Absorption-Enhancing Effects of Bile Salts

Molecules

Volumn 20, Issue 8, 2015, Pages 14451-14473

  Moghimipour, Eskandar ^a   Ameri, Abdulghani ^a   Handali, Somayeh ^a  

^a AHVAZ JUNDISHAPUR UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Absorption enhancers; Bile salts; Drug delivery

Indexed keywords

BILE ACID;

ABSORPTION; ANIMAL; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; HUMAN; PERMEABILITY; TRANSPORT AT THE CELLULAR LEVEL;

ABSORPTION, PHYSIOLOGICAL; ANIMALS; BILE ACIDS AND SALTS; BIOLOGICAL TRANSPORT; DRUG DELIVERY SYSTEMS; HUMANS; PERMEABILITY;

EID: 84941243020     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules200814451     Document Type: Review

References (117)

1. NavasDiaz, A.; GarciaSa'nchez, F.; GarciaPareja, A. Cholic acid behavior in water and organic solvent: Study of normal and inverted aggregates. Colloids Surf. A 1998, 142, 27-34.
2. Gunness, P.; Flanagan, B.M.; Shelat, K.; Gilbert, R.G.; Gidley, M.J. Kinetic analysis of bile salt passage across a dialysis membrane in the presence of cereal soluble dietary fiber polymers. Food Chem. 2012, 134, 2007-2013.
3. Yang, L.; Zhang, H.; Paul Fawcett, J.; Mikov, M.; Tucker, I.G. Effect of bile salts on the transport of morphine-6-glucuronide in rat brain endothelial cells. J. Pharm. Sci. 2011, 100, 1516-1524.
4. Hagey, L.R.; Vidal, N.; Hofmann, A.F.; Krasowski, M.D. Evolutionary diversity of bile salts in reptiles and mammals, including analysis of ancient human and extinct giant ground sloth coprolites. BMC Evol. Biol. 2010, 10, 1-23.
5. Yang, L.; Tucker, I.G.; Østergaard, J. Effects of bile salts on propranolol distribution into liposomes studied by capillary electrophoresis. J. Pharm. Biomed. Anal. 2011, 56, 553-559.
6. Senel, S.; Hincal, A.A. Drug permeation enhancement via buccal route: Possibilities and limitations. J. Control. Release 2001, 72, 133-144.
7. Kesarwani, K.; Gupta, R. Bioavailability enhancers of herbal origin: An overview. Asian Pac. J. Trop. Biomed. 2013, 3, 253-266.
8. Coufalová, L.; Mrózek, L.; Rárová, L.; Placek, L.; Opatrilová, R.; Dohnal, J.; Králová, K.; Paleta, O.; Král, V.; Drašar, P.; et al. New propanoyloxy derivatives of 5β-cholan-24-oic acid as drug absorption modifiers. Steroids 2013, 78, 435-453.
9. Holm, R.; Müllertz, A.; Mu, H. Bile salts and their importance for drug absorption. Int. J. Pharm. 2013, 453, 44-55.
10. Snigdha Mishra, S.; Subuddhi, U. Spectroscopic investigation of interaction of nile blue A, a potent photosensitizer, with bile salts in aqueous medium. J. Photochem. Photobiol. B Biol. 2014, 141, 67-75.
11. Poša, M.; Sebenji, A. Determination of number-average aggregation numbers of bile salts micelles with a special emphasis on their oxo derivatives-The effect of the steroid skeleton. Biochim. Biophys. Acta 2014, 1840, 1072-1082.
12. Roda, A.; Hofmann, A.F.; Mysels, K.J. The influence of bile salt structure on self-association in aqueous solutions. J. Biol. Chem. 1983, 258, 6362-6370.
13. Stamp, D.; Jenkins, G. An overview of bile-Acid synthesis, chemistry and function. In Bile Acids, Toxicology and Bioactivity; Royal Society of Chemistry; Jenkins, G., Hardie, L.J., Eds.; Springer: Berlin, Germany; Heidelberg, Germany, 2009; pp. 1-13.
14. AguiarVallim, T.Q.; Tarling, E.J.; Edwards, P.A. Pleiotropic roles of bile acids in metabolism. Cell Metab. 2013, 17, 657-669.
