Identification and quantitative assessment of uremic solutes as inhibitors of renal organic anion transporters, OAT1 and OAT3

Molecular Pharmaceutics

Volumn 13, Issue 9, 2016, Pages 3130-3140

  Hsueh, Chia Hsiang ^a,b   Yoshida, Kenta ^b   Zhao, Ping ^b   Meyer, Timothy W ^c   Zhang, Lei ^b   Huang, Shiew Mei ^b   Giacomini, Kathleen M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^c STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

chronic kidney disease; organic anion transporter; regulatory science; uremic solute

Indexed keywords

3 CARBOXY 4 METHYL 5 PROPYL 2 FURANPROPANOIC ACID; 4 CRESYL SULFATE; 6 CARBOXYFLUORESCEIN; CREATININE; HIPPURIC ACID; INDICAN; INDOLEACETIC ACID; INDOXYL BETA DEXTRO GLUCURONIDE; KYNURENIC ACID; N 2,N 2 DIMETHYLGUANOSINE; NONANAL; ORGANIC ANION TRANSPORTER 1; ORGANIC ANION TRANSPORTER 3; PHENOL; PHENYLACETIC ACID; PRESCRIPTION DRUG; PROTEIN INHIBITOR; UNCLASSIFIED DRUG; UREMIC TOXIN; URIC ACID; 6-CARBOXYFLUORESCEIN; FLUORESCEIN DERIVATIVE; ORGANIC ANION TRANSPORTER;

ARTICLE; CHRONIC KIDNEY DISEASE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG IDENTIFICATION; GLOMERULUS FILTRATION RATE; IC50; IN VITRO STUDY; KIDNEY FUNCTION; KIDNEY TUBULE EXCRETION; PRIORITY JOURNAL; PROTEIN TRANSPORT; QUANTITATIVE ANALYSIS; ANIMAL; BIOLOGICAL MODEL; CHRONIC KIDNEY FAILURE; HUMAN; METABOLISM;

ANIMALS; FLUORESCEINS; HUMANS; MODELS, BIOLOGICAL; ORGANIC ANION TRANSPORT PROTEIN 1; ORGANIC ANION TRANSPORTERS, SODIUM-INDEPENDENT; RENAL INSUFFICIENCY, CHRONIC;

EID: 84986253794     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.6b00332     Document Type: Article

References (80)

1. United States Renal Data System. 2015 United States Renal Data System Annual Data Report: Epidemiology of kidney disease in the United States; National Institutes of Health, National Institute of Diabetes and Digestive and Kidney Diseases: Bethesda, MD, 2015.
2. Manley, H. J.; Cannella, C. A.; Bailie, G. R.; St Peter, W. L. Medication-related problems in ambulatory hemodialysis patients: a pooled analysis Am. J. Kidney Dis. 2005, 46 (4) 669-80 10.1053/j.ajkd.2005.07.001
3. Morrissey, K. M.; Stocker, S. L.; Wittwer, M. B.; Xu, L.; Giacomini, K. M. Renal transporters in drug development Annu. Rev. Pharmacol. Toxicol. 2013, 53, 503-29 10.1146/annurev-pharmtox-011112-140317
4. Masereeuw, R.; Mutsaers, H. A.; Toyohara, T.; Abe, T.; Jhawar, S.; Sweet, D. H.; Lowenstein, J. The kidney and uremic toxin removal: glomerulus or tubule? Semin. Nephrol. 2014, 34 (2) 191-208 10.1016/j.semnephrol.2014.02.010
5. Lepist, E. I.; Ray, A. S. Renal drug-drug interactions: what we have learned and where we are going Expert Opin. Drug Metab. Toxicol. 2012, 8 (4) 433-48 10.1517/17425255.2012.667401
6. Tahara, H.; Kusuhara, H.; Endou, H.; Koepsell, H.; Imaoka, T.; Fuse, E.; Sugiyama, Y. A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters J. Pharmacol. Exp. Ther. 2005, 315 (1) 337-45 10.1124/jpet.105.088104
7. US Food and Drug Administration. Drug Interaction Studies-Study Design, Data Analysis, Implications for Dosing, and Labeling Recommendations, 2012. http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM292362.pdf.
