Effects of non-ionic surfactants on in vitro triglyceride digestion and their susceptibility to digestion by pancreatic enzymes

European Journal of Pharmaceutical Sciences

Volumn 41, Issue 2, 2010, Pages 376-382

  Christiansen, Anne ^a,b   Backensfeld, Thomas ^a   Weitschies, Werner ^b  

^a BAYER PHARMA AG   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Enzyme inhibition; Lipid digestion; Non ionic surfactants; PEG esters; Poorly water soluble drugs; Self emulsifying drug delivery system; Solubilization

Indexed keywords

ALPHA TOCOPHEROL; CREMOPHOR; FATTY ACID ESTER; NON IONIC SURFACTANT; OLIVE OIL; PANCREAS ENZYME; POLYSORBATE 80; SUCCINIC ACID; SUCROSE LAURATE; SURFACTANT; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; ENZYME DEGRADATION; ENZYME INHIBITION; HYDROLYSIS KINETICS; IN VITRO STUDY; INTESTINE FLUID; LIPID HYDROLYSIS; LIPID METABOLISM; PRIORITY JOURNAL; SOLUBILIZATION;

LIPASE; PANCREAS; SURFACE-ACTIVE AGENTS; TRIGLYCERIDES;

EID: 77955842200     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.07.005     Document Type: Article

References (43)

