Oral absorption of β-lactams by intestinal peptide transport proteins

Advanced Drug Delivery Reviews

Volumn 23, Issue 1-3, 1997, Pages 63-76

  Dantzig, Anne H ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

lactam; absorption; antibiotics; intestine; oral; peptide; transport

Indexed keywords

ANTIBIOTICS; CELL MEMBRANES; CLONING; IMMUNOLOGY; PROTEINS; PURIFICATION;

INTESTINAL PEPTIDE TRANSPORT PROTEINS; INTESTINE; LACTAMS; ORAL ABSORPTION; PEPTIDE; PHOTOAFFINITY LABELING; RECONSTITUTION;

DRUG THERAPY;

1 CARBACEPHEM DERIVATIVE; AMOXICILLIN; BETA LACTAM ANTIBIOTIC; CARRIER PROTEIN; CEFADROXIL; CEFALEXIN; CEFIXIME; CEFRADINE; CEFTIBUTEN; CEPHALOSPORIN DERIVATIVE; CYCLACILLIN; LORACARBEF; PENICILLIN DERIVATIVE; PENICILLIN G; PEPTIDE; PROTON;

APICAL MEMBRANE; BASOLATERAL MEMBRANE; BRUSH BORDER; CELL MEMBRANE; CELL STRAIN CACO 2; DRUG UPTAKE; HUMAN; INTESTINE ABSORPTION; INTESTINE CELL; MOLECULAR CLONING; MOLECULAR WEIGHT; NONHUMAN; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PURIFICATION; RABBIT; REGULATORY MECHANISM; REVIEW;

EID: 0031022687     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(96)00426-7     Document Type: Review

References (76)

