Effects of surfactants on lipase structure, activity, and inhibition

Pharmaceutical Research

Volumn 28, Issue 8, 2011, Pages 1831-1842

  Delorme, Vincent ^a,b   Dhouib, Rabeb ^a   Canaan, Stéphane ^a   Fotiadu, Frédéric ^b   Carrière, Frédéric ^a   Cavalier, Jean François ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b Ecole Centrale Marseille   (France)

Author keywords

inhibitor; interfacial enzymology; lipase; lipid protein interaction; surfactant

Indexed keywords

CETILISTAT; COLIPASE; DODECYL SULFATE SODIUM; FENFLURAMINE; GUM ARABIC; NONIONIC SURFACTANT; OCTYL GLUCOSIDE; PARAOXON; POLYSORBATE 80; RIMONABANT; SIBUTRAMINE; SORBITAN LAURATE; SURFACTANT; TAURODEOXYCHOLIC ACID; TETRAETHYLENE GLYCOL MONOOCTYL ETHER; TETRAHYDROLIPSTATIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ABDOMINAL PAIN; ADSORPTION KINETICS; CONFORMATIONAL TRANSITION; DEFECATION URGENCY; DIARRHEA; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DOSE COMPARISON; DRUG PROTEIN BINDING; DRUG STRUCTURE; EMULSION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME STRUCTURE; EQUILIBRIUM CONSTANT; HUMAN; HYDROPHOBICITY; LIPOLYSIS; LIVER INJURY; MICELLE; MICROEMULSION; NANOEMULSION; NONHUMAN; OBESITY; PATIENT COMPLIANCE; PHASE 3 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS;

ADSORPTION; ANIMALS; ANTI-OBESITY AGENTS; HUMANS; LIPASE; LIPOLYSIS; SURFACE-ACTIVE AGENTS;

EID: 79961169716     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-010-0362-9     Document Type: Review

References (94)

1. F Carrière C Renou S Ransac V Lopez J De Caro F Ferrato, et al. 2001 Inhibition of gastrointestinal lipolysis by Orlistat during digestion of test meals in healthy volunteers Am J Physiol Gastrointest Liver Physiol 281 1 G16 28 11408251
2. A Tiss H Lengsfeld R Verger 2010 A comparative kinetic study on human pancreatic and Thermomyces lanuginosa lipases: inhibitory effects of tetrahydrolipstatin in the presence of lipid substrates J Mol Catal B Enzym 62 19 26 10.1016/j.molcatb.2009.08.011 1:CAS:528:DC%2BD1MXhtlylsb%2FF
3. Lengsfeld H, Beaumier-Gallon G, Chahinian H, De Caro A, Verger R, Laugier R, et al. Physiology of gastrointestinal lipolysis and therapeutical use of lipases and digestive lipase inhibitors. In: Müller G, Petry S, editors. Lipases and phospholipases in drug development. Weinheim: Wiley-VCH; 2004. p. 195-223.
