Chemical approaches to improve the oral bioavailability of peptidergic molecules

Journal of Pharmacy and Pharmacology

Volumn 48, Issue 2, 1996, Pages 119-135

  Samanen, James ^a   Wilson, Glynn ^a   Smith, Philip L ^a   Lee, Chao Pin ^a   Bondinell, William ^a   Ku, Thomas ^a   Rhodes, Gerald ^a   Nichols, Andrew ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMPICILLIN; ANTITHROMBOCYTIC AGENT; CEFALEXIN; CEFRADINE; DRUG CARRIER; FIBRINOGEN RECEPTOR ANTAGONIST; GLYCOPROTEIN IIB; GLYCOPROTEIN IIB ANTAGONIST; HISTIDYL DEXTRO TRYPTOPHYLALANYLTRYPTOPHYL DEXTRO PHENYLALANYLLYSINAMIDE; MANNITOL; OLIGOPEPTIDE; PENICILLIN G; SB 207448; SB 208651; SKF 106760; SKF 107260; UNCLASSIFIED DRUG;

ANIMAL TISSUE; CHEMICAL MODIFICATION; CONFERENCE PAPER; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CONFORMATION; DRUG DESIGN; DRUG DEVELOPMENT; DRUG DIFFUSION; DRUG PENETRATION; DRUG TRANSPORT; INTESTINE MUCOSA PERMEABILITY; NONHUMAN; ORAL DRUG ADMINISTRATION; PEPTIDERGIC NERVOUS SYSTEM; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION INHIBITION; X RAY CRYSTALLOGRAPHY;

EID: 0029964082     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1996.tb07111.x     Document Type: Conference Paper

References (68)

1. Ali, F. E., Bennett, D. B., Calvo, R. R., Eilliott, J. D., Hwang, S.-M., Ku, T. W., Lago, M. A., Nichols, A. J., Romoff, T. T., Shah, D. H., Vasko, J. A., Wong, A. S., Yellin, T. O., Yuan, C.-K., Samanen, J. M. (1994) Conformationally constrained peptides and semipeptides derived from RGD as potent inhibitors of the platelet fibrinogen receptor and platelet aggregation. J. Med. Chem. 37: 769-780
2. Ali, F. E., Samanen, J. M., Calvo, R., Romoff, T., Yellin, T., Vasko, J., Powers, D., Stadel, J., Bennett, D., Berry, D., Nichols, A. (1992) Potent fibrinogen receptor antagonists bearing conformational constraints. In: Smith, J. A., Rivier, J. E. (eds) Proteins: Chemistry, Structure and Biology, Proc. 13th American Peptide Symposium. Escom Science Publishers, Leiden 761-762
3. Andrieux, A., Hudry-Clergeon, G., Ryckewaert, J.-J., Chapel, A., Ginsberg, M. H., Plow, E. F., Marguerie, G. (1989) Amino acid sequences in fibrinogen mediating its interaction with its platelet receptor, GPIIb/IIIa. J. Biol. Chem. 264: 9258-9265
4. Audus, K. L., Band, R. L., Hidalgo, I. J., Borchardt, R. T. (1990) The use of cultured epithelial and endothelial cells for drug transport and metabolism studies. Pharm. Res. 7: 435-451
5. Bach, A. C. I., Eyermann, C. J., Gross, J. D., Bower, M. J., Harlow, R. L., Weber, P. C., DeGrado, W. F. (1994) Structural studies of a family of high affinity ligands for GPIIb/IIIa. J. Am. Chem. Soc. 116: 3207-3219
6. Bean, J. W., Kopple, K. D., Peishoff, C. E. (1992) Conformational analysis of cyclic hexapeptides containing the D-Pro-L-Pro sequence to fix β-turn positions. J. Am. Chem. Soc 114: 5328-5334
7. Bondinell, W. E , Keenan, R. M., Miller, W. H , Ali, F. E., Allen, A. C., DeBrosse, C. W., Eggleston, D S., Erhard, K. F., Haltiwanger, R. C., Huffman, W. F., Hwang, S.-M., Jakas, D. R., Koster, P. F., Ku, T. W., Lee, C. P., Nichols, A. J., Ross, S. T., Samanen, J. M., Valocik, R. E., Vasko-Moser, J. A., Venslavsky, J. W., Wong, A. S., Yuan, C.-K. (1994) Design of a potent and orally active nonpeptide platelet fibrinogen receptor (GPIIB/IIIA) antagonist. Bioorg. Med. Chem. 2: 897-908