8. European Medicines Agency Guideline on the Investigation of Drug Interactions, 2012. http://www.ema.europa.eu/docs/en-GB/document-library/Scientific-guideline/2012/07/WC500129606.pdf.
9. Tweedie, D.; Polli, J. W.; Berglund, E. G.; Huang, S. M.; Zhang, L.; Poirier, A.; Chu, X.; Feng, B. International Transporter, C. Transporter studies in drug development: experience to date and follow-up on decision trees from the International Transporter Consortium Clin. Pharmacol. Ther. 2013, 94 (1) 113-25 10.1038/clpt.2013.77
10. Deguchi, T.; Kusuhara, H.; Takadate, A.; Endou, H.; Otagiri, M.; Sugiyama, Y. Characterization of uremic toxin transport by organic anion transporters in the kidney Kidney Int. 2004, 65 (1) 162-74 10.1111/j.1523-1755.2004.00354.x
11. Duranton, F.; Cohen, G.; De Smet, R.; Rodriguez, M.; Jankowski, J.; Vanholder, R.; Argiles, A.; European Uremic Toxin Work, G. Normal and pathologic concentrations of uremic toxins J. Am. Soc. Nephrol. 2012, 23 (7) 1258-70 10.1681/ASN.2011121175
12. Vanholder, R.; Glorieux, G.; De Smet, R.; Lameire, N. European Uremic Toxin Work, G. New insights in uremic toxins Kidney Int. 2003, 84, S6-10 10.1046/j.1523-1755.63.s84.43.x
13. Kido, Y.; Matsson, P.; Giacomini, K. M. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2 J. Med. Chem. 2011, 54 (13) 4548-58 10.1021/jm2001629
14. Shitara, Y.; Horie, T.; Sugiyama, Y. Transporters as a determinant of drug clearance and tissue distribution Eur. J. Pharm. Sci. 2006, 27 (5) 425-46 10.1016/j.ejps.2005.12.003
15. Begg, E. J.; Robson, R. A.; Bailey, R. R.; Lynn, K. L.; Frank, G. J.; Olson, S. C. The pharmacokinetics and pharmacodynamics of quinapril and quinaprilat in renal impairment Br. J. Clin. Pharmacol. 1990, 30 (2) 213-20 10.1111/j.1365-2125.1990.tb03767.x
16. He, G.; Massarella, J.; Ward, P. Clinical pharmacokinetics of the prodrug oseltamivir and its active metabolite Ro 64-0802 Clin. Pharmacokinet. 1999, 37 (6) 471-84 10.2165/00003088-199937060-00003
17. Horber, F. F.; Frey, F. J.; Descoeudres, C.; Murray, A. T.; Reubi, F. C. Differential effect of impaired renal function on the kinetics of clavulanic acid and amoxicillin Antimicrob. Agents Chemother. 1986, 29 (4) 614-9 10.1128/AAC.29.4.614
18. Kearney, B. P.; Yale, K.; Shah, J.; Zhong, L.; Flaherty, J. F. Pharmacokinetics and dosing recommendations of tenofovir disoproxil fumarate in hepatic or renal impairment Clin. Pharmacokinet. 2006, 45 (11) 1115-24 10.2165/00003088-200645110-00005
19. Kelloway, J. S.; Awni, W. M.; Lin, C. C.; Lim, J.; Affrime, M. B.; Keane, W. F.; Matzke, G. R.; Halstenson, C. E. Pharmacokinetics of Ceftibuten-cis and its trans metabolite in healthy volunteers and in patients with chronic renal insufficiency Antimicrob. Agents Chemother. 1991, 35 (11) 2267-74 10.1128/AAC.35.11.2267
