Orally Administered Drug Delivery Systems to the Colon

Oral Controlled Release Formulation Design and Drug Delivery: Theory to Practice

Volumn , Issue , 2010, Pages 225-243

  Nadler Milabuer, Mirela ^a   Kam, Yossi ^a   Rubinstein, Abraham ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Colon specific drug delivery system and polysaccharide mixtures with synthetic polymers; Design considerations in colonic drug delivery systems; Orally administered drug delivery systems to colon

Indexed keywords

EID: 84885559239     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470640487.ch14     Document Type: Chapter

References (205)

1. Davis SS. Formulation strategies for absorption windows. Drug Discov. Today 2005;10:249-257.
2. Hwang SJ, Park H, Park K. Gastric retentive drug-delivery systems. Crit. Rev. Ther. Drug Carrier Syst. 1998; 15:243-284.
3. Streubel A, Siepmann J, Bodmeier R. Gastroretentive drug delivery systems. Expert Opin. Drug Deliv. 2006;3:217-233.
4. Waterman KC.Acritical reviewof gastric retentive controlled drug delivery. Pharm. Dev. Technol. 2007;12:1-10.
5. Kesisoglou F, Zimmermann EM. Novel drug delivery strategies for the treatment of inflammatory bowel disease. Expert Opin. Drug Deliv. 2005;2:451-463.
6. Somerville KW, Richmond CR, Bell GD. Delayed release peppermint oil capsules (Colpermin) for the spastic colon syndrome: a pharmacokinetic study. Br. J. Pharmacol. 1984;18:638-640.
7. Passaretti S, Sorghi M, Colombo E, Mazzotti G, Tittobello A, Guslandi M. Motor effects of locally administered pinaverium bromide in the sigmoid tract of patients with irritable bowel syndrome. Int. J. Clin. Pharmacol. Ther. Toxicol. 1989;27:47-50.
8. Nolen HW. III Friend DR. Menthol-b-D-glucuronide: a potential prodrug for treatment of irritable bowel syndrome. Pharm. Res. 1994;11:1707-1711.
9. Arber N. Do NSAIDs prevent colorectal cancer?. Can. J. Gastroenterol. 2000;14:299-307.
10. Ciolino HP, Bass SE, MacDonald CJ, Cheng RY, Yeh GC. Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells. Int. J. Cancer 2008;122:990-998.
11. Williams CS, GoldmanAP, Sheng H, MorrowJD, DuBois RN. Sulindac sulfide, but not sulindac sulfone, inhibits colorectal cancer growth. Neoplasia 1999;1:170-176.
12. Glebov OK, Rodriguez LM, Lynch P, Patterson S, Lynch H, Nakahara K, Jenkins J, Cliatt J, Humbyrd CJ, Denobile J, Soballe P, Gallinger S, Buchbinder A, Gordon G, Hawk E, Kirsch IR. Celecoxib treatment alters the gene expression profile of normal colonic mucosa. Cancer Epidemiol. Biomarkers Prev. 2006;15:1382-1391.
13. Arber N, Eagle CJ, Spicak J, Racz I, Dite P, Hajer J, Zavoral M, Lechuga MJ, Gerletti P, Tang J, Rosenstein RB, Macdonald K, Bhadra P, Fowler R, Wittes J, Zauber AG, Solomon SD, Levin B. Celecoxib for the prevention of colorectal adenomatous polyps. N. Engl. J. Med. 2006; 355:885-895.
14. Haupt S, Zioni T, Gati I, Kleinstern J, Rubinstein A. Luminal delivery and dosing considerations of local celecoxib administration to colorectal cancer. Eur. J. Pharm. Sci. 2006; 28:204-211.
15. Torrance CJ, Jackson PE, Montgomery E, Kinzler KW, Vogelstein B, Wissner A, Nunes M, Frost P, Discafani CM. Combinatorial chemoprevention of intestinal neoplasia. Nat. Med. 2000;6:1024-1028.
16. Ishizawa T, Hayashi M, Awazu S. Enhancement of jejunal and colonic absorption of fosfomycin by promoters in the rat. J. Pharm. Pharmacol. 1987;39:892-895.
17. Tomita M, Shiga M, Hayashi M, Awazu S. Enhancement of colonic drug absorption by the paracellular permeation route. Pharm. Res. 1988;5:341-346.
18. Sintov A, Simberg M, Rubinstein A. Absorption enhancement of captopril in the rat colon as a putative method for captopril delivery by extended release formulations. Int. J. Pharm. 1996;143:101-106.
19. Haupt S, Rubinstein A. The colon as a possible target for orally administered peptides and proteins. Crit. Rev. Ther. Drug Carrier Syst. 2002;19:499-545.
20. Simon GL, Gorbach SL. Intestinal flora in health and disease. Gastroenterology 1984;86:174-193.
21. Scheline RR. Metabolism of foreign compounds by gastrointestinal microorganisms. Pharmacol. Rev. 1973;25: 451-523.
22. Phillips SF, Pemberton JH, Shorter RG, editors. The Large Intestine: Physiology, Pathophysiology, and Disease, Raven Press, New York, 1991.
23. Barkla DH, Gibson PR. The fate of epithelial cells in the human large intestine. Pathology 1999;31:230-238.
24. Fordtran JS, Rector FC Jr, Ewton MF, Soter N, Kinney J. Permeability characteristics of the human small intestine. J. Clin. Invest. 1965;44:1935-1944.
25. Pauletti GM, Gangwar S, Knipp GT, Nerurkar MM, Okumn FW, Tamura K, Siahaan TJ, Borchardt RT. Structural requirements for intestinal absorption of peptide drugs. J. Control. Release 1996;41:3-17.