8. Bowers, C. Y., Reynolds, G. A., Chang, D., Hong, A., Chang, K., Momany, F. A. (1980) A study of the regulation of growth hormone release from the pituitaries of rats in vitro. Endocrinology 108: 1071-1080
9. Burton, P. S., Conradi, R. A., Hilgers, A. R., Ho, N. F. H., Maggiora, L. L. (1992) The relationship between peptide structure and transport across epithelial cell monolayers. J. Contr. Rel. 19: 87-98
10. Burton, P. S., Conradi, R. A., Hilgers, A. R., Ho, N. F. H. (1993) Evidence for a polarized efflux system for peptides in the apical membrane of Caco-2 cells. Biochem. Biophys. Res. Commun. 190: 760-766
11. Callahan, J. F., Bean, J. W., Burgess, J. L., Eggleston, D. S., Hwang, S. M., Kopple, K., Koster, P. F., Nichols, A., Peishoff, C., Samanen, J., Vasko, J. A., Wong, A., Huffman, W. (1992) Design and Synthesis of a C7 mimetic for the predicted γ-turn conformation found in several constrained RGD antagonists. J. Med. Chem. 35: 3970-3972
12. Callahan, J. F., Newlander, K. A., Burgess, J. L., Eggleston, D., Nichols, A., Wong, A., Huffman, W. F. (1993) The use of γ-turn mimetics to define peptide secondary structure. Tetrahedron 49: 3479-3488
13. Conradi, R. A., Hilgers, A. R., Ho, N. F. H., Burton, P. S. (1991) The influence of peptide structure on transport across Caco-2 cells. Pharm. Res. 8: 1453-1459
14. Conradi, R. A., Hilgers, A. R., Ho, N. F. H., Burton, P S (1992) The influence of peptide structure on transport across Caco-2 cells. II. Peptide bond modification which results in improved permeability. Pharm. Res. 9: 435-439
15. Constantinides, P. P., Scalart, J., Lancaster, C., Marcello, J., Marks, G , Ellens, H., Smith, P. L. (1994) Formulation and intestinal absorption enhancement evaluation of water-in-oil microemulsions incorporating medium-chain glycerides. Pharm. Res. 11: 1385-1390
16. Dantzig, A. H., Bergin, L. (1988) Carrier-mediated uptake of cephalexin in human intestinal cells. Biochem. Biophys. Res. Commun. 155: 1082-1087
17. Dantzig, A. H., Bergin, L. (1990) Uptake of the cephalosporin cephalexin, by a dipeptide transport carrier in the human intestinal cell, Caco-2. Biochim. Biophys. Acta 1027: 211-217
18. Ganapathy, V., Leibach, F. H. (1985) Is intestinal peptide transport energized by a proton gradient? Am. J. Physiol. 249: G153-G160
19. Gartner, T. K., Bennett, J. S. (1985) The tetrapeptide analogue of the cell attachment site of fibronectin inhibits platelet aggregation and fibrinogen binding to activated platelets. J. Biol. Chem. 260: 11891-11894
20. Ginsberg, M. H., Pierschbacher, M. D., Ruoslahti, E., Marguerie, G. A., Plow, E. F (1985) Inhibition of fibronectin binding to platelets by proteolytic fragments and synthetic peptides which support fibroblast adhesion. J. Biol. Chem. 260: 3931-3936
21. Gochoco, C. H., Ryan, F. M., Miller, J., Smith, P. L., Hidalgo, I. J. (1994) Uptake and transepithelial transport of the orally-absorbed cephalosporin, cephalexin, in human intestinal cell line. Caco-2. Int. J. Pharm. 104: 187-202
22. Gunby, P. (1992) Cardiovascular diseases remain nation's leading cause of death. J. Am. Med. Assoc. 267: 335-336
23. Hann, M. M., Carter, B., Kitchin, J., Ward, P., Pipe, A., Broom-head, J., Hornby, E., Forster, M., Perry, C. (1992) An investigation of the bioactive conformation of Arg-Gly-Asp containing cyclic peptides and snake venom peptides which inhibit human platelet aggregation. In: Roberts, S. M. (ed.) Molecular Recognition: Chemical and Biochemical Problems II. The Royal Society of Chemistry, Cambridge, pp 145-159