1. Quay, J.F. (1972) Transport interaction of glycine and cephalexin in rat jejunum. Physiologist 15, 241.
2. Quay, J. (1975) Transport properties of microbiologically active 7 arylglycylamidocephem derivatives in isolated rat intestine. Physiologist 18, 359.
3. Harvengt, C., De Schepper, P., Lamy, F. and Hansen, J. (1973) Cephradine absorption and excretion in fasting and non-fasting volunteers. J. Clin. Pharmacol. New Drugs 13, 36-40.
4. D'Arcy, P.F. (1995) Nutrient-drug interactions. Adverse Drug React. Toxicol. Rev. 14, 223-254.
5. Ganapathy, V., Brandsch, M. and Leibach, F.H. (1994) Intestinal transport of amino acids and peptides. In: Johnson L.R., Ed., Physiology of the Gastrointestinal Tract. New York: Raven Press, pp. 1773-1794.
6. Amidon, G.L. and Lee, H.J. (1994) Absorption of peptide and peptidomimetic drugs. Annu. Rev. Pharmacol. Toxicol. 34, 321-341.
7. Boyd, C.A.R. (1995) Intestinal oligopeptide transport. Proc. Nutr. Soc. 54, 519-523.
8. Hediger, M.A., Kanai, Y., You, G. and Nussberger, S. (1995) Mammalian ion-coupled solute transporters. J. Physiol. 482, 7S-17S.
9. Tsuji, A. (1995) Intestinal absorption of β-lactam antibiotics. In: Taylor M.D., Amidon G.L., Eds., Peptide-Based Drug Design. Controlling Transport and Metabolism. Washington, DC: American Chemical Society, pp. 101-134.
10. Sadee, W., Drubbisch, V. and Amidon, G.L. (1995) Biology of membrane transport proteins. Pharm. Res. 12, 1823-1837.
11. Kramer, W., Girbig, F., Gutjahr, J. and Kowalewski, S. (1995) The intestinal oligopeptide transporter. Molecular characterization and substrate specificity. In: Taylor M.D., Amidon G.L., Eds., Peptide-Based Drug Design. Controlling Transport and Metabolism. Washington, DC: American Chemical Society, pp. 150-179.
12. Meredith, D. and Boyd, C.A.R. (1995) Oligopeptide transport by epithelial cells. J. Membr. Biol. 145, 1-12.
13. Lucas, M.L., Schneider, W., Haberich, F.J. and Blair, J.A. (1975) Direct measurement by pH-microelectrode of the pH microclimate in rat proximal jejunum. Proc. R. Soc. Lond. B 192, 39-48.
14. Ganapathy, V. and Leibach, F.H. (1991) Proton-coupled solute transport in the animal cell plasma membrane. Curr. Opin. Cell Biol. 3, 695-701.
15. Kramer, W., Girbig, F., Gutjahr, U., Kleeman, H.W., Leipe, I., Urbach, H. and Wagner, A. (1990) Interaction of renin inhibitors with the intestinal uptake system for oligopeptides and beta-lactam antibiotics. Biochim. Biophys. Acta 1027, 25-30.
16. Dantzig, A.H. and Bergin, L. (1990) Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2. Biochim. Biophys. Acta 1027, 211-217.
17. Dantzig, A.H., Duckworth, D.C. and Tabas, L.B. (1992) Mechanism for the absorption of loracarbef in human intestinal Caco-2 cells. 32nd Intersience Conference on Antimicrobial Agents and Chemotherapy, p. 354.
18. Dyer, J., Beechely, R.B., Gorvel, J.-P., Smith, R.T., Wootton, R. and Shirazi-Beechey, S.P. (1990) Glycyl-L-proline transport in rabbit enterocyte basolateral-membrane vesicles. Biochem. J. 269, 565-571.
19. + -coupled carriers at both apical and basal membranes. J. Biol. Chem. 268, 7640-7642.
20. Saito, H. and Inui, K. (1993) Dipeptide transporter in apical and basolateral membranes of the human intestinal-cell line Caco-2. Am. J. Physiol. 265, G289-G294.
21. Hu, M., Chen, J., Zhu, Y., Dantzig, A.H., Stratford, R.E., Jr. and Kuhfeld, M.T. (1994) Mechanism and kinetics of transcellular transport of a new β-lactam antibiotic loracarbef across an intestinal epithelial membrane model system (Caco-2). Pharm. Res. 11, 1405-1413.
22. Inui, K.-I., Yamamoto, M. and Saito, H. (1992) Trans-epithelial transport of oral cephalosporins by monolayers of intestinal epithelial cell line Caco-2: specific transport systems in apical and basolateral membranes. J. Pharmacol. Exp. Ther. 261, 195-201.
23. + -coupled dipeptide (glycylsarcosine) transport across apical and basal borders of human intestinal Caco-2 cell monolayers display distinctive characteristics. Biochim. Biophys. Acta 1151, 237-245.
24. Gochoco, C.H., Ryan, R.M., Miller, J., Smith, P.L. and Hidalgo, I.J. (1994) Uptake and transepithelial transport of the orally absorbed cephalosporin cephalexin, in the human intestinal cell line, Caco-2. Int. J. Pharm. 104, 187-202.
25. Matsumoto, S.-I., Saito, H. and Inui, K.I. (1994) Transcellular transport of oral cephalosporins in human intestinal eptihelial cells, Caco-2: interaction with dipeptide transport systems in apical and basolateral membranes. J. Pharm. Exp. Ther. 270, 498-504.
26. Kramer, W., Durckheimer, W., Girbig, F., Gutjahr, U., Leipe, I. and Oekonomopulos, R. (1990) Influence of amino acid side-chain modification on the uptake system for β-lactam antibiotics and dipeptides from rabbit small intestine. Biochim. Biophys. Acta 1028, 174-182.