20. Mita, A. C.; Sweeney, C. J.; Baker, S. D.; Goetz, A.; Hammond, L. A.; Patnaik, A.; Tolcher, A. W.; Villalona-Calero, M.; Sandler, A.; Chaudhuri, T.; Molpus, K.; Latz, J. E.; Simms, L.; Chaudhary, A. K.; Johnson, R. D.; Rowinsky, E. K.; Takimoto, C. H. Phase I and pharmacokinetic study of pemetrexed administered every 3 weeks to advanced cancer patients with normal and impaired renal function J. Clin. Oncol. 2006, 24 (4) 552-62 10.1200/JCO.2004.00.9720
21. Niemeyer, C.; Hasenfuss, G.; Wais, U.; Knauf, H.; Schafer-Korting, M.; Mutschler, E. Pharmacokinetics of hydrochlorothiazide in relation to renal function Eur. J. Clin. Pharmacol. 1983, 24 (5) 661-5 10.1007/BF00542218
22. Ohkawa, M.; Okasho, A.; Motoi, I.; Tokunaga, S.; Shoda, R.; Kawaguchi, S.; Sawaki, M.; Shimamura, M.; Hirano, S.; Kuroda, K.; Awazu, S. Elimination kinetics of cefotaxime and desacetyl cefotaxime in patients with renal insufficiency and during hemodialysis Chemotherapy 2004, 29 (1) 4-12 10.1159/000238166
23. Ohkawa, M.; Okasho, A.; Sugata, T.; Kuroda, K. Elimination kinetics of ceftizoxime in humans with and without renal insufficiency Antimicrob. Agents Chemother. 1982, 22 (2) 308-11 10.1128/AAC.22.2.308
24. Takabatake, T.; Ohta, H.; Maekawa, M.; Yamamoto, Y.; Ishida, Y.; Hara, H.; Nakamura, S.; Ushiogi, Y.; Kawabata, M.; Hashimoto, N. et al. Pharmacokinetics of famotidine, a new H2-receptor antagonist, in relation to renal function Eur. J. Clin. Pharmacol. 1985, 28 (3) 327-31 10.1007/BF00543332
25. Welling, P. G.; Craig, W. A.; Gordon, A. L.; Kunin, C. M. Pharmacokinetics of cefazolin in normal and uremic subjects Clin. Pharmacol. Ther. 1974, 15 (4) 344-53 10.1002/cpt1974154344
26. Wooley, M.; Miller, B.; Krishna, G.; Hershberger, E.; Chandorkar, G. Impact of renal function on the pharmacokinetics and safety of ceftolozane-tazobactam Antimicrob. Agents Chemother. 2014, 58 (4) 2249-55 10.1128/AAC.02151-13
27. Webb, D. B.; Roberts, D. E.; Williams, J. D.; Asscher, A. W. Pharmacokinetics of ciprofloxacin in healthy volunteers and patients with impaired kidney function J. Antimicrob. Chemother. 1986, 18 (Suppl D) 83-7
28. US Food and Drug Administration. VALCYTE (NDA 021304) Clinical Pharmacology and Biopharmaceutics Review(s), 2001. http://www.accessdata.fda.gov/drugsatfda-docs/nda/2001/21304.pdf-Valcyte-BioPharmr.pdf.
29. US Food and Drug Administration. Hepsera (NDA 21-449) Clinical Pharmacology and Biopharmaceutics Review(s), 2002, http://www.accessdata.fda.gov/drugsatfda-docs/nda/2002/21-449-Hepsera-biopharmr-P1.pdf.
30. US Food and Drug Administration. BARACLUDE (NDA 021797) Clinical Pharmacology and Biopharmaceutics Review(s), 2005, http://www.accessdata.fda.gov/drugsatfda-docs/nda/2005/21797-BARACLUDE-biopharmr.PDF.
31. US Food and Drug Administration. JANUVIA (NDA 21995) Clinical Pharmacology and Biopharmaceutics Review(s), 2006, http://www.accessdata.fda.gov/drugsatfda-docs/nda/2006/021995s000-ClinPharmR.pdf.
32. US Food and Drug Administration. AVYCAZ (NDA 206494) Clinical Pharmacology and Biopharmaceutics Review(s), 2015, http://www.accessdata.fda.gov/drugsatfda-docs/nda/2015/206494Orig1s000CllinPharmR.pdf.
