The molecular mechanism of human hormone-sensitive lipase inhibition by substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones

Biochimie

Volumn 94, Issue 1, 2012, Pages 137-145

  Ben Ali, Yassine ^a,b,c   Verger, Robert ^b   Carrire, Frédéric ^b   Petry, Stefan ^d   Muller, Günter ^d   Abousalham, Abdelkarim ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

^c UNIVERSITY OF SFAX   (Tunisia)

^d SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

3 Phenyl 5 alkoxy 1,3,4 oxadiazol 2 ones; Hormone sensitive lipase; Inhibition; Reactivation

Indexed keywords

3 PHENYL 5 ALKOXY 1,3,4 OXADIAZOL 2 ONES; 5 METHOXY 3 (3 METHYL 4 PHENYLACETAMIDOPHENYL)1,3,4 OXADIAZOL 2 3H ONE; 5 METHOXY 3 (3 PHENOXYPHENYL) 1,3,4 OXADIAZOL 2 3H ONE; CARBON DIOXIDE; ENZYME INHIBITOR; FATTY ACID; HORMONE SENSITIVE LIPASE; LIPID EMULSION; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; INCUBATION TIME; INHIBITION KINETICS; NUCLEOPHILICITY; REACTION TIME; STOICHIOMETRY; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, LIQUID; ENZYME INHIBITORS; HYDROLYSIS; KINETICS; MASS SPECTROMETRY; OXADIAZOLES; STEROL ESTERASE;

EID: 83555166285     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2011.09.028     Document Type: Article

References (41)

