Structure-affinity relationship in the interactions of human organic anion transporter 1 with caffeine, theophylline, theobromine and their metabolites

Biochimica et Biophysica Acta - Biomembranes

Volumn 1714, Issue 2, 2005, Pages 85-92

  Sugawara, Mitsuru ^a   Mochizuki, Takahiro ^a   Takekuma, Yoh ^a   Miyazaki, Katsumi ^a  

^a HOKKAIDO UNIVERSITY HOSPITAL   (Japan)

Author keywords

Caffeine; hOAT1; Interaction; Structure affinity relationship; Theophylline

Indexed keywords

4 AMINOHIPPURIC ACID; CAFFEINE; ORGANIC ANION TRANSPORTER; POLYCYCLIC AROMATIC HYDROCARBON; THEOBROMINE; THEOPHYLLINE; XANTHINE;

ANIMAL CELL; ARTICLE; CHO CELL; CONTROLLED STUDY; DRUG INHIBITION; DRUG POTENCY; DRUG RECEPTOR BINDING; LIPID SOLUBILITY; LIPOPHILICITY; NONHUMAN; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR OCCUPANCY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BIOLOGICAL TRANSPORT; CAFFEINE; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; MOLECULAR STRUCTURE; ORGANIC ANION TRANSPORT PROTEIN 1; P-AMINOHIPPURIC ACID; THEOBROMINE; THEOPHYLLINE; URIC ACID; XANTHINES;

EID: 23644457833     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2005.06.006     Document Type: Article

References (30)

