Using the reversible inhibition of gastric lipase by Orlistat for investigating simultaneously lipase adsorption and substrate hydrolysis at the lipid-water interface

Biochimie

Volumn 101, Issue 1, 2014, Pages 221-231

  Bénarouche, Anaïs ^a   Point, Vanessa ^a   Carrière, Frédéric ^a   Cavalier, Jean François ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Enzyme kinetics; Interfacial enzymology; Lipase; Lipase inhibition; Lipolysis; Monomolecular film

Indexed keywords

1,2-DIDECANOYLGLYCEROL; DIACYLGLYCEROL; LACTONE; LIPID; TETRAHYDROLIPSTATIN; TRIACYLGLYCEROL LIPASE; WATER;

ADSORPTION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOG; ENZYMOLOGY; HYDROLYSIS; KINETICS; STOMACH; SURFACE PROPERTY;

ADSORPTION; ANIMALS; DIGLYCERIDES; DOGS; HYDROLYSIS; KINETICS; LACTONES; LIPASE; LIPIDS; MODELS, MOLECULAR; STOMACH; SURFACE PROPERTIES; WATER;

EID: 84899415920     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2014.01.019     Document Type: Article

References (46)

1. F. Carrière, C. Renou, S. Ransac, V. Lopez, J. De Caro, F. Ferrato, A. De Caro, A. Fleury, P. Sanwald-Ducray, H. Lengsfeld, C. Beglinger, P. Hadvary, R. Verger, and R. Laugier Inhibition of gastrointestinal lipolysis by Orlistat during digestion of test meals in healthy volunteers Am. J. Physiol. Gastrointest. Liver Physiol. 281 2001 G16 G28
2. H. Lengsfeld, G. Beaumier-Gallon, H. Chahinian, A. De Caro, R. Verger, R. Laugier, and F. Carrière Physiology of gastrointestinal lipolysis and therapeutical use of lipases and digestive lipase inhibitors G. Müller, S. Petry, Lipases and Phospholipases in Drug Development 2004 Wiley-VCH Weinheim 195 223
3. B. Borgstrom Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin Biochim. Biophys. Acta 962 1988 308 316
4. P. Hadváry, H. Lengsfeld, and H. Wolfer Inhibition of pancreatic lipase in vitro by the covalent inhibitor tetrahydrolipstatin Biochem J. 256 1988 357
5. Y. Gargouri, H. Chahinian, H. Moreau, S. Ransac, and R. Verger Inactivation of pancreatic and gastric lipases by THL and C12: 0-TNB: a kinetic study with emulsified tributyrin Biochim. Biophys. Acta 1085 1991 322 328
6. P. Hadváry, 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
7. Q. Lüthi-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
8. A. Tiss, H. Lengsfeld, F. Carrière, and R. Verger Inhibition of human pancreatic lipase by tetrahydrolipstatin: further kinetic studies showing its reversibility J. Mol. Cat. B: Enzym. 58 2009 41 47
9. A. Tiss, H. Lengsfeld, and R. Verger A comparative kinetic study on human pancreatic and Thermomyces lanuginosa lipases: inhibitory effects of tetrahydrolipstatin in the presence of lipid substrates J. Mol. Cat. B Enzym. 62 2010 19 26
10. V. Belle, A. Fournel, M. Woudstra, S. Ranaldi, F. Prieri, V. Thomé, J. Currault, R. Verger, B. Guigliarelli, and F. Carrière Probing the opening of the pancreatic lipase lid using site-directed spin labeling and EPR spectroscopy Biochemistry 46 2007 2205 2214
11. A. Tiss, S. Ransac, H. Lengsfeld, P. Hadvary, A. Cagna, and R. Verger Surface behaviour of bile salts and tetrahydrolipstatin at air/water and oil/water interfaces Chem. Phys. Lipids 111 2001 73 85
12. A. Tiss, H. Lengsfeld, P. Hadvary, A. Cagna, and R. Verger Transfer of Orlistat through oil-water interfaces Chem. Phys. Lipids 119 2002 41 49