33. Vanholder, R.; De Smet, R. Pathophysiologic effects of uremic retention solutes J. Am. Soc. Nephrol 1999, 10 (8) 1815-23
34. Satoh, M.; Hayashi, H.; Watanabe, M.; Ueda, K.; Yamato, H.; Yoshioka, T.; Motojima, M. Uremic toxins overload accelerates renal damage in a rat model of chronic renal failure Nephron Exp Nephrol 2003, 95 (3) e111-8 10.1159/000074327
35. Ichida, K.; Hosoyamada, M.; Kimura, H.; Takeda, M.; Utsunomiya, Y.; Hosoya, T.; Endou, H. Urate transport via human PAH transporter hOAT1 and its gene structure Kidney Int. 2003, 63 (1) 143-55 10.1046/j.1523-1755.2003.00710.x
36. Sato, M.; Iwanaga, T.; Mamada, H.; Ogihara, T.; Yabuuchi, H.; Maeda, T.; Tamai, I. Involvement of uric acid transporters in alteration of serum uric acid level by angiotensin II receptor blockers Pharm. Res. 2008, 25 (3) 639-46 10.1007/s11095-007-9401-6
37. Eisner, C.; Faulhaber-Walter, R.; Wang, Y.; Leelahavanichkul, A.; Yuen, P. S.; Mizel, D.; Star, R. A.; Briggs, J. P.; Levine, M.; Schnermann, J. Major contribution of tubular secretion to creatinine clearance in mice Kidney Int. 2010, 77 (6) 519-26 10.1038/ki.2009.501
38. Vallon, V.; Eraly, S. A.; Rao, S. R.; Gerasimova, M.; Rose, M.; Nagle, M.; Anzai, N.; Smith, T.; Sharma, K.; Nigam, S. K.; Rieg, T. A role for the organic anion transporter OAT3 in renal creatinine secretion in mice Am. J. Physiol Renal Physiol 2012, 302 (10) F1293-9 10.1152/ajprenal.00013.2012
39. Ciarimboli, G.; Lancaster, C. S.; Schlatter, E.; Franke, R. M.; Sprowl, J. A.; Pavenstadt, H.; Massmann, V.; Guckel, D.; Mathijssen, R. H.; Yang, W.; Pui, C. H.; Relling, M. V.; Herrmann, E.; Sparreboom, A. Proximal tubular secretion of creatinine by organic cation transporter OCT2 in cancer patients Clin. Cancer Res. 2012, 18 (4) 1101-8 10.1158/1078-0432.CCR-11-2503
40. Imamura, Y.; Murayama, N.; Okudaira, N.; Kurihara, A.; Okazaki, O.; Izumi, T.; Inoue, K.; Yuasa, H.; Kusuhara, H.; Sugiyama, Y. Prediction of fluoroquinolone-induced elevation in serum creatinine levels: a case of drug-endogenous substance interaction involving the inhibition of renal secretion Clin. Pharmacol. Ther. 2011, 89 (1) 81-8 10.1038/clpt.2010.232
41. Lepist, E. I.; Zhang, X.; Hao, J.; Huang, J.; Kosaka, A.; Birkus, G.; Murray, B. P.; Bannister, R.; Cihlar, T.; Huang, Y.; Ray, A. S. Contribution of the organic anion transporter OAT2 to the renal active tubular secretion of creatinine and mechanism for serum creatinine elevations caused by cobicistat Kidney Int. 2014, 86 (2) 350-7 10.1038/ki.2014.66
42. Jankowski, J.; van der Giet, M.; Jankowski, V.; Schmidt, S.; Hemeier, M.; Mahn, B.; Giebing, G.; Tölle, M.; Luftmann, H.; Schlüter, H.; Zidek, W.; Tepel, M. Increased plasma phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression J. Clin. Invest. 2003, 112 (2) 256-264 10.1172/JCI200315524
43. Itoh, Y.; Ezawa, A.; Kikuchi, K.; Tsuruta, Y.; Niwa, T. Protein-bound uremic toxins in hemodialysis patients measured by liquid chromatography/tandem mass spectrometry and their effects on endothelial ROS production Anal. Bioanal. Chem. 2012, 403 (7) 1841-50 10.1007/s00216-012-5929-3
44. Chmielewski, M.; Cohen, G.; Wiecek, A.; Jesus Carrero, J. The peptidic middle molecules: is molecular weight doing the trick? Semin. Nephrol. 2014, 34 (2) 118-34 10.1016/j.semnephrol.2014.02.005