1. S. Khamdang, M. Takeda, R. Noshiro, S. Narikawa, A. Enomoto, N. Anzai, P. Piyachaturawat, and H. Endou Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs J. Pharmacol. Exp. Ther. 303 2002 534 539
2. M. Takeda, R. Nishiro, M.L. Onozato, A. Tojo, H. Hasannefad, X.-L. Huang, S. Narikawa, and H. Endou Evidence for a role of human organic anion transporters in the muscular side effects of HMG-CoA reductase inhibitors Eur. J. Pharmacol. 483 2004 133 138
3. M. Takeda, S. Khamdang, S. Narikawa, H. Kimura, M. Hosoyamada, S.H. Cha, T. Sekine, and H. Endou Characterization of methotrexate transport and its drug interactions with human organic anion transporters J. Pharmacol. Exp. Ther. 302 2002 666 671
4. H. Hassannejad, M. Takeda, K. Taki, H.J. Shin, E. Babu, P. Jutabha, S. Khamdang, M. Aleboyeh, M.L. Onozato, A. Tojo, A. Enomoto, N. Anzai, S. Narikawa, X.L. Huang, T. Niwa, and H. Endou Interactions of human organic anion transporters with diuretics J. Pharmacol. Exp. Ther. 308 2004 1021 1029
5. E. Babu, M. Takeda, S. Narikawa, Y. Kobayashi, T. Yamamoto, S.H. Cha, T. Sekine, D. Sakthisekaran, and H. Endou Human organic anion transporters mediate the transport of tetracycline Jpn. J. Pharmacol. 88 2002 69 76
6. T. Cihlar, D.C. Lin, J.B. Pritchard, M.D. Fuller, D.B. Mendel, and D.H. Sweet The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1 Mol. Pharmacol. 56 1999 570 580
7. E.S. Ho, D.C. Lin, D.B. Mendel, and T. Cihlar Cytotoxicity of antiviral nucleotides adefover and cidofovir is induced by the expression of human renal organic anion transporter 1 J. Am. Soc. Nephrol. 11 2000 383 393
8. M. Takeda, S. Khamdang, S. Narikawa, H. Kimura, Y. Kobayashi, T. Yamamoto, S.H. Cha, T. Sekine, and H. Endou Human organic anion transporters and human organic cation transporters mediate renal anti viral transport J. Pharmacol. Exp. Ther. 300 2002 918 924
9. B.C. Burckhardt, S. Brai, S. Wallis, W. Krick, N.A. Wolff, and G. Burckhardt Transport of cimetidine by flounder and human renal organic anion transporter 1 Am. J. Physiol.: Renal Physiol. 284 2003 F503 F509
10. H. Kimura, M. Takeda, S. Narikawa, A. Enomoto, K. Ichida, and H. Endou Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins J. Pharmacol. Exp. Ther. 301 2002 293 298
11. K. Ichida, M. Hosayamada, H. Kimara, M. Takeda, Y. Utsunomiya, T. Hosoya, and H. Endou Urate transport via human PAH transporter hOAT1 and its gene structure Kidney Int. 63 2003 143 155
12. M. Alebouyeh, M. Takeda, M.L. Onozato, A. Tojo, R. Noshiro, H. Hasannejad, J. Inatomi, S. Narikawa, X.-L. Huang, S. Khamdang, N. Anzai, and H. Endou Expression of human organic anion transporters in the choroid plexus and their interactions with neurotransmitter metabolites J. Pharmacol. Sci. 93 2003 430 436
13. T. Deguchi, H. Kusuhara, A. Takadate, H. Endou, M. Otagiri, and Y. Sugiyama Characterization of uremic toxin transport by organic anion transporters in the kidney Kidney Int. 65 2004 162 174
14. H. Motohashi, Y. Sakurai, H. Saito, S. Masuda, Y. Urakami, M. Goto, A. Fukatsu, O. Ogawa, and K. Inui Gene expression levels and immunolocalization of organic ion transporters in human kidney J. Am. Soc. Nephrol. 13 2002 866 874
15. S.H. Cha, T. Sekine, H. Kusuhara, E. Yu, J.Y. Kim, D.K. Kim, Y. Sugiyama, Y. Kanai, and H. Endou Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta J. Boil. Chem. 275 2000 4507 4512
16. S. Ekaratanawong, N. Anzai, P. Jutabha, H. Miyazaki, R. Noshiro, M. Takeda, Y. Kanai, S. Sophasan, and H. Endou Human organic anion transporter 4 is a renal apical organic anion/dicarboxylate exchanger in the proximal tubules J. Pharmacol. Sci. 94 2004 297 304
17. J.E. Race, S.M. Grassl, W.J. Williams, and E.J. Hotlzman Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3) Biochem. Biophys. Res. Commun. 255 1999 508 514
18. M. Hosoyamada, T. Sekine, Y. Kanai, and H. Endou Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney Am. J. Physiol.: Renal. Physiol. 276 1999 F122 F128
19. M. Hasegawa, H. Kusuhara, D. Sugiyama, K. Ito, S. Ueda, H. Endou, and Y. Sugiyama Functional involvement of rat organic anion transporter 3 (rOat3: Slc22a8) in the renal uptake of organic anions J. Pharmacol. Exp. Ther. 300 2002 746 753
20. M. Sugawara, T. Nakanishi, Y.-J. Fei, W. Huang, M.E. Ganapathy, F.H. Leibach, and V. Ganapathy Cloning of an amino acid transporter with functional characteristics and tissue expression pattern identical to that of system A J. Biol. Chem. 275 2000 16473 16477
21. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the Folin phenol reagent J. Biol. Chem. 193 1951 263 275
22. S.H. Cha, T. Sekine, J. Fukushima, Y. Kanai, Y. Kobayashi, T. Goya, and H. Endou Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney Mol. Pharmacol. 59 2001 1277 1286
23. + exchanger of rabbit renal brush border membranes Pfluegers Arch. 429 1995 313 324
24. 0 in the small intestine Drug Metab. Pharmacokineti. 18 2003 186 193
25. Q.M. Chen, and F.S. LaBella Inhibition of nitric oxide synthase by straight chain and cyclic alcohols Eur. J. Pharmacol. 321 1997 355 360
26. I. Roufos, S. Hays, and R.D. Schwarz A structure-Activity relationship study of novel phenylacetamides which are sodium channel blockers J. Med. Chem. 39 1996 1514 1520
27. B. Feng, Y. Shu, and K.M. Giacomini Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition Biochemistry 41 2002 8941 8947
28. W. Kalow, and B.-K. Tang The use of caffeine for enzyme assays: a critical appraisal Clin. Pharmacol. Ther. 53 1993 503 514
29. J. Kizu, S. Watanabe, N. Yasuno, Y. Arakawa, S. Uzu, S. Kanda, F. Komoda, T. Iwata, H. Hayakawa, T. Hayakawa, and K. Imai Development and clinical application of high performance liquid chromatography for the simultaneous determination of plasma levels of theophylline and its metabolites without interference from caffeine Biomed. Chromatogr. 13 1999 15 23
30. F. Vrtic, W.E. Haefeli, J. Drewe, S. Krahenbuhl, and M. Wenk Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug Br. J. Clin. Pharmacol. 55 2003 191 198