27. Kramer, W., Gutjahr, U. and Kowalewski, S. (1993) Interaction of the orally active dianionic cephalosporin cefixime with the uptake system for oligopeptides and alpha-amino-β-lactam antibiotics in rabbit small intestine. Biochem. Pharmacol. 46, 542-546.
28. Kramer, W., Girbig, F., Petzoldt, E. and Leipe, I. (1988) Inactivation of the intestinal uptake system for β-lactam antibiotics by diethylpyrocarbonate. Bichim. Biophys. Acta 943, 288-296.
29. + coupled transport of cephradine via dipeptide carriers in rabbit intestinal brush-border membranes: role of histidine residues. J. Pharmacol. Exp. Ther. 251, 745-749.
30. Kramer, W., Girbig, F., Gutjahr, U. and Leipe, I. (1990) Application of high-performance liquid chromatography to the purification of the putative intestinal peptide transporter. J. Chromatogr. 521, 199-210.
31. Kramer, W., Girbig, F., Gutjahr, U., Kowalewski, S., Adam, F. and Schiebler, W. (1992) Intestinal absorption of β-lactam antibiotics and oligopeptides. Functional and stereospecific reconstitution of the oligopeptide transport system from rabbit small intestine. Eur. J. Biochem. 204, 923-930.
32. Dantzig, A.H., Hoskins, J.A., Tabas, L.B., Bright, S., Shepard, R.L., Jenkins, I.L., Duckworth, D.C., Sportsman, J.R., Mackensen, D., Rosteck, P.R., Jr. and Skatrud, P.L. (1994) Association of intestinal peptide transport with a protein related to the cadherin superfamily. Science 264, 430-433.
33. Takeichi, M. (1990) Cadherins: a molecular family important in selective cell-cell adhesion. Annu. Rev. Biochem. 59, 237-252.
34. Erickson, R.H., Gum, J.R., Jr., Lindstrom, M.M., McKean, D. and Kim, Y.S. (1995) Regional expression and dietary regulation of rat small intestinal peptide and amino acid transporter mRNAs. Biochem. Biophys. Res. Commun. 216, 249-257.
35. 2+ -dependent cell adhesion molecule expressed in liver and intestine. J. Cell Biol. 125, 1353-1369.
36. Thomson, R.B., Igarashi, P., Biemesderfer, D., Kim, R., Abu-Alfa, A., Soleimani, M. and Aronson, P.S. (1995) Isolation and cDNA cloning of Ksp-cadherin, a novel kidney-specific member of the cadherin multigene family. J. Biol. Chem. 270, 17594-17601.
37. Tamai, K., Tomizawa, N., Kadowaki, A., Terasaki, T., Narkayama, K., Higashida, H. and Tsuji, A. (1994) Functional expression of intestinal dipeptide/β-lactam antibiotic transporter in Xenopus laevis oocytes. Biochem. Pharmacol. 48, 881-888.
38. Miyamoto, Y., Thompson, Y.G., Howard, E.F., Ganapathy, V. and Leibach, F.H. (1991) Functional expression of the intestinal peptide-proton co-transporter in Xenopus laevis oocytes. J. Biol. Chem. 266, 4742-4745.
39. Saito, H., Ishii, T. and Inui, K.-I. (1993) Expression of human intestinal dipeptide transporter in Xenopus laevis oocytes. Biochem. Pharmacol. 45, 776-779.
40. Fei, Y.-J., Kanai, Y., Nussberger, S., Ganapathy, V., Leibach, F.H., Romero, M.F., Singh, S.K., Boron, W.F. and Hediger, M.A. (1994) Expression cloning of a mammalian proton-coupled oligopeptide transporter. Nature 368, 563-566.
41. + /Di-tripeptide transporter (PepT1) expression in the rabbit intestine. Eur. J. Physiol. 430, 394-400.
42. Boll, M., Markovich, D., Weber, W.-M., Korte, H., Daniel, H. and Murer, H. (1994) Expression cloning of a cDNA from rabbit small intestine related to proton-coupled transport of peptides, β-lactam antibiotics and ACE-inhibitors. Pflugers Arch Eur. J Physiol. 429, 146-149.
43. Wenzel, U., Thwaites, D.T. and Daniel, H. (1995) Stereoselective uptake of β-lactam antibiotics by the intestinal peptide transporter. Br. J. Pharmacol. 3021-3027.
44. +/peptide cotransporter-cloning, functional expression, and chromosomal localization. J. Biol. Chem. 270, 6456-6463.
45. Liang, R., Fei, Y.J., Ramamoorthy, S., Prasad, P.D., Hediger, M.A., Ganapathy, V. and Leibach, F.H. (1994) Molecular cloning and functional expression of a peptide/proton cotransporter from human small intestine [abstract]. Gastroenterology, A617.
46. + /peptide cotransporter mediating absorption of β-lactam antibiotics in the intestine and kidney. J. Pharm. Exp. Ther. 275, 1631-1637.
47. Miyamoto, K.-I., Shiraga, T., Morita, K., Yamamoto, H., Haga, H., Taketani, Y., Tamai, I., Sai, Y., Tsuji, A. and Takeda, E. (1996) Sequence, tissue distribution and developmental changes in rat intestinal oligopeptide transporter. Biochim. Biophys. Acta 1305, 34-38.
48. + -coupled oligopeptide transporter hPEPT1. J. Biol. Chem. 271, 5430-5437.
49. Paulsen, I.T. and Skurray, R.A. (1994) The POT family of transport proteins. Trends Biochem. Sci. 19, 404.
50. Steiner, H.-Y., Naider, F. and Becker, J.M. (1995) The PTR family: a new group of peptide transporters. Mol. Microbiol. 16, 825-834.
