Mechanism-based inactivation of cytochrome P450 3A by evodol

References

• Backman JT, Olkkola KT, Aranko K, Himberg JJ, Neuvonen PJ. 1994. Dose of midazolam should be reduced during diltiazem and verapamil treatments. Br J Clin Pharmacol. 37(3):221–225.
   PubMed Web of Science ®Google Scholar
• Chen LJ, Hecht SS, Peterson LA. 1997. Characterization of amino acid and glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol. 10(8):866–874.
   PubMed Web of Science ®Google Scholar
• Cui T, Wang Q, Tian X, Zhang K, Peng Y, Zheng J. 2020. Piperine is a mechanism-based inactivator of CYP3A. Drug Metab Dispos. 48(2):123–134.
   PubMed Web of Science ®Google Scholar
• Filppula AM, Laitila J, Neuvonen PJ, Backman JT. 2012. Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4substrates. Br J Pharmacol. 165(8):2787–2798.
   PubMed Web of Science ®Google Scholar
• Guengerich PF. 2001. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol. 14(6):611–650.
   PubMed Web of Science ®Google Scholar
• Guengerich FP. 2003. Cytochromes P450, drugs, and diseases. Mol Interv. 3(4):194–204.
   PubMedGoogle Scholar
• Grimm SW, Einolf HJ, Hall SD, He K, Lim H-K, Ling K-HJ, Lu C, Nomeir AA, Seibert E, Skordos KW, et al. 2009. The conduct of in vitro studies to address time-dependent inhibition of drug-metabolizing enzymes: a perspective of the pharmaceutical research and manufacturers of America. Drug Metab Dispos. 37(7):1355–1370.
   PubMed Web of Science ®Google Scholar
• Guo X, Li W, Li Q, Chen Y, Zhao G, Peng Y, Zheng J. 2019. Tofacitinib is a mechanism-based inactivator of cytochrome P450 3A4. Chem Res Toxicol. 32(9):1791–1800.
   PubMed Web of Science ®Google Scholar
• Hu Z, Zhou S, Zhang N, Li W, Lin D, Peng Y, Zheng J. 2018. Development of polyclonal antibodies for detection of diosbulbin B-derived cis-enedial protein adducts. Chem Res Toxicol. 31(4):231–237.
   PubMed Web of Science ®Google Scholar
• Iwata H, Tezuka Y, Kadota S, Hiratsuka A, Watabe T. 2005. Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. Drug Metab Pharmacokinet. 20(1):34–45.
   PubMedGoogle Scholar
• Kent UM, Juschyshyn MI, Hollenberg PF. 2001. Mechanism-based inactivators as probes of cytochrome P450 structure and function. Curr Drug Metab. 2(3):215–243.
   PubMed Web of Science ®Google Scholar
• Lu D, Sullivan MM, Phillips MB, Peterson LA. 2009. Degraded protein adducts of cis-2-butene-1,4-dial are urinary and hepatocyte metabolites of furan. Chem Res Toxicol. 22(6):997–1007.
   PubMed Web of Science ®Google Scholar
• Lu D, Peterson LA. 2010. Identification of furan metabolites derived from cysteine-cis-2-butene-1,4-dial-lysine cross-links. Chem Res Toxicol. 23(1):142–151.
   PubMed Web of Science ®Google Scholar
• Liu ZL, Liu QZ, Du SS, Deng ZW. 2012. Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: culicidae). Parasitol Res. 111(3):991–996.
   PubMed Web of Science ®Google Scholar
• Lin D, Li C, Peng Y, Gao H, Zheng J. 2014. Cytochrome P450-mediated metabolic activation of diosbulbin B. Drug Metab Dispos. 42(10):1727–1736.
   PubMed Web of Science ®Google Scholar
• Lin D, Guo X, Gao H, Cheng L, Cheng M, Song S, Peng Y, Zheng J. 2015. In vitro and in vivo studies of the metabolic activation of 8-epidiosbulbin E acetate. Chem Res Toxicol. 28(9):1737–1746.
   PubMed Web of Science ®Google Scholar
• Lin D, Li W, Peng Y, Jiang C, Xu Y, Gao H, Zheng J. 2016. Role of metabolic activation in 8-epidiosbulbin E acetate-induced liver injury: mechanism of action of the hepatotoxic furanoid. Chem Res Toxicol. 29(3):359–366.
