Enhancers for enteral delivery of macromolecules with emphasis on surfactants

Enhancement in Drug Delivery

Volumn , Issue , 2006, Pages 36-56

  Godin, Biana ^a   Touitou, Elka ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84996515522     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (116)

1. Salamat-Miller, N., and T.P. Johnston. 2005. Current strategies used to enhance the paracellular transport of therapeutic polypeptides across the intestinal epithelium. Int J Pharm 294:201.
2. Turner, J.R. 2000. Show me the pathway! Regulation of paracellular permeability by Na+-glucose cotransport. Adv Drug Deliv Rev 41:265.
3. Nellans, H.N. 1991. Mechanism of peptide and protein absorption, paracellular intestinal transport:Modification of absorption. Adv Drug Deliv Rev 7:339.
4. Fasano, A., and S. Uzzau. 1997. Modulation of intestinal tight junctions by zonula occludens toxin permits enteral administration of insulin and other macromolecules in an animal model. J Clin Invest 99:1158.
5. Lane, M.E., C.M. O’Driscoll, and O.I. Corrigan. 1996. The relationship between rat intestinal permeability and hydrophilic probe size. Pharm Res 13:1554.
6. Tanaka, Y., et al. 1995. Characterization of drug transport through tight-junctional pathway in Caco-2 monolayer: Comparison with isolated rat jejunum and colon. Pharm Res 12:523.
7. Bak, A., et al. 1999. Acyloxyalkoxy-based cyclic prodrugs of opioid peptides: Evaluation of the chemical and enzymatic stability as well as their transport properties across Caco-2 cell monolayers. Pharm Res 16:24.
8. Salamat-Miller, N., et al. 2005. A randomly-coiled, high-molecular-weight polypeptide exhibits increased paracellular diffusion in vitro and in situ relative to the highly-ordered alpha-helix conformer. Pharm Res 22:245.
9. Bock, U., et al. 1998. Transport of proteolytic enzymes across Caco-2 cell monolayers. Pharm Res 15:1393.
10. Ward, P.D., T.K. Tippin, and D.R. Thakker. 2000. Enhancing paracellular permeability by modulating epithelial tight junctions. Pharm Sci Technol Today 3:346.
11. Sood, A., and R. Panchagnula. 2001. Peroral route: An opportunity for protein and peptide drug delivery. Chem Rev 101:3275.
12. Tomita, M., M. Hayashi, and S. Awazu. 1996. Absorption-enhancing mechanism of EDTA, caprate, and decanoylcarnitine in Caco-2 cells. J Pharm Sci 85:608.
13. Rosenblatt, D.E., D.G. Doyle, and A.L. Aronson. 1978. Calcium ethyl-enediaminetetraacetate (Ca EDTA) toxicity: Time- and dose-dependent studies on intestinal morphology in the rat. Exp Mol Pathol 28:215.
14. Junginger, H.E., and J.C. Verhoef. 1998. Macromolecules as safe penetration enhancers for hydrophilic drug-A fiction? Pharm Sci Technol Today 1:370.
15. Fasano, A. 1998. Novel approaches for oral delivery of macromolecules. J Pharm Sci 87:1351.
16. Fasano, A., et al. 1995. Zonula occludens toxin modulates tight junctions through protein kinase C-dependent actin reorganization, in vitro. J Clin Invest 96:710.
17. Fasano, A., et al. 1991. Vibrio cholerae produces a second enterotoxin, which affects intestinal tight junctions. Proc Natl Acad Sci USA 88:5242.
18. Salama, N.N., et al. 2004. The effect of delta G on the transport and oral absorption of macromolecules. J Pharm Sci 93:1310.
19. Wang, W., et al. 2000. Human zonulin, a potential modulator of intestinal tight junctions. J Cell Sci 113:4435.
20. Fasano, A. 2000. Regulation of intercellular tight junctions by zonula occludens toxin and its eukaryotic analogue zonulin. Ann NY Acad Sci 915:214.
21. Kotze, A.F., et al. 1999. Enhancement of paracellular drug transport with highly quaternized N-trimethyl chitosan chloride in neutral environments: In vitro evaluation in intestinal epithelial cells (Caco-2). J Pharm Sci 88:253.
22. Dodane, V., M. Amin Khan, and J.R. Merwin. 1999. Effect of chitosan on epithelial permeability and structure. Int J Pharm 182:21.
