Bibliography
- Nelson SD, Gordon WP. Mammalian drug metabolism. J Nat Prod 1983;46(1):71–8
- Nelson SD. Structure toxicity relationships--how useful are they in predicting toxicities of new drugs? Adv Exp Med Biol 2001;500:33–43
- Baillie TA. Metabolism and toxicity of drugs. Two decades of progress in industrial drug metabolism. Chem Res Toxicol 2008;21(1):129–37
- Kola I, Landis J. Can the pharmaceutical industry reduce attrition rates? Nat Rev Drug Discov 2004;3(8):711–15
- Guengerich FP, MacDonald JS. Applying mechanisms of chemical toxicity to predict drug safety. Chem Res Toxicol 2007;20(3):344–69
- Kumar S, Kassahun K, Tschirret-Guth RA, et al. Minimizing metabolic activation during pharmaceutical lead optimization: progress, knowledge gaps and future directions. Curr Opin Drug Discov Devel 2008;11(1):43–52
- Waring JF, Anderson MG. Idiosyncratic toxicity: mechanistic insights gained from analysis of prior compounds. Curr Opin Drug Discov Devel 2005;8(1):59–65
- Kalgutkar AS, Gardner I, Obach RS, et al. A comprehensive listing of bioactivation pathways of organic functional groups. Curr Drug Metab 2005;6(3):161–225
- Driscoll JP, Aliagas I, Harris JJ, et al. Formation of a quinoneimine intermediate of 4-fluoro-N-methylaniline by FMO1: carbon oxidation plus defluorination. Chem Res Toxicol 2010;23(5):861–3
- Walsh JS, Reese MJ, Thurmond LM. The metabolic activation of abacavir by human liver cytosol and expressed human alcohol dehydrogenase isozymes. Chem Biol Interact 2002;142(1-2):135–54
- Subramanyam B, Woolf T, Castagnoli NJr. Studies on the in vitro conversion of haloperidol to a potentially neurotoxic pyridinium metabolite. Chem Res Toxicol 1991;4(1):123–8
- Miller JA. Sulfonation in chemical carcinogenesis--history and present status. Chem Biol Interact 1994;92(1-3):329–41
- Uetrecht J. Screening for the potential of a drug candidate to cause idiosyncratic drug reactions. Drug Disc Today 2003;8(18):832–7
- Kalgutkar AS, Soglia JR. Minimising the potential for metabolic activation in drug discovery. Expert Opin Drug Metab Toxicol 2005;1(1):91–142
- Baillie TA. Future of toxicology-metabolic activation and drug design: challenges and opportunities in chemical toxicology. Chem Res Toxicol 2006;19(7):889–93
- Williams DP. Toxicophores: investigations in drug safety. Toxicology 2006;226(1):1–11
- Liebler DC. The poisons within: application of toxicity mechanisms to fundamental disease processes. Chem Res Toxicol 2006;19(5):610–13
- Godoy P, Hewitt NJ, Albrecht U, et al. Recent advances in 2D and 3D in vitro systems using primary hepatocytes, alternative hepatocyte sources and non-parenchymal liver cells and their use in investigating mechanisms of hepatotoxicity, cell signaling and ADME. Arch Toxicol 2013;87(8):1315–530
- Khetani SR, Kanchagar C, Ukairo O, et al. Use of micropatterned cocultures to detect compounds that cause drug-induced liver injury in humans. Toxicol Sci 2013;132(1):107–17
- Evans DC, Baillie TA. Minimizing the potential for metabolic activation as an integral part of drug design. Curr Opin Drug Discov Devel 2005;8(1):44–50
- Evans DC, Watt AP, Nicoll-Griffith DA, et al. Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem Res Toxicol 2004;17(1):3–16
- Mutlib A, Lam W, Atherton J, et al. Application of stable isotope labeled glutathione and rapid scanning mass spectrometers in detecting and characterizing reactive metabolites. Rapid Commun Mass Spectrom 2005;19(23):3482–92
