Oral drug delivery systems using chemical conjugates or physical complexes

Advanced Drug Delivery Reviews

Volumn 65, Issue 6, 2013, Pages 845-864

  Al Hilal, Taslim A ^a   Alam, Farzana ^b   Byun, Youngro ^b  

^a Seoul National University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

Chemical conjugation; Enhancer; Non complexation; Oral delivery; Physical complexation; Polymer; Therapeutics

Indexed keywords

ENHANCER; INTESTINAL EPITHELIUM; INTESTINAL PERMEABILITIES; NON-COMPLEXATION; ORAL DELIVERY; ORAL DRUG DELIVERY SYSTEM; THERAPEUTIC PROTEIN; THERAPEUTICS;

DIGESTIVE SYSTEM; DRUG DELIVERY; FUNCTIONAL POLYMERS; PEPTIDES; POLYMERS;

MOLECULES;

ACETIC ACID; AMPHOPHILE; ATORVASTATIN; BRAIN NATRIURETIC PEPTIDE; CALCITONIN DERIVATIVE; CHITOSAN; CYANOCOBALAMIN; EXENDIN 4; FLUOROURACIL; FUMAGILLOL CHLOROACETYLCARBAMATE; GLUCAGON LIKE PEPTIDE 1; GLUCAGON LIKE PEPTIDE 1 DERIVATIVE; INDOMETACIN; INSULIN; ITRACONAZOLE; KETOCONAZOLE; LACTOFERRIN; METFORMIN; N (2 HYDROXYPROPYL)METHACRYLAMIDE COPOLYMER; PHLORIZIN; PLACEBO; POLYACRYLAMIDE; POLYAMIDOAMINE; POLYETHYLENEIMINE; POLYGLUTAMIC ACID; PROINSULIN; RECOMBINANT BLOOD CLOTTING FACTOR 9; UNINDEXED DRUG; VALPROIC ACID; VANADIUM;

BIOLOGICAL ACTIVITY; COMPLEX FORMATION; CONJUGATE; CONJUGATION; DIABETES MELLITUS; DRUG ABSORPTION; DRUG ADMINISTRATION ROUTE; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG MECHANISM; DRUG SOLUBILITY; DRUG TRANSPORT; HUMAN; INTESTINE EPITHELIUM; INTESTINE MUCOSA PERMEABILITY; MACROMOLECULE; MOLECULAR RECOGNITION; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ADJUVANTS, PHARMACEUTIC; ADMINISTRATION, ORAL; BIOLOGICAL AVAILABILITY; BIOLOGICAL TRANSPORT; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; GASTROINTESTINAL TRACT; HUMANS; INTESTINAL ABSORPTION; POLYMERS; PROTEINS; RECEPTORS, CELL SURFACE;

EID: 84878829717     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2012.11.002     Document Type: Review

References (216)

1. Patton J.S., Byron P.R. Inhaling medicines: delivering drugs to the body through the lungs. Nat Rev Drug Discov 2007, 6:67-74.
2. Hearnden V., Sankar V., Hull K., Juras D.V., Greenberg M., Kerr A.R., 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.
3. Prausnitz M.R., Langer R. Transdermal drug delivery. Nat. Biotechnol. 2008, 26:1261-1268.
4. Balimane P.V., Chong S. Cell culture-based models for intestinal permeability: a critique. Drug Discov. Today 2005, 10:335-343.
5. Kraehenbuhl J.P., Neutra M.R. Epithelial M cells: differentiation and function. Annu. Rev. Cell Dev. Biol. 2000, 16:301-332.
6. Gebert A., Pabst R. M cells at locations outside the gut. Semin. Immunol. 1999, 11:165-170.
7. Spiekermann G.M., Finn P.W., Ward E.S., Dumont J., Dickinson B.L., Blumberg R.S., Lencer W.I. Receptor-mediated immunoglobulin G transport across mucosal barriers in adult life: functional expression of FcRn in the mammalian lung. J. Exp. Med. 2002, 196:303-310.
8. He W.Z., Ladinsky M.S., Huey-Tubman K.E., Jensen G.J., McIntosh J.R., Bjorkman P.J. FcRn-mediated antibody transport across epithelial cells revealed by electron tomography. Nature 2008, 455:542-546.
9. Azizi A., Kumar A., Diaz-Mitoma F., Mestecky J. Enhancing oral vaccine potency by targeting intestinal M cells. Plos Pathog. 2010, 6.
10. Chionh Y.T., Wee J.L.K., Every A.L., Ng G.Z., Sutton P. M-cell targeting of whole killed bacteria induces protective immunity against gastrointestinal pathogens. Infect. Immun. 2009, 77:2962-2970.
11. Hartsock A., Nelson W.J. Adherens and tight junctions: structure, function and connections to the actin cytoskeleton. Biochim. Biophys. Acta 2008, 1778:660-669.
12. Harder J.L., Margolis B. SnapShot: tight and adherens junction signaling. Cell 2008, 133:1118. (1118 e1111-1112).
13. Fihn B.M., Sjoqvist A., Jodal M. Permeability of the rat small intestinal epithelium along the villus-crypt axis: effects of glucose transport. Gastroenterology 2000, 119:1029-1036.
14. Van Itallie C.M., Holmes J., Bridges A., Gookin J.L., Coccaro M.R., Proctor W., Colegio O.R., Anderson J.M. The density of small tight junction pores varies among cell types and is increased by expression of claudin-2. J. Cell Sci. 2008, 121:298-305.
15. Bendayan M., Ziv E., Gingras D., Ben-Sasson R., Bar-On H., Kidron M. Biochemical and morpho-cytochemical evidence for the intestinal absorption of insulin in control and diabetic rats. Comparison between the effectiveness of duodenal and colon mucosa. Diabetologia 1994, 37:119-126.
16. Rosenthal R., Gunzel D., Finger C., Krug S.M., Richter J.F., Schulzke J.D., Fromm M., Amasheh S. The effect of chitosan on transcellular and paracellular mechanisms in the intestinal epithelial barrier. Biomaterials 2012, 33:2791-2800.
17. Lee E., Lee J., Lee I.H., Yu M., Kim H., Chae S.Y., Jon S. Conjugated chitosan as a novel platform for oral delivery of paclitaxel. J. Med. Chem. 2008, 51:6442-6449.
18. Eriksson U., Hilfinger J.M., Kim J.S., Mitchell S., Kijek P., Borysko K.Z., Breitenbach J.M., Drach J.C., Kashemirov B.A., McKenna C.E. Synthesis and biological activation of an ethylene glycol-linked amino acid conjugate of cyclic cidofovir. Bioorg. Med. Chem. Lett. 2007, 17:583-586.
19. Clardy S.M., Allis D.G., Fairchild T.J., Doyle R.P. Vitamin B12 in drug delivery: breaking through the barriers to a B12 bioconjugate pharmaceutical. Expert Opin. Drug Deliv. 2011, 8:127-140.