23. Yen, W.C., and V.H.L. Lee. 1995. Penetration enhancement effect of Pz-peptide, a paracellularly transported peptide, in rabbit intestinal segments and Caco-2 cell monolayers. J Control Release 36:25.
24. Bernkop-Schnurch, A., C.E. Kast, and D. Guggi. 2003. Permeation enhancing polymers in oral delivery of hydrophilic macromolecules: Thiomer/GSH systems. J Control Release 93:95.
25. Wong, V., and B.M. Gumbiner. 1997. A synthetic peptide corresponding to the extracellular domain of occludin perturbs the tight junction permeability barrier. J Cell Biol 136:399.
26. Mathiowitz, E., et al. 1997. Biologically erodable microspheres as potential oral drug delivery systems. Nature 386:410.
27. Carino, G.P., and E. Mathiowitz. 1999. Oral insulin delivery. Adv Drug Deliv Rev 35:249.
28. Ford, J., J. Woolfe, and A.T. Florence. 1999. Nanospheres of cyclosporin A: Poor oral absorption in dogs. Int J Pharm 183:3.
29. Lee, J.H., T.G. Park, and H.K. Choi. 1999. Development of oral drug delivery system using floating microspheres. J Microencapsul 16:715.
30. Damge, C., et al. 1997. Poly(alkyl cyanoacrylate) nanospheres for oral administration of insulin. J Pharm Sci 86:1403.
31. Pinto-Alphandary, H., et al. 2003. Visualization of insulin-loaded nanocapsules: In vitro and in vivo studies after oral administration to rats. Pharm Res 20:1071.
32. Peppas, N.A. 2004. Devices based on intelligent biopolymers for oral protein delivery. Int J Pharm 277:11.
33. Mesiha, M.S., M.B. Sidhom, and B. Fasipe. 2005. Oral and subcutaneous absorption of insulin poly(isobutylcyanoacrylate) nanoparticles. Int J Pharm 288:289.
34. Morcol, T., et al. 2004. Calcium phosphate-PEG-insulin-casein (CAPIC) particles as oral delivery systems for insulin. Int J Pharm 277:91.
35. Morishita, M., et al. 2006. Novel oral insulin delivery systems based on complexation polymer hydrogels: Single and multiple administration studies in type 1 and 2 diabetic rats. J Control Release 110:587.
36. Peppas, N.A., K.M. Wood, and J.O. Blanchette. 2004. Hydrogels for oral delivery of therapeutic proteins, Expert Opin Biol Ther 4:881.
37. Zhang, N., et al. 2005. Investigation of lectin-modified insulin liposomes as carriers for oral administration. Int J Pharm 294:247.
38. Al-Achi, A., and R. Greenwood. 1998. Erythrocytes as oral delivery systems for human insulin. Drug Dev Ind Pharm 24:67.
39. Katayama, K., et al. 2003. Double liposomes: Hypoglycemic effects of liposomal insulin on normal rats. Drug Dev Ind Pharm 29:725.
40. Shao, Z., et al. 1994. Cyclodextrins as mucosal absorption promoters of insulin. II. Effects of betacyclodextrin derivatives on alpha-chymotryptic degradation and enteral absorption of insulin in rats. Pharm Res 11:1174.
41. Knipp, G.T., et al. 1997. The effect of b-turn structure on the passive diffusion of peptides across Caco-2 cell monolayers. Pharm Res 14:1332.
42. Werner, U., T. Kissel, and W. Stuber. 1997. Effects of peptide structure on transport properties of seven thyrotropin releasing hormone (TRH) analogues in a human intestinal cell line (Caco-2). Pharm Res 14:246.
43. Camenisch, G., et al. 1998. Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs’ lipophilicity and molecular weight. Eur J Pharm Sci 6:317.
44. Leone-Bay, A., et al. 1996. 4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric acid as a novel oral delivery agent for recombinant human growth hormone. J Med Chem 39:2571.
45. Leone-Bay, A., et al. 2001. Oral delivery of biologically active parathyroid hormone. Pharm Res 18:964.
46. Leone-Bay, A., et al. 1998. Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 41:1163.
47. Leone-Bay, A., et al. 1996. Oral delivery of rhGH: Preliminary mechanistic considerations. Drug News Perspect 9:586.
48. Emisphere technologies official Web site: http://www.emisphere.com.
49. Gibaldi, M., and S. Feldman. 1970. Mechanisms of surfactant effects on drug absorption. J Pharm Sci 59:579.
50. Feldman, S., M. Salvino, and M. Gibaldi. 1970. Physiologic surface-active agents and drug absorption. VII. Effect of sodium deoxycholate on phenol red absorption in the rat. J Pharm Sci 59:705.
