Oral peptide delivery by tetraether lipid liposomes

International Journal of Pharmaceutics

Volumn 415, Issue 1-2, 2011, Pages 150-157

  Parmentier, Johannes ^a   Thewes, Bernhard ^b   Gropp, Felix ^b   Fricker, Gert ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b Bernina Plus GmbH   (Germany)

Author keywords

Bioavailability; GI tract; Oral delivery; Protein; Stability

Indexed keywords

AF 1; DIGLYCERYL TETRAETHER; DIPALMITOYLPHOSPHATIDYLCHOLINE; GLYCERYLCALDITYL TETRAETHER; LIPOSOME; OCTREOTIDE; TETRAETHER LIPID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; MALE; NONHUMAN; PARTICLE SIZE; PRIORITY JOURNAL; RADIOACTIVITY; RAT; SULFOLOBUS ACIDOCALDARIUS;

ANIMALS; BIOLOGICAL AVAILABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIGLYCERIDES; DRUG CARRIERS; DRUG COMPOUNDING; DRUG STABILITY; GLYCOLIPIDS; LIPOSOMES; MALE; MOLECULAR STRUCTURE; OCTREOTIDE; PARTICLE SIZE; PEPTIDES; RATS; RATS, WISTAR; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFOLOBUS ACIDOCALDARIUS; TISSUE DISTRIBUTION;

EID: 79960193011     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.05.066     Document Type: Article

References (51)