26. Cereijido M, Contreras RG, Flores-Benitez D, Flores-Maldonado C, Larre I, Ruiz A, Shoshani L. New diseases derived or associated with the tight junction. Arch. Med. Res. 2007;38:465-478.
27. Hollander D. Intestinal permeability, leaky gut, and intestinal disorders. Curr. Gastroenterol. Rep. 1999;1:410-416.
28. Sarna SK. Physiology and pathophysiology of colonic motor activity. Part 1. Dig. Dis. Sci. 1991;36:827-862.
29. Sarna SK. Physiology and pathophysiology of colonic motor activity. Part 2. Dig. Dis. Sci. 1991;36:998-1018.
30. Podolsky DK. Oligosaccharide structures of human colonic mucin. J. Biol. Chem. 1985;260:8262-8271.
31. Azab AK, Kleinstern J, Srebnik M, Rubinstein A. The metastatic stage-dependent mucosal expression of sialic acid is a potential marker for targeting colon cancer with cationic polymers. Pharm. Res. 2008;25:379-386.
32. Salyers AA. Bacteroides of the human lower intestinal tract. Annu. Rev. Microbiol. 1984;38:293-313.
33. JiaW, Li H, Zhao L, Nicholson JK. Gut microbiota: a potential new territory for drug targeting. Nat. Rev. Drug Discov. 2008;7:123-129.
34. Eckburg PB, Bik EM, Bernstein CN, Purdom E, Dethlefsen L, Sargent M, Gill SR, Nelson KE, Relman DA. Diversity of the human intestinal microbial flora. Science 2005;308:1635-1638.
35. Macfarlane GT, Macfarlane S. Human colonic microbiota: ecology, physiology and metabolic potential of intestinal bacteria. Scand. J. Gastroenterol. Suppl. 1997;222:3-9.
36. Cummings JH, Englyst HN. Fermentation in the human large intestine and the available substrates. Am. J. Clin. Nutr. 1987;45:1243-1255.
37. Fallingborg J. Intraluminal pH of the human gastrointestinal tract. Dan. Med. Bull. 1999;46:183-196.
38. Rowland IR. Factors affecting metabolic activity of the intestinal microflora. Drug Metab. Rev. 1988;19:243-261.
39. Rubinstein A. Microbially controlled drug delivery to the colon. Biopharm. Drug Dispos. 1990;11:465-475.
40. Sinha VR, Kumria R. Microbially triggered drug delivery to the colon. Eur. J. Pharm. Sci. 2003;18:3-18.
41. Friend DR, ChangGW.Acolon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria. J. Med. Chem. 1984;27:261-266.
42. Friend DR, Chang GW. Drug glycosides: potential prodrugs for colon-specific drug delivery. J. Med. Chem. 1985; 28:51-57.
43. SaffranM, Kumar GS, Savariar C, Burnham JC,Williams F, Neckers DC. A new approach to the oral administration of insulin and other peptide drugs. Science 1986;233:1081-1084.
44. Russell TL, Berardi RR, Barnett JL, Dermentzoglou LC, Jarvenpaa KM, Schmaltz SP, Dressman JB. Upper gastrointestinal pH in seventy-nine healthy, elderly, North American men and women. Pharm. Res. 1993;10:187-196.
45. Dressman JB, Berardi RR, Dermentzoglou LC, Russell TL, Schmaltz SP, Barnett JL, Jarvenpaa KM. Upper gastrointestinal (GI) pH in young, healthy men and women. Pharm. Res. 1990;7:756-761.
46. Evans DF, Pye G, Bramley R, ClarkAG, Dyson TJ, Hardcastle JD. Measurement of gastrointestinal pH profiles in normal ambulant human subjects. Gut 1988;29:1035-1041.
47. Charalambides D, Segal I. Colonic pH: a comparison between patients with colostomies due to trauma and colorectal cancer. Am. J. Gastroenterol. 1992;87:74-78.
48. Fallingborg J, Christensen LA, Jacobsen BA, Rasmussen SN. Very low intraluminal colonic pH in patients with active ulcerative colitis. Dig. Dis. Sci. 1993;38:1989-1993.
49. Dew MJ, Hughes PJ, Lee MG, Evans BK, Rhodes J. An oral preparation to release drugs in the human colon. Br. J. Clin. Pharmacol. 1982;14:405-408.
50. Klotz U, Maier KE, Fischer C, Bauer KH. A new slow-release form of 5-aminosalicylic acid for the oral treatment of inflammatory bowel disease. Biopharmaceutic and clinical pharmacokinetic characteristics. Arzneimittelforschung 1985;33:636-639.
51. Levine DS, RaisysVA, AinardiV. Coating of oral beclomethasone dipropionate capsules with cellulose acetate phthalate enhances delivery of topically active antiinflammatory drug to the terminal ileum. Gastroenterology 1987;92:1037-1044.
52. Ritschel WA. Targeting in the gastrointestinal tract: new approaches. Methods Find. Exp. Clin. Pharmacol. 1991;13:313-336.
53. Ashford M, Fell JT, Attwood D, Woodhead PJ. An in vitro investigation into the suitability of pH dependent polymers for colonic targeting. Int. J. Pharm. 1993;91:241-245.
54. Ashford M, Fell JT, Attwood D, Sharma H, Woodhead PJ. An in vivo investigation into the suitability of pH dependent polymers for colonic targeting. Int. J. Pharm. 1993;95:193-199.