20. Lee E., Kim H., Lee I.H., Jon S. In vivo antitumor effects of chitosan-conjugated docetaxel after oral administration. J. Control. Release 2009, 140:79-85.
21. Yang L., Chen L., Zeng R., Li C., Qiao R., Hu L., Li Z. Synthesis, nanosizing and in vitro drug release of a novel anti-HIV polymeric prodrug: chitosan-O-isopropyl-5'-O-d4T monophosphate conjugate. Bioorg. Med. Chem. 2010, 18:117-123.
22. Hancock B.C., Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 1997, 86:1-12.
23. Amidi M., Mastrobattista E., Jiskoot W., Hennink W.E. Chitosan-based delivery systems for protein therapeutics and antigens. Adv. Drug Deliv. Rev. 2010, 62:59-82.
24. Thanou M., Verhoef J.C., Junginger H.E. Chitosan and its derivatives as intestinal absorption enhancers. Adv. Drug Deliv. Rev. 2001, 50:S91-S101.
25. Kean T., Thanou M. Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliv. Rev. 2010, 62:3-11.
26. Werle M., Takeuchi H., Bernkop-Schnurch A. Modified chitosans for oral drug delivery. J. Pharm. Sci. 2009, 98:1643-1656.
27. Anwar M., Warsi M.H., Mallick N., Akhter S., Gahoi S., Jain G.K., Talegaonkar S., Ahmad F.J., Khar R.K. Enhanced bioavailability of nano-sized chitosan-atorvastatin conjugate after oral administration to rats. Eur. J. Pharm. Sci. 2011, 44:241-249.
28. Nam H.Y., Kwon S.M., Chung H., Lee S.Y., Kwon S.H., Jeon H., Kim Y., Park J.H., Kim J., Her S., Oh Y.K., Kwon I.C., Kim K., Jeong S.Y. Cellular uptake mechanism and intracellular fate of hydrophobically modified glycol chitosan nanoparticles. J. Control. Release 2009, 135:259-267.
29. Bonferoni M.C., Sandri G., Rossi S., Ferrari F., Caramella C. Chitosan and its salts for mucosal and transmucosal delivery. Expert Opin. Drug Deliv. 2009, 6:923-939.
30. Duhem N., Rolland J., Riva R., Guillet P., Schumers J.M., Jerome C., Gohy J.F., Preat V. Tocol modified glycol chitosan for the oral delivery of poorly soluble drugs. Int. J. Pharm. 2012, 423:452-460.
31. Miller M.A., Malkar N.B., Severynse-Stevens D., Yarbrough K.G., Bednarcik M.J., Dugdell R.E., Puskas M.E., Krishnan R., James K.D. Amphiphilic conjugates of human brain natriuretic peptide designed for oral delivery: in vitro activity screening. Bioconjug. Chem. 2006, 17:267-274.
32. Cataliotti A., Chen H.H., Schirger J.A., Martin F.L., Boerrigter G., Costello-Boerrigter L.C., James K.D., Polowy K., Miller M.A., Malkar N.B., Bailey K.R., Burnett J.C. Chronic actions of a novel oral B-type natriuretic peptide conjugate in normal dogs and acute actions in angiotensin II-mediated hypertension. Circulation 2008, 118:1729-1736.
33. Sudoh T., Kangawa K., Minamino N., Matsuo H. A new natriuretic peptide in porcine brain. Nature 1988, 332:78-81.
34. Porter J.G., Arfsten A., Palisi T., Scarborough R.M., Lewicki J.A., Seilhamer J.J. Cloning of a cDNA encoding porcine brain natriuretic peptide. J. Biol. Chem. 1989, 264:6689-6692.
35. Hosoda K., Nakao K., Mukoyama M., Saito Y., Jougasaki M., Shirakami G., Suga S., Ogawa Y., Yasue H., Imura H. Expression of brain natriuretic peptide gene in human heart. Production in the ventricle. Hypertension 1991, 17:1152-1155.
36. Mukoyama M., Nakao K., Hosoda K., Suga S., Saito Y., Ogawa Y., Shirakami G., Jougasaki M., Obata K., Yasue H., et al. Brain natriuretic peptide as a novel cardiac hormone in humans. Evidence for an exquisite dual natriuretic peptide system, atrial natriuretic peptide and brain natriuretic peptide. J. Clin. Investig. 1991, 87:1402-1412.
37. Yan W., Sheng N., Seto M., Morser J., Wu Q. Corin, a mosaic transmembrane serine protease encoded by a novel cDNA from human heart. J. Biol. Chem. 1999, 274:14926-14935.
38. Yan W., Wu F., Morser J., Wu Q. Corin, a transmembrane cardiac serine protease, acts as a pro-atrial natriuretic peptide-converting enzyme. Proc. Natl. Acad. Sci. U. S. A. 2000, 97:8525-8529.
39. Yoshimura M., Yasue H., Morita E., Sakaino N., Jougasaki M., Kurose M., Mukoyama M., Saito Y., Nakao K., Imura H. Hemodynamic, renal, and hormonal responses to brain natriuretic peptide infusion in patients with congestive heart failure. Circulation 1991, 84:1581-1588.
40. Levin E.R., Gardner D.G., Samson W.K. Natriuretic peptides. N. Engl. J. Med. 1998, 339:321-328.
41. Cataliotti A., Schirger J.A., Martin F.L., Chen H.H., McKie P.M., Boerrigter G., Costello-Boerrigter L.C., Harty G., Heublein D.M., Sandberg S.M., James K.D., Miller M.A., Malkar N.B., Polowy K., Burnett J.C. Oral human brain natriuretic peptide activates cyclic guanosine 3',5'-monophosphate and decreases mean arterial pressure. Circulation 2005, 112:836-840.
42. Clement S., Still J.G., Kosutic G., McAllister R.G. Oral insulin product hexyl-insulin monoconjugate 2 (HIM2) in type 1 diabetes mellitus: the glucose stabilization effects of HIM2. Diabetes Technol. Ther. 2002, 4:459-466.
43. Kipnes M., Dandona P., Tripathy D., Still J.G., Kosutic G. Control of postprandial plasma glucose by an oral insulin product (HIM2) in patients with type 2 diabetes. Diabetes Care 2003, 26:421-426.
44. Mansoor S., Youn Y.S., Lee K.C. Oral delivery of mono-PEGylated sCT (Lys18) in rats: regional difference in stability and hypocalcemic effect. Pharm. Dev. Technol. 2005, 10:389-396.
45. Youn Y.S., Jung J.Y., Oh S.H., Yoo S.D., Lee K.C. Improved intestinal delivery of salmon calcitonin by Lys18-amine specific PEGylation: stability, permeability, pharmacokinetic behavior and in vivo hypocalcemic efficacy. J. Control. Release 2006, 114:334-342.