24. Hashimoto, N., Fujioka, T., Hayashi, K., Odasuchi, K., Toyoda, T., Nakamura, M., Hirano, K. (1994) Renin inhibitor, relationship between molecular structure and oral absorption. Pharm. Res. 11: 1443-1447
25. Hidalgo, I. J., Raub, T. J., Borchardt, R. T. (1989) Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96: 736-749
26. Hidalgo, I. H., Ryan, F. M., Marks, G. J., Smith, P. L. (1993) pH-Dependent transcellular transport of cephalexin in rabbit intestinal mucosa. Int. J. Pharm. 98: 83-92
27. Hidalgo, I. J., Bhatnagar, P., Lee, C., Miller, J., Cucollino, G., Smith, P. L. (1995) Structural requirements for interaction with the oligopeptide transporter in Caco-2 cells. Pharm. Res. 12: 317-319
28. Holzemann, G. (1991) Peptide conformation mimetics Part 1. Kontakte (Darmstadt) 1: 3-12
29. Horwell, D. C., Birchmore, B., Boden, P. R., Higginbottom, M., Ping Ho, Y., Hughes, J., Hunter, J. C , Richardson, R. S. (1990) α-Methyl tryptophanylphenylalanines and their aryl ethylamine "dipeptoid" analogues of the tetrapeptide cholecystokinin (30-33). Eur. J. Med. Chem. 25: 53-60
30. Hunter, J., Hirst, B. H., Simmons, N. L. (1991) Transepithelial vinblastine secretion mediated by P-glycoprotein is inhibited by forskolin derivatives. Biochem. Biophys. Res. Commun. 181: 671-676
31. Jung, G., Beck-Sickinger, A. G. (1992) Multiple peptide synthesis methods and their applications. Angew. Chem. Int. Ed. Engl. 31: 367-486
32. Karls, M. S., Rush, B. D., Wilkinson, K. F., Vidmar, T. J., Burton, P. S., Ruwart, M. J. (1991) Desolvation energy: a major determinant of absorption, but not clearance, of peptides in rats. Pharm. Res. 8: 1477-1481
33. Kleeman, H. W., Heitsch, H., Henning, R., Kramer, W., Kocher, U., Lerch, U., Linz, W., Nickel, W. U., Ruppert, D., Urbach, H., Utz, R., Wagner, A., Weck, R., Wiegand, F. (1992) Renin inhibitory pentols showing improved enteral bioavailability. J. Med. Chem. 35: 559-567
34. Kloczewiak, M., Timmons, S., Bednarek, M. A., Sakon, M., Hawiger, J. (1989) Platelet receptor recognition domain on the γ chain of human fibrinogen and its synthetic peptide analogues. Biochemistry 28: 2915-2919
35. Kloczewiak, M., Timmons, S., Lukas, T. J., Hawiger. J. (1984) Recognition site for the platelet receptor is present on the 15-residue fragment of the γ chain of human fibrinogen and is not involved in the fibrin polymerization reaction. Biochemistry 23: 1767-1774
36. Kopple, K. D., Baures, P. W., Bean, J. W., D'Ambrosio, C. A., Hughes, J. L., Peishoff, C. E., Eggleston, D. S. (1992) Conformations of Arg-Gly-Asp containing heterodetic cyclic peptides: solution and crystal studies. J. Am. Chem. Soc. 114: 9615-9623
37. Ku, T. W., Ali, F. E., Barton, L. S., Bean, J. W., Bondinell, W. E., Burgess, J. L., Callahan, J. F., Calvo, R. R., Chen, L., Eggleston, D. S., Gleason, J. G., Huffman, W. F., Hwang, S. M., Jakas, D. R., Karash, C. B., Keenan, R. M., Kopple, K. D., Miller, W. M., Newlander, K. A., Nichols, A., Parker, M. F., Peishoff, C. E., Samanen, J. M., Uzinskas, I., Venslavsky, J. W. (1993) Direct design of a potent non-peptide fibrinogen receptor antagonist based on the structure and conformation of a highly constrained cyclic RGD peptide. J. Am. Chem. Soc. 115: 8861-8862