15. Torchia, E.C.; Stolz, A.; Agellon, L.B. Differential modulation of cellular death and survival pathways by conjugated bile acids. BMC Biochem. 2001, 2, 11, doi:10.1186/1471-2091-2-11.
16. Monte, M.J.; Marin, J.J.G.; Antelo, A.; Vazquez-Tato, J. Bile acids: Chemistry, physiology, and pathophysiology. World J. Gastroenterol. 2009, 15, 804-816.
17. KullakUblick, G.A.; Stieger, B.; Meier, P.J. Enterohepatic bile salt transporters in normal physiology and liver disease. Gastroenterology 2004, 126, 322-342.
18. Mukhopadhyay, S.; Maitra, U. Chemistry and biology of bile acids. Curr. Sci. 2004, 87, 1666-1683.
19. Merkus, F.W.H.M.; Schipper, N.G.M.; Verhoef, J.C. The influence of absorption enhancers on intranasal insulin absorption in normal and diabetic subjects. J. Control. Release 1996, 41, 69-75.
20. Kim, N.D.; Im, E.K.; Hyun Choi, Y.; Hyun Yoo, Y. Synthetic bile acids: Novel mediators of apoptosis. J. Biochem. Mol. Biol. 2002, 35, 134-141.
21. Dial, E.J.; Rooijakkers, S.H.M.; Darling, R.L.; Romero, J.J.; Lichtenberger, L.M. Role of phosphatidylcholine saturation in preventing bile salt toxicity to gastrointestinal epithelia and membranes. J. Gastroenterol. Hepatol. 2008, 23, 430-436.
22. Garidel, P.; Hildebrand, A.; Knauf, K.; Blume, A. Membranolytic activity of bile salts: Influence of biological membrane properties and composition. Molecules 2007, 12, 2292-2326.
23. Zughaid, H.; Forbes, B.; Martin, G.P.; Patel, N. Bile salt composition is secondary to bile salt concentration in determining hydrocortisone and progesterone solubility in intestinal mimetic fluids. Int. J. Pharm. 2012, 422, 295-301.
24. Wiedmann, T.S.; Kamel, L. Examination of the solubilization of drugs by bile salt micelles. J. Pharm. Sci. 2002, 91, 1743-1764.
25. Small, D.M.; Admirand, W. Solubility of bile salts. Nature 1969, 221, 265-267.
26. Russell, D.W. Fifty years of advances in bile acid synthesis and metabolism. J. Lipid Res. 2009, S120-S125, doi:10.1194/jlr.R800026-JLR200.
27. Hofmann, A.F.; Mysels, K.J. Bile salts as biological surfactants. Colloid Surf. 1987, 30, 145-173.
28. Ravichandran, G.; Gopinath, D. Ultrasonic relaxation studies on micelle formation in aqueous solutions of some bile salts. J. Mol. Liq. 2014, 198, 122-127.
29. Barrasa, J.I.; Olmo, N.; Lizarbe, M.A.; Turnay, J. Bile acids in the colon, from healthy to cytotoxic molecules. Toxicol. In Vitro 2013, 27, 964-977.
30. Claro da Silva, T.; Polli, J.E.; Swaan, P.W. The solute carrier family 10 (SLC10): Beyond bile acid transport. Mol. Asp. Med. 2013, 34, 252-269.
31. Qi, Y.; Jiang, C.; Cheng, J.; Krausz, K.W.; Li, T.; Ferrell, J.M.; Gonzalez, F.J.; Chiang, J.Y.L. Bile acid signaling in lipid metabolism: Metabolomic and lipidomic analysis of lipid and bile acid markers linked to anti-obesity and anti-diabetes in mice. Biochim. Biophys. Acta 2015, 1851, 19-29.
32. Cremers, C.M.; Knoefler, D.; Vitvitsky, V.; Banerjee, R.; Jakob, U. Bile salts act as effective protein-unfolding agents and instigators of disulfide stress in vivo. Proc. Natl. Acad. Sci. USA 2014, 4, E1610-E1619.
33. Yin, S.; Zhai, Z.; Wang, G.; An, H.; Luo, Y.; Hao, Y. A novel vector for lactic acid bacteria that uses a bile salt hydrolase gene as apotential food-grade selection marker. J. Biotechnol. 2011, 152, 49-53.