55. Hanauer SB. Medical therapy of ulcerative colitis. Lancet 1993;342:412-417.
56. Edwards CA. Anatomical and physiological basis: physiological factors influencing drug absorption. In Bieck PR, editor. Colonic Drug Absorption and Metabolism, Marcel Dekker, New York, 1993, pp. 1-28.
57. Caldwell L, Nishihata T, Rytting JH, Higuchi T. Lymphatic uptake of water-soluble drugs after rectal administration. J. Pharm. Pharmacol. 1982;34:520-522.
58. Kararli TT. Gastrointestinal absorption of drugs. Crit. Rev. Ther. Drug Carrier Syst. 1989;6:39-86.
59. Ichihashi T, Kinoshita H, Yamada H. Absorption and disposition of epithiosteroids in rats. 2. Avoidance of first-pass metabolism of mepitiostane by lymphatic absorption. Xenobiotica 1991;21:873-880.
60. Florence AT. The oral absorption of micro- and nanoparticulates: neither exceptional nor unusual. Pharm. Res. 1997;14:259-266.
61. Gershkovich P, Hoffman A. Uptake of lipophilic drugs by plasma derived isolated chylomicrons: linear correlation with intestinal lymphatic bioavailability. Eur. J. Pharm. Sci. 2005;26:394-404.
62. Rubinstein A. Approaches and opportunities in colon-specific drug delivery. Crit. Rev. Ther. Drug Carrier Syst. 1995;12:101-149.
63. Hardcastle JD,Wilkins JL. The action of sennoside and related compounds on human colon and rectum. Gut 1970;11:1038-1042.
64. Staumont G, Frexinos J, Fioramonti J, Bueno L. Sennoside and human colonic motility. Pharmacology 1988;36(Suppl.1):49-56.
65. Hattori M, Namba T, Akao T, Kobashi K. Metabolism of sennosides by human intestinal bacteria. Pharmacology 1988;36(Suppl. 1):172-179.
66. Moreto M, Gonalons E, Mylonakis N, Giraldez A, Torralba A. 3,3-bis-(4-hydroxyphenyl)-7-methyl-2-indolinone (BHMI), the active metabolite of the laxative sulisatin. Arzneim Forsch/Drug Res. 1979;29:1561-1564.
67. Gullikson GW, Bass P. Mechanisms of action of laxative drugs. In Csaky TZ, editor. Pharmacology of Intestinal Permeation II, Springer-Verlag, Heidelberg, 1984, pp. 419-459.
68. Bennett A, Eley KG. Intestinal pH and propulsion: an explanation of diarrhoea in lactase deficiency and laxation by lactulose. J. Pharm. Pharmacol. 1976;28:192-195.
69. SimpkinsJW, Smulkowski M, Dixon R, Tuttle R. Evidence for the delivery of narcotic antagonists to the colon as their glucuronide conjugates. J. Pharmacol. Exp. Ther. 1988;244:195-205.
70. Ryde ME. Low-molecular-weight azo compounds. In Friend DR, editor. Oral Colon-Specific Drug Delivery, CRC Press, Boca Raton, 1992, pp. 143-152.
71. Hanngren A, Hansson E, Svartz N, Ullberg S. Distribution and metabolism of salicyl-azo-sulfapyridine. I. A study with C-14-5-amino-salicylic acid. Acta Med. Scand. 1963;173:61-72.
72. Hanngren A, Hansson E, Svartz N, Ullberg S. Distribution and metabolism of salicyl-azo-sulfapyridine. II.Astudy with S35-salicyl-azo-sulfapyridine and S35-sulfapyridine. Acta Med. Scand. 1963;173:391-399.
73. Klotz U. Clinical pharmacokinetics of sulphasalazine, its metabolites and other prodrugs of 5-aminosalicylic acid. Clin. Pharmacokinet. 1985;10:285-302.
74. Peppercorn MA, Goldman P. The role of intestinal bacteria in the metabolism of salicylazosulfapyridine. J. Pharmacol. Exp. Ther. 1972;181:555-562.
75. McIntyre PB, Rodrigues CA, Lennard-Jones JE, Barrison IG, Walker JG, Baron JH, Thornton PC. Balsalazide in the maintenance treatment of patients with ulcerative colitis, a doubleblind comparison with sulphasalazine. Aliment. Pharmacol. Ther. 1988;2:237-243.
76. Willoughby CP, Aronson JK, Agback H, Bodin NO, Truelove SC. Distribution and metabolism in healthy volunteers of disodium azodisalicylate, a potential therapeutic agent for ulcerative colitis. Gut 1982;23:1081-1087.
77. Bartalsky A. Salicylazobenzoic acid in ulcerative colitis. Lancet 1982;1:960.
78. Travis SPL, Tysk C, de Silva HJ, Sandberg Gertzen H, Jewell DP, Jarnerot G. Optimum dose of olsalazine for maintaining remission in ulcerative colitis. Gut 1994;35:1282-1286.
79. Agyilirah GA, Banker GS. Polymers for enteric coating applications. In Tarcha PJ, editor. Polymers for Controlled Drug Delivery, CRC Press, Boca Raton, 1991, pp. 39-66.
80. Hardy JG, Healy JNC, Lee SW, Reynolds JR. Gastrointestinal transit of an enteric-coated delayed release 5-aminosalicylic acid tablet. Aliment. Pharmacol. Ther. 1987;1:209-216.
81. Myers B, Evans DN, Rhodes J, Evans BK, Hughes BR, Lee MG, Richens A, Richards D. Metabolism and urinary excretion of 5-amino salicylic acid in healthy volunteers when given intravenously or released for absorption at different sites in the gastrointestinal tract. Gut 1987;28:196-200.