13. H. Stalder, G. Oesterhelt, and B. Borgström Tetrahydrolipstatin: degradation products produced by human carboxyl-ester lipase Helv. Chim. Acta 75 1992 1593 1603
14. H. Stalder, P.R. Schneider, and G. Oesterhelt Tetrahydrolipstatin: thermal and hydrolytic degradation Helv. Chim. Acta 73 1990 1022 1036
15. A. Aloulou, J.A. Rodriguez, S. Fernandez, D. van Oosterhout, D. Puccinelli, and F. Carrière Exploring the specific features of interfacial enzymology based on lipase studies Biochim. Biophys. Acta 1761 2006 995 1013
16. H. Singh, A. Ye, and D. Horne Structuring food emulsions in the gastrointestinal tract to modify lipid digestion Prog. Lipid Res. 48 2009 92 100
17. M. Golding, and T.J. Wooster The influence of emulsion structure and stability on lipid digestion Curr. Opin. Colloid Interface Sci. 15 2010 90 101
18. J.F. Cavalier, S. Ransac, R. Verger, and G. Buono Inhibition of human gastric and pancreatic lipases by chiral alkylphosphonates. A kinetic study with 1,2-didecanoyl-sn-glycerol monolayer Chem. Phys. Lipids 100 1999 3 31
19. V. Delorme, R. Dhouib, S. Canaan, F. Fotiadu, F. Carrière, and J.-F. Cavalier Effects of surfactants on lipase structure, activity and inhibition Pharm. Res. 28 2011 1831 1842
20. H. Haiker, H. Lengsfeld, P. Hadvary, and F. Carrière Rapid exchange of pancreatic lipase between triacylglycerol droplets Biochim. Biophys. Acta (BBA) Lipids Lipid Metab. 1682 2004 72 79
21. G. Pieroni, and R. Verger Hydrolysis of mixed monomolecular films of triglyceride/lecithin by pancreatic lipase J. Biol. Chem. 254 1979 10090 10094
22. Y. Gargouri, G. Piéroni, C. Rivière, L. Sarda, and R. Verger Inhibition of lipases by proteins: a binding study using dicaprin monolayers Biochemistry 25 1986 1733 1738
23. M. Aoubala, M. Ivanova, I. Douchet, A. De Caro, and R. Verger Interfacial binding of human gastric lipase to lipid monolayers, measured with an ELISA Biochemistry 34 1995 10786 10793
24. F. Marguet, I. Douchet, J.F. Cavalier, G. Buono, and R. Verger Interfacial and or molecular recognition by lipases of mixed monomolecular films of 1,2-dicaprin and chiral organophosphorus glyceride analogues? Colloids Surf. B: Biointerfaces 13 1999 37 45
25. A. Tiss, F. Carrière, I. Douchet, S. Patkar, A. Svendsen, and R. Verger Interfacial binding and activity of lipases at the lipid-water interface: effects of Gum Arabic and surface pressure Colloids Surf. B Biointerfaces 26 2002 135 145
26. J.-C. Bakala N'Goma, S. Amara, K. Dridi, V. Jannin, and F. Carrière Understanding the lipid-digestion processes in the GI tract before designing lipid-based drug-delivery systems Ther. Deliv. 3 2011 105 124
27. A. Roussel, N. Miled, L. Berti-Dupuis, M. Rivière, S. Spinelli, P. Berna, V. Gruber, R. Verger, and C. Cambillau Crystal structure of the open form of dog gastric lipase in complex with a phosphonate inhibitor J. Biol. Chem. 277 2002 2266 2274
28. S. Fernandez, S. Chevrier, N. Ritter, B. Mahler, F. Demarne, F. Carrière, and V. Jannin In vitro gastrointestinal lipolysis of four formulations of piroxicam and cinnarizine with the self emulsifying excipients Labrasol and Gelucire 44/14 Pharm. Res. 26 2009 1901 1910
29. V. Gruber, P. Berna, T. Arnaud, P. Bournat, C. Clément, D. Mison, B. Olagnier, L. Philippe, M. Theisen, S. Baudino, C. Bénicourt, C. Cudrey, C. Bloës, N. Duchateau, S. Dufour, C. Gueguen, S. Jacquet, C. Ollivo, C. Poncetta, N. Zorn, D. Ludevid, A. Van Dorsselaer, R. Verger, A. Doherty, B. Mérot, and C. Danzin Large-scale production of a therapeutic protein in transgenic tobacco plants: effect of subcellular targeting on quality of a recombinant dog gastric lipase Mol. Breed. 7 2001 329 340