51. Gouda, M.W., N. Khalafalah, and S.A. Khalil. 1977. Effect of surfactants on absorption through membranes V: Concentration-dependent effect of a bile salt (sodium deoxycholate) on absorption of a poorly absorbable drug, phenolsulfonphthalein, in humans. J Pharm Sci 66:727.
52. Malik, S.N., D.H. Canaham, and M.W. Gouda. 1975. Effect of surfactants on absorption through membranes III: Effects of dioctyl sodium sulfosuccinate and poloxalene on absorption of a poorly absorbable drug, phenolsulfonphthalein, in rats. J Pharm Sci 64:987.
53. Khalafallah, N., M.W. Gouda, and S.A. Khalil. 1975. Effect of surfactants on absorption through membranes IV: Effects of dioctyl sodium sulfosuccinate on absorption of a poorly absorbable drug, phenolsulfonphthalein, in humans. J Pharm Sci 64:991.
54. Utsumi, I., K. Kono, and Y. Takeuchi. 1973. Effect of surfactants on drug absorption. IV. Mechanism of the action of sodium glycocholate on the absorption of benzoylthiamine disulfide in the presence of sodium laurylsulfate and polysorbate 80. Chem Pharm Bull (Tokyo) 21:2161.
55. Levy, G., and A. Perala. 1970. Effect of polysorbate 80 and oleic acid on drug absorption from the rat intestine. J Pharm Sci 59:874.
56. Engel, R.H., and M.J. Fahrenbach. 1968. Intestinal absorption of heparin in the rat and gerbil. Proc Soc Exp Biol Med 129:772.
57. Engel, R.H., and S.J. Riggi. 1969. Effect of sulfated and sulfonated surfactants on the intestinal absorption of heparin. Proc Soc Exp Biol Med 130:879.
58. Engel, R.H., and S.J. Riggi. 1969. Intestinal absorption of heparin facilitated by sulfated or sulfonated surfactants. J Pharm Sci 58:706.
59. Touitou, E., M. Donbrow, and E. Azaz. 1978. New hydrophilic vehicle enabling rectal and vaginal absorption of insulin, heparin, phenol red and gentamicin. J Pharm Pharmacol 30:662.
60. Shichiri, M., et al. 1978. Increased intestinal absorption of insulin: An insulin suppository. J Pharm Pharmacol 30:806.
61. Whitmore, D.A., L.G. Brookes, and K.P. Wheeler. 1979. Relative effects of different surfactants on intestinal absorption and the release of proteins and phospholipids from the tissue. J Pharm Pharmacol 31:277.
62. Anderberg, E.K., C. Nystrom, and P. Artursson. 1992. Epithelial transport of drugs in cell culture. VII: Effects of pharmaceutical surfactant excipients and bile acids on transepithelial permeability in monolayers of human intestinal epithelial (Caco-2) cells. J Pharm Sci 81:879.
63. Touitou, E., M. Donbrow, and A. Rubinstein. 1980. Effective intestinal absorption of insulin in diabetic rats using a new formulation approach. J Pharm Pharmacol 32:108.
64. Touitou, E., and M. Donbrow. 1983. Promoted rectal absorption of insulin: Formulative parameters involved in the absorption from hydrophilic bases. Int J Pharm 15:13.
65. Bar-On, H., et al. 1981. Enteral administration of insulin in the rat. Br J Pharmacol 73:21.
66. Rubinstein, A., et al. 1981. Increase of the intestinal absorption of gentamicin and amikacin by a nonionic surfactant. Antimicrob Agents Chemother 19:696.
67. Touitou, E. 1992. Enhancement of intestinal peptide absorption. J Control Release 21:139.
68. Guzman, A., and R. Garcia. 1990. Effects of fatty ethers and stearic acid on the gastrointestinal absorption of insulin. P R Health Sci J 9:155.
69. Prasad, Y.V., et al. 2003. Enhanced intestinal absorption of vancomycin with Labrasol and D-alpha-tocopheryl PEG 1000 succinate in rats. Int J Pharm 250:181.