82. Rasmussen SN, Rondesen S, Hvidberg EF, Hansen S, Binder V, Halskov S, Flachs H. 5-Aminosalicylic acid in a slow-release preparation: bioavailability, plasma level, and excretion in humans. Gastroenterology 1982;83:1062-1070.
83. Thomas P, Richards D, Richards A, Rogers L, Evans BK, Dew MJ, Rhodes J. Absorption of delayed-release prednisolone in ulcerative colitis and Crohn's disease. J. Pharm. Pharmacol. 1985;37:757-758.
84. Ford GA, Oliver PS, Shepherd NA, Wilkinson SP. An Eudragit-coated prednisolone preparation for ulcerative colitis: pharmacokinetics and preliminary therapeutic use. Aliment. Pharmacol. Ther. 1992;6:31-40.
85. Harris DM. Properties and therapeutic uses of some corticosteroids with enhanced topical potency. J. Steroid Biochem. 1975;6:711-716.
86. Fedorak RN, Bistritz L. Targeted delivery, safety, and efficacy of oral enteric-coated formulations of budesonide. Adv. Drug Deliv. Rev. 2005;57:303-316.
87. Marin-Jimenez I, Pena AS. Budesonide for ulcerative colitis. Rev. Esp. Enferm. Dig. 2006;98:362-373.
88. Hanauer SB. Review: evolving concepts in treatment and disease modification in ulcerative colitis. Aliment. Pharmacol. Ther. 2008;27(Suppl. 1):15-21.
89. White DA, Thompson SP, Wilson CG, Bell GD. A pharmacokinetic comparison of two delayed-release peppermint oil preparations, Colpermin and Mintec, for treatment of the irritable bowel syndrome. Int. J. Pharm. 1987;40:151-155.
90. Wilding IR, Davis SS, Pozzi F, Furlani P, Gazzaniga A. Enteric coating timed release system for colonic targeting. Int. J. Pharm. 1994;111:99-102.
91. Gazzaniga A, Maroni A, Foppoli A, Palugan L. Oral colon delivery: rationale and time-based drug design strategy. Discov. Med. 2006;6:223-228.
92. Maggi L, Bruni R, Conte U. High molecular weight polyethylene oxides (PEOs) as an alternative to HPMC in controlled release dosage forms. Int. J. Pharm. 2000;195:229-238.
93. Conte U, Maggi L, Colombo P, La Manna A. Multi-layered hydrophilic matrices as constant release devices (Geomatrix systems). J. Control. Release 1993;26:39-47.
94. Ueda Y, Hata T, Yamaguchi H, Ueda S, Kodani M. Timecontrolled explosion systems and processes for preparing the same. US Patent 4,871,549, 1989.
95. Proano M, Camilleri M, Phillips SF, Brown ML, Thomforde GM. Transit of solids through the human colon: regional quantification in the unprepared bowel. Am. J. Physiol. 1990;258:G856-G862.
96. McLean RG, Smart RC, Gaston-Parry D, Barbagallo S, Baker J, Lyons NR, Bruck CE, King DW, Lubowski DZ, Talley NA. Colon transit scintigraphy in health and constipation using oral iodine-131-cellulose. J. Nucl. Med. 1990; 31:985-989.
97. Saffran M, Field JB, Pena J, Jones RH, Okuda Y. Oral insulin in diabetic dogs. J. Endocrinol. 1991;131:267-278.
98. Brondsted H, Kopecek J. Hydrogels for site-specific oral drug delivery: synthesis and characterization. Biomaterials 1991; 12:584-592.
99. Kopecek J, Kopeckova P, Brondsted H, Rathi R, Rihova R, Yeh P-Y, Ikesue K. Polymers for colon-specific drug delivery. J. Control. Release 1992;19:121-130.
100. Van den Mooter G, Samyn C, Kinget R. Azo polymers for colon-specific drug delivery. Int. J. Pharm. 1992;87:37-46.
101. Van den Mooter G, Samyn C, Kinget R. Azo polymers for colon-specific drug delivery. II. Influence of the type of azo polymer on the degradation by intestinal microflora. Int. J. Pharm. 1993;97:133-139.
102. Van den Mooter G, Samyn C, Kinget R. Characterization of colon-specific polymers: a study of the swelling properties and the permeability of isolated polymer films. Int. J. Pharm. 1994;111:127-136.
103. Kopecek J, Kopeckova P. N-(2-hydroxypropyl)methacrylamide copolymers for colon-specific drug delivery. In Friend DR, editor. Oral Colon-Specific Drug Delivery, CRC Press, Boca Raton, 1992, pp. 189-212.
104. Gingell R,Walker R. Mechanisms of azo reduction by Streptococcus faecalis. II. The role of soluble flavins. Xenobiotica 1971;1:231-239.
105. Lloyd AW, Martin GP, Soozandehfar SH. Azopolymers: a means of colon specific drug delivery?. Int. J. Pharm. 1994;106:255-260.
106. Hawksworth G, Drasar BS, Hill MJ. Intestinal bacteria and the hydrolysis of glycosidic bonds. J. Med. Microbiol. 1971;4:451-459.
107. Conchie J, Macdonald DC. Glycosidase in the mammalian alimentary tract. Nature 1959;184(Suppl. 16):1233.
108. Englyst HN, Hay S, Macfarlane GT. Polysaccharide breakdown by mixed populations of human fecal bacteria. FEMS Microbiol. Ecol. 1987;95:163-171.
109. Cummings JH, Southgate DAT, Branch WJ,Wiggins HS. The digestion of pectin in human gut and its effect on calcium absorption and large bowel function. Br. J. Nutr. 1979;41:477-485.