45. Watanabe, H.; Sakaguchi, Y.; Sugimoto, R.; Kaneko, K.; Iwata, H.; Kotani, S.; Nakajima, M.; Ishima, Y.; Otagiri, M.; Maruyama, T. Human organic anion transporters function as a high-capacity transporter for p-cresyl sulfate, a uremic toxin Clin. Exp. Nephrol. 2014, 18 (5) 814-20 10.1007/s10157-013-0902-9
46. Uwai, Y.; Honjo, H.; Iwamoto, K. Interaction and transport of kynurenic acid via human organic anion transporters hOAT1 and hOAT3 Pharmacol. Res. 2012, 65 (2) 254-60 10.1016/j.phrs.2011.11.003
47. 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 (8) 5072-83 10.1074/jbc.M508050200
48. Eraly, S. A.; Vallon, V.; Rieg, T.; Gangoiti, J. A.; Wikoff, W. R.; Siuzdak, G.; Barshop, B. A.; Nigam, S. K. Multiple organic anion transporters contribute to net renal excretion of uric acid Physiol. Genomics 2008, 33 (2) 180-92 10.1152/physiolgenomics.00207.2007
49. Wikoff, W. R.; Nagle, M. A.; Kouznetsova, V. L.; Tsigelny, I. F.; Nigam, S. K. Untargeted metabolomics identifies enterobiome metabolites and putative uremic toxins as substrates of organic anion transporter 1 (Oat1) J. Proteome Res. 2011, 10 (6) 2842-51 10.1021/pr200093w
50. Ingraham, L.; Li, M.; Renfro, J. L.; Parker, S.; Vapurcuyan, A.; Hanna, I.; Pelis, R. M. A plasma concentration of alpha-ketoglutarate influences the kinetic interaction of ligands with organic anion transporter 1 Mol. Pharmacol. 2014, 86 (1) 86-95 10.1124/mol.114.091777
51. Bohle, A.; Christ, H.; Grund, K. E.; Mackensen, S. The role of the interstitium of the renal cortex in renal disease Contrib. Nephrol. 1979, 16, 109-14 10.1159/000402883
52. Thomas, M. E.; Schreiner, G. F. Contribution of proteinuria to progressive renal injury: consequences of tubular uptake of fatty acid bearing albumin Am. J. Nephrol. 1993, 13 (5) 385-98 10.1159/000168653
53. Dixon, R. J.; Young, K.; Brunskill, N. J. Lysophosphatidic acid-induced calcium mobilization and proliferation in kidney proximal tubular cells Am. J. Physiol. 1999, 276 (2 Pt 2) F191-8
54. Ji, L.; Masuda, S.; Saito, H.; Inui, K. Down-regulation of rat organic cation transporter rOCT2 by 5/6 nephrectomy Kidney Int. 2002, 62 (2) 514-24 10.1046/j.1523-1755.2002.00464.x
55. Aoyama, I.; Enomoto, A.; Niwa, T. Effects of oral adsorbent on gene expression profile in uremic rat kidney: cDNA array analysis Am. J. Kidney Dis. 2003, 41 (3 Suppl 1) S8-14 10.1053/ajkd.2003.50075
56. Habu, Y.; Yano, I.; Takeuchi, A.; Saito, H.; Okuda, M.; Fukatsu, A.; Inui, K.-i. Decreased activity of basolateral organic ion transports in hyperuricemic rat kidney: roles of organic ion transporters, rOAT1, rOAT3 and rOCT2 Biochem. Pharmacol. 2003, 66 (6) 1107-1114 10.1016/S0006-2952(03)00466-0
57. Deguchi, T.; Takemoto, M.; Uehara, N.; Lindup, W. E.; Suenaga, A.; Otagiri, M. Renal clearance of endogenous hippurate correlates with expression levels of renal organic anion transporters in uremic rats J. Pharmacol. Exp. Ther. 2005, 314 (2) 932-8 10.1124/jpet.105.085613
58. Habu, Y.; Yano, I.; Okuda, M.; Fukatsu, A.; Inui, K. Restored expression and activity of organic ion transporters rOAT1, rOAT3 and rOCT2 after hyperuricemia in the rat kidney Biochem. Pharmacol. 2005, 69 (6) 993-9 10.1016/j.bcp.2004.12.004