4. A Ballinger S Peikin 2002 Orlistat: its current status as an anti-obesity drug Eur J Pharmacol 440 2-3 109 17 12007529 10.1016/S0014-2999(02)01422-X 1:CAS:528:DC%2BD38XjsVSktLw%3D (Pubitemid 34458018)
5. P Kopelman A Bryson R Hickling A Rissanen S Rossner S Toubro, et al. 2007 Cetilistat (ATL-962), a novel lipase inhibitor: a 12-week randomized, placebo-controlled study of weight reduction in obese patients Int J Obes Lond 31 3 494 9 16953261 10.1038/sj.ijo.0803446 1:CAS:528:DC%2BD2sXitVKhsrc%3D
6. A Bryson S de la Motte C Dunk 2009 Reduction of dietary fat absorption by the novel gastrointestinal lipase inhibitor cetilistat in healthy volunteers Br J Clin Pharmacol 67 3 309 15 19220279 10.1111/j.1365-2125.2008.03311.x 1:CAS:528:DC%2BD1MXlt1Gmsb0%3D
7. Y Yamada T Kato H Ogino S Ashina K Kato 2008 Cetilistat (ATL-962), a novel pancreatic lipase inhibitor, ameliorates body weight gain and improves lipid profiles in rats Horm Metab Res 40 8 539 43 18500680 10.1055/s-2008- 1076699 1:CAS:528:DC%2BD1cXht1agu7vE
8. P Kopelman H Groot Gde A Rissanen S Rossner S Toubro R Palmer, et al. 2010 Weight loss, HbA1c reduction, and tolerability of cetilistat in a randomized, placebo-controlled phase 2 trial in obese diabetics: comparison with orlistat (Xenical) Obesity (Silver Spring) 18 1 108 15 10.1038/oby.2009.155 1:CAS:528:DC%2BD1MXhs1Sqt7vE
9. S Tucci E Boyland J Halford 2010 The role of lipid and carbohydrate digestive enzyme inhibitors in the management of obesity: a review of current and emerging therapeutic agents Diabetes Metab Syndr Obes 3 125 43 21437083 10.2147/DMSOTT.S7005 1:CAS:528:DC%2BC3cXmtl2jtr8%3D
10. V Salem S Bloom 2010 Approaches to the pharmacological treatment of obesity Expert Rev Clin Pharmacol 3 1 73 88 10.1586/ecp.09.54
11. Y Ben Ali H Chahinian S Petry G Muller R Lebrun R Verger, et al. 2006 Use of an inhibitor to identify members of the hormone-sensitive lipase family Biochemistry 45 47 14183 91 17115713 10.1021/bi0613978 1:CAS:528: DC%2BD28XhtFCqt77F (Pubitemid 44846207)
12. Petry S, Baringhaus K-H, Schoenafinger K, Jung C, Kleine H, Müller G. High-throughput screening of hormone-sensitive lipase and subsequent. In: Müller G, Petry S, editors. Lipases and phospholipases in drug development. Weinheim: Wiley-VCH; 2004. p. 121-37.
13. W Jin JS Millar U Broedl JM Glick DJ Rader 2003 Inhibition of endothelial lipase causes increased HDL cholesterol levels in vivo J Clin Invest 111 3 357 62 12569161 1:CAS:528:DC%2BD3sXpvFSntg%3D%3D (Pubitemid 36182212)
14. K Cotes JC Bakala N'goma R Dhouib I Douchet D Maurin F Carriere, et al. 2008 Lipolytic enzymes in Mycobacterium tuberculosis Appl Microbiol Biotechnol 78 5 741 9 18309478 10.1007/s00253-008-1397-2 1:CAS:528:DC%2BD1cXjsFGhtb4%3D
15. KC Mishra C de Chastellier Y Narayana P Bifani AK Brown GS Besra, et al. 2008 Functional role of the PE domain and immunogenicity of the Mycobacterium tuberculosis triacylglycerol hydrolase LipY Infect Immun 76 1 127 40 17938218 10.1128/IAI.00410-07 1:CAS:528:DC%2BD1cXisVKgsA%3D%3D
16. Seibert G, Toti L, Wink J, inventors; Sanofi-Aventis, assignee. Use of cyclipostin derivatives for the treatment of mycobacterial infectious diseases. United States patent US 20090233884. 2009 Sep 17.