- Baillie TA, Davis MR. Mass spectrometry in the analysis of glutathione conjugates. Biol Mass Spectrom 1993;22(6):319–25
- Dieckhaus CM, Fernandez-Metzler CL, King R, et al. Negative ion tandem mass spectrometry for the detection of glutathione conjugates. Chem Res Toxicol 2005;18(4):630–8
- Zhang C, Wong S, Delarosa EM, et al. Inhibitory properties of trapping agents: glutathione, potassium cyanide, and methoxylamine, against major human cytochrome p450 isoforms. Drug Metab Lett 2009;3(2):125–9
- Day SH, Mao A, White R, et al. A semi-automated method for measuring the potential for protein covalent binding in drug discovery. J Pharmacol Toxicol Methods 2005;52(2):278–85
- Uetrecht J. Evaluation of which reactive metabolite, if any, is responsible for a specific idiosyncratic reaction. Drug Metab Rev 2006;38(4):745–53
- Doss GA, Baillie TA. Addressing metabolic activation as an integral component of drug design. Drug Metab Rev 2006;38(4):641–9
- Nelson SD. Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury. Drug Metab Rev 1995;27(1-2):147–77
- Jollow DJ, Mitchell JR, Potter WZ, et al. Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J Phramacol Exp Ther 1973;187(1):195–202
- Fisher R, Brendel K, Hanzlik RP. Correlation of metabolism, covalent binding and toxicity for a series of bromobenzene derivatives using rat liver slices in vitro. Chem Biol Interact 1993;88(2-3):191–8
- Satoh H, Fukuda Y, Anderson DK, et al. Immunological studies on the mechanism of halothane-induced hepatotoxicity: immunohistochemical evidence of trifluoroacetylated hepatocytes. J Pharmacol Exp Ther 1985;233(3):857–62
- Timbrell JA, Mitchell JR, Snodgrass WR, et al. Isoniazid hepatoxicity: the relationship between covalent binding and metabolism in vivo. J Pharmacol Exp Ther 1980;213(2):364–9
- Pohl LR, Branchflower RV. Covalent binding of electrophilic metabolites to macromolecules. Methods Enzymol 1981;77:43–50
- Monks TJ, Hinson JA, Gillette JR. Bromobenzene and p-bromophenol toxicity and covalent binding in vivo. Life Sci 1982;30(10):841–8
- Matthews AM, Hinson JA, Roberts DW, et al. Comparison of covalent binding of acetaminophen and the regioisomer 3’-hydroxyacetanilide to mouse liver protein. Toxicol Lett 1997;90(1):77–82
- Tirmenstein MA, Nelson SD. Subcellular binding and effects on calcium homeostasis produced by acetaminophen and a nonhepatotoxic regioisomer, 3’-hydroxyacetanilide, in mouse liver. J Biol Chem 1989;264(17):9814–19
- Obach RS, Kalgutkar AS, Ryder TF, et al. In vitro metabolism and covalent binding of enol-carboxamide derivatives and anti-inflammatory agents sudoxicam and meloxicam: insights into the hepatotoxicity of sudoxicam. Chem Res Toxicol 2008;21(9):1890–9
- Zhao SX, Dalvie DK, Kelly JM, et al. NADPH-dependent covalent binding of [3H]paroxetine to human liver microsomes and S-9 fractions: identification of an electrophilic quinone metabolite of paroxetine. Chem Res Toxicol 2007;20(11):1649–57
- Dalvie D, Kang P, Zientek M, et al. Effect of intestinal glucuronidation in limiting hepatic exposure and bioactivation of raloxifene in humans and rats. Chem Res Toxicol 2008;21(12):2260–71
- Thompson RA, Isin EM, Li Y, et al. In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. Chem Res Toxicol 2012;25(8):1616–32
- Nakayama S, Atsumi R, Takakusa H, et al. A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding. Drug Metab Dispos 2009;37(9):1970–7
- Uetrecht JP. New concepts in immunology relevant to idiosyncratic drug reactions: the "danger hypothesis" and innate immune system. Chem Res Toxicol 1999;12(5):387–95