1. P. Arner Insulin resistance in type 2 diabetes: role of fatty acids Diabetes. Metab. Res. Rev. 18 Suppl. 2 2002 S5 S9
2. Y.T. Kruszynska, D.S. Worrall, J. Ofrecio, J.P. Frias, G. Macaraeg, and J.M. Olefsky Fatty acid-induced insulin resistance: decreased muscle PI3K activation but unchanged Akt phosphorylation J. Clin. Endocrinol. Metab. 87 2002 226 234 (Pubitemid 34084695)
3. M. Roden, T.B. Price, G. Perseghin, K.F. Petersen, D.L. Rothman, G.W. Cline, and G.I. Shulman Mechanism of free fatty acid-induced insulin resistance in humans J. Clin. Invest. 97 1996 2859 2865 (Pubitemid 26197099)
4. C. Holm, T. Osterlund, H. Laurell, and J.A. Contreras Molecular mechanisms regulating hormone-sensitive lipase and lipolysis Annu. Rev. Nutr. 20 2000 365 393
5. G. Haemmerle, R. Zimmermann, M. Hayn, C. Theussl, G. Waeg, E. Wagner, W. Sattler, T.M. Magin, E.F. Wagner, and R. Zechner Hormone-sensitive lipase deficiency in mice causes diglyceride accumulation in adipose tissue, muscle, and testis J. Biol. Chem. 277 2002 4806 4815 (Pubitemid 34968514)
6. F.B. Kraemer, and W.J. Shen Hormone-sensitive lipase: control of intracellular tri-(di-)acylglycerol and cholesteryl ester hydrolysis J. Lipid. Res. 43 2002 1585 1594 (Pubitemid 35168272)
7. F.B. Kraemer, W.J. Shen, K. Harada, S. Patel, J. Osuga, S. Ishibashi, and S. Azhar Hormone-sensitive lipase is required for high-density lipoprotein cholesteryl ester-supported adrenal steroidogenesis Mol. Endocrinol. 18 2004 549 557 (Pubitemid 38328202)
8. J. Osuga, S. Ishibashi, T. Oka, H. Yagyu, R. Tozawa, A. Fujimoto, F. Shionoiri, N. Yahagi, F.B. Kraemer, O. Tsutsumi, and N. Yamada Targeted disruption of hormone-sensitive lipase results in male sterility and adipocyte hypertrophy, but not in obesity Proc. Natl. Acad. Sci. U S A 97 2000 787 792 (Pubitemid 30070388)
9. S.P. Wang, N. Laurin, J. Himms-Hagen, M.A. Rudnicki, E. Levy, M.F. Robert, L. Pan, L. Oligny, and G.A. Mitchell The adipose tissue phenotype of hormone-sensitive lipase deficiency in mice Obes. Res. 9 2001 119 128 (Pubitemid 33603838)
10. J.A. Rodriguez, Y. Ben Ali, S. Abdelkafi, L.D. Mendoza, J. Leclaire, F. Fotiadu, G. Buono, F. Carriere, and A. Abousalham In vitro stereoselective hydrolysis of diacylglycerols by hormone-sensitive lipase Biochim. Biophys. Acta 1801 2010 77 83
11. Y. Ben Ali, F. Carriere, R. Verger, S. Petry, G. Muller, and A. Abousalham Continuous monitoring of cholesterol oleate hydrolysis by hormone-sensitive lipase and other cholesterol esterases J. Lipid. Res. 46 2005 994 1000
12. R. Zimmermann, J.G. Strauss, G. Haemmerle, G. Schoiswohl, R. Birner-Gruenberger, M. Riederer, A. Lass, G. Neuberger, F. Eisenhaber, A. Hermetter, and R. Zechner Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase Science 306 2004 1383 1386 (Pubitemid 39532517)
13. R. Lehner, and D.E. Vance Cloning and expression of a cDNA encoding a hepatic microsomal lipase that mobilizes stored triacylglycerol Biochem. J. 343 Pt 1 1999 1 10 (Pubitemid 29473871)
14. R. Birner-Gruenberger, H. Susani-Etzerodt, M. Waldhuber, G. Riesenhuber, H. Schmidinger, G. Rechberger, M. Kollroser, J.G. Strauss, A. Lass, R. Zimmermann, G. Haemmerle, R. Zechner, and A. Hermetter The lipolytic proteome of mouse adipose tissue Mol. Cell. Proteomics 4 2005 1710 1717 (Pubitemid 41749264)
15. V.W. Dolinsky, S. Sipione, R. Lehner, and D.E. Vance The cloning and expression of a murine triacylglycerol hydrolase cDNA and the structure of its corresponding gene Biochim. Biophys. Acta 1532 2001 162 172 (Pubitemid 32706436)
16. E. Wei, Y. Ben Ali, J. Lyon, H. Wang, R. Nelson, V.W. Dolinsky, J.R. Dyck, G. Mitchell, G.S. Korbutt, and R. Lehner Loss of TGH/Ces3 in mice decreases blood lipids, improves glucose tolerance, and increases energy expenditure Cell Metab. 11 2010 183 193
17. L. Vertesy, B. Beck, M. Bronstrup, K. Ehrlich, M. Kurz, G. Muller, D. Schummer, and G. Seibert Cyclipostins, novel hormone-sensitive lipase inhibitors from Streptomyces sp. DSM 13381. II. Isolation, structure elucidation and biological properties J. Antibiot. (Tokyo) 55 2002 480 494 (Pubitemid 34746670)
18. D. Wagle, S.D. Fang, I. Terlecky, J. Resek, and J. Egan Preparation and formulation of eudesmanolides for use as glucose and lipid lowering compounds PCT Int. Appl. 2000 41 WO 0027388 A1
19. S. Ebdrup, L.G. Sorensen, O.H. Olsen, and P. Jacobsen Synthesis and structure-activity relationship for a novel class of potent and selective carbamoyl-triazole based inhibitors of hormone sensitive lipase J. Med. Chem. 47 2004 400 410 (Pubitemid 38057883)
