Species difference in the inhibitory potentials of non-steroidal anti-inflammatory drugs on the hepatic sulfation and glucuronidation of bioactive flavonoids: differential observations among common inhibition parameters

References

• Boobis AR, Sesardic D, Murray BP, et al. (1990). Species variation in the response of the cytochrome P-450-dependent monooxygenase system to inducers and inhibitors. Xenobiotica 20:1139–61
   PubMed Web of Science ®Google Scholar
• Chu X, Korzekwa K, Elsby R, et al. (2013). Intracellular drug concentrations and transporters: measurement, modeling, and implications for the liver. Clin Pharmacol Ther 94:126–41
   PubMed Web of Science ®Google Scholar
• Cornish-Bowden A. (1974). A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors. Biochem J 137:143–4
   PubMed Web of Science ®Google Scholar
• Crook PR, Willis JV, Kendall MJ, et al. (1982). The pharmacokinetics of diclofenac sodium in patients with active rheumatoid disease. Eur J Clin Pharmacol 21:331--4
   Google Scholar
• Davies E, Avery GS. (1971). Ibuprofen: a review of its pharmacological properties and therapeutic efficacy in rheumatic disorders. Drugs 2:416--46
   Google Scholar
• Dunn RT, Klaassen CD. (1998). Tissue-specific expression of rat sulfotransferase messenger RNAs. Drug Metab Dispos 26:598–604
   PubMed Web of Science ®Google Scholar
• Eagling VA, Tjia JF, Back DJ. (1998). Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. Br J Clin Pharmacol 45:107–14
   PubMed Web of Science ®Google Scholar
• Fong YK, Li CR, Wo SK, et al. (2012). In vitro and in situ evaluation of herb–drug interactions during intestinal metabolism and absorption of Baicalein. J Ethnopharmacol 141:742–53
   PubMed Web of Science ®Google Scholar
• Gaganis P, Miners JO, Knights KM. (2007). Glucuronidation of fenamates: kinetic studies using human kidney cortical microsomes and recombinant UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. Biochem Pharmacol 73:1683–91
   PubMed Web of Science ®Google Scholar
• Gamage N, Barnett A, Hempel N, et al. (2006). Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5–22
   PubMed Web of Science ®Google Scholar
• Herman RJ, Loewen GR, Antosh DM, et al. (1994). Analysis of polymorphic variation in drug metabolism: III. Glucuronidation and sulfation of diflunisal in man. Clin Invest Med 17:297–307
   PubMed Web of Science ®Google Scholar
• Honma W, Kamiyama Y, Yoshinari K, et al. (2001). Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. Drug Metab Dispos 29:274–81
   PubMed Web of Science ®Google Scholar
• Houin G, Tremblay D, Bree F, et al. (1983). The pharmacokinetics and availability of niflumic acid in humans. Int J Clin Pharmacol Ther Toxicol 21:130--4
   Google Scholar
• Insel PA. (1990). Analgesic-antipyretics and antiinflammatory agents: drugs employed in the treatment of rheumatoid arthritis and gout. In: Gillman AG, Rall TW, Nies AS, Taylor P, eds. Goodman and Gillman's: the pharmacological basis of therapeutics. 8th ed. New York: Pergamon Press, 638--81
   Google Scholar
• Kaneko T, Chiba H, Horie N, et al. (2009). Effect of Scutellariae Radix ingredients on prostaglandin E2 production and COX-2 expression by LPS-activated macrophage. In Vivo 23:577–81
   PubMed Web of Science ®Google Scholar
• Kiang TKL, Ensom MHH, Chang TKH. (2005). UDP-glucuronosyltransferases and clinical drug--drug interactions. Pharmacol Ther 106:97–132
   PubMed Web of Science ®Google Scholar
• Kim YH, Jeong DW, Paek IB, et al. (2006). Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma. J Chromatogr B 844:261–7
   PubMed Web of Science ®Google Scholar
• King CD, Green MD, Rios GR, et al. (1996). The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1. Arch Biochem Biophys 332:92–100
   PubMed Web of Science ®Google Scholar
• Kotani A, Kojima S, Hakamata H, Kusu F. (2006). HPLC with electrochemical detection to examine the pharmacokinetics of baicalin and baicalein in rat plasma after oral administration of a Kampo medicine. Anal Biochem 350:99–104