1. Anton A., Barlow S., Boskou D., Castle L., Crebelli R., Dekant W., Engel K.-H., Forsythe S., Grunow W., Heinonen M., Laarsen J.C., Leclercq C., Mennes W., Milana M.-R., Pratt I., Rietjens I., Svensson K., Tobback P., Toldrá F. Opinion of the scientific panel on foods additives, flavourings, processing aids and materials in contact with food on sucrose esters of fatty acids, E 473 and sucroglycerides, E 474 based on a request from the commission related to sucrose esters of fatty acids (E 473). EFSA J. 2004, 106:1-24.
2. Borgström B. The action of bile salts and other detergents on pancreatic lipase and the interaction with colipase. Biochim. Biophys. Acta 1977, 488:381-391.
3. Christensen J.Ø., Schultz K., Mollgaard B., Kristensen H.G., Müllertz A. Solubilisation of poorly water-soluble drugs during in vitro lipolysis of medium- and long-chain triacylglycerols. Eur. J. Pharm. Sci. 2004, 23:287-296.
4. Clark D.C., Wilde P.J., Wilson D.R., Wustneck R. The interaction of sucrose esters with β-lactoglobulin and β-casein from bovine milk. Food Hydrocoll. 1992, 6:173-186.
5. Cuiné J.F., Charman W., Pouton C., Edwards G.A., Porter C.J.H. Increasing the proportional content of surfactant (Cremophor EL) relative to lipid in self-emulsifying lipid-based formulations of danazol reduces oral bioavailability in beagle dogs. Pharm. Res. 2007, 24:748-757.
6. Cuiné J.F., McEvoy C.L., Charman W.N., Pouton C.W., Edwards G.A., Benameur H., Porter C.J.H. Evaluation of the impact of surfactant digestion on the bioavailability of danazol after oral administration of lipidic self-emulsifying formulations to dogs. J. Pharm. Sci. 2008, 97:995-1012.
7. Dahan A., Hoffman A. Use of a dynamic in vitro lipolysis model to rationalize oral formulation development for poor water soluble drugs: correlation with in vivo data and the relationship to intra-enterocyte processes in rats. Pharm. Res. 2006, 23:2165-2174.
8. de Caro J., Sias B., Grandval P., Ferrato F., Halimi H., Carriere F., Donald M.S. Characterization of pancreatic lipase-related protein 2 isolated from human pancreatic juice. Biochim. Biophys. Acta 2004, 1701:89-99.
9. Devani M., Ashford M., Craig D.Q.M. The emulsification and solubilisation properties of polyglycolised oils in self-emulsifying formulations. J. Pharm. Pharmacol. 2004, 56:307-316.
10. Embleton J.K., Pouton C.W. Structure and function of gastro-intestinal lipases. Adv. Drug Deliv. Rev. 1997, 25:15-32.
11. ® 44/14. Pharm. Res. 2009, 26:1901-1910.
12. ®, medium chain glycerides and PEG esters. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2007, 1771:633-640.
13. Folmer B.M., Barron D., Hughes E., Miguet L., Sanchez B., Heudi O., Rouvet M., Sagalowicz L., Callier P., Michel M., Williamson G. Monocomponent hexa- and dodecaethylene glycol succinyl-tocopherol esters: self-assembly structures, cellular uptake and sensitivity to enzyme hydrolysis. Biochem. Pharmacol. 2009, 78:1464-1474.
14. Gargouri Y., Julien R., Bois A.G., Verger R., Sarda L. Studies on the detergent inhibition of pancreatic lipase activity. J. Lipid Res. 1983, 24:1336-1342.
15. Giller T., Buchwald P., Blum-Kaelin D., Hunziker W. Two novel human pancreatic lipase related proteins, hPLRP1 and hPLRP2. Differences in colipase dependence and in lipase activity. J. Biol. Chem. 1992, 267:16509-16516.
16. Gursoy N.R., Benita S. Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs. Biomed. Pharmacother. 2004, 58:173-182.
17. Guy O., Figarella C. The proteins of human pancreatic external secretion. Scand. J. Gastroenterol. 1981, 16:59-61.
18. Hadváry P., Sidler W., Meister W., Vetter W., Wolfer H. The lipase inhibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase. J. Biol. Chem. 1991, 266:1021-1027.
19. Harp J.B. An assessment of the efficacy and safety of orlistat for the long-term management of obesity. J. Nutr. Biochem. 1998, 9:516-521.
20. Hermoso J., Pignol D., Kerfelec B., Crenon I., Chapus C., Fontecilla-Camps J.C. Lipase activation by nonionic detergents. J. Biol. Chem. 1996, 271:18007-18016.
21. Humberstone A.J., Charman W.N. Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv. Drug Deliv. Rev. 1997, 25:103-128.
22. Johnston T.P., Goldberg I.J. Inhibition of pancreatic lipase by poloxamer 407 may provide an adjunct treatment strategy for weight loss. J. Pharm. Pharmacol. 2006, 58:1099-1105.
23. Kang B.K., Lee J.S., Chon S.K., Jeong S.Y., Yuk S.H., Khang G., Lee H.B., Cho S.H. Development of self-microemulsifying drug delivery systems (SMEDDS) for oral bioavailability enhancement of simvastatin in beagle dogs. Int. J. Pharm. 2004, 274:65-73.
24. Kaukonen A., Boyd B., Charman W., Porter C. Drug solubilization behavior during in vitro digestion of suspension formulations of poorly water-soluble drugs in triglyceride lipids. Pharm. Res. 2004, 21:254-260.
25. Kossena G.A., Boyd B.J., Porter C.J.H., Charman W.N. Separation and characterization of the colloidal phases produced on digestion of common formulation lipids and assessment of their impact on the apparent solubility of selected poorly water-soluble drugs. J. Pharm. Sci. 2003, 92:634-648.
26. Lennernäs H., Abrahamsson B. The use of biopharmaceutic classification of drugs in drug discovery and development: current status and future extension. J. Pharm. Pharmacol. 2005, 57:273-285.
27. Li P., Ghosh A., Wagner R.F., Krill S., Joshi Y.M., Serajuddin A.T.M. Effect of combined use of nonionic surfactant on formation of oil-in-water microemulsions. Int. J. Pharm. 2005, 288:27-34.
28. Lipinski C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44:235-249.
29. Lombardo D., Fauvel J., Guy O. Studies on the substrate specificity of a carboxyl ester hydrolase from human pancreatic juice. Biochim. Biophys. Acta 1980, 611:136-146.
30. MacGregor K.J., Embleton J.K., Lacy J.E., Perry E.A., Solomon L.J., Seager H., Pouton C.W. Influence of lipolysis on drug absorption from the gastro-intestinal tract. Adv. Drug Deliv. Rev. 1997, 25:33-46.
31. Nerurkar M.M., Ho N.F., Burton P.S., Vidmar T.J., Borchardt R.T. Mechanistic roles of neutral surfactants on concurrent polarized and passive membrane transport of a model peptide in Caco-2 cells. J. Pharm. Sci. 1997, 86:813-821.
32. Niizu, E.C., 1991, Food Deterioration Inhibitor, Japanese Patent No. 03112473 A, 14 May.
33. Nishiyama J., Shizu Y., Kuninori T. Inhibition of soybean Lipoxygenase-1 by sucrose esters of fatty esters. Biosci. Biotechnol. Biochem. 1993, 57:557-560.
34. Porter C.J.H., Kaukonen A.M., Boyd B.J., Edwards G.A., Charman W.N. Susceptibility to lipase-mediated digestion reduces the oral bioavailability of danazol after administration as a medium-chain lipid-based microemulsion formulation. Pharm. Res. 2004, 21:1405-1412.
35. Solomon L.J., Embleton J.K., Pouton C.W. Inhibition of lipolysis of medium-chain triglycerides by non-ionic surfactants, a structure/activity study. Formulation of Poorly-available Drugs for Oral Administration (Minutes of the European Symposium) 1996, 437-440. Editions de Santé, Paris. P. Couvreur, D. Duchene, I. Kalles (Eds.).
36. Sousa T., Paterson R., Moore V., Carlsson A., Abrahamsson B., Basit A.W. The gastrointestinal microbiota as a site for the biotransformation of drugs. Int. J. Pharm. 2008, 363:1-25.
37. Subramanian N., Ray S., Ghosal S.K., Bhadra R., Moulik S.P. Formulation design of self-microemulsifying drug delivery systems for improved oral bioavailability of celecoxib. Biol. Pharm. Bull. 2004, 27:1993-1999.
38. Tagiri M., Endo Y., Fujimoto K., Suzuki T. Hydrolysis of triglycerides of branched-chain fatty acids and castor oil derivatives by pancreatic lipase. Biosci. Biotechnol. Biochem. 1992, 56:1490-1491.
39. Traber M.G., Thellman C.A., Rindler M.J., Kayden H.J. Uptake of intact TPGS (d-α-tocopheryl polyethylene glycol 1000 succinate) a water-miscible form of vitamin E by human cells in vitro. Am. J. Clin. Nutr. 1988, 48:605-611.
40. Villalobos A.P., Gunturi S.R., Heavner G.A. Interaction of polysorbate 80 with erythropoietin: a case study in protein-surfactant interactions. Pharm. Res. 2005, 22:1186-1194.
41. Wan L.S.C., Lee P.F.S. CMC of polysorbates. J. Pharm. Sci. 1974, 63:136-137.
42. Wignot T.M., Stewart R.P., Schray K.J., Das S., Sipos T. In vitro studies of the effects of HAART drugs and excipients on activity of digestive enzymes. Pharm. Res. 2004, 21:420-427.
43. Zangenberg N.H., Müllertz A., Kristensen H.G., Hovgaard L. A dynamic in vitro lipolysis model II: evaluation of the model. Eur. J. Pharm. Sci. 2001, 14:237-244.