59. Di Giusto, G.; Anzai, N.; Endou, H.; Torres, A. M. Elimination of organic anions in response to an early stage of renal ischemia-reperfusion in the rat: role of basolateral plasma membrane transporters and cortical renal blood flow Pharmacology 2008, 81 (2) 127-36 10.1159/000110555
60. Matsuzaki, T.; Morisaki, T.; Sugimoto, W.; Yokoo, K.; Sato, D.; Nonoguchi, H.; Tomita, K.; Terada, T.; Inui, K.; Hamada, A.; Saito, H. Altered pharmacokinetics of cationic drugs caused by down-regulation of renal rat organic cation transporter 2 (Slc22a2) and rat multidrug and toxin extrusion 1 (Slc47a1) in ischemia/reperfusion-induced acute kidney injury Drug Metab. Dispos. 2008, 36 (4) 649-54 10.1124/dmd.107.019869
61. Naud, J.; Michaud, J.; Beauchemin, S.; Hebert, M. J.; Roger, M.; Lefrancois, S.; Leblond, F. A.; Pichette, V. Effects of chronic renal failure on kidney drug transporters and cytochrome P450 in rats Drug Metab. Dispos. 2011, 39 (8) 1363-9 10.1124/dmd.111.039115
62. Brandoni, A.; Torres, A. M. Altered Renal Expression of Relevant Clinical Drug Transporters in Different Models of Acute Uremia in Rats. Role of Urea Levels Cell. Physiol. Biochem. 2015, 36 (3) 907-16 10.1159/000430265
63. Lin, J. H.; Lin, T. H. Renal handling of drugs in renal failure. I: Differential effects of uranyl nitrate- and glycerol-induced acute renal failure on renal excretion of TEAB and PAH in rats J. Pharmacol Exp Ther 1988, 246 (3) 896-901
64. Gloff, C. A.; Benet, L. Z. Differential effects of the degree of renal damage on p-aminohippuric acid and inulin clearances in rats J. Pharmacokinet. Biopharm. 1989, 17 (2) 169-77 10.1007/BF01059026
65. Jamei, M.; Dickinson, G. L.; Rostami-Hodjegan, A. A framework for assessing inter-individual variability in pharmacokinetics using virtual human populations and integrating general knowledge of physical chemistry, biology, anatomy, physiology and genetics: A tale of 'bottom-up' vs 'top-down' recognition of covariates Drug Metab. Pharmacokinet. 2009, 24 (1) 53-75 10.2133/dmpk.24.53
66. Bergman, A. J.; Cote, J.; Yi, B.; Marbury, T.; Swan, S. K.; Smith, W.; Gottesdiener, K.; Wagner, J.; Herman, G. A. Effect of renal insufficiency on the pharmacokinetics of sitagliptin, a dipeptidyl peptidase-4 inhibitor Diabetes Care 2007, 30 (7) 1862-4 10.2337/dc06-2545
67. Wishart, D. S.; Jewison, T.; Guo, A. C.; Wilson, M.; Knox, C.; Liu, Y.; Djoumbou, Y.; Mandal, R.; Aziat, F.; Dong, E.; Bouatra, S.; Sinelnikov, I.; Arndt, D.; Xia, J.; Liu, P.; Yallou, F.; Bjorndahl, T.; Perez-Pineiro, R.; Eisner, R.; Allen, F.; Neveu, V.; Greiner, R.; Scalbert, A. HMDB 3.0 - The Human Metabolome Database in 2013 Nucleic Acids Res. 2013, 41, D801-7 10.1093/nar/gks1065
68. Tavazzi, B.; Lazzarino, G.; Leone, P.; Amorini, A. M.; Bellia, F.; Janson, C. G.; Di Pietro, V.; Ceccarelli, L.; Donzelli, S.; Francis, J. S.; Giardina, B. Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism Clin. Biochem. 2005, 38 (11) 997-1008 10.1016/j.clinbiochem.2005.08.002
69. van Dorsten, F. A.; Grun, C. H.; van Velzen, E. J.; Jacobs, D. M.; Draijer, R.; van Duynhoven, J. P. The metabolic fate of red wine and grape juice polyphenols in humans assessed by metabolomics Mol. Nutr. Food Res. 2010, 54 (7) 897-908 10.1002/mnfr.200900212