110. Werch SC, Ivy AC. On the fate of ingested pectin. Am. J. Dig. Dis. 1941;8:101-105.
111. Macfarlane GT, Hay S, Macfarlane S, Gibson GR. Effect of different carbohydrates on growth, polysaccharidase and glycosidase production by Bacteroides ovatus, in batch and continuous culture. J. Appl. Bacteriol. 1990;68:179-187.
112. Macfarlane GT, Cummings JH. The colonic flora, and large bowel digestive function. In Phillips SF, Pemberton JH, Shorter RG, editor. The Large Intestine: Physiology, Pathophysiology and Disease, Raven Press, New York, 1991, pp. 51-92.
113. Sinha VR, Kumria R. Polysaccharides in colon-specific drug delivery. Int. J. Pharm. 2001;224:19-38.
114. Rubinstein A. Natural polysaccharides as targeting tools of drugs to the human colon. Drug Dev. Res. 2000;50:435-439.
115. Hovgaard L, Brondsted H. Current applications of polysaccharides in colon targeting. Crit. Rev. Ther. Drug Carrier Syst. 1996;13:185-223.
116. Rubinstein A, Nakar D, Sintov A. Colonic drug delivery: enhanced release of indomethacin from cross-linked chondroitin matrix in rat cecal content. Pharm. Res. 1992;9:276-278.
117. Sintov A, Di Capua N, Rubinstein A. Crosslinked chondroitin sulfate: characterization for drug delivery purposes. Biomaterials 1995;16:473-478.
118. Rubinstein A, Radai R, Ezra M, Pathak S, Rokem JS. In vitro evaluation of calcium pectinate: a potential colon-specific drug delivery carrier. Pharm. Res. 1993;10:258-263.
119. Rubinstein A, Radai R. In vitro and in vivo analysis of colonspecificity of calcium pectinate formulations. Eur. J. Pharm. Biopharm. 1995;41:291-295.
120. Gliko-Kabir I, Yagen B, Penhasi A, Rubinstein A. Crosslinking guar with glutaraldehyde: a new method for preparing hydrogels for colon-specific drug delivery. In Ottenbrite RM, editor. Frontiers in Biomedical Polymer Applications, Technomic, Basel, 1998, pp. 83-93.
121. Gliko-Kabir I, Penhasi A, Rubinstein A. Characterization of crosslinked guar by thermal analysis. Cabohydr. Res. 1999;316:1-8.
122. Gliko-Kabir I, Yagen B, Penhasi A, Rubinstein A. Phosphated crosslinked guar for colon-specific drug delivery. I. Preparation and physical and chemical characterization. J. Control. Release 2000;63:121-127.
123. Gliko-Kabir I,Yagen B, Baluom M, Rubinstein A. Phosphated crosslinked guar for colon-specific drug delivery. II. In vitro and in vivo evaluation. J. Control. Release 2000;63:129-134.
124. Adkin DA, Kenyon CJ, Lerner EI, Landau I, Strauss E, Caron D, Penhasi A, Rubinstein A, Wilding IR. The use of scintigraphy to provide.proof of concept. for novel polysaccharide preparations designed for colonic drug delivery. Pharm. Res. 1997;14:103-107.
125. Ashford M, Fell JT, Attwood D, Sharma H, Woodhead P. An evaluation of pectin as a carrier for drug targeting to the colon. J. Control. Release 1993;26:213-220.
126. Ashford M, Fell J, Attwood D, Sharma H, Woodhead P. Studies on pectin formulations for colonic drug delivery. J. Control. Release 1994;30:225-232.
127. Salyers AA, O'brien M. Cellular location of enzymes involved in chondroitin sulfate breakdown by Bacteroides thetaiotaomicron. J. Bacteriol. 1980;143:772-780.
128. Kuritza AP, Salyers AA. Digestion of proteoglycan by Bacteroides thetaiotaomicron. J. Bacteriol. 1983;153:1180-1186.
129. Macfarlane S,Woodmansey EJ, Macfarlane GT. Colonization of mucin by human intestinal bacteria and establishment of biofilm communities in a two-stage continuous culture system. Appl. Environ. Microbiol. 2005;71:7483-7492.
130. Rubinstein A, Ezra M, Rokem JS. Adhesion of bacteria on pectin casted films. Microbiosis 1992;73:163-170.
131. Rubinstein A, Radai R, Friedman M, Fischer P, Rokem JS. The effect of intestinal bacteria adherence on drug diffusion through solid films under stationary condition. Pharm. Res. 1997;14:503-507.
132. Lehmann KOR, Dreher KD. Methacrylate-galactomannan coating for colon-specific drug delivery. In Proceedings of the International Symposium on Controlled Release of Bioactive Materials 1991;331-332.
133. Siefke V,Weckenmann HP, Bauer KH. b-Cyclodextrin matrix films for colon-specific drug delivery. In Proceedings of the International Symposium on Controlled Release of Bioactive Materials 1993;182-183.
134. Sarlikiotis AW, Bauer KH. Synthese und untersuchung von polyurethanen mit galactomannan-segmenten als hilfsstoffe zur freisetzung von peptid-arzneistoffen im dickdarm. Pharm. Ind. 1992;54:873-880.
135. Sintov A, Ankol S, Levy DP, Rubinstein A. Enzymatic cleavage of disaccharide side groups in insoluble synthetic polymers: a new method for specific delivery of drugs to the colon. Biomaterials 1993;14:483-490.