46. Nojima Y., Suzuki Y., Iguchi K., Shiga T., Iwata A., Fujimoto T., Yoshida K., Shimizu H., Takeuchi T., Sato A. Development of poly(ethylene glycol) conjugated lactoferrin for oral administration. Bioconjug. Chem. 2008, 19:2253-2259.
47. Takeuchi T., Kitagawa H., Harada E. Evidence of lactoferrin transportation into blood circulation from intestine via lymphatic pathway in adult rats. Exp. Physiol. 2004, 89:263-270.
48. Kakizawa Y., Kataoka K. Block copolymer micelles for delivery of gene and related compounds. Adv. Drug Deliv. Rev. 2002, 54:203-222.
49. Nishiyama N., Kataoka K. Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol. Therapeut. 2006, 112:630-648.
50. Benny O., Fainaru O., Adini A., Cassiola F., Bazinet L., Adini I., Pravda E., Nahmias Y., Koirala S., Corfas G., D'Amato R.J., Folkman J. An orally delivered small-molecule formulation with antiangiogenic and anticancer activity. Nat. Biotechnol. 2008, 26:799-807.
51. Francis M.F., Cristea M., Winnik F.M. Exploiting the vitamin B12 pathway to enhance oral drug delivery via polymeric micelles. Biomacromolecules 2005, 6:2462-2467.
52. Norris D.A., Puri N., Sinko P.J. The effect of physical barriers and properties on the oral absorption of particulates. Adv. Drug Deliv. Rev. 1998, 34:135-154.
53. Zhu S., Huang R., Hong M., Jiang Y., Hu Z., Liu C., Pei Y. Effects of polyoxyethylene (40) stearate on the activity of P-glycoprotein and cytochrome P450. Eur. J. Pharm. Sci. 2009, 37:573-580.
54. Grabovac V., Guggi D., Bernkop-Schnurch A. Comparison of the mucoadhesive properties of various polymers. Adv. Drug Deliv. Rev. 2005, 57:1713-1723.
55. Iqbal J., Shahnaz G., Dunnhaupt S., Muller C., Hintzen F., Bernkop-Schnurch A. Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials 2012, 33:1528-1535.
56. Cone R.A. Barrier properties of mucus. Adv. Drug Deliv. Rev. 2009, 61:75-85.
57. Gum J.R., Hicks J.W., Toribara N.W., Rothe E.M., Lagace R.E., Kim Y.S. The human Muc2 intestinal mucin has cysteine-rich subdomains located both upstream and downstream of its central repetitive region. J. Biol. Chem. 1992, 267:21375-21383.
58. Tolle-Sander S., Lentz K.A., Maeda D.Y., Coop A., Polli J.E. Increased acyclovir oral bioavailability via a bile acid conjugate. Mol. Pharm. 2004, 1:40-48.
59. Wu S., Campbell C., Koda Y., Blanchfield J.T., Toth I. Investigation of the route of absorption of lipid and sugar modified leu-enkephalin analogues and their enzymatic stability using the caco-2 cell monolayer system. Med. Chem. 2006, 2:203-211.
60. Rouquayrol M., Gaucher B., Roche D., Greiner J., Vierling P. Transepithelial transport of prodrugs of the HIV protease inhibitors saquinavir, indinavir, and nelfinavir across Caco-2 cell monolayers. Pharm. Res. 2002, 19:1704-1712.
61. Bergeon J.A., Chan Y.N., Charles B.G., Toth I. Oral absorption enhancement of dipeptide L-Glu-L-Trp-OH by lipid and glycosyl conjugation. Biopolymers 2008, 90:633-643.
62. Chalasani K.B., Russell-Jones G.J., Yandrapu S.K., Diwan P.V., Jain S.K. A novel vitamin B12-nanosphere conjugate carrier system for peroral delivery of insulin. J. Control. Release 2007, 117:421-429.
63. Sockolosky J.T., Tiffany M.R., Szoka F.C. Engineering neonatal Fc receptor-mediated recycling and transcytosis in recombinant proteins by short terminal peptide extensions. Proc. Natl. Acad. Sci. U. S. A. 2012, 109:16095-16100.
64. Bai Y., Ann D.K., Shen W.C. Recombinant granulocyte colony-stimulating factor-transferrin fusion protein as an oral myelopoietic agent. Proc. Natl. Acad. Sci. U. S. A. 2005, 102:7292-7296.
65. Amet N., Wang W., Shen W.C. Human growth hormone-transferrin fusion protein for oral delivery in hypophysectomized rats. J. Control. Release 2010, 141:177-182.
66. Meier Y., Eloranta J.J., Darimont J., Ismair M.G., Hiller C., Fried M., Kullak-Ublick G.A., Vavricka S.R. Regional distribution of solute carrier mRNA expression along the human intestinal tract. Drug Metab. Dispos. 2007, 35:590-594.
67. Rais R., Fletcher S., Polli J.E. Synthesis and in vitro evaluation of gabapentin prodrugs that target the human apical sodium-dependent bile acid transporter (hASBT). J. Pharm. Sci. 2011, 100:1184-1195.
68. Mukherjee R., Donnay E.G., Radomski M.A., Miller C., Redfern D.A., Gericke A., Damron D.S., Brasch N.E. Vanadium-vitamin B12 bioconjugates as potential therapeutics for treating diabetes. Chem. Commun. (Camb) 2008, 3783-3785.
69. Wuerges J., Garau G., Geremia S., Fedosov S.N., Petersen T.E., Randaccio L. Structural basis for mammalian vitamin B12 transport by transcobalamin. Proc. Natl. Acad. Sci. U. S. A. 2006, 103:4386-4391.
70. Olesen H., Hippe E., Haber E. Nature of vitamin B 12 binding. I. Covalent coupling of hydroxocobalamin to soluble and insoluble carriers. Biochim. Biophys. Acta 1971, 243:66-74.
71. Petrus A.K., Vortherms A.R., Fairchild T.J., Doyle R.P. Vitamin B12 as a carrier for the oral delivery of insulin. ChemMedChem 2007, 2:1717-1721.
72. Petrus A.K., Fairchild T.J., Doyle R.P. Traveling the vitamin B12 pathway: oral delivery of protein and peptide drugs. Angew. Chem. Int. Ed. Engl. 2009, 48:1022-1028.
73. Fishburn C.S. The pharmacology of PEGylation: balancing PD with PK to generate novel therapeutics. J. Pharm. Sci. 2008, 97:4167-4183.
74. Veronese F.M. Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 2001, 22:405-417.
75. Shaunak S., Godwin A., Choi J.W., Balan S., Pedone E., Vijayarangam D., Heidelberger S., Teo I., Zloh M., Brocchini S. Site-specific PEGylation of native disulfide bonds in therapeutic proteins. Nat. Chem. Biol. 2006, 2:312-313.