17. S Dowling J Cox RJ Cenedella 2009 Inhibition of fatty acid synthase by Orlistat accelerates gastric tumor cell apoptosis in culture and increases survival rates in gastric tumor bearing mice in vivo Lipids 44 6 489 98 19381703 10.1007/s11745-009-3298-2 1:CAS:528:DC%2BD1MXmtlOmt7w%3D
18. K-E Jaeger S Ransac BW Dijkstra C Colson M Vanheuvel O Misset 1994 Bacterial lipases FEMS Microbiol Rev 15 1 29 63 7946464 10.1111/j.1574-6976. 1994.tb00121.x 1:CAS:528:DyaK2cXmsV2js7s%3D (Pubitemid 24290299)
19. EJ Gilbert 1993 Pseudomonas lipases: biochemical properties and molecular cloning Enzyme Microb Technol 15 8 634 45 7763958 10.1016/0141-0229(93)90062-7 1:CAS:528:DyaK3sXlvFyisbY%3D (Pubitemid 23225964)
20. Huang AHC. Plant lipases. In: Borgström B, Brockman HL, editors. Lipases. Amsterdam: Elsevier; 1984. p. 419-42.
21. Mukherjee KD, Hills MJ. Lipases from plants. In: Woolley P, Petersen SB, editors. Lipases: their structure, biochemistry and application. Cambridge: Cambridge University Press; 1994. p. 49-75.
22. F Carrière S Bezzine R Verger 1997 Molecular evolution of the pancreatic lipase and two related enzymes towards different substrate selectivities J Mol Catal B Enzym 3 55 64 10.1016/S1381-1177(96)00049-5 (Pubitemid 27276653)
23. Carrière F, Gargouri Y, Moreau H, Ransac S, Rogalska E, Verger R. Gastric lipases: cellular, biochemical and kinetic aspects. In: Wooley P, Petersen SB, editors. Lipases: Their structure, biochemistry and application. Cambridge: Cambridge University Press; 1994. p. 181-205.
24. Alberghina L, Schmid RD, Verger R. Lipases: structure, mechanism, and genetic engineering. Weinheim: VCH; 1991.
25. Wooley P, Petersen SB. Lipases: their structure, biochemistry and applications. Cambridge: Cambridge University Press; 1994.
26. Brockerhoff H, Jensen RG. In: Brockerhoff H, Jensen RG, editors. Lipolytic enzymes. New York: Academic; 1974.
27. Borgström B, Erlanson C. In: Borgström B, Brockman HL, editors. Lipases. Amsterdam: Elsevier; 1984.
28. A Aloulou JA Rodriguez S Fernandez D Van Oosterhout D Puccinelli F Carriere 2006 Exploring the specific features of interfacial enzymology based on lipase studies Biochim Biophys Acta, Mol Cell Biol Lipids 1761 995 1013 1:CAS:528:DC%2BD28Xps1Ghsbg%3D (Pubitemid 44354291)
29. R Verger MCE Mieras GH de Haas 1973 Action of phospholipase A at interfaces J Biol Chem 248 11 4023 34 4736081 1:CAS:528:DyaE3sXktl2ltb0%3D
30. Panaitov I, Verger R. Enzymatic reactions at interfaces: interfacial and temporal organization of enzymatic lipolysis. In: Baszkin A, Norde W, editors. Physical chemistry of biological interfaces. New York: Marcel Dekker, Inc; 2000. p. 359-400.