70. Rama Prasad, Y.V., et al. 2003. Evaluation of oral formulations of gentamicin containing Labrasol in beagle dogs. Int J Pharm 268:13.
71. Rama Prasad, Y.V., et al. 2004. In situ intestinal absorption studies on low molecular weight heparin in rats using Labrasol as absorption enhancer. Int J Pharm 271:225.
72. Hu, Z., et al. 2002. Diethyl ether fraction of Labrasol having a stronger absorption enhancing effect on gentamicin than Labrasol itself. Int J Pharm 234:223.
73. Eaimtrakarn, S., et al. 2002. Absorption enhancing effect of Labrasol on the intestinal absorption of insulin in rats. J Drug Target 10:255.
74. Mori, S., et al. 2004. Studies on the intestinal absorption of low molecular weight heparin using saturated fatty acids and their derivatives as an absorption enhancer in rats. Biol Pharm Bull 27:418.
75. Ito, Y., et al. 2005. Effect of adsorbents on the absorption of lansoprazole with surfactant. Int J Pharm 289:69.
76. Venkatesan, N., et al. 2005. Liquid filled nanoparticles as a drug delivery tool for protein therapeutics. Biomaterials 26:7154.
77. Venkatesan, N., et al. 2006. Gastro-intestinal patch system for the delivery of erythropoietin. J Control Release 111:19.
78. Hu, Z., et al. 2001. A novel emulsifier, Labrasol, enhances gastrointestinal absorption of gentamicin. Life Sci 69:2899.
79. Sechter, I., E. Touitou, and M. Donbrow. 1989. The influence of a non-ionic surfactant on rectal absorption of virus particles. Arch Virol 106:141.
80. Hofmann, A.F., and A. Roda. 1984. Physicochemical properties of bile acids and their relationship to biological properties: An overview of the problem. J Lipid Res 25:1477.
81. Swenson, E.S., and W.J. Curatolo. 1992. Means to enhance penetration: (2) Intestinal permeability enhancement for proteins, peptides and other polar drugs: Mechanisms and potential toxicity. Adv Drug Deliv Rev 8:39.
82. Chadwick, V.S., et al. 1979. Effect of molecular structure on bile acid-induced alterations in absorptive function, permeability and morphology in the perfused rabbit colon. J Lab Clin Med Sci 94:661.
83. Gullikson, G.W., et al. 1977. Effects of anionic surfactants on hamster small intestinal membrane structure and function: Relationship to surface activity. Gastroenterology 73:501.
84. Guarini, S., and W. Ferrari. 1985. Olive oil-provoked bile-dependent absorption of heparin from gastro-intestinal tract in rats. Pharmacol Res Commun 17:685.
85. Guarini, S., and W. Ferrari. 1985. Sodium deoxycholate promotes the absorption of heparin administered orally, probably by acting on gastrointestinal mucosa, in rats. Experientia 41:350.
86. Guarini, S., and W. Ferrari. 1984. Structural restriction in bile acids and non-ionic detergents for promotion of heparin absorption from rat gastro-intestinal tract. Arch Int Pharmacodyn Ther 271:4.
87. Hosny, E.A., H.I. Al-Shora, and M.M. Elmazar. 2001. Effect of different bile salts on the relative hypoglycemia of witepsol W35 suppositories containing insulin in diabetic beagle dogs. Drug Dev Ind Pharm 27:837.
88. Hosny, E.A., et al. 1997. Hypoglycemic effect of oral insulin in diabetic rabbits using pHdependent coated capsules containing sodium salicylate without and with sodium cholate. Pharm Acta Helv 72:203.
89. Hosny, E.A., et al. 1998. Hypoglycemic effect of oral insulin in diabetic rabbits using pHdependent coated capsules containing sodium salicylate without and with sodium cholate. Drug Dev Ind Pharm 24:307.
90. Hosny, E.A., et al. 2003. Evaluation of efficiency of insulin suppository formulations containing sodium salicylate or sodium cholate in insulin dependent diabetic patients. Boll Chim Farm 142:361.
91. Small, D.M. 1970. The formation of gallstones. Adv Intern Med 16:243.
92. Lowes, S., and N.L. Simmons. 2001. Human intestinal cell monolayers are preferentially sensitive to disruption of barrier function from basolateral exposure to cholic acid: Correlation with membrane transport and transepithelial secretion. Pflugers Arch 443:265.