76. Veronese F.M., Mero A. The impact of PEGylation on biological therapies. BioDrugs 2008, 22:315-329.
77. Chapman A.P. PEGylated antibodies and antibody fragments for improved therapy: a review. Adv. Drug Deliv. Rev. 2002, 54:531-545.
78. Keefe A.J., Jiang S. Poly(zwitterionic)protein conjugates offer increased stability without sacrificing binding affinity or bioactivity. Nat. Chem. 2011, 4:59-63.
79. Tamai I. Oral drug delivery utilizing intestinal OATP transporters. Adv. Drug Deliv. Rev. 2012, 64:508-514.
80. Zempleni J. Uptake, localization, and noncarboxylase roles of biotin. Annu. Rev. Nutr. 2005, 25:175-196.
81. Ramanathan S., Pooyan S., Stein S., Prasad P.D., Wang J., Leibowitz M.J., Ganapathy V., Sinko P.J. Targeting the sodium-dependent multivitamin transporter (SMVT) for improving the oral absorption properties of a retro-inverso Tat nonapeptide. Pharm. Res. 2001, 18:950-956.
82. Cetin M., Youn Y.S., Capan Y., Lee K.C. Preparation and characterization of salmon calcitonin-biotin conjugates. AAPS PharmSciTech 2008, 9:1191-1197.
83. Chae S.Y., Jin C.H., Shin H.J., Youn Y.S., Lee S., Lee K.C. Preparation, characterization, and application of biotinylated and biotin-PEGylated glucagon-like peptide-1 analogues for enhanced oral delivery. Bioconjug. Chem. 2008, 19:334-341.
84. Jin C.H., Chae S.Y., Son S., Kim T.H., Um K.A., Youn Y.S., Lee S., Lee K.C. A new orally available glucagon-like peptide-1 receptor agonist, biotinylated exendin-4, displays improved hypoglycemic effects in db/db mice. J. Control. Release 2009, 133:172-177.
85. Ikumi Y., Kida T., Sakuma S., Yamashita S., Akashi M. Polymer-phloridzin conjugates as an anti-diabetic drug that inhibits glucose absorption through the Na+/glucose cotransporter (SGLT1) in the small intestine. J. Control. Release 2008, 125:42-49.
86. Sakuma S., Sagawa T., Masaoka Y., Kataoka M., Yamashita S., Shirasaka Y., Tamai I., Ikumi Y., Kida T., Akashi M. Stabilization of enzyme-susceptible glucoside bonds of phloridzin through conjugation with poly(gamma-glutamic acid). J. Control. Release 2009, 133:125-131.
87. Lee Y., Nam J.H., Shin H.C., Byun Y. Conjugation of low-molecular-weight heparin and deoxycholic acid for the development of a new oral anticoagulant agent. Circulation 2001, 104:3116-3120.
88. Hyers T.M., Hull R.D., Weg J.G. Antithrombotic therapy for venous thromboembolic disease. Chest 1995, 108:335S-351S.
89. Mackman N. Triggers, targets and treatments for thrombosis. Nature 2008, 451:914-918.
90. Weitz J.I. Low-molecular-weight heparins. N. Engl. J. Med. 1997, 337:688-698.
91. Windsor E., Cronheim G.E. Gastro-intestinal absorption of heparin and synthetic heparinoids. Nature 1961, 190:263-264.
92. Ross B.P., Toth I. Gastrointestinal absorption of heparin by lipidization or coadministration with penetration enhancers. Curr. Drug Deliv. 2005, 2:277-287.
93. Kim S.K., Huh J., Kim S.Y., Byun Y., Lee D.Y., Moon H.T. Physicochemical conjugation with deoxycholic acid and dimethylsulfoxide for heparin oral delivery. Bioconjug. Chem. 2011, 22:1451-1458.
94. Park J.W., Jeon O.C., Kim S.K., Al-Hilal T.A., Moon H.T., Kim C.Y., Byun Y. Anticoagulant efficacy of solid oral formulations containing a new heparin derivative. Mol. Pharm. 2010, 7:836-843.
95. Kim S.K., Kim K., Lee S., Park K., Park J.H., Kwon I.C., Choi K., Kim C.Y., Byun Y. Evaluation of absorption of heparin-DOCA conjugates on the intestinal wall using a surface plasmon resonance. J. Pharmaceut. Biomed. 2005, 39:861-870.
96. Kim S.K., Lee D.Y., Lee E., Lee Y.K., Kim C.Y., Moon H.T., Byun Y. Absorption study of deoxycholic acid-heparin conjugate as a new form of oral anti-coagulant. J. Control. Release 2007, 120:4-10.
97. Park J.W., Jeon O.C., Kim S.K., Al-Hilal T.A., Lim K.M., Moon H.T., Kim C.Y., Byun Y. Pharmacokinetic evaluation of an oral tablet form of low-molecular-weight heparin and deoxycholic acid conjugate as a novel oral anticoagulant. Thromb. Haemost. 2011, 105:1060-1071.
98. Kim S.K., Lee D., Kim C., Moon H.T., Byun Y. Prevention effect of orally active heparin derivative on deep vein thrombosis. Thromb. Haemost. 2006, 96:149-153.
99. Lee D.Y., Kim S.K., Kim Y.S., Son D.H., Nam J.H., Kim I.S., Park R.W., Kim S.Y., Byun Y. Suppression of angiogenesis and tumor growth by orally active deoxycholic acid-heparin conjugate. J. Control. Release 2007, 118:310-317.
100. Lee D.Y., Park K., Kim S.K., Park R.W., Kwon I.C., Kim S.Y., Byun Y. Antimetastatic effect of an orally active heparin derivative on experimentally induced metastasis. Clin. Cancer Res. 2008, 14:2841-2849.
101. Dahan A., Amidon G.L. Segmental dependent transport of low permeability compounds along the small intestine due to P-glycoprotein: the role of efflux transport in the oral absorption of BCS class III drugs. Mol. Pharm. 2009, 6:19-28.
102. Masaoka Y., Tanaka Y., Kataoka M., Sakuma S., Yamashita S. Site of drug absorption after oral administration: assessment of membrane permeability and luminal concentration of drugs in each segment of gastrointestinal tract. Eur. J. Pharm. Sci. 2006, 29:240-250.
103. Mudie D.M., Amidon G.L., Amidon G.E. Physiological parameters for oral delivery and in vitro testing. Mol. Pharm. 2010, 7:1388-1405.
104. Edwards C. Physiology of the colorectal barrier. Adv. Drug Deliv. Rev. 1997, 28:173-190.
105. Di Maio S., Carrier R.L. Gastrointestinal contents in fasted state and post-lipid ingestion: In vivo measurements and in vitro models for studying oral drug delivery. J. Control. Release 2011, 151:110-122.
106. Maroni A., Zema L., Del Curto M.D., Foppoli A., Gazzaniga A. Oral colon delivery of insulin with the aid of functional adjuvants. Adv. Drug Deliv. Rev. 2012, 64:540-556.