   PubMed Web of Science ®Google Scholar
• Krippendorff B-F, Neuhaus R, Lienau P, et al. (2009). Mechanism-based inhibition: deriving KI and kinact directly from time-dependent IC50 values. J Biomol Screening 14:913–23
   PubMedGoogle Scholar
• Kulkarni KH, Wang S, Hu M. (2006). Gender difference affects metabolism of isoflavones in rat intestinal and liver microsomes. 14th North American International Society for the Study of Xenobiotics Meeting. Rio Grande, PR
   Google Scholar
• Lahoz A, Gombau L, Donato MT, et al. (2006). In vitro ADME medium/high-throughput screening in drug preclinical development. Mini-Rev Med Chem 6:1053–62
   PubMed Web of Science ®Google Scholar
• Lam W, Loi C-M, Atherton J, et al. (2007). Application of in-line liquid chromatography-accurate radioisotope counting-mass spectrometry (LC-ARC-MS) to evaluate metabolic profile of [3H]-mefenamic acid in rat plasma. Drug Metab Lett 1:179–88
   PubMedGoogle Scholar
• Lee BH, Lee SJ, Kang TH, et al. (2000). Baicalein: an in vitro antigenotoxic compound from Scutellaria baicalensis. Planta Med 66:70–1
   PubMed Web of Science ®Google Scholar
• Li CR, Zhang L, Lin G, Zuo Z. (2011). Identification and quantification of baicalein, wogonin, oroxylin A and their major glucuronide conjugated metabolites in rat plasma after oral administration of Radix scutellariae product. J Pharm Biomed Anal 54:750–8
   PubMed Web of Science ®Google Scholar
• Li CR, Zhang L, Wo SK, et al. (2012). Pharmacokinetic interactions among major bioactive components in Radix Scutellariae via metabolic competition. Biopharm Drug Dispos 33:487–500
   PubMed Web of Science ®Google Scholar
• Mackenzie PI, Walter Bock K, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–85
   PubMed Web of Science ®Google Scholar
• Mano Y, Usui T, Kamimura H. (2006). In vitro inhibitory effects of non-steroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP-glucuronosyltransferase 1A9–potent inhibition by niflumic acid. Biopharm Drug Dispos 27:1–6
   PubMed Web of Science ®Google Scholar
• Mano Y, Usui T, Kamimura H. (2007). Inhibitory potential of nonsteroidal anti-inflammatory drugs on UDP-glucuronosyltransferase 2B7 in human liver microsomes. Eur J Clin Pharmacol 63:211–16
   PubMed Web of Science ®Google Scholar
• Mano Y, Usui T, Kamimura H. (2008). Species differences in inhibition potential of nonsteroidal anti-inflammatory drugs against estradiol 3β-glucuronidation between rats, dogs, and humans. J Pharm Sci 97:2805–10
   PubMed Web of Science ®Google Scholar
• Martignoni M, Groothuis GM, de Kanter R. (2006). Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metabol Toxicol 2:875–94
   PubMed Web of Science ®Google Scholar
• McEvoy GK. (2003). Nonsteroidal anti-inflammatory agents. AHFS drug handbook. Bethesda: American Society of Health-System Pharmacists, 1902--2021
   Google Scholar
• Montvale NJ. (1999). Physicians' desk reference. Medical Economics Co
   Google Scholar
• Obach RS, Walsky RL, Venkatakrishnan K, et al. (2006). The utility of in vitro cytochrome P450 inhibition data in the prediction of drug--drug interactions. J Pharmacol Exp Ther 316:336–48
   PubMed Web of Science ®Google Scholar
• Pai TG, Suiko M, Sakakibara Y, Liu M-C. (2001). Sulfation of flavonoids and other phenolic dietary compounds by the human cytosolic sulfotransferases. Biochem Biophys Res Commun 285:1175–9
   PubMed Web of Science ®Google Scholar
• Pfeiffer E, Treiling CR, Hoehle SI, Metzler M. (2005). Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. Carcinogenesis 26:2172–8
   PubMed Web of Science ®Google Scholar
• Pritchard M, Fournel-Gigleux S, Siest G, et al. (1994). A recombinant phenobarbital-inducible rat liver UDP-glucuronosyltransferase (UDP-glucuronosyltransferase 2B1) stably expressed in V79 cells catalyzes the glucuronidation of morphine, phenols, and carboxylic acids. Mol Pharmacol 45:42–50