31. L Sarda P Desnuelle 1958 Action de la lipase pancréatique sur les esters en émulsion Biochim Biophys Acta 30 513 21 13618257 10.1016/0006-3002(58)90097-0 1:CAS:528:DyaG1MXjsFWjug%3D%3D
32. V Belle A Fournel M Woudstra S Ranaldi F Prieri V Thome, et al. 2007 Probing the opening of the pancreatic lipase lid using site-directed spin labeling and EPR spectroscopy Biochemistry 46 2205 14 17269661 10.1021/bi0616089 1:CAS:528:DC%2BD2sXhtFalsb8%3D (Pubitemid 46355329)
33. R Verger 1976 Interfacial enzyme kinetics of lipolysis Annu Rev Biophys Bioeng 5 77 117 782347 10.1146/annurev.bb.05.060176.000453 1:CAS:528: DyaE28Xksleqt78%3D
34. B Entressangles P Desnuelle 1968 Action of pancreatic lipase on aggregated glyceride molecules in an isotropic system Biochim Biophys Acta 159 2 285 95 5657459 1:CAS:528:DyaF1cXktFKgtbw%3D
35. A Antipova M Semenova L Belyakova M Il'in 2001 On relationships between molecular structure, interaction and surface behavior in mixture: small-molecule surfactant+ protein Colloids Surf B Biointerfaces 21 1-3 217 30 11377950 10.1016/S0927-7765(01)00174-6 1:CAS:528:DC%2BD3MXjslemtr0%3D (Pubitemid 32500321)
36. R Miller V Fainerman A Makievski J Krägel D Grigoriev V Kazakov, et al. 2000 Dynamics of protein and mixed protein/surfactant adsorption layers at the water/fluid interface Adv Colloid Interface Sci 86 1-2 39 82 10798350 10.1016/S0001-8686(00)00032-4 1:CAS:528:DC%2BD3cXitFyrtrY%3D (Pubitemid 30582777)
37. JE Mogensen P Sehgal DE Otzen 2005 Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents Biochemistry 44 5 1719 30 15683256 10.1021/bi0479757 1:CAS:528:DC%2BD2MXitVKhsg%3D%3D (Pubitemid 40204413)
38. Holmberg K, Jönsson B, Kronberg B, Lindman B. Surfactants and polymers in aqueous solution. Chischester: Wiley; 2002.
39. J Reynolds C Tanford 1970 Binding of dodecyl sulfate to proteins at high binding ratios. Possible implications for the state of proteins in biological membranes Proc Natl Acad Sci U S A 66 3 1002 5269225 10.1073/pnas.66.3.1002 1:CAS:528:DyaE3cXkvFCltbw%3D
40. D Otzen M Oliveberg 2002 Burst-phase expansion of native protein prior to global unfolding in SDS J Mol Biol 315 5 1231 40 11827490 10.1006/jmbi.2001. 5300 1:CAS:528:DC%2BD38XpsVSltw%3D%3D (Pubitemid 34729300)
41. D Otzen 2002 Protein unfolding in detergents: effect of micelle structure, ionic strength, pH, and temperature Biophys J 83 4 2219 30 12324439 10.1016/S0006-3495(02)73982-9 1:CAS:528:DC%2BD38XnslSrt74%3D
42. B Borgström J Donner 1976 Interactions of pancreatic lipase with bile salts and dodecyl sulfate J Lipid Res 17 5 491 7 965841
43. AM Brzozowski U Derewenda ZS Derewenda GG Dodson DM Lawson JP Turkenburg, et al. 1991 A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex Nature 351 6326 491 4 2046751 10.1038/351491a0 1:CAS:528:DyaK3MXksVGis7o%3D (Pubitemid 21896627)
44. U Derewenda AM Brzozowski DM Lawson ZS Derewenda 1992 Catalysis at the interface: the anatomy of a conformational change in a triglyceride lipase Biochemistry 31 5 1532 41 1737010 10.1021/bi00120a034 1:CAS:528: DyaK38XnvFaqsw%3D%3D
45. AM Brzozowski H Savage CS Verma JP Turkenburg DM Lawson A Svendsen, et al. 2000 Structural origins of the interfacial activation in Thermomyces (Humicola) lanuginosa lipase Biochemistry 39 49 15071 82 11106485 10.1021/bi0013905 1:CAS:528:DC%2BD3cXnvVKns7Y%3D
46. AM Brzozowski 1993 Crystallization of a Humicola lanuginosa lipase-inhibitor complex with the use of polyethylene glycol monomethyl ether Acta Crystallogr D Biol Crystallogr 49 Pt 3 352 4 15299525 10.1107/ S0907444993000952 1:STN:280:DC%2BD2czpsVOqsw%3D%3D