107. Udo K., Hokonohara K., Motoyama K., Arima H., Hirayama F., Uekama K. 5-Fluorouracil acetic acid/beta-cyclodextrin conjugates: drug release behavior in enzymatic and rat cecal media. Int. J. Pharm. 2010, 388:95-100.
108. Gao S.Q., Lu Z.R., Kopeckova P., Kopecek J. Biodistribution and pharmacokinetics of colon-specific HPMA copolymer-9-aminocamptothecin conjugate in mice. J. Control. Release 2007, 117:179-185.
109. Gao S.Q., Sun Y., Kopeckova P., Peterson C.M., 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.
110. Dahan A., Duvdevani R., Dvir E., Elmann A., Hoffman A. A novel mechanism for oral controlled release of drugs by continuous degradation of a phospholipid prodrug along the intestine: in-vivo and in-vitro evaluation of an indomethacin-lecithin conjugate. J. Control. Release 2007, 119:86-93.
111. Dahan A., Duvdevani R., Shapiro I., Elmann A., Finkelstein E., Hoffman A. The oral absorption of phospholipid prodrugs: in vivo and in vitro mechanistic investigation of trafficking of a lecithin-valproic acid conjugate following oral administration. J. Control. Release 2008, 126:1-9.
112. Schwarze S.R., Ho A., Vocero-Akbani A., Dowdy S.F. In vivo protein transduction: delivery of a biologically active protein into the mouse. Science 1999, 285:1569-1572.
113. Foged C., Nielsen H.M. Cell-penetrating peptides for drug delivery across membrane barriers. Expert Opin. Drug Deliv. 2008, 5:105-117.
114. Liang J.F., Yang V.C. Insulin-cell penetrating peptide hybrids with improved intestinal absorption efficiency. Biochem. Biophys. Res. Commun. 2005, 335:734-738.
115. Jones S.W., Christison R., Bundell K., Voyce C.J., Brockbank S.M., Newham P., Lindsay M.A. Characterisation of cell-penetrating peptide-mediated peptide delivery. Br. J. Pharmacol. 2005, 145:1093-1102.
116. Kang S.K., Woo J.H., Kim M.K., Woo S.S., Choi J.H., Lee H.G., Lee N.K., Choi Y.J. Identification of a peptide sequence that improves transport of macromolecules across the intestinal mucosal barrier targeting goblet cells. J. Biotechnol. 2008, 135:210-216.
117. Fievez V., Plapied L., Plaideau C., Legendre D., des Rieux A., Pourcelle V., Freichels H., Jerome C., Marchand J., Preat V., Schneider Y.J. In vitro identification of targeting ligands of human M cells by phage display. Int. J. Pharm. 2010, 394:35-42.
118. Jin Y., Song Y., Zhu X., Zhou D., Chen C., Zhang Z., Huang Y. Goblet cell-targeting nanoparticles for oral insulin delivery and the influence of mucus on insulin transport. Biomaterials 2012, 33:1573-1582.
119. Langridge W., Denes B., Fodor I. Cholera toxin B subunit modulation of mucosal vaccines for infectious and autoimmune diseases. Curr. Opin. Invest. Dr. 2010, 11:919-928.
120. Milletti F. Cell-penetrating peptides: classes, origin, and current landscape. Drug Discov. Today 2012, 17:850-860.
121. Amet N., Wang W., Shen W.C. Human growth hormone-transferrin fusion protein for oral delivery in hypophysectomized rats. J. Control. Release 2010, 141:177-182.
122. Merritt E.A., Sixma T.K., Kalk K.H., van Zanten B.A., Hol W.G. Galactose-binding site in Escherichia coli heat-labile enterotoxin (LT) and cholera toxin (CT). Mol. Microbiol. 1994, 13:745-753.
123. Verma D., Moghimi B., LoDuca P.A., Singh H.D., Hoffman B.E., Herzog R.W., Daniell H. Oral delivery of bioencapsulated coagulation factor IX prevents inhibitor formation and fatal anaphylaxis in hemophilia B mice. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:7101-7106.
124. Gong Z.H., Jin Y.F., Zhang Y.Z. Suppression of diabetes in non-obese diabetic (NOD) mice by oral administration of a cholera toxin B subunit-insulin B chain fusion protein vaccine produced in silkworm. Vaccine 2007, 25:1444-1451.
125. Ruhlman T., Ahangari R., Devine A., Samsam M., Daniell H. Expression of cholera toxin B-proinsulin fusion protein in lettuce and tobacco chloroplasts - oral administration protects against development of insulitis in non-obese diabetic mice. Plant Biotechnol. J. 2007, 5:495-510.
126. Shah D., Shen W.C. Transcellular delivery of an insulin-transferrin conjugate in enterocyte-like Caco-2 cells. J. Pharm. Sci. 1996, 85:1306-1311.
127. Kavimandan N.J., Losi E., Wilson J.J., Brodbelt J.S., Peppas N.A. Synthesis and characterization of insulin-transferrin conjugates. Bioconjug. Chem. 2006, 17:1376-1384.
128. Lee S., Kim K., Kumar T.S., Lee J., Kim S.K., Lee D.Y., Lee Y.K., Byun Y. Synthesis and biological properties of insulin-deoxycholic acid chemical conjugates. Bioconjug. Chem. 2005, 16:615-620.
129. Ovadia O., Greenberg S., Chatterjee J., Laufer B., Opperer F., Kessler H., Gilon C., Hoffman A. The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides. Mol. Pharm. 2011, 8:479-487.
130. Doedens L., Opperer F., Cai M., Beck J.G., Dedek M., Palmer E., Hruby V.J., Kessler H. Multiple N-methylation of MT-II backbone amide bonds leads to melanocortin receptor subtype hMC1R selectivity: pharmacological and conformational studies. J. Am. Chem. Soc. 2010, 132:8115-8128.
131. Biron E., Chatterjee J., Ovadia O., Langenegger D., Brueggen J., Hoyer D., Schmid H.A., Jelinek R., Gilon C., Hoffman A., Kessler H. Improving oral bioavailability of peptides by multiple N-methylation: somatostatin analogues. Angew. Chem. Int. Ed. Engl. 2008, 47:2595-2599.
132. He Y.B., Huang Z.W., Raynor K., Reisine T., Goodman M. Syntheses and conformations of somatostatin-related cyclic hexapeptides incorporating specific alpha-methylated and beta-methylated residues. J. Am. Chem. Soc. 1993, 115:8066-8072.
133. Hruby V.J. Designing peptide receptor agonists and antagonists. Nat. Rev. Drug Discov. 2002, 1:847-858.
134. Vlieghe P., Lisowski V., Martinez J., Khrestchatisky M. Synthetic therapeutic peptides: science and market. Drug Discov. Today 2010, 15:40-56.
