Quantitative structure activity relationship for inhibition of human organic cation/carnitine transporter

Molecular Pharmaceutics

Volumn 7, Issue 6, 2010, Pages 2120-2131

  Diao, Lei ^a   Ekins, Sean ^a,b,c   Polli, James E ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b Collaborations in Chemistry ^*  (United States)

^c RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; AMLODIPINE; ATENOLOL; ATROPINE; BROMOCRIPTINE; CARNITINE; CARVEDILOL; CEFALORIDINE; CERIVASTATIN; CETIRIZINE; CLOZAPINE; DESLORATADINE; DULOXETINE; GUANOSINE; HYDROCHLOROTHIAZIDE; INHIBITOR PROTEIN; LOMEFLOXACIN; ORGANIC CATION TRANSPORTER; ORGANIC CATION TRANSPORTER 5; ORGANIC CATION TRANSPORTER 5 INHIBITOR; PRAMIPEXOLE; PROCHLORPERAZINE; PROPANTHELINE BROMIDE; RALOXIFENE; SULFANILAMIDE; THIORIDAZINE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL; VINBLASTINE;

ANIMAL TISSUE; ARTICLE; BAYESIAN LEARNING; CONTROLLED STUDY; DRUG CLEARANCE; DRUG ELIMINATION; DRUG UPTAKE; HOMEOSTASIS; HYDROGEN BOND; HYDROPHOBICITY; INHIBITION KINETICS; IONIZATION; KIDNEY CLEARANCE; MATHEMATICAL MODEL; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RHABDOMYOLYSIS; THREE DIMENSIONAL IMAGING;

CELLS, CULTURED; CEPHALORIDINE; CETIRIZINE; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; ORGANIC CATION TRANSPORT PROTEINS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78649929750     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100226q     Document Type: Article

References (36)