- Sakatis MZ, Reese MJ, Harrell AW, et al. Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds. Chem Res Toxicol 2012;25(10):2067–82
- Usui T, Mise M, Hashizume T, et al. Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. Drug Metab Dispos 2009;37(12):2383–92
- Bauman JN, Kelly JM, Tripathy S, et al. Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from nonhepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction. Chem Res Toxicol 2009;22(2):332–40
- Carlson RM. Assessment of the propensity for covalent binding of electrophiles to biological substrates. Environ Health Perspect 1990;87:227–32
- Lopachin RM, Gavin T, Decaprio A, et al. Application of the Hard and Soft, Acids and Bases (HSAB) theory to toxicant--target interactions. Chem Res Toxicol 2012;25(2):239–51
- Masubuchi N, Makino C, Murayama N. Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans. Chem Res Toxicol 2007;20(3):455–64
- Banks AT, Zimmerman HJ, Ishak KG, et al. Diclofenac-associated hepatotoxicity: analysis of 180 cases reported to the Food and Drug Administration as adverse reactions. Hepatology 1995;22(3):820–7
- Boelsterli UA. Diclofenac-induced liver injury: a paradigm of idiosyncratic drug toxicity. Toxicol Appl Pharmacol 2003;192(3):307–22
- Tang W. The metabolism of diclofenac--enzymology and toxicology perspectives. Curr Drug Metab 2003;4(4):319–29
- Kassahun K, Pearson PG, Tang W, et al. Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission. Chem Res Toxicol 2001;14(1):62–70
- Jin L, Davis MR, Hu P, Baillie TA. Identification of novel glutathione conjugates of disulfiram and diethyldithiocarbamate in rat bile by liquid chromatography-tandem mass spectrometry. Evidence for metabolic activation of disulfiram in vivo. Chem Res Toxicol 1994;7(4):526–33
- Wen B, Ma L, Nelson SD, et al. High-throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry. Anal Chem 2008;80(5):1788–99
- Zhu M, Ma L, Zhang H, et al. Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering. Anal Chem 2007;79(21):8333–41
- Mulder GJ, Le CT. A rapid, simple in vitro screening test, using [(3)H]glutathione and l-[(35)S]cysteine as trapping agents, to detect reactive intermediates of xenobiotics. Toxicol In Vitro 1988;2(3):225–30
- Hartman NR, Cysyk RL, Bruneau-Wack C, et al. Production of intracellular 35S-glutathione by rat and human hepatocytes for the quantification of xenobiotic reactive intermediates. Chem Biol Interact 2002;142(1-2):43–55
- Takakusa H, Masumoto H, Makino C, et al. Quantitative assessment of reactive metabolite formation using 35S-labeled glutathione. Drug Metab Pharmacokinet 2009;24(1):100–7
- Lim HK, Chen J, Cook K, et al. A generic method to detect electrophilic intermediates using isotopic pattern triggered data-dependent high-resolution accurate mass spectrometry. Rapid Commun Mass Spectrom 2008;22(8):1295–311
- Yan Z, Caldwell GW, Maher N. Unbiased high-throughput screening of reactive metabolites on the linear ion trap mass spectrometer using polarity switch and mass tag triggered data-dependent acquisition. Anal Chem 2008;80(16):6410–22
- Soglia JR, Harriman SP, Zhao S, et al. The development of a higher throughput reactive intermediate screening assay incorporating micro-bore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent. J Pharmaceut Biomed Anal 2004;36(1):105–16
- Gan J, Harper TW, Hsueh MM, et al. Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites. Chem Res Toxicol 2005;18(5):896–903