30. V. Point, K.V.P. Pavan Kumar, S. Marc, V. Delorme, G. Parsiegla, S. Amara, F. Carrière, G. Buono, F. Fotiadu, S. Canaan, J. Leclaire, and J.-F. Cavalier Analysis of the discriminative inhibition of mammalian digestive lipases by 3-phenyl substituted 1,3,4-oxadiazol-2(3H)-ones Eur. J. Med. Chem. 58 2012 452 463
31. R. Verger, M.C. Mieras, and G.H. de Haas Action of phospholipase A at interfaces J. Biol. Chem. 248 1973 4023 4034
32. L. Wilhelmy Ueber die Abhängigkeit der Capillaritäts Constanten des Alkohols von Substanz und Gestalt des benetzten festen Körpers Ann. Phys. 195 1863 177 217
33. I. Panaiotov, and R. Verger Enzymatic reactions at interfaces: interfacial and temporal organization of enzymatic lipolysis W. Norde, Physical Chemistry of Biological Interfaces 2000 Marcel Dekker, Inc New York, Basel 359 400
34. R. Verger, and G.H. De Haas Enzyme reactions in a membrane model. 1. A new technique to study enzyme reactions in monolayers Chem. Phys. Lipids 10 1973 127 136
35. A. Bénarouche, V. Point, G. Parsiegla, F. Carrière, and J.-F. Cavalier New insights into the pH-dependent interfacial adsorption of dog gastric lipase using the monolayer technique Colloids Surf. B Biointerfaces 111 2013 306 312
36. R. Verger, and G.H. De Haas Interfacial enzyme kinetics of lipolysis Annu. Rev. Biophys. Bioeng. 5 1976 77 117
37. R. Verger, J. Rietsch, M. Van Dam-Mieras, and G. De Haas Comparative studies of lipase and phospholipase A2 acting on substrate monolayers J. Biol. Chem. 251 1976 3128 3133
38. D.J.C. Pappin, P. Hojrup, and A.J. Bleasby Rapid identification of proteins by peptide-mass fingerprinting Curr. Biol. 3 1993 327 332
39. S. Ransac, Y. Gargouri, H. Moreau, and R. Verger Inactivation of pancreatic and gastric lipases by tetrahydrolipstatin and alkyl-dithio-5-(2- nitrobenzoic acid). A kinetic study with 1,2-didecanoyl-sn-glycerol monolayers Eur. J. Biochem. 202 1991 395 400
40. Y. Gargouri, S. Ransac, and R. Verger Covalent inhibition of digestive lipases: an in vitro study Biochim. Biophys. Acta 1344 1997 6 37
41. 2 Eur. J. Biochem. 132 1983 639 644
42. P. Vainio, J.A. Virtanen, P.K.J. Kinnunen, J. Gotto, M. Antonio, J.T. Sparrow, F. Pattus, P. Bougis, and R. Verger Action of lipoprotein lipase on mixed triacylglycerol/phosphatidylcholine monolayers. Activation by apolipoprotein C-II J. Biol. Chem. 258 1983 5477 5482
43. I. Arimoto, M. Fujita, H. Saito, T. Handa, and K. Miyajima Activation and inhibition of lipoprotein lipase in mixed monolayers of medium or long chain-triglycerides and phospholipids Colloid Polym. Sci. 275 1997 60 66
44. G.H. Peters, U. Dahmen-Levison, K. de Meijere, G. Brezesinski, S. Toxvaerd, H. Möhwald, A. Svendsen, and P.K.J. Kinnunen Influence of surface properties of mixed monolayers on lipolytic hydrolysis Langmuir 16 2000 2779 2788
45. H. Chahinian, T. Snabe, C. Attias, P. Fojan, S.B. Petersen, and F. Carrière How gastric lipase, an interfacial enzyme with a Ser-His-Asp catalytic triad, acts optimally at acidic pH Biochemistry 45 2006 993 1001
46. P. Bougis, H. Rochat, G. Pieroni, and R. Verger Penetration of phospholipid monolayers by cardiotoxins Biochemistry 20 1981 4915 4920