J. Influence of the degree of unsaturation of the acyl side chain upon the interaction of analogues of 1-arachidonoylglycerol with monoacylglycerol lipase and fatty acid amide hydrolase. Biochem. Biophys. Res. Commun. 337 (2005) 104-109
16. Brengdahl J., and Fowler C.J. A novel assay for monoacylglycerol hydrolysis suitable for high-throughput screening. Anal. Biochem. 359 (2006) 40-44
17. Matuszak N., Muccioli G.G., Labar G., and Lambert D.M. Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors. J. Med. Chem. 52 (2009) 7410-7420
18. L. Even, C. Hoornaert, Triazolopyridine carboxamide derivatives and triazolopyrimidine carboxamide derivatives, preparatin thereof, and therapeutic use thereof, WO2008/145839, 2008.
19. Blankman J.L., Simon G.M., and Cravatt B.F. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem. Biol. 14 (2007) 1347-1356
20. King A.R., Duranti A., Tontini A., Rivara S., Rosengarth A., Clapper J.R., Astarita G., Geaga J.A., Luecke H., Mor M., Tarzia G., and Piomelli D. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices. Chem. Biol. 14 (2007) 1357-1365
21. King A.R., Lodola A., Carmi C., Fu J., Mor M., and Piomelli D. A critical cysteine residue in monoacylglycerol lipase is targeted by a new class of isothiazolinone-based enzyme inhibitors. Br. J. Pharmacol. 157 (2009) 974-983
22. Saario S.M., Savinainen J.R., Laitinen J.T., Järvinen T., and Niemi R. Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes. Biochem. Pharmacol. 67 (2004) 1381-1387
23. Saario S.M., Salo O.M., Nevalainen T., Poso A., Laitinen J.T., Järvinen T., and Niemi R. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem. Biol. 12 (2005) 649-656
24. Minkkilä A., Myllymäki M.J., Saario S.M., Castillo-Melendez J.A., Koskinen A.M., Fowler C.J., Leppänen J., and Nevalainen T. The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors. Eur. J. Med. Chem. 44 (2009) 2994-3008
25. Muccioli G.G., Labar G., and Lambert D.M. CAY10499, a novel monoglyceride lipase inhibitor evidenced by an expeditious MGL assay. ChemBioChem 9 (2008) 2704-2710
26. Wang Y., Chanda P., Jones P.G., and Kennedy J.D. A fluorescence-based assay for monoacylglycerol lipase compatible with inhibitor screening. Assay Drug Dev. Technol. 6 (2008) 387-393
27. Forster L., Schulze Elfringhoff A., and Lehr M. High performance liquid chromatographic assay with fluorescence detection for the evaluation of inhibitors against fatty acid amide hydrolase. Anal. Bioanal. Chem. 394 (2009) 1679-1685
28. Parkkari T., Salo O.M., Huttunen K.M., Savinainen J.R., Laitinen J.T., Poso A., Nevalainen T., and Järvinen T. Synthesis and CB1 receptor activities of dimethylheptyl derivatives of 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE). Bioorg. Med. Chem. 14 (2006) 2850-2858
29. 2. Anal. Biochem. 222 (1994) 110-115
30. 2: structure-function studies with vesicle, micelle, and membrane assays. Biochim. Biophys. Acta 1420 (1999) 45-56
31. Boswinkel G., Derksen J.T.P., van't Riet1 K., and Cuperus F.P. Kinetics of acyl migration in monoglycerides and dependence on acyl chain length. J. Am. Oil Chem. Soc. 73 (1996) 707-711
32. Vogeser M., and Schelling G. Pitfalls in measuring the endocannabinoid 2-arachidonoyl glycerol in biological samples. Clin. Chem. Lab. Med. 45 (2007) 1023-1025
33. Pan B., Wang W., Long J., Sun D., Hillard C.J., Cravatt B.F., and Liu Q.S. Blockade of 2-arachidonoylglycerol hydrolysis by selective monoacylglycerol lipase inhibitor 4-nitrophenyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)piperidine-1-carboxylate (JZL184) enhances retrograde endocannabinoid signaling. J. Pharmacol. Exp. Ther. 331 (2009) 591-597
34. 2-mediated arachidonic acid release by several indole-2-carboxylic acids and 3-(pyrrol-2-yl)propionic acids in bovine and in human platelets. Arch. Pharm. (Weinheim) 333 (2000) 312-314
35. 2. J. Pharm. Biomed. Anal. 35 (2004) 135-142
36. 2. J. Chromatogr. B 783 (2003) 327-333
37. Schmolke M., Fabian J., and Lehr M. High-performance liquid chromatographic assay with ultraviolet spectrometric detection for the evaluation of inhibitors of phosphatidylinositol-specific phospholipase C. Anal. Biochem. 375 (2008) 291-298
38. 2 synthase-1 inhibitor screening. J. Chromatogr. B 875 (2008) 557-561