47. P Grochulski F Bouthillier RJ Kazlauskas AN Serreqi JD Schrag E Ziomek, et al. 1994 Analogs of reaction intermediates identify a unique substrate binding site in Candida rugosa lipase Biochemistry 33 12 3494 500 8142346 10.1021/bi00178a005 1:CAS:528:DyaK2cXis1CntL4%3D (Pubitemid 24115996)
48. 11 alkyl phosphonate Biochemistry 34 9 2751 62 7893686 10.1021/bi00009a003 1:CAS:528:DyaK2MXjvFOks78%3D
49. A Roussel S Canaan MP Egloff M Riviere L Dupuis R Verger, et al. 1999 Crystal structure of human gastric lipase and model of lysosomal acid lipase, two lipolytic enzymes of medical interest J Biol Chem 274 24 16995 7002 10358049 10.1074/jbc.274.24.16995 1:CAS:528:DyaK1MXjvVGktLY%3D (Pubitemid 29275155)
50. A Roussel N Miled L Berti-Dupuis M Riviere S Spinelli P Berna, et al. 2002 Crystal structure of the open form of dog gastric lipase in complex with a phosphonate inhibitor J Biol Chem 277 3 2266 74 11689574 10.1074/jbc.M109484200 1:CAS:528:DC%2BD38XosFekuw%3D%3D (Pubitemid 34968814)
51. H van Tilbeurgh M-P Egloff C Martinez N Rugani R Verger C Cambillau 1993 Interfacial activation of the lipase-procolipase complex by mixed micelles revealed by X-Ray crystallography Nature 362 6423 814 20 8479519 10.1038/362814a0 (Pubitemid 23132155)
52. H Gonzalez-Navarro MC Bano C Abad 2001 The closed/open model for lipase activation. Addressing intermediate active forms of fungal enzymes by trapping of conformers in water-restricted environments Biochemistry 40 10 3174 83 11258933 10.1021/bi002202d 1:CAS:528:DC%2BD3MXhtVyms7w%3D (Pubitemid 32205362)
53. J Hermoso D Pignol B Kerfelec I Crenon C Chapus JC Fontecilla-Camps 1996 Lipase activation by nonionic detergents. The crystal structure of the porcine lipase-colipase-tetraethylene glycol monooctyl ether complex J Biol Chem 271 18007 16 8663362 10.1074/jbc.271.30.18007 1:CAS:528:DyaK28XksFyiurY%3D (Pubitemid 26250786)
54. N Miled A Roussel C Bussetta L Berti-Dupuis M Riviere G Buono, et al. 2003 Inhibition of dog and human gastric lipases by enantiomeric phosphonate inhibitors: a structure-activity study Biochemistry 42 40 11587 93 14529268 10.1021/bi034964p 1:CAS:528:DC%2BD3sXntlyqs74%3D (Pubitemid 37243618)
55. M Rouard H Sari S Nurit B Entressangles P Desnuelle 1978 Inhibition of pancreatic lipase by mixed micelles of diethyl p-nitrophenyl phosphate and the bile salts Biochim Biophys Acta 530 227 35 667092 1:CAS:528:DyaE1cXlsF2gtrc%3D (Pubitemid 9000144)
56. J Hermoso D Pignol S Penel M Roth C Chapus JC Fontecilla-Camps 1997 Neutron crystallographic evidence of lipase-colipase complex activation by a micelle EMBO J 16 18 5531 6 9312012 10.1093/emboj/16.18.5531 1:CAS:528:DyaK2sXmsFWmsLc%3D (Pubitemid 27399845)
57. H Moreau A Moulin Y Gargouri J-P Noël R Verger 1991 Inactivation of gastric and pancreatic lipases by diethyl p-nitrophenyl phosphate Biochemistry 30 4 1037 41 1989675 10.1021/bi00218a022 1:CAS:528:DyaK3MXmt1Krsbs%3D
58. C Cudrey H van Tilbeurgh Y Gargouri R Verger 1993 Inactivation of pancreatic lipases by amphiphilic reagents 5-(Dodecyldithio)-2-nitrobenzoic acid and tetrahydrolipstatin. Dependence upon partitioning between micellar and oil phases Biochemistry 32 50 13800 8 8268155 10.1021/bi00213a008 1:CAS:528:DyaK2cXjtlGn (Pubitemid 24018230)
59. Tiss A, Miled N, Verger R, Gargouri Y, Abousalham A. Digestive lipases inhibition: an in vitro study. In: Müller G, editor. Lipases and phospholipases in drug development. Weinheim: Wiley-VCH; 2004. p. 155-93.