38. Laker, M. F., Bull, H. J., Menzies, I. S. (1982) Evaluation of mannitol for use as a probe marker of gastrointestinal permeability in man. Eur J. Clin. Invest. 12: 485-491
39. Marks, G. I., Ryan, F. M., Hidalgo, I. J., Smith, P. L. (1991) Mannitol, as a marker for intestinal integrity in in vitro absorption studies. Gastroenterology 100: A697
40. Matuszewska, B., Liversidge, G. G., Ryan, F., Dent, J., Smith, P. L. (1988) In vitro study of intestinal absorption and metabolism of 8-L-argenme vasopressin and its analogues Int. J. Pharm. 46: 111-120
41. Meunier, L. D., Kissinger, J. T., Marcello, J., Nichols, A. J., Smith, P. L. (1993) A chronic access model for direct delivery of drugs into the intestine of conscious dogs. J. Lab. Animal Sci. 43: 466-470
42. Nichols, A. J., Ruffolo, R. R., Huffman, W. F., Poste, G., Samanen, J. (1992) Development of GpIIb/IIIa Antagonist as antithrombotic drugs. Trends Pharmacol. Sci. 13: 413-417
43. Nichols, A. J., Vasko, F A., Koster, P. F., Valocik, R. E., Samanen, J. M. (1994a) GPIIb/IIIa Antagonists as novel antithrombotic drugs: potential therapeutic agents. In: Metcalf, B.W , Dalton, B. J., Poste, G. (eds) Cellular Adhesion: Molecular Definition to Therapeutic Potential. Plenum Press, New York, pp 213-237
44. Nichols, A. J., Vasko, J. A., Koster, P. F., Valocik, R. E., Rhodes, G. R., Miller-Stein, C., Boppana, V., Samanen, J. M. (1994b) The in vivo pharmacological profile of the novel glycoprotein IIb/IIIa antagonist, SK&F 106760. J. Pharm. Exp. Ther. 270: 614-621
45. Peishoff, C. E., Ali, F. E., Bean, J. W., Calvo, R., D'Ambrosio, C. A., Eggleston, D. S., Kline, T. P., Koster, P. F., Nichols, A., Powers, D., Romoff, T., Samanen, J. M., Stadel, J., Vasko, J. A., Wong, A., Kopple, K. D. (1992) Investigation of conformational specificity at GPIIb/IIIa. evaluation of conformationally constrained RGD peptide analogs. J. Med. Chem. 35: 3962-3969
46. Plow, E. F., Pierschbacher, M. D., Ruoslahti, E., Marguerie, G., Ginsberg, M. H. (1987) Arginyl-glycyl-aspartic acid sequences and fibrinogen binding to platelets. Blood: 110-115
47. Rosenberg, S. H., Spina, K. P., Condon, S. L., Polakowski, J., Yao, Z., Kovar, P., Stein, H. H., Cohen, J., Barlow, J. L., Klinghofer, V , Egan, D. A., Tricarico, K. A., Perrun, T. J., Baker, W. R., Kleinert, H. D. (1993b) Studies directed toward the design of orally active renin inhibitors. J. Med. Chem. 36: 460-467
48. Rosenberg, S. H., Spina, K. P., Woods, K. W., Polakowski, J., Martin, D. L., Yao, Z., Stein, H. H., Cohen, J., Barlow, J. L., Egan, D. A., Tricarico, K. A., Baker, W. R., Kleinert, H. D. (1993a) Studies directed toward the design of orally active renin inhibitors. J. Med. Chem. 36: 449-459
49. Saffran, M., Kumar, G. S., Savariar, C., Burnham, J. C., Williams, F , Neckers, D. C. (1986) A new approach to the oral administration of insulin and other peptide drugs. Science 233: 1081-1084
50. Samanen, J. (1985) Biomedical polypeptides - A wellspring of pharmaceuticals. In: Gebelein, C. G, Carraher, C. E. J. (eds) Bioactive Polymeric Systems, An Overview . Plenum Press, New York, pp 279-382
51. Samanen, J., Ali, F. E., Romoff, T., Calvo, R., Sorenson, E., Vasko, J., Berry, D., Bennett, D., Strohsacker, M., Powers, D., J., S., Nichols, A. (1991) Development of an RGD-peptide fibrinogen receptor antagonist with potent antiaggregatory activity in vitro. J. Med. Chem. 34: 3114-3125