51. Silbernagl, S. (1988) The renal handling of amino acids and oligopeptides. Physiol. Rev. 68, 911-1007.
52. Skopicki, H.A., Fisher, K., Zikos, D., Bloch, R., Flouret, G. and Peterson, D.R. (1991) Multiple carriers for dipeptide transport: carrier-mediated transport of glycyl-L-proline in renal BBMV. Am. J. Physiol. 261, F670-678.
53. Daniel, H., Morse, E.L. and Adibi, S.A. (1991) The high and low affinity transport systems for dipeptides in kidney brush border membrane respond differently to alterations in pH gradient and membrane potential. J. Biol. Chem. 266, 19 917-19 924.
54. Ganapathy, M.E., Brandsch, M., Prasad, P.D., Ganapathy, V. and Leibach, F.H. (1995) Differential recognition of βlactam antibiotics by intestinal and renal peptide transporters, PepT1 and PepT2. J. Biol. Chem. 270, 25 672-25 677.
55. + /peptide cotransporter family, from human kidney. Biochim. Biophys. Acta 1235, 461-466.
56. Ramamoorthy, S., Liu, W., Ma, Y.-Y., Yang-Feng, T.L., Ganapathy, V. and Leibach, F.H. (1995) Proton/peptide cotransporter (PERT 2) from human kidney: Functional characterization and chromosomal localization. Biochim. Biophys. Acta 1240, 1-4.
57. Boll, M., Herget, M., Wagener, M., Weber, W.M., Markovich, D., Biber, J., Clauss, W., Murer, H. and Daniel, H. (1996) Expression cloning and functional characterization of the kidney cortex high-affinity proton-coupled peptide transporter. Proc. Natl. Acad. Sci. USA 93, 284-289.
58. + -symporter in kidney brush-border membranes. Biochim. Biophys. Acta 1233, 145-152.
59. Ferraris, R.P., Diamond, J. and Kwan, W.W. (1988) Dietary regulation of intestinal transport of the dipeptide carnosine. Am. J. Physiol. 255, G143-G150.
60. + -dependent bile acid transport activity in rabbit small intestine correlates with the coexpression of an integral 93-kDa and a peripheral 14-kDa bile acid-binding membrane protein along the duodenum-ileum axis. J. Biol. Chem. 268, 18 035-18 046.
61. + /dipeptide cotransporter and distribution of the transport activity in isolated rabbit intestinal epithelial cells. J. Pharm. Exp. Ther. 272, 63-69.
62. Hidalgo, I.J., Ryan, F.M., Marks, G.J. and Smith, P.L. (1993) pH-Dependent transepithelial transport of cephalexin in rabbit intestinal mucosa. Int. J. Pharm. 98, 83-92.
63. Buddington, R.K. and Diamond, J.M. (1989) Ontogenetic development of intestinal nutrient transporters. Annu. Rev. Physiol. 51, 601-619.
64. Stein, E.D., Chang, S.D. and Diamond, J.M. (1987) Comparison of different dietary amino acids as inducers of intestinal amino acid transport. Am. J. Physiol. 252, G626-G635.
65. + co-transport system in the Caco-2 human colon carcinoma cell line. Biochem. J. 299, 253-260.
66. +/dipeptide cotransport system in human intestinal cell line Caco-2, Regulation by cell growth. Pharm. Res. 12, 1483-1487.
67. Hu, M., Zheng, L., Chen. J., Liu, L., Li, Y., Dantzig, A.H. and Stratford, R.E., Jr. (1995) Peptide transporter function and prolidase activities in Caco-2 cells: a lack of coordinated expression. J. Drug Targ. 3, 291-300.
68. +/peptide cotransporter in the human intestial cell line Caco-2 by cyclic AMP. Biochem. Biophys. Res. Commun. 218, 461-465.
69. + transport in human jejunal brush-border membrane vesicles. Am. J. Physiol. 255, G206-G211.
70. Ganapathy, V. and Leibach, F.H. (1985) Is intestinal peptide transport energized by a proton gradient? Am. J. Physiol. 249, G153-G160.
71. + exchanger. Clin. Pharmacol. Ther. 57, 257-264.
72. Whestphal, J.F., Brogard, J.M., Jehl, F. and Carbon, C. (1995) Role of enterocyte ionic exchanges in amoxicillin intestinal absorption: evaluation through interaction with amiloride. Path. Biol. 43, 590-595.
73. Westphal, J.-F., Trouvin, J.-H., Deslandes, A. and Carbon, C. (1990) Nifedipine enhances amoxicillin absorption kinetics and bioavailability in humans. J. Pharm. Exp. Ther. 255, 312-317.
74. Duverne, C., Boutern, A., Deslandes, A., Westphal, J.-F., Trouvin, J.-H., Farinotti, R. and Carbon, C. (1992) Modification of cefixime bioavailability by nifedipine in humans: involvement of the dipeptide carrier system. Antimicrob. Agents Chemother. 36, 2462-2467.
75. Sugawara, M., Toda, T., Iseki, K., Miyazaki, K., Shiroto, H., Kondo, Y. and Uchino, J.I. (1992) Transport characteristics of cephalosporin antibiotics across intestinal brush-border membrane in man, rat and rabbit. J. Pharm Pharmacol 44, 968.
76. Yuasa, H., Fleisher, D. and Amidon, G.L. (1994) Noncompetitive inhibition of cephradine uptake by enalapril in rabbit intestinal brush-border membrane vesicles: an enalapril specific inhibitory binding site on the peptide carrier. J. Pharmacol. Exp. Ther. 269, 1107-1111.