60. Y Ben Ali H Chahinian S Petry G Muller F Carriere R Verger, et al. 2004 Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain? Biochemistry 43 29 9298 306 15260473 10.1021/bi049479o 1:CAS:528:DC%2BD2cXltFGgurs%3D (Pubitemid 38955463)
61. P Desnuelle L Sarda G Ailhaud 1960 Inhibition de la lipase pancréatique par le diéthyl-p-nitrophényl phosphate en émulsion Biochim Biophys Acta 37 570 1 13816167 10.1016/0006-3002(60) 90532-1 1:CAS:528:DyaF3cXmvVGmsA%3D%3D
62. Y Gargouri H Chahinian H Moreau S Ransac R Verger 1991 Inactivation of pancreatic and gastric lipases by THL and C12:0-TNB: a kinetic study with emulsified tributyrin Biochim Biophys Acta 1085 3 322 8 1911866 1:CAS:528:DyaK38XhslKmtA%3D%3D
63. P Hadvary H Lengsfeld H Wolfer 1988 Inhibition of pancreatic lipase in vitro by the covalent inhibitor tetrahydrolipstatin Biochem J 256 2 357 61 3223916 1:CAS:528:DyaL1MXitVCiug%3D%3D (Pubitemid 19005994)
64. B Borgström 1988 Mode of action of tetrahydrolipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin Biochim Biophys Acta 962 3 308 16 3167082
65. S Hogan A Fleury P Hadvary H Lengsfeld MK Meier J Triscari, et al. 1987 Studies on the antiobesity activity of tetrahydrolipstatin, a potent and selective inhibitor of pancreatic lipase Int J Obes 11 Suppl 3 35 42 3440690 1:CAS:528:DyaL1cXoslyktA%3D%3D (Pubitemid 18012894)
66. E Hochuli E Kupfer R Maurer W Meister Y Mercadal K Schmidt 1987 Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation J Antibiot (Tokyo) 40 8 1086 91 1:CAS:528:DyaL2sXmtFyjsbo%3D (Pubitemid 17141407)
67. EK Weibel P Hadvary E Hochuli E Kupfer H Lengsfeld 1987 Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity J Antibiot (Tokyo) 40 8 1081 5 1:CAS:528:DyaL2sXlvFKnsbc%3D (Pubitemid 17141406)
68. C Martinez A Nicolas H van Tilbeurgh M-P Egloff C Cudrey R Verger, et al. 1994 Cutinase, a lipolytic enzyme with a preformed oxyanion hole Biochemistry 33 1 83 9 8286366 10.1021/bi00167a011 1:CAS:528:DyaK2cXkvVyrtg%3D%3D (Pubitemid 24046499)
69. C Withers-Martinez F Carriere R Verger D Bourgeois C Cambillau 1996 A pancreatic lipase with a phospholipase A1 activity: crystal structure of a chimeric pancreatic lipase-related protein 2 from guinea pig Structure 4 11 1363 74 8939760 10.1016/S0969-2126(96)00143-8 1:CAS:528:DyaK28XntFOnt7c%3D (Pubitemid 26420504)
70. Q Lüthi-Peng FK Winkler 1992 Large spectral changes accompany the conformational transition of human pancreatic lipase induced by acylation with the inhibitor tetrahydrolipstatin Eur J Biochem 205 1 383 90 1555598 10.1111/j.1432-1033.1992.tb16791.x
71. A Tiss F Carriere R Verger 2001 Effects of gum arabic on lipase interfacial binding and activity Anal Biochem 294 1 36 43 11412003 10.1006/abio.2001.5095 1:CAS:528:DC%2BD3MXksVWqsLg%3D (Pubitemid 32612547)