1. Y. Aramaki, H. Tomizawa, T. Hara, K. Yachi, H. Kikuchi, and S. Tsuchiya Stability of liposomes in vitro and their uptake by rat Peyer's patches following oral administration Pharm. Res. 10 1993 1228 1231 (Pubitemid 23244182)
2. J. Arts, P. Caenepeel, R. Bisschops, D. Dewulf, L. Holvoet, H. Piessevaux, S. Bourgeois, D. Sifrim, J. Janssens, and J. Tack Efficacy of the long-acting repeatable formulation of the somatostatin analogue octreotide in postoperative dumping Clin. Gastroenterol. Hepatol. 7 2009 432 437
3. C.S. Bal, S.K. Gupta, and J.J. Zaknun Radiolabeled somatostatin analogs for radionuclide imaging and therapy in patients with gastroenteropancreatic neuroendocrine tumors Trop. Gastroenterol. 31 2010 87 95
4. A.D. Bangham, M.M. Standish, and J.C. Watkins Diffusion of univalent ions across the lamellae of swollen phospholipids J. Mol. Biol. 13 1965 238 252
5. P. Batershill, and S. Clissold Octreotide - a review of its pharmacodynamic and pharmacokinetik properties, and therapeutic potential in conditions associated with excessive peptide secretion Drugs 38 1989 658 702 (Pubitemid 19285390)
6. G. Beschiaschvili, and J. Seelig Peptide binding to lipid bilayers. Binding isotherms and zeta-potential of a cyclic somatostatin analogue Biochemistry 29 1990 10995 11000
7. F. Cavagnetto, A. Relini, Z. Mirghani, A. Gliozzi, D. Bertoia, and A. Gambacorta Molecular packing parameters of bipolar lipids Biochim. Biophys. Acta 1106 1992 273 281
8. E.L. Chang Unusual thermal stability of liposomes made from bipolar tetraether lipids Biochem. Biophy. Res. Commun. 202 1994 673 679 (Pubitemid 24259267)
9. C. Chiang, and N. Weiner Gastrointestinal uptake of liposomes. I: in vitro and in situ studies Int. J. Pharm. 37 1987 75 85 (Pubitemid 17084951)
10. C. Chiang, and N. Weiner Gastrointestinal uptake of liposomes. II: in vivo studies Int. J. Pharm. 40 1987 143 150
11. G. Dapergolas, and G. Gregoriadis Hypoglycaemic effect of liposome-entrapped insulin administered intragastrically into rats Lancet 2 1976 824 827
12. A. des Rieux, V. Fievez, M. Garinot, Y.-J. Schneider, and V. Préat Nanoparticles as potential oral delivery systems of proteins and vaccines: a mechanistic approach J. Control. Release 116 2006 1 27 (Pubitemid 44792295)
13. J. Drewe, G. Fricker, J. Vonderscher, and C. Beglinger Enteral absorption of octreotide - absorption enhancement by polyoxyethylene-24-cholesterol ether Br. J. Pharmacol. 108 1993 298 303 (Pubitemid 23032529)
14. M.G. Elferink, J. van Breemen, W.N. Konings, A.J. Driessen, and J. Wilschut Slow fusion of liposomes composed of membrane-spanning lipids Chem. Phys. Lipids 88 1997 37 43 (Pubitemid 27395412)
15. G. Fricker, C. Bruns, J. Munzer, U. Briner, R. Albert, T. Kissel, and J. Vonderscher Intestinal-absorption of the octapeptide SMS-201-995 visulaized by fluorescene derivatization Gastroenterology 100 1991 1544 1552
16. G. Fricker, and J. Drewe Enteral absorption of octreotide: modulation of intestinal permeability by distinct carbohydrates J. Pharmacol. Exp. Ther. 274 1995 826 832
17. G. Fricker, and J. Drewe Current concepts in intestinal peptide absorption J. Pept. Sci. 2 1996 195 211
18. G. Fricker, J. Drewe, J. Vonderscher, T. Kissel, and C. Beglinger Enteral absorption of octreotide Brit. J. Pharmacol. 105 4 1992 783 786
19. H.S. Fuessl, J. Domin, and S.R. Bloom Oral absorption of the somatostatin analogue SMS 201-995: theoretical and practical implications Clin. Sci. 72 2 1987 255 257 (Pubitemid 17231153)
20. A. Gambacorta, A. Gliozzi, and M. Rosa Archaeal lipids and their biotechnological applications World J. Microbiol. Biotechnol. 11 1995 115 131
21. B. Groner Peptides as Drugs: Discovery and Development 2009 VCH-Wiley Weinheim
22. B. Haeberlin, T. Gengenbacher, A. Meinzer, and G. Fricker Cyclodextrins - Useful excipients for oral peptide administration? Int. J. Pharm. 137 1996 103 110 (Pubitemid 26238517)
23. J. Hamman, G. Enslin, and A. Kotzé Oral delivery of peptide drugs: barriers and developments BioDrugs 19 2006 165 177
24. P. Jani, G. Halbert, J. Langridge, and A. Florence Nanoparticle uptake by the rat gastrointestinal mucosa - quantitation and particle-size dependency J. Pharm. Pharmacol. 42 1990 821 826
25. A. Jesorka, and O. Orwar Liposomes: technologies and analytical applications Annu. Rev. Anal. Chem. 1 2008 801 832
26. E. Köhler, M. Duberow-Drewe, J. Drewe, G. Ribes, M.M. Loubatiéres-Mariani, N. Mazer, K. Gyr, and C. Beglinger Absorption of an aqueous solution of a new synthetic somatostatin analogue administered to man by gavage Eur. J. Clin. Pharmacol. 33 2 1987 167 171 (Pubitemid 17149230)
27. T.R.S. Kumar, K. Soppimath, and S.K. Nachaegari Novel delivery technologies for protein and peptide therapeutics Curr. Pharm. Biotechnol. 7 2006 261 276 (Pubitemid 44194386)