20. D.H. Slee, A.S. Bhat, T.N. Nguyen, M. Kish, K. Lundeen, M.J. Newman, and S.J. McConnell Pyrrolopyrazinedione-based inhibitors of human hormone-sensitive lipase J. Med. Chem. 46 2003 1120 1122 (Pubitemid 36428216)
21. J.C. de Jong, L.G. Sorensen, H. Tornqvist, and P. Jacobsen Carbazates as potent inhibitors of hormone-sensitive lipase Bioorg. Med. Chem. Lett. 14 2004 1741 1744 (Pubitemid 38340678)
22. Y. Ben Ali, H. Chahinian, S. Petry, G. Muller, R. Lebrun, R. Verger, F. Carriere, L. Mandrich, M. Rossi, G. Manco, L. Sarda, and A. Abousalham Use of an inhibitor to identify members of the hormone-sensitive lipase family Biochemistry 45 2006 14183 14191 (Pubitemid 44846207)
23. K. Schoenafinger, S. Petry, G. Müller, and K.-H. Baringhaus Preparation of 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones as hormone-sensitive lipase inhibitors PCT Int. Appl. 2001 80 WO 0351841 A2
24. Y. Ben Ali, H. Chahinian, S. Petry, G. Muller, F. Carriere, R. Verger, and A. Abousalham Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain? Biochemistry 43 2004 9298 9306 (Pubitemid 38955463)
25. M.M. Bradford A rapid and sensitive method for quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254
26. A. Tiss, F. Carriere, and R. Verger Effects of gum arabic on lipase interfacial binding and activity Anal. Biochem. 294 2001 36 43 (Pubitemid 32612547)
27. S. Ransac, Y. Gargouri, F. Marguet, G. Buono, C. Beglinger, P. Hildebrand, H. Lengsfeld, P. Hadvary, and R. Verger Covalent inactivation of lipases Meth. Enzymol. 286 1997 190 231 (Pubitemid 27408194)
28. R. Verger, M.C. Mieras, and G.H. de Haas Action of phospholipase A at interfaces J. Biol. Chem. 248 1973 4023 4034
29. S. Petry, Y. Ben Ali, H. Chahinian, H. Jordan, H. Kleine, G. Muller, F. Carriere, and A. Abousalham Sensitive assay for hormone-sensitive lipase using NBD-labeled monoacylglycerol to detect low activities in rat adipocytes J. Lipid. Res. 46 2005 603 614 (Pubitemid 43109797)
30. S. Longhi, M. Czjzek, V. Lamzin, A. Nicolas, and C. Cambillau Atomic resolution (1.0 A) crystal structure of Fusarium solani cutinase: stereochemical analysis J. Mol. Biol. 268 1997 779 799 (Pubitemid 27214437)
31. A. Tiss, H. Lengsfeld, F. Carrire, and R. Verger Inhibition of human pancreatic lipase by tetrahydrolipstatin: further kinetic studies showing its reversibility J. Mol. Catal. B Enzym. 58 2009 41 47
32. A. Tiss, N. Miled, R. Verger, Y. Gargouri, and A. Abousalham Digestive lipases inhibition: an in vitro study G. Müller, S. Petry, Lipases and Phospholipases in Drug Development 2004 Wiley-VCH 155 193
33. B. Borgström Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin Biochim. Biophys. Acta 962 1988 308 316
34. A. Lookene, N. Skottova, and G. Olivecrona Interactions of lipoprotein lipase with the active-site inhibitor tetrahydrolipstatin (Orlistat) Eur. J. Biochem. 222 1994 395 403 (Pubitemid 24204908)
35. A.P. Potthoff, L. Haalck, and F. Spener Inhibition of lipases from Chromobacterium viscosum and Rhizopus oryzae by tetrahydrolipstatin Biochim. Biophys. Acta 1389 1998 123 131 (Pubitemid 28022472)
36. P. Hadvry, W. Sidler, W. Meister, W. Vetter, and H. Wolfer The lipase inhibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase J. Biol. Chem. 266 1991 2021 2027 (Pubitemid 21909023)
37. Q. Luthi-Peng, H.P. Marki, and P. Hadvary Identification of the active-site serine in human pancreatic lipase by chemical modification with tetrahydrolipstatin FEBS Lett. 299 1992 111 115
38. M. Cygler, P. Grochulski, R.J. Kazlauskas, J.D. Schrag, F. Bouthillier, B. Rubin, A.N. Serreqi, and A.K. Gupta A structural basis for the chiral preferences of lipases J. Am. Chem. Soc. 116 1994 3180 3186
39. M.-P. Egloff, F. Marguet, G. Buono, R. Verger, C. Cambillau, and H. van Tilbeurgh The 2.46 resolution structure of the pancreatic lipase-colipase complex inhibited by a C11 alkyl phosphonate Biochemistry 34 1995 2751 2762
40. J. Uppenberg, N. Ohrner, M. Norin, K. Hult, G.J. Kleywegt, S. Patkar, V. Waagen, T. Anthonsen, and T.A. Jones Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols Biochemistry 34 1995 16838 16851
41. S. Yapoudjian, M.G. Ivanova, A.M. Brzozowski, S.A. Patkar, J. Vind, A. Svendsen, and R. Verger Binding of Thermomyces (Humicola) lanuginosa lipase to the mixed micelles of cis-parinaric acid/NaTDC Eur. J. Biochem. 269 2002 1613 1621