72. A Lookene N Skottova G Olivecrona 1994 Interactions of lipoprotein lipase with the active-site inhibitor tetrahydrolipstatin (Orlistat)(R) Eur J Biochem 222 2 395 403 8020477 10.1111/j.1432-1033.1994.tb18878.x 1:CAS:528: DyaK2cXkslOjsrk%3D (Pubitemid 24204908)
73. A Tiss H Lengsfeld F Carrière R Verger 2009 Inhibition of human pancreatic lipase by tetrahydrolipstatin: further kinetic studies showing its reversibility J Mol Catal B Enzym 58 1-4 41 7 10.1016/j.molcatb.2008.11.003 10.1016/j.molcatb.2008.11.003 1:CAS:528:DC%2BD1MXkt1Snt7c%3D
74. A Tiss S Ransac H Lengsfeld P Hadvary A Cagna R Verger 2001 Surface behaviour of bile salts and tetrahydrolipstatin at air/water and oil/water interfaces Chem Phys Lipids 111 1 73 85 11438285 10.1016/S0009-3084(01)00149-9 1:CAS:528:DC%2BD3MXkvVemsb8%3D (Pubitemid 32595645)
75. A Tiss H Lengsfeld P Hadvary A Cagna R Verger 2002 Transfer of orlistat through oil-water interfaces Chem Phys Lipids 119 1-2 41 9 12270672 10.1016/S0009-3084(02)00051-8 1:CAS:528:DC%2BD38XntVeisbw%3D (Pubitemid 35247916)
76. Y Gargouri G Piéroni PA Lowe L Sarda R Verger 1986 Human gastric lipase. The effect of amphiphiles Eur J Biochem 156 305 10 3699017 10.1111/j.1432-1033.1986.tb09583.x 1:CAS:528:DyaL28XktValtL4%3D (Pubitemid 16077768)
77. Y Gargouri G Piéroni C Rivière J-F Saunière PA Lowe L Sarda, et al. 1986 Kinetic assay of human gastric lipase on short- and long-chain triacylglycerol emulsions Gastroenterology 91 4 919 25 3743968 1:CAS:528:DyaL28XlvVKmsLY%3D (Pubitemid 16014599)
78. S Bezzine F Ferrato MG Ivanova V Lopez R Verger F Carriere 1999 Human pancreatic lipase: colipase dependence and interfacial binding of lid domain mutants Biochemistry 38 17 5499 510 10220337 10.1021/bi982601x 1:CAS:528:DyaK1MXit1Kgsr4%3D (Pubitemid 29211235)
79. Y Gargouri R Julien AG Bois R Verger L Sarda 1983 Studies on the detergent inhibition of pancreatic lipase activity J Lipid Res 24 1336 42 6644184 1:CAS:528:DyaL2cXis1Om
80. M Wahlgren T Arnebrant 1991 Protein adsorption to solid surfaces Trends Biotechnol 9 1 201 8 1367245 10.1016/0167-7799(91)90064-O 1:CAS:528: DyaK3MXltlSrsbo%3D (Pubitemid 121003109)
81. A Aloulou D Puccinelli A De Caro Y Leblond F Carriere 2007 A comparative study on two fungal lipases from Thermomyces lanuginosus and Yarrowia lipolytica shows the combined effects of detergents and pH on lipase adsorption and activity Biochim Biophys Acta 1771 12 1446 56 18022403 1:CAS:528: DC%2BD1cXptlSqsg%3D%3D
82. H Chahinian T Snabe C Attias P Fojan SB Petersen F Carriere 2006 How gastric lipase, an interfacial enzyme with a Ser-His-Asp catalytic triad, acts optimally at acidic pH Biochemistry 45 3 993 1001 16411775 10.1021/bi0518803 1:CAS:528:DC%2BD2MXhtlClsLfJ (Pubitemid 43122263)
83. S Ranaldi V Belle M Woudstra J Rodriguez B Guigliarelli J Sturgis, et al. 2009 Lid opening and unfolding in human pancreatic lipase at low pH revealed by site-directed spin labeling EPR and FTIR spectroscopy Biochemistry 48 3 630 8 19113953 10.1021/bi801250s 1:CAS:528:DC%2BD1cXhsFCrt73J