34. Strauch, E.D.; Yamaguchi, J.; Bass, B.L.; Wang, J.Y. Bile salts regulate intestinal epithelial cell migration by nuclear factor-K β-induced expression of transforming growth factor-β. J. Am. Coll. Surg. 2003, 197, 974-984.
35. Keating, N.; Keely, S.J. Bile acids in regulation of intestinal physiology. Curr. Gastroenterol. Rep. 2009, 11, 375-382.
36. Soroka, C.J.; Boyer, J.L. Biosynthesis and trafficking of the bile salt export pump, BSEP: Therapeutic implications of BSEP mutations. Mol. Asp. Med. 2014, 37, 3-14.
37. Kumar, D.P.; Rajagopal, S.; Mahavadi, S.; Mirshahi, F.; Grider, J.R.; Murthy, K.S.; Sanyal, A.J. Activation of transmembrane bile acid receptor TGR5 stimulates insulin secretion in pancreatic β cells. Biochem. Biophys. Res. Commun. 2012, 427, 600-605.
38. Torcello-Gómez, A.; Foster, T.J. Interactions between cellulose ethers and a bile salt in the control of lipid digestion of lipid-based systems. Carbohydr. Polymers 2014, 113, 53-61.
39. Elnaggar, Y.S. Multifaceted applications of bile salts in pharmacy: An emphasis on nanomedicine. Int. J. Nanomed. 2015, 10, 3955-3971.
40. Goldberg, A.A.; Titorenko, V.I.; Beach, A.; Sanderson, J.T. Bile acids induce apoptosis selectively inandrogen-dependent and -independentprostate cancer cells. Peer J. 2013, 1, e122, doi:10.7717/peerj.122.
41. Hussain, A.; Arnold, J.J.; Khan, M.A.; Ahsan, F. Absorption enhancers in pulmonary protein delivery. J. Control. Release 2004, 94, 15-24.
42. Goto, T.; Holzinger, F.; Hagey, L.R.; Cerrè, C.; Ton-Nu, H.T.; Schteingart, C.D.; Steinbach, J.H.; Shneider, B.L.; Hofmann, A.F. Physicochemical and physiological properties of 5α-cyprinol sulfate the toxic bile salt of cyprinid fish. J. Lipid Res. 2003, 44, 1643-1651.
43. Ananthapadmanabhan, K.P.; Goddard, E.D.; Turro, N.J.; Kuo, P.L. Fluorescence probes for critical micelle concentration. Langmuir 1985, 1, 352-355.
44. Charman, W.N.; Porter, C.J.H.; Mithani, S.; Dressman, J.B. Physicochemical and physiological mechanisms for the effects of food on drug absorption: The role of lipids and pH. J. Pharm. Sci. 1997, 86, 269-282.
45. Hofmann, A.F.; Rods, A. Physicochemical properties of bile acids and their relationship to biological properties: An overview of the problem. J. Lipid Res. 1984, 25, 1477-1489.
46. Mills, C.O.; Martin, G.H.; Elias, E. The effect of tyrosine conjugation on the critical micellar concentration of free and glycine-conjugated bile salts. Biochim. Biophys. Acta 1986, 876, 677-683.
47. Meaneya, C.M.; O'Driscoll, C.M. A comparison of the permeation enhancement potential of simple bile salt and mixed bile salt: Fatty acid micellar systems using the CaCo-2 cell culture model. Int. J. Pharm. 2000, 207, 21-30.
48. Senel, S.; Duchene, D.; Hncal, A.A.; Capan, Y.; Ponchel, G. In vitro studies on enhancing effect of sodium glycocholate on transbuccal permeation of morphine hydrochloride. J. Control. Release 1998, 51, 107-113.
49. Spivak, W.; Morrison, C.; Devinuto, D.; Yuey, W. Spectrophotometric determination of the critical micellar concentration of bile salts using bilirubin monoglucuronide as a micellar probe. Biochem. J. 1988, 252, 275-281.
50. Mahalingam, R.; Ravivarapu, H.; Redkar, S.; Li, X.; Jasti, B.R. Transbuccal delivery of 5-Aza-2?-deoxycytidine: Effects of drug concentration, buffer solution, and bile salts on permeation. AAPS Pharm. Sci. Technol. 2007, 8, E1-E6.