1. Koepsell, H.; Lips, K.; Volk, C. Polyspecific Organic Cation Transporters: Structure, Function, Physiological Roles, and Biopharmaceutical Implications Pharm. Res. 2007, 24, 1227-1251
2. Nezu, J. I.; Tamai, I.; Oku, A.; Ohashi, R.; Yabuuchi, H.; Hashimoto, N.; Nikaido, H.; Sai, Y.; Koizumi, A.; Shoji, Y.; Takada, G.; Matsuishi, T.; Yoshino, M.; Kato, H.; Ohura, T.; Tsujimoto, G.; Hayakawa, J. i.; Shimane, M.; Tsuji, A. Primary systemic carnitine deficiency is caused by mutations in a gene encoding sodium ion-dependent carnitine transporter Nat. Genet. 1999, 21, 91-94
3. Tein, I. Carnitine transport: Pathophysiology and metabolism of known molecular defects J. Inherited Metab. Dis. 2003, 26, 147-169
4. Nakamura, T.; Nakanishi, T.; Haruta, T.; Shirasaka, Y.; Keogh, J. P.; Tamai, I. Transport of Ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by Organic Cation/Carnitine Transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption Mol. Pharmaceutics 2009, 7, 187-195
5. Kano, T.; Kato, Y.; Ito, K.; Ogihara, T.; Kubo, Y.; Tsuji, A. Carnitine/Organic Cation Transporter OCTN2 (Slc22a5) is responsible for renal secretion of cephaloridine in mice Drug Metab. Dispos. 2009, 37, 1009-1016
6. Grube, M.; Meyer zu Schwabedissen, H. E. U.; Prager, D.; Haney, J.; Moritz, K. U.; Meissner, K.; Rosskopf, D.; Eckel, L.; Bohm, M.; Jedlitschky, G.; Kroemer, H. K. Uptake of cardiovascular drugs into the human heart: expression, regulation, and function of the carnitine transporter OCTN2 (SLC22A5) Circulation 2006, 113, 1114-1122
7. Ganapathy, M. E.; Huang, W.; Rajan, D. P.; Carter, A. L.; Sugawara, M.; Iseki, K.; Leibach, F. H.; Ganapathy, V. Beta-lactam antibiotics as substrates for OCTN2, an Organic Cation/Carnitine Transporter J. Biol. Chem. 2000, 275, 1699-1707
8. Tune, B. M. Effects of L-carnitine on the renal tubular transport of cephaloridine Biochem. Pharmacol. 1995, 50, 562-564
9. Diao, L.; Ekins, S.; Polli, J. Novel inhibitors of human Organic Cation/Carnitine Transporter (hOCTN2) via computational modeling and in vitro testing Pharm. Res. 2009, 26, 1890-1900
10. Chang, C.; Bahadduri, P. M.; Polli, J. E.; Swaan, P. W.; Ekins, S. Rapid identification of P-glycoprotein substrates and inhibitors Drug Metab. Dispos. 2006, 34, 1976-1984
11. Hassan, M.; Brown, R.; Varma-O'Brien, S.; Rogers, D. Cheminformatics analysis and learning in a data pipelining environment Mol. Diversity 2006, 10, 283-299
12. Zientek, M.; Stoner, C.; Ayscue, R.; Klug-McLeod, J.; Jiang, Y.; West, M.; Collins, C.; Ekins, S. Integrated in silico-in vitro strategy for addressing cytochrome P450 3A4 time-dependent inhibition Chem. Res. Toxicol. 2010, 23, 664-676
13. Chang, C.; Pang, K. S.; Swaan, P. W.; Ekins, S. Comparative pharmacophore modeling of organic anion transporting polypeptides: a meta-analysis of rat Oatp1a1 and human OATP1B1 J. Pharmacol. Exp. Ther. 2005, 314, 533-41
14. Arimoto, R.; Prasad, M. A.; Gifford, E. M. Development of CYP3A4 inhibition models: Comparisons of machine-learning techniques and molecular descriptors J. Biomol. Screening 2005, 10, 197-205
15. Ekins, S.; Andreyev, S.; Ryabov, A.; Kirillov, E.; Rakhmatulin, E. A.; Sorokina, S.; Bugrim, A.; Nikolskaya, T. A combined approach to drug metabolism and toxicity assessment Drug Metab. Dispos. 2006, 34, 495-503
16. Product Information: XYZAL(R) oral tablets, levocetirizine dihydrochloride oral tablets. UCB Pharma, Inc, May 1, 2007.
17. Polli, J. W.; Baughman, T. M.; Humphreys, J. E.; Jordan, K. H.; Mote, A. L.; Salisbury, J. A.; Tippin, T. K.; Serabjit-Singh, C. J. P-glycoprotein influences the brain concentrations of cetirizine (Zyrtec (R)), a second-generation non-sedating antihistamine J. Pharm. Sci. 2003, 92, 2082-2089
18. Tilstone, W. J.; Semple, P. F.; Lawson, D. H.; Boyle, J. A. Effects of furosemide on glomerular filtration rate and clearance of practolol, digoxin, cephaloridine, and gentamicin Clin. Pharmacol. Ther. 1977, 22, 389-394
