Photoaffinity labeling of the anionic sites in Caco-2 cells mediating saturable transport of hydrophilic cations ranitidine and famotidine

Journal of Medicinal Chemistry

Volumn 47, Issue 11, 2004, Pages 2935-2938

  Bourdet, David L ^a   Lee, Kiho ^a,b   Thakker, Dhiren R ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FAMOTIDINE; HISTAMINE H2 RECEPTOR ANTAGONIST; RANITIDINE;

ARTICLE; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG TRANSPORT; ELECTRIC RESISTANCE; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROPHILICITY; INTESTINE; PHOTOAFFINITY LABELING; STRUCTURE ANALYSIS; ULTRAVIOLET RADIATION;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; CARRIER PROTEINS; ELECTRIC CONDUCTIVITY; FAMOTIDINE; HISTAMINE H2 ANTAGONISTS; HUMANS; PHOTOAFFINITY LABELS; RANITIDINE; ULTRAVIOLET RAYS;

EID: 2442654057     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030433n     Document Type: Article

References (14)

1. Gan, L. S.; Hsyu, P. H.; Pritchard, J. F.; Thakker, D. Mechanism of intestinal absorption of ranitidine and ondansetron: transport across Caco-2 cell monolayers. Pharm. Res. 1993,10, 1722-1725.
2. Lee, K.; Thakker, D. R. Saturable transport of H2-antagonists ranitidine and famotidine across Caco-2 cell monolayers. J. Pharm. Sci. 1999, 88, 680-687.
3. Collett, A.; Higgs, N. B.; Sims, E.; Rowland, M.; Warhurst, G. Modulation of the permeability of H2 receptor antagonists cimetidine and ranitidine by P-glycoprotein in rat intestine and the human colonic cell line Caco-2. J. Pharmacol. Exp. Ther. 1999, 288, 171-178.
4. Brandquist, C. M.; Ng, C.; Thakker, D. R.; Brouwer, K. L. Novel Interactions in the Oral Absorption of Hydrophilic Cations: A Clinical Study with Ranitidine and Famotidine. Clin. Pharmacol. Ther. 2003, 73, 19.
5. Bayley, H.; Knowles, J. R. Photoaffinity labeling. Methods Enzymol. 1977, 46, 69-114.
6. Gilman, D. J.; Wardleworth, J. M.; Yellin, T. O. Guanidine derivatives of imidazoles and thiazoles; ICI Americas Inc.: United States Patent 4,165,378, 1979.
7. Yanagisawa, I.; Hirata, Y.; Ishii, Y. Histamine H2 receptor antagonists. 1. Synthesis of N-cyano and N-carbamoyl amidine derivatives and their biological activities. J. Med. Chem. 1984, 27, 849-857.
8. Brown, T.; Blakemore, R.; Durant, G.; Ganellin, C.; Parsons, M. et al. Isocytosine H2-receptor histamine antagonists. IV. The synthesis and biological activity of donetidine (SK&F 93574) and related compounds. Eur. J. Med. Chem. 1993, 28, 601-608.
9. Gan, L. S.; Yanni, S.; Thakker, D. R. Modulation of the tight junctions of the Caco-2 cell monolayers by H2-antagonists. Pharm. Res. 1998, 15, 53-57.
10. Morita, K.; Furuse, M.; Fujimoto, K.; Tsukita, S. Claudin multigene family encoding four-transmembrane domain protein components of tight junction strands. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 511-516.
11. Colegio, O. R.; Van Itallie, C. M.; McCrea, H. J.; Rahner, C.; Anderson, J. M. Claudius create charge-selective channels in the paracellular pathway between epithelial cells. Am. J. Physiol. Cell Physiol. 2002, 283, C142-147.
12. Kimura, M.; Nabekura, T.; Katsura, T.; Takano, M.; Hori, R. Identification of organic cation transporter in rat renal brush-border membrane by photoaffinity labeling. Biol. Pharm. Bull. 1995, 18, 388-395.
13. Daoud, R.; Desneves, J.; Deady, L. W.; Tilley, L.; Scheper, R. J. et al. The multidrug resistance protein is photoaffinity labeled by a quinoline-based drug at multiple sites. Biochemistry 2000, 39, 6094-6102.
14. Daoud, R.; Kast, C.; Gros, P.; Georges, E. Rhodamine 123 binds to multiple sites in the multidrug resistance protein (MRP1). Biochemistry 2000, 39, 15344-15352.