51. Dias, R.; Sakhare, S.; Mali. K. In vitro absorption studies of mucoadhesive tablets of Acyclovir. Indian J. Pharm. Educ. Res. 2010, 44, 183-188.
52. Salama, N.N.; Eddington, N.D.; Fasano, A. Tight junction modulation and its relationship to drug delivery. Adv. Drug Deliv. Rev. 2006, 58, 15-28.
53. Song, K.H.; Chung, S.J.; Shim, C.K. Enhanced intestinal absorption of salmon calcitonin (sCT) from proliposomes containing bile salts. J. Control. Release 2005, 106, 298-308.
54. Cetin1, M.; Sinan Aktas, M.; Vural, I.; Ozturk, M. Salmon calcitonin-loaded Eudragit® and Eudragit® -PLGAnanoparticles: In vitro and in vivo evaluation. J. Microencapsul. 2012, 29, 156-166.
55. Moghimipour, E.; Jalali, A.; SajjadiTabassi, S.A.; Löbenberg, R. The enhancing effect of sodium glycocholate and sodium salicylate on rats gastro-intestinal permeability to insulin. Iran. J. Pharm. Res. 2004, 2, 87-91.
56. Jalali, A.; Moghimipour, E.; Akhgari, A. Enhancing effect of bile salts on gastrointestinal absorption of insulin. Trop. J. Pharm. Res. 2014, 13, 1797-1802.
57. Kavitha, K.; More, R.M.; Patel, D.M.; Sandeep, D.S.; Ganesh, N.S. Chemical permeation enhancers for transdermal drug delivery: A brief review. Der Pharm. Lett. 2010, 2, 358-365.
58. Shembale, A.I.; Borole, D.K.; Lohiya, R.T. Useful permeation enhancers for transdermal drug delivery: A review. Int. J. Pharm. Res. Dev. 2010, 2, 1-6.
59. Jain, H. Effect of penetration enhancer on in vitro release of diclofenac sodium gel formulation. Int. J. Pharm. Res. Dev. 2011, 2, 62-72.
60. Valenta, C.; Nowack, E.; Bernkop-Schnurch, A. Deoxycholate-hydrogels: Novel drug carrier systems for topical use. Int. J. Pharm. 1999, 185, 103-111.
61. Senyigit, T.; Tekmen, I.; Sönmez, U.; Santi, P.; Özer, O. Deoxycholate hydrogels of betamethasone-17-valerate intended for topical use: In vitro and in vivo evaluation. Int. J. Pharm. 2011, 403, 123-129.
62. Kouchak, M.; Handali, S. Effects of various penetration enhancers on penetration of aminophylline through shed snake skin. Jundishapur J. Nat. Pharm. Prod. 2014, 9, 24-29.
63. Moghimipour, E.; SajjadiTabassi, S.A.; Kouchak, M.; Varghaei, H. Combination strategies for enhancing transdermal absorption of theophylline through shed snake skin. Asian J. Pharm. Clin. Res. 2012, 5, 30-34.
64. Benson, H.A. Transdermal drug delivery: Penetration enhancement techniques. Curr. Drug Deliv. 2005, 2, 23-33.
65. Hamman, J.H.; Stander, M.; Kotze, A.F. Effect of the degree of quaternisation of N-trimethyl chitosan chloride on absorption enhancement: In vivo evaluation in rat nasal epithelia. Int. J. Pharm. 2002, 232, 235-242.
66. Merkus, F.W.H.M.; Schipper, N.G.M.; Hermens, W.A.J.J.; Romeijn, S.G.; Verhoef, J.C. Absorption enhancers in nasal drug delivery: Efficacy and safety. J. Control. Release 1993, 24, 201-208.
67. Kushwaha, S.K.S.; Kumar Keshari, R.; Rai, A.K. Advances in nasal trans-mucosal drug delivery. J. Appl. Pharm. Sci. 2011, 1, 21-28.