136. Fedorak RN, Haeberlin B, Empey LR, Cui N, Nolen H III Jewell LD, Friend DR. Colonic delivery of dexamethasone from a prodrug accelerates healing of colitis in rats without adrenal suppression. Gastroenterology 1995;108: 1688-1699.
137. Cui N, Friend DR, Fedorak RN. A budesonide prodrug accelerates treatment of colitis in rats. Gut 1994; 35:1439-1446.
138. Mahkam M, Doostie L, Siadat SO. Synthesis and characterization of acrylic type hydrogels containing azo derivatives of 5-amino salicylic acid for colon-specific drug delivery. Inflammopharmacology 2006;14:72-75.
139. Garretto M, Riddel RH, Winans CS. Treatment of chronic ulcerative colitis with poly-ASA: a new nonabsorbable carrier for release of 5-aminosalicylate in the colon. Gastroenterology 1983;84:1162.
140. Duncan R, Hume IC, Kopeckova P, Uldrich K, Strohalm J, Kopecek J. Anticancer agents coupled to N-(2-hydroxypropyl) methacrylamide copolymers. 3. Evaluation of adriamycin conjugates against mouse leukaemia L1210 in vivo. J. Control. Release 1989;10:51-63.
141. Ashkenazi S. Adherence of non-fimbriate entero-invasive Escherichia coli O124 to guinea pig intestinal tract in vitro and in vivo. J. Med. Microbiol. 1986;21:117-123.
142. Rihova B, Rathi RC, Kopeckova P, Kopecek J. In vitro bioadhesion of carbohydrate-containing N-(2-hydroxypropyl) methacrylamide copolymers to the GI tract of guinea pigs. Int. J. Pharm. 1992;87:105-116.
143. McLeod AD, Friend DR, Tozer TN. Glucocorticoid-dextran conjugates as potential prodrugs for colon-specific delivery: hydrolysis in rat gastrointestinal tract contents. J. Pharm. Sci. 1994;83:1284-1288.
144. Hehre EJ, Servy TW. Dextran-splitting anaerobic bacteria from the human intestine. J. Bacteriol. 1952;63:424.
145. Harboe E, Larsen C, Johansen M, Olsen HP. Macromolecular prodrugs. XV. Colon-targeted delivery-bioavailability of naproxen from orally administered dextran-naproxen ester prodrugs varying in molecular size in the pig. Pharm. Res. 1989;6:919-923.
146. Larsen C, Harboe E, Johansen M, Olsen HP. Macromolecular prodrugs. XVI. Colon-targeted delivery-comparison of the rate of release of naproxen from dextran ester prodrugs in homogenates of various segments of the pig gastrointestinal tract. Pharm. Res. 1989;6:995-999.
147. Nielsen LS,Weibel H, Johnsen M, Larsen C. Macromolecular prodrugs. XX. Factors influencing model dextranase-mediated depolymerization of dextran derivatives in vitro. Acta Pharm. Nord 1992;4:23-30.
148. Inoue M, Morikawa M, Tsuboi M, Yamada T, Sugiura M. Hydrolysis of ester-type drugs by the purified esterase from human intestinal mucosa. Jpn. J. Pharmacol. 1979;29:17-25.
149. McLeod AD, Fedorak RN, Friend DR, Tozer TN, Cui N. A glucocorticoid prodrug facilitates normal mucosal function in rat colitis without adrenal suppression. Gastroenterology 1994;106:405-413.
150. Steidler L, Hans W, Schotte L, Neirynck S, Obermeier F, Falk W, Fiers W, Remaut E. Treatment of murine colitis by Lactococcus lactis secreting interleukin-10. Science 2000;289:1352-1355.
151. Mardini HA, Lindsay DC, Deighton CM, Record CO. Effect of polymer coating on fecal recovery of ingested 5-amino salicylic acid in patients with ulcerative colitis. Gut 1987;28:1084-1089.
152. Li Y, Li HJ, Yang GR, Gu WP, Ma YK, Zhang MH, Sun J, Sun SJ. Colon-specific delivery tablets of sodium 4-aminosalicylic acid. Yao Xue Xue Bao 2006;41:927-932.
153. Khan MZ, Prebeg Z, Kurjakovic N. A pH-dependent colon targeted oral drug delivery system using methacrylic acid copolymers. I. Manipulation of drug release using Eudragit L100-55 and Eudragit S100 combinations. J. Control. Release 1999;58:215-222.
154. Norlander B, Gotthard R, Strom M. Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet in patients with Crohn's disease or ulcerative colitis and in healthy volunteers. Aliment. Pharmacol. Ther. 1990;4:497-505.
155. RudolphMW, Klein S, Beckert TE, Petereit H, Dressman JB. A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis. Eur. J. Pharm. Biopharm. 2001;51:183-190.
156. Iruin A, Fernandez-Arevalo M, Alvarez-Fuentes J, Fini A, Holgado MA. Elaboration and.in vitro. characterization of 5-ASA beads. Drug Dev. Ind. Pharm. 2005;31:231-239.
157. Lorenzo-Lamosa ML, Remunan-Lopez C,Vila-Jato JL, Alonso MJ. Design of microencapsulated chitosan microspheres for colonic drug delivery. J. Control. Release 1998; 52:109-118.
158. Jain A, Gupta Y, Jain SK. Potential of calcium pectinate beads for target specific drug release to colon. J. Drug Target. 2007;15:285-294.
159. Ghaffari A, Navaee K, Oskoui M, Bayati K, Rafiee-Tehrani M. Preparation and characterization of free mixed-film of pectin/ chitosan/Eudragit RS intended for sigmoidal drug delivery. Eur. J. Pharm. Biopharm. 2007;67:175-186.