93. Ward, P.D., T.K. Tippin, and D.R. Thakker. 2000. Enhancing paracellular permeability by modulating epithelial tight junctions. Pharm Sci Technol Today 3:346.
94. Yamamoto, A., E. Hayakawa, and V.H.L. Lee. 1990. Insulin and proinsulin proteolysis in mucosal homogenates of the albino rabbit: Implications in peptide delivery from nonoral routes. Life Sci 47:2465.
95. Morishita, M., et al. 1993. Site-dependent effect of aprotinin, sodium caprate, Na2EDTA and sodium glycocholate on intestinal absorption of insulin. Biol Pharm Bull 16:68.
96. Touitou, E., and A. Rubinstein. 1986. Targeted enteral delivery of insulin to rats. Int J Pharm 30:95.
97. Ziv, E., et al. 1994. Oral administration of insulin in solid form to nondiabetic and diabetic dogs. J Pharm Sci 83:792.
98. Ziv, E., O. Lior, and M. Kidron. 1987. Absorption of protein via the intestinal wall. A quantitative model. Biochem Pharmacol 36:1035.
99. Raoof, A.A., et al. 2002. Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs. Eur J Pharm Sci 17:131.
100. Raoof, A.A., et al. 2004. Oral bioavailability and multiple dose tolerability of an antisense oligonucleotide tablet formulated with sodium caprate. J Pharm Sci 93:1431.
101. Lennernas, H., et al. 2002. The influence of caprate on rectal absorption of phenoxymethylpenicillin:Experience from an in-vivo perfusion in humans. J Pharm Pharmacol 54:499.
102. Takatsuka, S., et al. 2006. Enhancement of intestinal absorption of poorly absorbed hydrophilic compounds by simultaneous use of mucolytic agent and non-ionic surfactant. Eur J Pharm Biopharm 62:52.
103. Muranishi, S. 1990. Absorption enhancers. Crit Rev Ther Drug Carrier Syst 7:1.
104. Swenson, E.S., W.B. Milisen, and W. Curatolo. 1994. Intestinal permeability enhancement:Efficacy, acute local toxicity, and reversibility. Pharm Res 11:1132.
105. Nissim, J.A. 1960. Action of some surface-active compounds on the gastro-intestinal mucosa. Nature 187:305.
106. Feldman, S., and M. Reinhard. 1976. Interaction of sodium alkyl sulfates with everted rat small intestinal membrane. J Pharm Sci 65:1460.
107. Whitmore, D.A., L.G. Brookes, and K.P. Wheeler. 1979. Relative effects of different surfactants on intestinal absorption and the release of proteins and phospholipids from the tissue. J Pharm Pharmacol 31:277.
108. Potter, G.D. 1998. Bile acid diarrhea. Dig Dis 16:118.
109. Casellas, F., et al. 1991. Human jejunal LTC4 response to irritant bile-acids. Eur J Gastroenterol Hepatol 3:393.
110. Quist, R.G., et al. 1991. Activation of mast cells by bile-acids. Gastroenterology 101:446.
111. Shah, R.B., A. Palamakula, and M.A. Khan. 2004. Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin. J Pharm Sci 93:1070.
112. Yamamoto, A., et al. 1996. Effectiveness and toxicity screening of various absorption enhancers in the rat small intestine: Effects of absorption enhancers on the intestinal absorption of phenol red and the release of protein and phospholipids from the intestinal membrane. J Pharm Pharmacol 48:1285.
113. Uchiyama, T., et al. 1999. Enhanced permeability of insulin across the rat intestinal membrane by various absorption enhancers: Their intestinal mucosal toxicity and absorption-enhancing mechanism of n-lauryl-beta-D-maltopyranoside. J Pharm Pharmacol 51:1241.
114. Swenson, E.S., W.B. Milisen, and W. Curatolo. 1994. Intestinal permeability enhancement:Structure-activity and structure-toxicity relationships for nonylphenoxypolyoxyethylene surfactant permeability enhancers. Pharm Res 11:1501.
115. Oberle, R.L., T.J. Moore, and D.A. Krummel. 1995. Evaluation of mucosal damage of surfactants in rat jejunum and colon. J Pharmacol Toxicol Meth 33:75.
116. Xia, W.J., and H. Onyuksel. 2000. Mechanistic studies on surfactant-induced membrane permeability enhancement. Pharm Res 17:612.