135. Gong N., Ma A.N., Zhang L.J., Luo X.S., Zhang Y.H., Xu M., Wang Y.X. Site-specific PEGylation of exenatide analogues markedly improved their glucoregulatory activity. Br. J. Pharmacol. 2011, 163:399-412.
136. Bailon P., Won C.Y. PEG-modified biopharmaceuticals. Expert Opin. Drug Deliv. 2009, 6:1-16.
137. Smorenburg S.M., Van Noorden C.J.F. The complex effects of heparins on cancer progression and metastasis in experimental studies. Pharmacol. Rev. 2001, 53:93-105.
138. Lever R., Page C.R. Novel drug development opportunities for heparin. Nat. Rev. Drug Discov. 2002, 1:140-148.
139. Park J.W., Jeon O.C., Kim S.K., Al-Hilal T.A., Jin S.J., Moon H.T., Yang V.C., Kim S.Y., Byun Y. High antiangiogenic and low anticoagulant efficacy of orally active low molecular weight heparin derivatives. J. Control. Release 2010, 148:317-326.
140. Engelman D.M., Steitz T.A. The spontaneous insertion of proteins into and across membranes - the helical hairpin hypothesis. Cell 1981, 23:411-422.
141. Meier P.J., Stieger B. Bile salt transporters. Annu. Rev. Physiol. 2002, 64:635-661.
142. Swenson E.S., Curatolo W.J. Intestinal permeability enhancement for proteins, peptides and other polar drugs - mechanisms and potential toxicity. 2. Adv. Drug Deliv. Rev. 1992, 8:39-92.
143. Lee S., Lee J., Lee D.Y., Kim S.K., Lee Y., Byun Y. A new drug carrier, Nalpha-deoxycholyl-L: -lysyl-methylester, for enhancing insulin absorption in the intestine. Diabetologia 2005, 48:405-411.
144. Lee S., Kim S.K., Lee D.Y., Chae S.Y., Byun Y. Pharmacokinetics of a new, orally available ceftriaxone formulation in physical complexation with a cationic analogue of bile acid in rats. Antimicrob. Agents Chemother. 2006, 50:1869-1871.
145. Lee S., Kim S.K., Lee D.Y., Park K., Kumar T.S., Chae S.Y., Byun Y. Cationic analog of deoxycholate as an oral delivery carrier for ceftriaxone. J. Pharm. Sci. 2005, 94:2541-2548.
146. Lee D.Y., Lee J., Lee S., Kim S.K., Byun Y. Liphophilic complexation of heparin based on bile acid for oral delivery. J. Control. Release 2007, 123:39-45.
147. Leone-Bay A., Leipold H., Sarubbi D., Variano B., Rivera T., Baughman R.A. Oral delivery of sodium cromolyn: preliminary studies in vivo and in vitro. Pharm. Res. 1996, 13:222-226.
148. Gonze M.D., Salartash K., Sternbergh W.C., Baughman R.A., Leone-Bay A., Money S.R. Orally administered unfractionated heparin with carrier agent is therapeutic for deep venous thrombosis. Circulation 2000, 101:2658-2661.
149. Goldberg M., Gomez-Orellana I. Challenges for the oral delivery of macromolecules. Nat. Rev. Drug Discov. 2003, 2:289-295.
150. Hoffman A., Qadri B. Eligen insulin - a system for the oral delivery of insulin for diabetes. IDrugs 2008, 11:433-441.
151. Steinert R.E., Poller B., Castelli M.C., Friedman K., Huber A.R., Drewe J., Beglinger C. Orally administered glucagon-like peptide-1 affects glucose homeostasis following an oral glucose tolerance test in healthy male subjects. Clin. Pharmacol. Ther. 2009, 86:644-650.
152. Castelli M.C., Wong D.F., Friedman K., Riley M.G. Pharmacokinetics of oral cyanocobalamin formulated with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate (SNAC): an open-label, randomized, single-dose, parallel-group study in healthy male subjects. Clin. Ther. 2011, 33:934-945.
153. Carrier R.L., Miller L.A., Ahmed I. The utility of cyclodextrins for enhancing oral bioavailability. J. Control. Release 2007, 123:78-99.
154. Agueros M., Zabaleta V., Espuelas S., Campanero M.A., Irache J.M. Increased oral bioavailability of paclitaxel by its encapsulation through complex formation with cyclodextrins in poly(anhydride) nanoparticles. J. Control. Release 2010, 145:2-8.
155. Kiss T., Fenyvesi F., Bacskay I., Varadi J., Fenyvesi E., Ivanyi R., Szente L., Tosaki A., Vecsernyes M. Evaluation of the cytotoxicity of beta-cyclodextrin derivatives: evidence for the role of cholesterol extraction. Eur. J. Pharm. Sci. 2010, 40:376-380.
156. Fenyvesi F., Kiss T., Fenyvesi E., Szente L., Veszelka S., Deli M.A., Varadi J., Feher P., Ujhelyi Z., Tosaki A., Vecsernyes M., Bacskay I. Randomly methylated beta-cyclodextrin derivatives enhance taxol permeability through human intestinal epithelial Caco-2 cell monolayer. J. Pharm. Sci. 2011, 100:4734-4744.
157. Z.M.Z., Bergeon Julie A., Abdelrahim Adel S., Pernevi Niklas U., Moss Anne R., Toth Istvan In vitro and in vivo evaluation of positively charged liposaccharide derivatives as oral absorption enhancers for the delivery of anionic drugs. J. Pharm. Sci. 2009, 99.
158. Abdelrahim A.S., Ziora Z.M., Bergeon J.A., Moss A.R., Toth I. Design and synthesis of a series of novel, cationic liposaccharide derivatives as potential penetration enhancers for oral drug delivery. Tetrahedron 2009, 65:9436-9442.
159. Lee H.E., Lee M.J., Park C.R., Kim A.Y., Chun K.H., Hwang H.J., Oh D.H., Jeon S.O., Kang J.S., Jung T.S., Choi G.J., Lee S. Preparation and characterization of salmon calcitonin-sodium triphosphate ionic complex for oral delivery. J. Control. Release 2010, 143:251-257.
160. Heerklotz H. Interactions of surfactants with lipid membranes. Q. Rev. Biophys. 2008, 41:205-264.
161. 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., Amidon G.L., Choe S.Y., Walker S., Kahne D. Design of compounds that increase the absorption of polar molecules. Proc. Natl. Acad. Sci. U. S. A. 1997, 94:12218-12223.
162. Zhu X.X., Nichifor M. Polymeric materials containing bile acids. Accounts Chem. Res. 2002, 35:539-546.
163. Imai T., Sakai M., Ohtake H., Azuma H., Otagiri M. In vitro and in vivo evaluation of the enhancing activity of glycyrrhizin on the intestinal absorption of drugs. Pharm. Res. 1999, 16:80-86.
164. Zhao L., Ding J., He P., Xiao C., Tang Z., Zhuang X., Chen X. An efficient pH sensitive oral insulin delivery system enhanced by deoxycholic acid. J. Control. Release 2011, 152(Suppl. 1):e184-e186.