68. Ozsoy, Y.; Gungor, S.; Cevher, E. Nasal delivery of high molecular weight drugs. Molecules 2009, 14, 3754-3779.
69. Pillion, D.J.; Amsden, J.A.; Kensil, C.R.; Recchia, J. Structure-function relationship among Quillaja saponins serving as excipients for nasal and ocular delivery of Insulin. J. Pharm. Sci. 1996, 85, 518-524.
70. Hirai, S.; Yashiki, T.; Mima, H. Mechanisms for the enhancement of the nasal absorption of insulin by surfactants. Int. J. Pharm. 1981, 9, 173-184.
71. Gordon, G.S.; Moses, A.C.; Silver, R.D.; Flier, J.S.; Carey, M.C. Nasal absorption of insulin: Enhancement by hydrophobic bile salts. Proc. Natl. Acad. Sci. USA 1985, 82, 7419-7423.
72. Türker. S.; Onur, E.; Özer, Y. Nasal route and drug delivery systems. Pharm. World Sci. 2004, 26, 137-142.
73. Uchida, N.; Maitani, Y.; Machida, Y.; Nakagaki, M.; Nagai, T. Influence of bile salts on the permeability of insulin through the nasal mucosa of rabbits in comparison with dextran derivatives. Int. J. Pharm. 1991, 74, 95-103.
74. Bagger, M.A.; Wulff Nielsen, H.; Bechgaard, E. Nasal bioavailability of peptide T in rabbits: Absorption enhancement by sodium glycocholate and glycofurol. Eur. J. Pharm. Sci. 2001, 14, 69-74.
75. Bowe, C.L.; Mokhtarzadeh, L.; Venkatesan, P.; Babu, S.; Axelrod, H.R.; Sofia, M.J.; Kakarla, R.; Chan, T.Y.; Kim, J.S.; Lee, H.J.; et al. Design of compounds that increase the absorption of polar molecules. Proc. Natl. Acad. Sci. USA 1997, 94, 12218-12223.
76. Aungst, B.J.; Rogers, N.J.; Shefter, E. Comparison of nasal, rectal, buccal, sublingual and intramuscular insulin efficacy and the effects of a bile salt absorption promoter. J. Pharmacol. Exp. Ther. 1998, 244, 23-27.
77. Dondeti, P.; Zia, H.; Needham, T.E. In vivo evaluation of spray formulations of human insulin for nasal delivery. Int. J. Pharm. 1995, 122, 91-105.
78. Harai, S.; Ikenaga, T.; Matsuzawa, T. Nasal absorption ofinsulin in dogs. Diabetes 1978, 27, 296-299.
79. SajadiTabassi, S.A.; Hosseinzadeh, H.; Ramezani, M.; Moghimipour, E.; Mohajeri, S.A. Isolation, characterization and study of enhancing effects on nasal absorption of insulin in rat of the total saponin from Acanthophyllumsquarrosum. Indian J. Pharmacol. 2007, 39, 226-230.
80. Dodla, S.; Velmurugan, S. Buccal penetration enhancers-an review. Asian J. Pharm. Clin. Res. 2013, 6, 39-47.
81. Hearnden, V.; Sankar, V.; Hull, K.; VidovíJuras, D.; Greenberg, M.; Ross Kerr, A.; Lockhart, P.B.; Patton, L.L.; Porter. S.; Thornhill, M.H. New developments and opportunities in oral mucosal drug delivery for local and systemic disease. Adv. Drug Deliv. Rev. 2012, 64, 16-28.
82. Oh, D.H.; Chun. K.H.; Jeon, S.O.; Kang, J.W.; Lee, S. Enhanced transbuccal salmon calcitonin (sCT) delivery: Effect of chemical enhancers and electrical assistance on in vitro sCTbuccal permeation. Eur J. Pharm. Biopharm. 2011, 79, 357-363.
83. Hoogstraate, A.J.; Senel, S.; Cullander, C.; Verhoef, J.; Junginger, H.E.; Bodd, H.E. Effects of bile salts on transport rates and routes of FITC-labelled compounds across porcine buccal epithelium in vitro. J. Control. Release 1996, 40, 211-221.
84. Bernstein, G. Delivery of insulin to the buccal mucosa utilizing the RapidMistTM system. Expert Opin. Drug Deliv. 2008, 5, 1047-1055.