160. Oosegi T, Onishi H, Machida Y. Novel preparation of entericcoated chitosan-prednisolone conjugate microspheres and in vitro evaluation of their potential as a colonic delivery system. Eur. J. Pharm. Biopharm. 2008;68:260-266.
161. Akhgari A, Farahmand F, Afrasiabi Garekani H, Sadeghi F, Vandamme TF. Permeability and swelling studies on free films containing inulin in combination with different polymethacrylates aimed for colonic drug delivery. Eur. J. Pharm. Sci. 2006;28:307-314.
162. Theeuwes F, Wong PL, Burkoth TL, Fox DA. Osmotic systems for colon-targeted drug delivery. In Bieck PR, editor. Colonic Drug Absorption and Metabolism, Marcel Dekker, New York, 1993, p 137.
163. Chacko A, Szaz KF, Howard J, Cummings JH. Non-invasive method for delivery of tracer substances or small quantities of other materials to the colon. Gut 1990;31:106-110.
164. Liu H, Yang XG, Nie SF, Wei LL, Zhou LL, Liu H, Tang R, Pan WS. Chitosan-based controlled porosity osmotic pump for colon-specific delivery system: screening of formulation variables and in vitro investigation. Int. J. Pharm. 2007; 332:115-124.
165. Wilding IR, Davis SS, Bakhshaee M, Stevens HNE, Sparrow RA, Brennan JB. Gastrointestinal transit and systemic absorption of captopril from a pulsed-release formulation. Pharm. Res. 1992;9:654-657.
166. Stevens HN,Wilson CG,Welling PG, Bakhshaee M, Binns JS, Perkins AC, Frier M, Blackshaw EP, FrameMW, Nichols DJ, Humphrey MJ,Wicks SR. Evaluation of Pulsincap to provide regional delivery of dofetilide to the human GI tract. Int. J. Pharm. 2002;236:27-34.
167. Roldo M, Barbu E, Brown JF, Laight DW, Smart JD, Tsibouklis J. Orally administered, colon-specific mucoadhesive azopolymer particles for the treatment of inflammatory bowel disease: An in vivo study. J. Biomed. Mater. Res. A 2006;79:706-715.
168. Kakoulides EP, Smart JD, Tsibouklis J. Azocrosslinked poly (acrylic acid) for colonic delivery and adhesion specificity: in vitro degradation and preliminary ex vivo bioadhesion studies. J. Control. Release 1998;54:95-109.
169. Van den Mooter G, Samyn C, KingetR. In vitro evaluation of a colon-specific drug delivery systems: an absorption study of theophylline from capsules coated with azo polymers in rats. Pharm. Res. 1995;12:244-247.
170. Yamaoka T, Makita Y, Sasatani H, Kim SI, Kimura Y. Linear type azo-containing polyurethane as drug-coating material for colon-specific delivery: its properties, degradation behavior, and utilization for drug formulation. J. Control. Release 2000;66:187-197.
171. Brondsted H, Kopecek J. Hydrogels for site-specific drug delivery to the colon: in vitro and in vivo degradation. Pharm. Res. 1992;12:1540-1545.
172. Shantha KL, Ravichandran P, Rao KP. Azo polymeric hydrogels for colon targeted drug delivery. Biomaterials 1995;16:1313-1318.
173. Maris B, Verheyden L, Van Reeth K, Samyn C, Augustijns P, Kinget R, Van den Mooter G. Synthesis and characterisation of inulin-azo hydrogels designed for colon targeting. Int. J. Pharm. 2001;213:143-152.
174. Chen WB, Wang LF, Chen JS, Fan SY. Characterization of polyelectrolyte complexes between chondroitin sulfate and chitosan in the solid state. J. Biomed. Mater. Res. A 2005;75:128-137.
175. Brondsted H, Andersen C, Hovgaard L. Crosslinked dextran- a new capsule material for colon targeting of drugs. J. Control. Release 1998;53:7-13.
176. Chiu HC, Hsiue GH, Lee YP, Huang LW. Synthesis and characterization of pH-sensitive dextran hydrogels as a potential colon-specific drug delivery system. J. Biomater. Sci. Polym. Ed. 1999;10:591-608.
177. Basan H, Gumusderelioglu M, Orbey Tevfik M. Release characteristics of salmon calcitonin from dextran hydrogels for colon-specific delivery. Eur. J. Pharm. Biopharm. 2007; 65:39-46.
178. Calinescu C, Mateescu MA. Carboxymethyl high amylose starch: chitosan self-stabilized matrix for probiotic colon delivery. Eur. J. Pharm. Biopharm. 2008;70(2):582-589.
179. Hirsch S, Binder V, Schehlmann V, Kolter K, Bauer KH. Lauroyldextran and crosslinked galactomannan as coating materials for site-specific drug delivery to the colon. Eur. J. Pharm. Biopharm. 1999;47:61-71.
180. Wakerly Z, Fell J, Attwood D, Parkins D. Studies on amidated pectins as potential carriers in colonic drug delivery. J. Pharm. Pharmacol. 1997;49:622-625.
181. Munjeri O, Fell JT, Collett JH. Hydrogel beads based on amidated pectins for colon-specific drug delivery: the role of chitosan in modifying drug release. J. Control. Release 1997;46:273-278.
182. Tozaki H, Komoike J, Tada C, Maruyama T, Terabe A, Suzuki T, Yamamoto A, Muranishi S. Chitosan capsules for colonspecific drug delivery: improvement of insulin absorption from the rat colon. J. Pharm. Sci. 1997;86:1016-1021.