165. Anderberg E.K., Lindmark T., Artursson P. Sodium caprate elicits dilatations in human intestinal tight junctions and enhances drug absorption by the paracellular route. Pharm. Res. 1993, 10:857-864.
166. Leonard T.W., Lynch J., McKenna M.J., Brayden D.J. Promoting absorption of drugs in humans using medium-chain fatty acid-based solid dosage forms: GIPET. Expert Opin. Drug Deliv. 2006, 3:685-692.
167. Bernkop-Schnurch A. Low molecular mass permeation enhancers in oral delivery of macromolecular drugs 2009, Springer.
168. Maher S., Feighery L., Brayden D.J., McClean S. Melittin as an epithelial permeability enhancer I: Investigation of its mechanism of action in Caco-2 monolayers. Pharm. Res. 2007, 24:1336-1345.
169. Maher S., McClean S. Melittin exhibits necrotic cytotoxicity in gastrointestinal cells which is attenuated by cholesterol. Biochem. Pharmacol. 2008, 75:1104-1114.
170. Maher S., Devocelle M., Ryan S., McClean S., Brayden D.J. Impact of amino acid replacements on in vitro permeation enhancement and cytotoxicity of the intestinal absorption promoter, melittin. Int. J. Pharm. 2010, 387:154-160.
171. Fasano A., Fiorentini C., Donelli G., Uzzau S., Kaper J.B., Margaretten K., Ding X., Guandalini S., Comstock L., Goldblum S.E. Zonula occludens toxin modulates tight junctions through protein kinase C-dependent actin reorganization, in vitro. J. Clin. Investig. 1995, 96:710-720.
172. Fasano A., Uzzau S. Modulation of intestinal tight junctions by Zonula occludens toxin permits enteral administration of insulin and other macromolecules in an animal model. J. Clin. Investig. 1997, 99:1158-1164.
173. Di Pierro M., Lu R.L., Uzzau S., Wang W.L., Margaretten K., Pazzani C., Maimone F., Fasano A. Zonula occludens toxin structure-function analysis - identification of the fragment biologically active on tight junctions and of the zonulin receptor binding domain. J. Biol. Chem. 2001, 276:19160-19165.
174. Salama N.N., Fasano A., Thakar M., Eddington N.D. The impact of DeltaG on the oral bioavailability of low bioavailable therapeutic agents. J. Pharmacol. Exp. Ther. 2005, 312:199-205.
175. Song K.H., Fasano A., Eddington N.D. Effect of the six-mer synthetic peptide (AT1002) fragment of zonula occludens toxin on the intestinal absorption of cyclosporin A. Int. J. Pharm. 2008, 351:8-14.
176. Goldblum S.E., Rai U., Tripathi A., Thakar M., De Leo L., Di Toro N., Not T., Ramachandran R., Puche A.C., Hollenberg M.D., Fasano A. The active Zot domain (aa 288-293) increases ZO-1 and myosin 1C serine/threonine phosphorylation, alters interaction between ZO-1 and its binding partners, and induces tight junction disassembly through proteinase activated receptor 2 activation. FASEB J. 2011, 25:144-158.
177. Yamamoto A., Tatsumi H., Maruyama M., Uchiyama T., Okada N., Fujita T. Modulation of intestinal permeability by nitric oxide donors: implications in intestinal delivery of poorly absorbable drugs. J. Pharmacol. Exp. Ther. 2001, 296:84-90.
178. Fetih G., Habib F., Katsumi H., Okada N., Fujita T., Attia M., Yamamoto A. Excellent absorption enhancing characteristics of NO donors for improving the intestinal absorption of poorly absorbable compound compared with conventional absorption enhancers. Drug Metab. Pharmacol. 2006, 21:222-229.
179. Duncan R. Polymer therapeutics as nanomedicines: new perspectives. Curr. Opin. Biotech. 2011, 22:492-501.
180. Aghemo A., Rumi M.G., Colombo M. Pegylated interferons alpha2a and alpha2b in the treatment of chronic hepatitis C. Nat. Rev. Gastroenterol. Hepatol. 2010, 7:485-494.
181. Sadekar S., Ghandehari H. Transepithelial transport and toxicity of PAMAM dendrimers: Implications for oral drug delivery. Adv. Drug Deliv. Rev. 2012, 64:571-588.
182. Dodou D., Breedveld P., Wieringa P.A. Mucoadhesives in the gastrointestinal tract: revisiting the literature for novel applications. Eur. J. Pharm. Biopharm. 2005, 60:1-16.
183. Thanou M., Verhoef J.C., Nihot M.T., Verheijden J.H.M., Junginger H.E. Enhancement of the intestinal absorption of low molecular weight heparin (LMWH) in rats and pigs using Carbopol (R) 934P. Pharm. Res. 2001, 18:1638-1641.
184. Bernkop-Schnurch A. Thiomers: a new generation of mucoadhesive polymers. Adv. Drug Deliv. Rev. 2005, 57:1569-1582.
185. Clausen A.E., Kast C.E., Bernkop-Schnurch A. The role of glutathione in the permeation enhancing effect of thiolated polymers. Pharm. Res. 2002, 19:602-608.
186. Perera G., Barthelmes J., Vetter A., Krieg C., Uhlschmied C., Bonn G.K., Bernkop-Schnurch A. Thiolated polycarbophil/glutathione: defining its potential as a permeation enhancer for oral drug administration in comparison to sodium caprate. Drug Deliv. 2011, 18:415-423.
187. Leitner V.M., Walker G.F., Bernkop-Schnurch A. Thiolated polymers: evidence for the formation of disulphide bonds with mucus glycoproteins. Eur. J. Pharm. Biopharm. 2003, 56:207-214.
188. Saremi S., Atyabi F., Akhlaghi S.P., Ostad S.N., Dinarvand R. Thiolated chitosan nanoparticles for enhancing oral absorption of docetaxel: preparation, in vitro and ex vivo evaluation. Int. J. Nanomedicine 2011, 6:119-128.
189. Foger F., Schmitz T., Bernkop-Schnurch A. In vivo evaluation of an oral delivery system for P-gp substrates based on thiolated chitosan. Biomaterials 2006, 27:4250-4255.
190. Kitchens K.M., Kolhatkar I.B., Swaan P.W., Ghandehari H. Endocytosis inhibitors prevent poly(amidoamine) dendrimer internalization and permeability across Ceco-2 cells. Mol. Pharm. 2008, 5:364-369.
191. Lin Y.L., Fujimori T., Kawaguchi N., Tsujimoto Y., Nishimi M., Dong Z.Q., Katsumi H., Sakane T., Yamamoto A. Polyamidoamine dendrimers as novel potential absorption enhancers for improving the small intestinal absorption of poorly absorbable drugs in rats. J. Control. Release 2011, 149:21-28.