70. van Velzen, E. J.; Westerhuis, J. A.; van Duynhoven, J. P.; van Dorsten, F. A.; Grun, C. H.; Jacobs, D. M.; Duchateau, G. S.; Vis, D. J.; Smilde, A. K. Phenotyping tea consumers by nutrikinetic analysis of polyphenolic end-metabolites J. Proteome Res. 2009, 8 (7) 3317-30 10.1021/pr801071p
71. Hanhineva, K.; Lankinen, M. A.; Pedret, A.; Schwab, U.; Kolehmainen, M.; Paananen, J.; de Mello, V.; Sola, R.; Lehtonen, M.; Poutanen, K.; Uusitupa, M.; Mykkanen, H. Nontargeted metabolite profiling discriminates diet-specific biomarkers for consumption of whole grains, fatty fish, and bilberries in a randomized controlled trial J. Nutr. 2015, 145 (1) 7-17 10.3945/jn.114.196840
72. MacArthur, R. B.; Altincatal, A.; Tuchman, M. Pharmacokinetics of sodium phenylacetate and sodium benzoate following intravenous administration as both a bolus and continuous infusion to healthy adult volunteers Mol. Genet. Metab. 2004, 81, S67-73 10.1016/j.ymgme.2003.12.011
73. Camacho, L. H.; Olson, J.; Tong, W. P.; Young, C. W.; Spriggs, D. R.; Malkin, M. G. Phase I dose escalation clinical trial of phenylbutyrate sodium administered twice daily to patients with advanced solid tumors Invest. New Drugs 2007, 25 (2) 131-8 10.1007/s10637-006-9017-4
74. Cudkowicz, M. E.; Andres, P. L.; Macdonald, S. A.; Bedlack, R. S.; Choudry, R.; Brown, R. H., Jr.; Zhang, H.; Schoenfeld, D. A.; Shefner, J.; Matson, S.; Matson, W. R.; Ferrante, R. J.; Northeast, A. L. S.; National, V. A. A. L. S. R. C. Phase 2 study of sodium phenylbutyrate in ALS Amyotrophic Lateral Scler. 2009, 10 (2) 99-106 10.1080/17482960802320487
75. Tanihara, Y.; Masuda, S.; Sato, T.; Katsura, T.; Ogawa, O.; Inui, K. Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters Biochem. Pharmacol. 2007, 74 (2) 359-71 10.1016/j.bcp.2007.04.010
76. Mutsaers, H. A.; van den Heuvel, L. P.; Ringens, L. H.; Dankers, A. C.; Russel, F. G.; Wetzels, J. F.; Hoenderop, J. G.; Masereeuw, R. Uremic toxins inhibit transport by breast cancer resistance protein and multidrug resistance protein 4 at clinically relevant concentrations PLoS One 2011, 6 (4) e18438 10.1371/journal.pone.0018438
77. Strobel, J.; Muller, F.; Zolk, O.; Endress, B.; Konig, J.; Fromm, M. F.; Maas, R. Transport of asymmetric dimethylarginine (ADMA) by cationic amino acid transporter 2 (CAT2), organic cation transporter 2 (OCT2) and multidrug and toxin extrusion protein 1 (MATE1) Amino Acids 2013, 45 (4) 989-1002 10.1007/s00726-013-1556-3
78. Liu, T.; Meng, Q.; Wang, C.; Liu, Q.; Guo, X.; Sun, H.; Peng, J.; Ma, X.; Kaku, T.; Liu, K. Changes in expression of renal Oat1, Oat3 and Mrp2 in cisplatin-induced acute renal failure after treatment of JBP485 in rats Toxicol. Appl. Pharmacol. 2012, 264 (3) 423-30 10.1016/j.taap.2012.08.019
79. Laouari, D.; Yang, R.; Veau, C.; Blanke, I.; Friedlander, G. Two apical multidrug transporters, P-gp and MRP2, are differently altered in chronic renal failure Am. J. Physiol Renal Physiol 2001, 280 (4) F636-45
80. Sharma, K.; Karl, B.; Mathew, A. V.; Gangoiti, J. A.; Wassel, C. L.; Saito, R.; Pu, M.; Sharma, S.; You, Y. H.; Wang, L.; Diamond-Stanic, M.; Lindenmeyer, M. T.; Forsblom, C.; Wu, W.; Ix, J. H.; Ideker, T.; Kopp, J. B.; Nigam, S. K.; Cohen, C. D.; Groop, P. H.; Barshop, B. A.; Natarajan, L.; Nyhan, W. L.; Naviaux, R. K. Metabolomics reveals signature of mitochondrial dysfunction in diabetic kidney disease J. Am. Soc. Nephrol. 2013, 24 (11) 1901-12 10.1681/ASN.2013020126