183. Zhao XL, Li KX, Zhao XF, Pang DH, Chen DW. Study on colon-specific 5-Fu pH-enzyme Di-dependent chitosan microspheres. Chem. Pharm. Bull. (Tokyo) 2008;56: 963-968.
184. Kenyon CJ, Nardi RV,Wong D, Hooper G,Wilding IR, Friend DR. Colonic delivery of dexamethasone: a pharmacoscintigraphic evaluation. Aliment. Pharmacol. Ther. 1997; 11:205-213.
185. Prasad YV, Krishnaiah YS, Satyanarayana S. In vitro evaluation of guar gum as a carrier for colon-specific drug delivery. J. Control. Release 1998;51:281-287.
186. Krishnaiah YSR, Satyanarayana S, Rama Prasad YV, Narashima Rao S. Evaluation of guar as a compression coat for drug targeting to the colon. Int. J. Pharm. 1998;171:137-146.
187. Gliko-Kabir I, Yagen B, Penhasi A, Rubinstein A. Low swelling, crosslinked guar and its potential use as colonspecific drug carrier. Pharm. Res. 1998;15:1019-1025.
188. Graff S, Hussain S, Chaumeil JC, Charrueau C. Increased intestinal delivery of viable Saccharomyces boulardii by encapsulation in microspheres. Pharm. Res. 2008;25: 1290-1296.
189. Xu Y, Zhan C, Fan L, Wang L, Zheng H. Preparation of dual crosslinked alginate-chitosan blend gel beads and in vitro controlled release in oral site-specific drug delivery system. Int. J. Pharm. 2007;336:329-337.
190. Vervoort L, Van den Mooter G, Augustijns P, Busson R, Toppet S, Kinget R. Inulin hydrogels as carriers for colonic drug targeting. I. Synthesis and characterization of methacrylated inulin and hydrogel formation. Pharm. Res. 1997; 14:1730-1737.
191. Pitarresi G, Casadei MA, Mandracchia D, Paolicelli P, Palumbo FS, Giammona G. Photocrosslinking of dextran and polyaspartamide derivatives: a combination suitable for colon- specific drug delivery. J. Control. Release 2007;119: 328-338.
192. Siew LF, Basit AW, Newton JM. The potential of organicbased amylose-ethylcellulose film coatings as oral colonspecific drug delivery systems. AAPS PharmSciTech 2000;1:E22.
193. Wakerly Z, Fell JT, Attwood D, Parkins D. Pectin/ethylcellulose film coating formulations for colonic drug delivery. Pharm. Res. 1996;13:1210-1212.
194. Fan LF, He W, Bai M, Du Q, Xiang B, Chang YZ, Cao DY. Biphasic drug release: permeability and swelling of pectin/ ethylcellulose films, and in vitro and in vivo correlation of film-coated pellets in dogs. Chem. Pharm. Bull. (Tokyo) 2008;56:1118-1125.
195. Yin L, Fei L, Cui F, Tang C, Yin C. Superporous hydrogels containing poly(acrylic acid-co-acrylamide)/O-carboxymethyl chitosan interpenetrating polymer networks. Biomaterials 2007;28:1258-1266.
196. Tsai MF, Tsai HY, Peng YS, Wang LF, Chen JS, Lu SC. Characterization of hydrogels prepared from copolymerization of the different degrees of methacrylate-grafted chondroitin sulfate macromers and acrylic acid. J. Biomed. Mater. Res. A 2008;84:727-739.
197. Lee JS, Jung YJ, Doh MJ, Kim YM. Synthesis and properties of dextran-nalidixic acid ester as a colon-specific prodrug of nalidixic acid. Drug Dev. Ind. Pharm. 2001; 27:331-336.
198. Pang YN, Zhang Y, Zhang ZR. Synthesis of an enzymedependent prodrug and evaluation of its potential for colon targeting. World J. Gastroenterol. 2002;8:913-917.
199. Ahmad S, Tester RF, Corbett A, Karkalas J. Dextran and 5-aminosalicylic acid (5-ASA) conjugates: synthesis, characterisation and enzymic hydrolysis. Carbohydr. Res. 2006;341:2694-2701.
200. Minami K, Hirayama F, Uekama K. Colon-specific drug delivery based on a cyclodextrin prodrug: release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration. J. Pharm. Sci. 1998;87:715-720.
201. Yano H, Hirayama F, Arima H, Uekama K. Prednisoloneappended alpha-cyclodextrin: alleviation of systemic adverse effect of prednisolone after intracolonic administration in 2,4,6-trinitrobenzenesulfonic acid-induced colitis rats. J. Pharm. Sci. 2001;90:2103-2112.
202. Zou M, Okamoto H, Cheng G, Hao X, Sun J, Cui F, Danjo K. Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems. Eur. J. Pharm. Biopharm. 2005;59:155-160.
203. Cai QX, Zhu KJ, Chen D, Gao LP. Synthesis, characterization and in vitro release of 5-aminosalicylic acid and 5-acetyl aminosalicylic acid of polyanhydride-P(CBFAS). Eur. J. Pharm. Biopharm. 2003;55:203-208.
204. Gao SQ, Sun Y, Kopeckova P, Peterson CM, Kopecek J. Pharmacokinetic modeling of absorption behavior of 9-aminocamptothecin (9-AC) released from colon-specific HPMA copolymer-9-AC conjugate in rats. Pharm. Res. 2008;25:218-226.
205. Luo Y, Bernshaw NJ, Lu ZR, Kopecek J, Prestwich GD. Targeted delivery of doxorubicin by HPMA copolymerhyaluronan bioconjugates. Pharm. Res. 2002;19:396-402.