52. Samanen, J., Weinstock, J., Hempel, J., Keenan, R. M., Hill, D. T., Ohlstein, E. H., Weidley, E. F., Aiyar, N., Edwards, R. (1992) A molecular model of angiotensin II (Ang II) for rational design of small Ang II antagonists with increased potency. In: Riviere, J. E., Smith, J. A. (eds) Peptides: Structure and Biology; Proceedings of the 12th American Peptide Symposium. Leiden: ESCOM Science Publishers, pp 386-388
53. Samanea, J. M., Peishoff, C. E., Keenan, R. M., Weinstock, J. M. (1993) Refinement of a molecular model of angiotensin II (AII) employed in the discovery of potent nonpeptide antagonists. Bioorg. Med. Chem. Lett. 3: 909-914
54. Samanen, J., Ali, F., Bean, J , Callahan, J., Huffman, W., Kopple, K., Peishoff, C , Nichols, A. (1994) Peptide mimetics as adhesion molecule antagonists. In: Metcalf, B. W., Dalton, B. J., Poste, G. (eds) Cellular Adhesion: Molecular Definition to Therapeutic Potential Plenum Press, New York pp 259-290
55. Smith, J. W. (1994) The structural basis of integrin-ligand (RGD) interaction. In: Cheresh, D. A., Mecham, R. P. (ed.) Integrins, Molecular and Biological Response to the Extracellular Matrix. Academic Press, New York, pp 1-32
56. Smith, P. L. (1995) Intestinal absorption and secretion: in vivo studies. In: Gaginella, T S. (ed.) Methods in Gastrointestinal Pharmacology. CRC, New York, pp 85-99
57. Smith, P. L., Mirabelli, C., Fondacaro, J., Ryan, F., Dent, J. (1988) Intestinal 5-fiuorouracil absorption: use of Ussing chambers to assess transport and metabolism. Pharm. Res. 5: 598-603
58. Smith, P. L., Wall, D. A., Gochoco, C. H., Wilson, G. Routes of Delivery: Case Studies; (5) (1992) Oral absorption of peptides and proteins. Advanced Drug Delivery Reviews 8: 253-290
59. Smith, P. L., Eddy, E. P., Lee, C., Wilson, G. (1993) Exploitation of the intestinal oligopeptide transporter to enhance drug absorption. Drug Del. I: 103-111
60. Smith, P. L., Yeulet, S. E., Citerone, D. R., Drake, F., Cook, M., Wall, D. A., Marcello, J. (1994) SK&F 110679: Comparison of absorption following oral or respiratory administration. J. Contr. Rel. 28: 67-77
61. Swaan, P. W., Marks, G J., Ryan, F. M., Smith, P. L. (1994) Determination of transport rates for arginine and acetaminophen in rabbit intestinal tissues in-vitro. Pharm. Res. 11: 283-287
62. +-coupled dipeptide (glycylsarcosine) transport across apical and basal membranes of human intestinal Caco-2 cell monolayers display distinct characteristics. Biochim. Biophys. Acta 1151: 237-245
63. Toniolo, C. (1989) Structure of conformationally constrained peptides: from model compounds to bioactive peptides. Biopolymers 28: 247-257
64. Toniolo, C. (1990) Conformationally restricted peptides through short-range cyclizations. Int. J. Pept. Protein Res. 35: 287-300
65. Ussing, H. H., Zerahn, K. (1951) Active transport of sodium as the source of electric current in the short-circuited isolated frog skin. Acta Physiol. Scand. 23: 110-127
66. 2) in rats, dogs and monkeys. Life Sci. 47: 29-36
67. Wilson, G., Hasson, I. F., Dix, C. J., Williamson, I., Shah, R., Mackay, M., Arturssou, P. (1990) Transport and permeability properties of human Caco-2 cells: an in vitro model of the intestinal epithelial cell barrier. J. Contr. Rel. 11: 25-40
68. Yeh, P.-Y., Smith, P. L., Ellens, H. (1994) Effect of medium-chain glycerides on physiological properties of rabbit intestinal epithelium in vitro. Pharm. Res. 11: 1148-1154