84. RN Gursoy S Benita 2004 Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs Biomed Pharmacother 58 3 173 82 15082340 10.1016/j.biopha.2004.02.001 (Pubitemid 38479922)
85. CA Lipinski 2000 Drug-like properties and the causes of poor solubility and poor permeability J Pharmacol Toxicol Methods 44 1 235 49 11274893 10.1016/S1056-8719(00)00107-6 1:CAS:528:DC%2BD3MXitF2ksrc%3D (Pubitemid 32239479)
86. W Charman C Porter S Mithani J Dressman 1997 Physicochemical and physiological mechanisms for the effects of food on drug absorption: the role of lipids and pH J Pharm Sci 86 3 269 82 9050793 10.1021/js960085v 1:CAS:528:DyaK2sXhtVGit7Y%3D (Pubitemid 27113759)
87. CW Pouton CJ Porter 2008 Formulation of lipid-based delivery systems for oral administration: materials, methods and strategies Adv Drug Deliv Rev 60 6 625 37 18068260 10.1016/j.addr.2007.10.010 1:CAS:528:DC%2BD1cXitVOnu7s%3D
88. SA Charman WN Charman MC Rogge TD Wilson FJ Dutko CW Pouton 1992 Self-emulsifying drug delivery systems: formulation and biopharmaceutic evaluation of an investigational lipophilic compound Pharm Res 9 1 87 93 1589415 10.1023/A:1018987928936 1:CAS:528:DyaK38XptFaluw%3D%3D
89. Attwood D, Florence AT. Surfactant systems: their chemistry, pharmacy and biology. London: Chapman and Hall; 1983.
90. Strickley R. Currently marketed oral lipid-based dosage forms: drug products and excipients. In: Hauss DJ, editor. Oral lipid-based formulations: enhancing the bioavailability of poorly water soluble drugs. New York: Informa Healthcare, Inc.; 2007. p. 1-31.
91. S Fernandez V Jannin JD Rodier N Ritter B Mahler F Carriere 2007 Comparative study on digestive lipase activities on the self emulsifying excipient Labrasol®, medium chain glycerides and PEG esters Biochim Biophys Acta, Mol Cell Biol Lipids 1771 633 40 1:CAS:528:DC%2BD2sXkvFGqurc%3D (Pubitemid 46670793)
92. S Fernandez JD Rodier N Ritter B Mahler F Demarne F Carrière, et al. 2008 Lipolysis of the semi-solid self-emulsifying excipient Gelucire 44/14 by digestive lipases Biochim Biophys Acta, Mol Cell Biol Lipids 1781 367 75 1:CAS:528:DC%2BD1cXps1Gls7o%3D
93. S Fernandez S Chevrier N Ritter B Mahler F Demarne F Carriere, et al. 2009 In vitro gastrointestinal lipolysis of four formulations of piroxicam and cinnarizine with the self emulsifying excipients Labrasol and Gelucire 44/14 Pharm Res 26 8 1901 10 19452130 10.1007/s11095-009-9906-2 1:CAS:528: DC%2BD1MXmtVOqsrw%3D
94. A Christiansen T Backensfeld W Weitschies 2010 Effects of non-ionic surfactants on in vitro triglyceride digestion and their susceptibility to digestion by pancreatic enzymes Eur J Pharm Sci 41 2 376 82 20633646 10.1016/j.ejps.2010.07.005 1:CAS:528:DC%2BC3cXhtVKhtb7F