19. Norrby, R.; Stenqvist, K.; Elgefors, B. action between cephaloridine and furosemide in man Scand. J. Infect. Dis. 1976, 8, 209-212
20. Simpson, I. J. Nephrotoxicity and acute renal failure associated with cephalothin and cephaloridine N.Z. Med. J. 1971, 74, 312-315
21. Gabriel, R.; Foord, R. D.; Joekes, A. M. Reversible encephalopathy and acute renal failure after cephaloridine Br. Med. J. 1970, 4, 283-284
22. Dodds, M. G.; Foord, R. D. Enhancement by potent diuretics of renal tubular necrosis induced by cephaloridine Br. J. Pharmacol. 1970, 40, 227-236
23. Hasannejad, H.; Takeda, M.; Taki, K.; Shin, H. J.; Babu, E.; Jutabha, P.; Khamdang, S.; Aleboyeh, M.; Onozato, M. L.; Tojo, A.; Enomoto, A.; Anzai, N.; Narikawa, S.; Huang, X. L.; Niwa, T.; Endou, H. Interactions of human organic anion transporters with diuretics J. Pharmacol. Exp. Ther. 2004, 308, 1021-1029
24. Eraly, S. A.; Vallon, V.; Vaughn, D. A.; Gangoiti, J. A.; Richter, K.; Nagle, M.; Monte, J. C.; Rieg, T.; Truong, D. M.; Long, J. M.; Barshop, B. A.; Kaler, G.; Nigam, S. K. Decreased renal organic anion secretion and plasma accumulation of endogenous organic anions in OAT1 knock-out mice J. Biol. Chem. 2006, 281, 5072-5083
25. Ueo, H.; Motohashi, H.; Katsura, T.; Inui, K. Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1 Biochem. Pharmacol. 2005, 70, 1104-1113
26. Jung, K. Y.; Takeda, M.; Shimoda, M.; Narikawa, S.; Tojo, A.; Kim, D. K.; Chairoungdua, A.; Choi, B. K.; Kusuhara, H.; Sugiyama, Y.; Sekine, T.; Endou, H. Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1 Life Sci. 2002, 70, 1861-1874
27. Takeda, M.; Babu, E.; Narikawa, S.; Endou, H. Interaction of human organic anion transporters with various cephalosporin antibiotics Eur. J. Pharmacol. 2002, 438, 137-142 (Pubitemid 34241501)
28. Glube, N.; Closs, E.; Langguth, P. OCTN2-mediated carnitine uptake in a newly discovered human proximal tubule cell line (Caki-1) Mol. Pharmaceutics 2006, 4, 160-168
29. Wagner, C. A.; Lukewille, U.; Kaltenbach, S.; Moschen, I.; Broer, A.; Risler, T.; Broer, S.; Lang, F. Functional and pharmacological characterization of human Na+-carnitine cotransporter hOCTN2 Am. J. Physiol. 2000, 279, F584-F591
30. Georges, B.; Galland, S.; Rigault, C.; Borgne, F. L.; Demarquoy, J. Beneficial effects of L-carnitine in myoblastic C2C12 cells: Interaction with zidovudine Biochem. Pharmacol. 2003, 65, 1483-1488
31. Pochini, L.; Scalise, M.; Indiveri, C. Inactivation by omeprazole of the carnitine transporter (OCTN2) reconstituted in liposomes Chem. Biol. Interact. 2009, 179, 394-401
32. Hirano, T.; Yasuda, S.; Osaka, Y.; Asari, M.; Kobayashi, M.; Itagaki, S.; Iseki, K. The inhibitory effects of fluoroquinolones on L-carnitine transport in placental cell line BeWo Int. J. Pharm. 2008, 351, 113-118
33. Sung, J. H.; Yu, K. H.; Park, J. S.; Tsuruo, T.; Kim, D. D.; Shim, C. K.; Chung, S. J. Saturable distribution of tacrine into the striatal extracellular fluid of the rat: evidence of involvement of multiple organic cation transporters in the transporter Drug Metab. Dispos. 2005, 33, 440-448
34. Haschke, M.; Vitins, T.; Lude, S.; Todesco, L.; Novakova, K.; Herrmann, R.; Krahenbuhl, S. Urinary excretion of carnitine as a marker of proximal tubular damage associated with platin-based antineoplastic drugs Nephrol., Dial., Transplant. 2010, 25, 426-433
35. Todesco, L.; Bur, D.; Brooks, H.; Török, M.; Landmann, L.; Stieger, B.; Krähenbühl, S. Pharmacological manipulation of L-carnitine transport into L6 cells with stable overexpression of human OCTN2 Cell. Mol. Life Sci. 2008, 65, 1596-1608
36. Kato, Y.; Sugiura, M.; Sugiura, T.; Wakayama, T.; Kubo, Y.; Kobayashi, D.; Sai, Y.; Tamai, I.; Iseki, S.; Tsuji, A. Organic cation/carnitine transporter OCTN2 (Slc22a5) is responsible for carnitine transport across apical membranes of small intestinal epithelial cells in mouse Mol. Pharmacol. 2006, 70, 829-837