85. Gandhi, R.; Robinson, J. Mechanisms of penetration enhancement for transbuccal delivery of salicylic acid. Int. J. Pharm.1992, 85, 129-140.
86. Ganem-Quintanara, A.; Kalia, Y.N.; Falson-Rieg, F.; Buri, P. Mechanisms of oral permeation enhancement. Int. J. Pharm. 1997, 156, 127-142.
87. Yamamoto, A.; Hayakawa, E.; Kato, Y.; Nishiura, A.; Lee, V.H. A mechanistic study on enhancement of rectal permeability to insulin in albino rabbits. J. Pharmacol. Exp. Ther. 1992, 263, 25-31.
88. Kim1, D.W.; Ramasamy, T.; Choi, J.Y.; Kim, J.H.; Yong, C.S.; Kim, J.O.; Choi, H.G. The influence of bile salt on the chemotherapeutic response of docetaxelloaded thermosensitive nanomicelles. Int. J. Nanomed. 2014, 9, 3815-3824.
89. Saettone, M.F.; Chetoni, P.; Cerbai, R.; Mazzanti, G.; Braghiroli, L. Evaluation of ocular permeation enhancers: In vitro effects on corneal transport of fourß-blockers, and in vitro/in vivo toxic activity. Int. J. Pharm. 1996, 142, 103-113.
90. Yamamoto, A.; Luo, A.; Dodda-Kashi, S.; Lee, V. The ocular route for systemic insulin delivery in the albino rabbit. J. Pharmacol. Exp. Ther. 1989, 249, 249-255.
91. Nicolazzo, J.A.; Reed, B.L.; Finnin, B.C. Buccal penetration enhancers-How do they really work? J. Control. Release 2005, 105, 1-15.
92. Stojancevic, M.; Pavlovic, N.; Golocorbin-Kon, S.; Mikov, M. Application of bile acids in drug formulation and delivery. Front. Life Sci. 2013, 7, 112-122.
93. Wang, Y.; Zuo, Z.; Chow, M.S.S. HO-1-u-1 model for screening sublingual drug delivery-Influence of pH, osmolarity and permeation enhancer. Int. J. Pharm. 2009, 370, 68-74.
94. Shaikh, M.S.I.; Derle, N.D.; Bhamber, R. Permeability enhancement techniques for poorly permeable drugs: A review. J. Appl. Pharm. Sci. 2012, 2, 34-39.
95. Hinchcliffe, M.; Illum, L. Intranasal insulin delivery and therapy. Adv. Drug Deliv. Rev. 1999, 35, 199-234.
96. Lin, H.; Gebhardt, M.; Bian, S.; Kwon, K.A.; Shim, C.K.; Chung, S.J.; Kim, D.D. Enhancing effect of surfactants on fexofenadine. HCltransportacross the human nasal epithelial cell monolayer. Int. J. Pharm. 2007, 330, 23-31.
97. Lee, V.H.L.; Yamamoto, A. Penetration and enzymatic barriers to peptide and protein absorption. Adv. Drug Deliv. Rev. 1990, 4, 171-207.
98. Alpar, H.O.; Eyles, J.E.; Williamson, E.D.; Somavarapu, S. Intranasal vaccination against plague, tetanus and diphtheria. Adv. Drug Deliv. Rev. 2001, 51, 173-201.
99. Naveen, C.; Kiran Kumar, Y.; Venkateshwar Rao, P.; Rama Rao, T. Chemical enhancers in buccal and sublingual delivery. Int. J. Pharm. Sci. Nanothecnol. 2011, 4, 1307-1319.
100. Yamamoto, A.; Hayakawa, E.; Lee, V.H.L. Insulin and proinsulin proteolysis in mucosal homogenates of the albino rabbit: Implications in peptide delivery from nonoral routes. Life Sci. 1990, 47, 2465-2474.
101. Nakada, Y.; Awata, C.; Nakamichi, C.; Sugimoto, I. The effectof additives on the oral mucosal absorption of humancalcitonin in rats. J. Pharmacobiol. Dyn. 1988, 11, 395-401.
102. Duchateau, G.S.M.J.E.; Zuidema, J.; Merkus, F.W.H.M. Bile salts and intranasal drug absorption. Int. J. Pharm. 1986, 31, 193-199.