   PubMed Web of Science ®Google Scholar
• Liu Y, Liu C, Liu Y, Ge Q, Sun C. 2020. Cytochrome P450 mediated bioactivation of rutaevin, a bioactive and potentially hepatotoxic component of Evodia rutaecarpa. Chem Res Toxicol. 33(12):3054–3064.
   PubMed Web of Science ®Google Scholar
• Moruno-Dávila MA, Garrido-del Solo C, García-Moreno M, Havsteen BH, Garcia-Sevilla F, Garcia-Cánovas F, Varón R. 2001. Kinetic analysis of enzyme systems with suicide substrate in the presence of a reversible competitive inhibitor, tested by simulated progress curves. Int J Biochem Cell Biol. 33(2):181–191.
   PubMed Web of Science ®Google Scholar
• Masubuchi Y, Horie T. 2007. Toxicological significance of mechanism-based inactivation of cytochrome P450 enzymes by drugs. Crit Rev Toxicol. 37(5):389–412.
   PubMed Web of Science ®Google Scholar
• O'Brien SG, Meinhardt P, Bond E, Beck J, Peng B, Dutreix C, Mehring G, Milosavljev S, Huber C, Capdeville R, et al. 2003. Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome P450 3A4 substrate, in patients with chronic myeloid leukaemia. Br J Cancer. 89(10):1855–1859.
   PubMed Web of Science ®Google Scholar
• Peterson LA. 2013. Reactive metabolites in the biotransformation of molecules containing a furan ring. Chem Res Toxicol. 26(1):6–25.
   PubMed Web of Science ®Google Scholar
• Phillips MB, Sullivan MM, Villalta PW, Peterson LA. 2014. Covalent modification of cytochrome c by reactive metabolites of furan. Chem Res Toxicol. 27(1):129–135.
   PubMed Web of Science ®Google Scholar
• Qin J, Liao C-N, Chen W-W, Li H-Y, Su J, Wu X-D, He J-B, Zhang G-H. 2021. New limonoids and quinolone alkaloids with cytotoxic and anti-platelet aggregation activities from Evodia rutaecarpa (Juss.) Benth. Fitoterapia. 152:104875.
   PubMed Web of Science ®Google Scholar
• Rodrigues AD. 1999. Integrated P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol. 57(5):465–480.
   PubMed Web of Science ®Google Scholar
• Taxak N, Kalra S, Bharatam PV. 2013. Mechanism-based inactivation of cytochromes by furan epoxide: unraveling the molecular mechanism. Inorg Chem. 52(23):13496–13508.
   PubMed Web of Science ®Google Scholar
• Thompson RA, Isin EM, Ogese MO, Mettetal JT, Williams DP. 2016. Reactive metabolites: current and emerging risk and hazard assessments. Chem Res Toxicol. 29(4):505–533.
   PubMed Web of Science ®Google Scholar
• Wang YH, Jones DR, Hall SD. 2004. Prediction of cytochromeP4503A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 32(2):259–266.
   PubMed Web of Science ®Google Scholar
• Wang T-Y, Wu J-B, Hwang T-L, Kuo Y-H, Chen J-J. 2010. A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses. Chem Biodivers. 7(7):1828–1834.
   PubMed Web of Science ®Google Scholar
• Werk AN, Cascorbi I. 2014. Functional gene variants of CYP3A4. Clin Pharmacol Ther. 96(3):340–348.
   PubMed Web of Science ®Google Scholar
• Yu H, Jin H, Gong W, Wang Z, Liang H. 2013. Liang HP. Pharmacological actions of multi-target directed evodiamine. Molecules. 18(2):1826–1843.
   PubMed Web of Science ®Google Scholar
• Yang X-B, Qian P, Yang X-W, Liu J-X, Gong N-B, Lv Y. 2013. Limonoid constituents of Euodia rutaecarpa var. bodinieri and their inhibition on NO production in lipopolysaccharide-activated RAW264.7 macrophages. J Asian Nat Prod Res. 15(10):1130–1138.
   PubMed Web of Science ®Google Scholar
• Yu J, Deng P, Zhong D, Chen X. 2014. Identification of amino acid and glutathione N-conjugates of toosendanin: bioactivation of the furan ring mediated by CYP3A4. Chem Res Toxicol. 27(9):1598–1609.
   PubMed Web of Science ®Google Scholar