   PubMed Web of Science ®Google Scholar
• Rao SI, Duffel MW. (1991). Inhibition of aryl sulfotransferase by carboxylic acids. Drug Metab Dispos: Biological Fate Chem 19:543–5
   PubMed Web of Science ®Google Scholar
• Riches Z, Stanley EL, Bloomer JC, Coughtrie MWH. (2009). Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT “Pie”. Drug Metab Dispos 37:2255–61
   PubMed Web of Science ®Google Scholar
• Scott G, Nierenberg D. (1992). Pharmacokinetic data for commonly used drugs. In: Melmon KL, Morelli HF, Hoffman BB, Nierenberg DW, eds. Clinical pharmacology. Basic principles in therapeutics. 3rd ed. New York: McGraw-Hill, 1029--72
   Google Scholar
• Small RE, Cox SR, Adams WJ. (1990). Influence of H2 receptor antagonists on the disposition of flurbiprofen enantiomers. J Clin Pharmacol 30:660--4
   Google Scholar
• Su YL, Huang Y, Chen ZY. (2004). Isolation and elucidation of antioxidant constituents from acetone extract in root of Scutellaria rehderiana. China J Chin Mater Med 29:863–4
   Google Scholar
• Vietri M, De Santi C, Pietrabissa A, et al. (2000a). Inhibition of human liver phenol sulfotransferase by nonsteroidal anti-inflammatory drugs. Eur J Clin Pharmacol 56:81–7
   PubMed Web of Science ®Google Scholar
• Vietri M, Pietrabissa A, Mosca F, Pacifici GM. (2000b). Mycophenolic acid glucuronidation and its inhibition by non-steroidal anti-inflammatory drugs in human liver and kidney. Eur J Clin Pharmacol 56:659–64
   PubMed Web of Science ®Google Scholar
• Williamson G, Barron D, Shimoi K, Terao J. (2005). In vitro biological properties of flavonoid conjugates found in vivo. Free Radical Res 39:457–69
   PubMed Web of Science ®Google Scholar
• Yang CH, Tang L, Lv C, et al. (2011). Sulfation of selected mono-hydroxyflavones by sulfotransferases in vitro: a species and gender comparison. J Pharm Pharmacol 63:967–70
   PubMed Web of Science ®Google Scholar
• Yang X, Gandhi Y, Duignan D, Morris M. (2009). Prediction of biliary excretion in rats and humans using molecular weight and quantitative structure–pharmacokinetic relationships. AAPS J 11:511–25
   PubMed Web of Science ®Google Scholar
• Yuan R, Parmelee T, Balian JD, et al. (1999). In vitro metabolic interaction studies: experience of the Food and Drug Administration. Clin Pharmacol Ther 66:9–15
   PubMed Web of Science ®Google Scholar
• Yuen AW, Land G, Weatherley BC, Peck AW. (1992). Sodium valproate acutely inhibits lamotrigine metabolism. Br J Clin Pharmacol 33:511–13
   PubMed Web of Science ®Google Scholar
• Zhai S, Dai R, Friedman FK, Vestal RE. (1998). Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Drug Metab Dispos 26:989–92
   PubMed Web of Science ®Google Scholar
• Zhang D, Chando TJ, Everett DW, et al. (2005). In vitro inhibition of UDP glucuronosyltransferases bu Atazanavir and other HIV protease inhibitiors and the relationship of this propertu to in vivo bilirubin glucuronidation. Drug Metab Dispos 33:1729–39
   PubMed Web of Science ®Google Scholar
• Zhang H, Cui D, Wang B, et al. (2007a). Pharmacokinetic drug interactions involving 17α-ethinylestradiol. Clin Pharmacokinet 46:133–57
   PubMed Web of Science ®Google Scholar
• Zhang L, Li C, Lin G, et al. (2011). Hepatic metabolism and disposition of baicalein via the coupling of conjugation enzymes and transporters – in vitro and in vivo evidences. AAPS J 13:378–89
   PubMed Web of Science ®Google Scholar
• Zhang L, Lin G, Zuo Z. (2007b). Involvement of UDP-glucuronosyltransferases in the extensive liver and intestinal first-pass metabolism of flavonoid baicalein. Pharm Res 24:81–9
   PubMed Web of Science ®Google Scholar
• Zhou Q, Zheng Z, Xia B, et al. (2010). Use of isoform-specific UGT metabolism to determine and describe rates and profiles of glucuronidation of wogonin and oroxylin A by human liver and intestinal microsomes. Pharm Res 27:1568–83
   PubMed Web of Science ®Google Scholar