103. Wheatley, M.A.; Dent, J.; Wheeldon, E.B.; Smith, P.L. Nasal drug delivery: An in vitro characterization of transepitehlial electrical properties and fluxes in the presence or absence of enhancers. J. Control. Release 1998, 8, 167-177.
104. Radwana, M.A.; Aboul-Enein, H.Y. The effect of absorption enhancers on the initialdegradation kinetics of insulin by α-chymotrypsin. Int. J. Pharm. 2001, 217, 111-120.
105. Morimoto, K.; Uehara, Y.; Iwanaga, K.; Kakemi, M.; Ohashi, Y.; Tanaka, A.; Nakai, Y. Influence of absorption enhancers (bile salts) and the preservative (benzalkonium chloride) on mucociliary function and permeation barrier function in rabbit tracheas. Eur. J. Pharm. Sci. 1998, 6, 225-230.
106. Greenwood, J.; Adu, J.; Davey, A.J.; Abbott, N.J.; Bradbury, M.W.B. The effect of bile salts on the permeability and ultrastructure of the perfused, energy-depleted, rat blood-brain barrier. J. Cereb. Blood Flow Metab. 1991, 11, 644-654.
107. Barrios, J.M.; Lichtenberger, L.M. Role of biliary phosphatidylcholine in bile acid protection and NSAID injury of the ileal mucosa in rats. Gastroenterology 2000, 118, 1179-1186.
108. Tan, Y.; Qi, J.; Lu, Y.; Hu, F.; Yin, Z.; Wu, W. Lecithin in mixed micelles attenuates the cytotoxicity of bile salts in Caco-2 cells. Toxicol. in Vitro 2013, 27, 714-720.
109. Zhang, Y.; Jiang, X.G.; Yao, J. Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins. Acta Pharmacol. Sin. 2001, 22, 1051-1056.
110. Muheem, A.; Shakeel, F.; Jahangir, M.A.; Anwara, M.; Mallick, N.; Kumar Jain, G.; Husain Warsia, M.; Jalees Ahmad, F. A review on the strategies for oral delivery of proteins and peptides and their clinical perspectives. Saudi Pharm. J. 2014, doi:10.1016/j.jsps.2014.06.004.
111. Kim, H.; Kim, Y.; Lee, J. Liposomal formulations for enhanced lymphatic drug delivery. Asian J. Pharm. Sci. 2013, 8, 96-103.
112. Niua, M.; Lu, Y.;Hovgaard, L.; Guan, P.; Tan, Y.; Lian, R.; Qi, J.; Wu, W. Hypoglycemic activity and oral bioavailability of insulin-loaded liposomes containing bile salts in rats: The effect of cholate type, particle size and administered dose. Eur. J. Pharm. Biopharm. 2012, 81, 265-272.
113. Mann, J.F.; Ferro, V.A.; Mullen, A.B.; Tetley, L.; Mullen, M.; Carter, K.C.; Alexander, J.; Stimson, W.H. Optimisation of a lipid based oral delivery system containing A/Panama influenza haemagglutinin. Vaccine 2004, 22, 2425-2429.
114. Guan, P.; Lu, Y.; Qi, J.;Niu, M.;Lian, R.; Hu, F.; Wu, W. Enhanced oral bioavailability of cyclosporine A by liposomes containing a bile salt. Int. J. Nanomed. 2011, 6, 965-974.
115. Conacher, M.; Alexander, J.; Brewer, J.M. Oral immunisation with peptide and protein antigens by formulation in lipid vesicles incorporating bile salts (bilosomes). Vaccine 2001, 19, 2965-2974.
116. Mann, J.F.; Scales, H.E.; Shakir, E.; Alexander, J.; Carter, K.C.; Mullen, A.B.; Ferro, V.A. Oral delivery of tetanus toxoid using vesicles containing bile salts (bilosomes) induces significant systemic and mucosal immunity. Methods 2006, 38, 90-95.
117. Shukla, A.; Khatri, K.; Gupta, P.N.; Goyal, A.K.; Mehta, A.; Vyas, S.P. Oral immunization against hepatitis B using bile salt stabilized vesicles (bilosomes). J. Pharm. Pharm. Sci. 2008, 11, 58-66.