192. Rossi S., Ferrari F., Bonferoni M.C., Caramella C. Characterization of chitosan hydrochloride-mucin rheological interaction: influence of polymer concentration and polymer:mucin weight ratio. Eur. J. Pharm. Sci. 2001, 12:479-485.
193. Alan Yu S.L. Claudins, in: Current Topics in Membranes 2010, Academia Press, New York.
194. Heiskala M., Peterson P.A., Yang Y. The roles of claudin superfamily proteins in paracellular transport. Traffic 2001, 2:92-98.
195. Yeh T.H., Hsu L.W., Tseng M.T., Lee P.L., Sonjae K., Ho Y.C., Sung H.W. Mechanism and consequence of chitosan-mediated reversible epithelial tight junction opening. Biomaterials 2011, 32:6164-6173.
196. Chae S.Y., Jang M.K., Nah J.W. Influence of molecular weight on oral absorption of water soluble chitosans. J. Control. Release 2005, 102:383-394.
197. Thanou M., Verhoef J.C., Marbach P., Junginger H.E. Intestinal absorption of octreotide: N-trimethyl chitosan chloride (TMC) ameliorates the permeability and absorption properties of the somatostatin analogue in vitro and in vivo. J. Pharm. Sci. 2000, 89:951-957.
198. van der Merwe S.M., Verhoef J.C., Verheijden J.H., Kotze A.F., Junginger H.E. Trimethylated chitosan as polymeric absorption enhancer for improved peroral delivery of peptide drugs. Eur. J. Pharm. Biopharm. 2004, 58:225-235.
199. Dorkoosh F.A., Stokkel M.P.M., Blok D., Borchard G., Rafiee-Tehrani A., Verhoef J.C., Junginger H.E. Feasibility study on the retention of superporous hydrogel composite polymer in the intestinal tract of man using scintigraphy. J. Control. Release 2004, 99:199-206.
200. Nguyen H.N., Wey S.P., Juang J.H., Sonaje K., Ho Y.C., Chuang E.Y., Hsu C.W., Yen T.C., Lin K.J., Sung H.W. The glucose-lowering potential of exendin-4 orally delivered via a pH-sensitive nanoparticle vehicle and effects on subsequent insulin secretion in vivo. Biomaterials 2011, 32:2673-2682.
201. Su F.Y., Lin K.J., Sonaje K., Wey S.P., Yen T.C., Ho Y.C., Panda N., Chuang E.Y., Maiti B., Sung H.W. Protease inhibition and absorption enhancement by functional nanoparticles for effective oral insulin delivery. Biomaterials 2012, 33:2801-2811.
202. Sung H.W., Sonaje K., Liao Z.X., Hsu L.W., Chuang E.Y. pH-responsive nanoparticles shelled with chitosan for oral delivery of insulin: from mechanism to therapeutic applications. Acc. Chem. Res. 2012, 45:619-629.
203. Sadeghi A.M.M., Dorkoosh F.A., Avadi M.R., Saadat P., Rafiee-Tehrani M., Junginger H.E. Preparation, characterization and antibacterial activities of chitosan, N-trimethyl chitosan (TMC) and N-diethylmethyl chitosan (DEMC) nanoparticles loaded with insulin using both the ionotropic gelation and polyelectrolyte complexation methods. Int. J. Pharm. 2008, 355:299-306.
204. Pein F., Pinkerton R., Berthaud P., Pritchard-Jones K., Dick G., Vassal G. Dose finding study of oral PSC 833 combined with weekly intravenous etoposide in children with relapsed or refractory solid tumours. Eur. J. Cancer 2007, 43:2074-2081.
205. Friedenberg W.R., Rue M., Blood E.A., Dalton W.S., Shustik C., Larson R.A., Sonneveld P., Greipp P.R. Phase III study of PSC-833 (Valspodar) in combination with vincristine, doxorubicin, and dexamethasone (Valspodar/VAD) versus VAD alone in patients with recurring or refractory multiple myeloma (E1A95) - a Trial of the Eastern Cooperative Oncology Group. Cancer 2006, 106:830-838.
206. Kimura Y., Aoki J., Kohno M., Ooka H., Tsuruo T., Nakanishi O. P-glycoprotein inhibition by the multidrug resistance-reversing agent MS-209 enhances bioavailability and antitumor efficacy of orally administered paclitaxel. Cancer Chemother. Pharmacol. 2002, 49:322-328.
207. Mistry P., Stewart A.J., Dangerfield W., Okiji S., Liddle C., Bootle D., Plumb J.A., Templeton D., Charlton P. In vitro and in vivo reversal of P-glycoprotein-mediated multidrug resistance by a novel potent modulator, XR9576. Cancer Res. 2001, 61:749-758.
208. Majumdar S., Mitra A.K. Chemical modification and formulation approaches to elevated drug transport across cell membranes. Expert Opin. Drug Deliv. 2006, 3:511-527.
209. Batrakova E.V., Li S., Alakhov V.Y., Miller D.W., Kabanov A.V. Optimal structure requirements for pluronic block copolymers in modifying P-glycoprotein drug efflux transporter activity in bovine brain microvessel endothelial cells. J. Pharmacol. Exp. Ther. 2003, 304:845-854.
210. Batrakova E.V., Li S., Brynskikh A.M., Sharma A.K., Li Y., Boska M., Gong N., Mosley R.L., Alakhov V.Y., Gendelman H.E., Kabanov A.V. Effects of pluronic and doxorubicin on drug uptake, cellular metabolism, apoptosis and tumor inhibition in animal models of MDR cancers. J. Control. Release 2010, 143:290-301.
211. Wu G.D., Chen J., Hoffmann C., Bittinger K., Chen Y.Y., Keilbaugh S.A., Bewtra M., Knights D., Walters W.A., Knight R., Sinha R., Gilroy E., Gupta K., Baldassano R., Nessel L., Li H.Z., Bushman F.D., Lewis J.D. Linking long-term dietary patterns with gut microbial enterotypes. Science 2011, 333:105-108.
212. Faith J.J., McNulty N.P., Rey F.E., Gordon J.I. Predicting a human gut microbiota's response to diet in gnotobiotic mice. Science 2011, 333:101-104.
213. Koropatkin N.M., Cameron E.A., Martens E.C. How glycan metabolism shapes the human gut microbiota. Nat. Rev. Microbiol. 2012, 10:323-335.
214. Yang L., Zhang H., Mikov M., Tucker I.G. Physicochemical and biological characterization of monoketocholic acid, a novel permeability enhancer. Mol. Pharm. 2009, 6:448-456.
215. Phillips M.C., Graham D.E., Hauser H. Lateral compressibility and penetration into phospholipid monolayers and bilayer membranes. Nature 1975, 254:154-156.
216. Hu N.J., Iwata S., Cameron A.D., Drew D. Crystal structure of a bacterial homologue of the bile acid sodium symporter ASBT. Nature 2011, 478:408-411.