28. P. Lelkes, D. Goldenberg, A. Gliozzi, M.D. Rosa, A. Gambacorta, and I. Miller Vesicles from mixtures of bipolar archaebacterial lipids with egg phosphatidylcholine BBa-Biomembrane 1983 s714 718
29. Z. Li, J. Chen, W. Sun, and Y. Xu Investigation of archaeosomes as carriers for oral delivery of peptides Biochem. Biophy. Res. Commun. 394 2010 412 417
30. J. Liang, and V. Yang Insulin-cell penetrating peptide hybrids with improved intestinal absorption efficiency Biochem. Biophy. Res. Commun. 335 2005 734 738 (Pubitemid 41188260)
31. S.L. Lo, and E.L. Chang Purification and characterization of a liposomal-forming tetraether lipid fraction Biochem. Biophy. Res. Commun. 167 1990 238 243 (Pubitemid 20085375)
32. S.L. Lo, C.E. Montague, and E.L. Chang Purification of glycerol dialkyl nonitol tetraether from Sulfolobus acidocaldarius J. Lipid Res. 30 1989 944 949
33. D. Malkov, R. Angelo, H.-z. Wang, E. Flanders, H. Tang, and I. Gomez-Orellana Oral delivery of insulin with the eligen technology: mechanistic studies Curr. Drug Deliv. 2 2005 191 197 (Pubitemid 40488628)
34. S. Michael, M. Thole, R. Dillmann, A. Fahr, J. Drewe, and G. Fricker Improvement of intestinal peptide absorption by a synthetic bile acid derivative, cholylsarcosine Eur. J. Pharm. Sci. 10 2000 133 140 (Pubitemid 30155935)
35. T.L. Miller, and M.J. Wolin Enumeration of Methanobrevibacter smithii in human feces Arch. Microbiol. 131 1982 14 18 (Pubitemid 12153065)
36. G.B. Patel, B.J. Agnew, L. Deschatelets, L.P. Fleming, and G.D. Sprott In vitro assessment of archaeosome stability for developing oral delivery systems Int. J. Pharm. 194 2000 39 49
37. H.M. Patel, R.W. Stevenson, J.A. Parsons, and B.E. Ryman Use of liposomes to aid intestinal absorption of entrapped insulin in normal and diabetic dogs Biochim. Biophys. Acta 716 1982 188 193 (Pubitemid 12057561)
38. J. Pless, W. Bauer, U. Briner, W. Doepfner, P. Marbach, R. Maurer, T.J. Petcher, J.C. Reubi, and J. Vonderscher Chemistry and pharmacology of SMS 201-995, a long-acting octapeptide analogue of somatostatin Scand. J. Gastroenterol. Suppl. 119 1986 54 64 (Pubitemid 16057844)
39. E.E. Prommer Established and potential therapeutic applications of octreotide in palliative care Support. Care Cancer 16 2008 1117 1123
40. G. Rouser, S. Fleischer, and A. Yamamoto Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots Lipids 5 1970 494 496
41. R.N. Rowland, and J.F. Woodley The uptake of distearoylphosphatidylcholine/cholesterol liposomes by rat intestinal sacs in vitro Biochim. Biophys. Acta 673 1981 217 223 (Pubitemid 11144184)
42. R.N. Rowland, and J.F. Woodley Uptake of free and liposome-entrapped 125I-labelled PVP by rat intestinal sacs in vitro: evidence for endocytosis Biosci. Rep. 1 1981 399 406 (Pubitemid 11036472)
43. R.N. Rowland, and J.F. Woodley Uptake of free and liposome-entrapped insulin by rat intestinal sacs in vitro Biosci. Rep. 1 1981 345 352 (Pubitemid 11082882)
44. S. Schouten, M.T.J. Van Der Meer, E.C. Hopmans, W.I.C. Rijpstra, A.-L. Reysenbach, D.M. Ward, and J.S. Sinninghe Damste Archaeal and bacterial glycerol dialkyl glycerol tetraether lipids in hot springs of yellowstone national park Appl. Environ. Microbiol. 73 2007 6181 6191 (Pubitemid 47548028)
45. G. Sprott, C. Dicaire, L. Fleming, and G. Patel Stability of liposomes prepared from archaeobacterial lipids and phosphatidylcholine mixtures Cells Mater. 6 1996 143 155
46. G.D. Sprott, J. Brisson, C.J. Dicaire, A.K. Pelletier, L.A. Deschatelets, L. Krishnan, and G.B. Patel A structural comparison of the total polar lipids from the human archaea Methanobrevibacter smithii and Methanosphaera stadtmanae and its relevance to the adjuvant activities of their liposomes Biochim. Biophys. Acta 1440 1999 275 288 (Pubitemid 29424192)
47. B.R. Stoll, H.R. Leipold, S. Milstein, and D.A. Edwards A mechanistic analysis of carrier-mediated oral delivery of protein therapeutics J. Control. Release 64 2000 217 228 (Pubitemid 30035321)
48. H. Takeuchi, Y. Matsui, H. Sugihara, H. Yamamoto, and Y. Kawashima Effectiveness of submicron-sized, chitosan-coated liposomes in oral administration of peptide drugs Int. J. Pharm. 303 2005 160 170 (Pubitemid 41318033)
49. J. Thongborisute, H. Takeuchi, H. Yamamoto, and Y. Kawashima Visualization of the penetrative and mucoadhesive properties of chitosan and chitosan-coated liposomes through the rat intestine J. Liposome Res. 16 2006 127 141 (Pubitemid 43861149)
50. S. van der Merwe, J. Verhoef, J. Verheijden, A. Kotze, and H. Junginger Trimethylated chitosan as polymeric absorption enhancer for improved peroral delivery of peptide drugs Eur. J. Pharm. Biopharm. 58 2004 225 235 (Pubitemid 39037231)
51. E. Ziv, and M. Bendayan Intestinal absorption of peptides through the enterocytes Microsc. Res. Tech. 49 2000 346 352 (Pubitemid 30407770)