- Soglia JR, Contillo LG, Kalgutkar AS, et al. A semiquantitative method for the determination of reactive metabolite conjugate levels in vitro utilizing liquid chromatography-tandem mass spectrometry and novel quaternary ammonium glutathione analogues. Chem Res Toxicol 2006;19(3):480–90
- Doss GA, Miller RR, Zhang Z, et al. Metabolic activation of a 1,3-disubstituted piperazine derivative: evidence for a novel ring contraction to an imidazoline. Chem Res Toxicol 2005;18(2):271–6
- Lenz EM, Martin S, Schmidt R, et al. Reactive metabolite trapping screens and potential pitfalls: bioactivation of a homomorpholine and formation of an unstable thiazolidine adduct. Chem Res Toxicol 2014;27(6):968–80
- Jian W, Yao M, Zhang D, et al. Rapid detection and characterization of in vitro and urinary N-acetyl-L-cysteine conjugates using quadrupole-linear ion trap mass spectrometry and polarity switching. Chem Res Toxicol 2009;22(7):1246–55
- Tate SS, Meister A. gamma-Glutamyl transpeptidase from kidney. Methods Enzymol 1985;113:400–19
- Jones DP, Moldfus P, Stead AH, et al. Metabolism of glutathione and a glutathione conjugate by isolated kidney cells. J Biol Chem 1979;254(8):2787–92
- Aigner A, Jager M, Pasternack R, et al. Purification and characterization of cysteine-S-conjugate N-acetyltransferase from pig kidney. Biochem J 1996;317(Pt 1):213–18
- van Welie RT, van Dijck RG, Vermeulen NP, et al. Mercapturic acids, protein adducts, and DNA adducts as biomarkers of electrophilic chemicals. Crit Rev Toxicol 1992;22(5-6):271–306
- Scholz K, Dekant W, Volkel W, et al. Rapid detection and identification of N-acetyl-L-cysteine thioethers using constant neutral loss and theoretical multiple reaction monitoring combined with enhanced product-ion scans on a linear ion trap mass spectrometer. J Am Soc for Mass Spectrom 2005;16(12):1976–84
- Ding YS, Blount BC, Valentin-Blasini L, et al. Simultaneous determination of six mercapturic acid metabolites of volatile organic compounds in human urine. Chem Res Toxicol 2009;22(6):1018–25
- Grillo MP, Lohr MT, Khera S. Interaction of gamma-glutamyltranspeptidase with ibuprofen-S-acyl-glutathione in vitro and in vivo in human. Drug Metab Dispos 2013;41(1):111–21
- Grillo MP, Hua F, March KL, et al. Gamma-glutamyltranspeptidase-mediated degradation of diclofenac-S-acyl-glutathione in vitro and in vivo in rat. Chem Res Toxicol 2008;21(10):1933–8
- Fitch WL, Berry PW, Tu Y, et al. Identification of glutathione-derived metabolites from an IP receptor antagonist. Drug Metab Dispos 2004;32(12):1482–90
- Grillo MP. Drug-S-acyl-glutathione thioesters: synthesis, bioanalytical properties, chemical reactivity, biological formation and degradation. Curr Drug Metab 2011;12(3):229–44
- Argoti D, Liang L, Conteh A, et al. Cyanide trapping of iminium ion reactive intermediates followed by detection and structure identification using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Chem Res Toxicol 2005;18(10):1537–44
- Murphy PJ. Enzymatic oxidation of nicotine to nicotine 1’(5’) iminium ion. A newly discovered intermediate in the metabolism of nicotine. J Biol Chem 1973;248(8):2796–800
- Gorrod JW, Aislaitner G. The metabolism of alicyclic amines to reactive iminium ion intermediates. Eur J Drug Metab Pharmacokinet 1994;19(3):209–17
- Gorrod JW, Whittlesea CM, Lam SP. Trapping of reactive intermediates by incorporation of 14C-sodium cyanide during microsomal oxidation. Adv Exp Med Biol 1991;283:657–64
- Meneses-Lorente G, Sakatis MZ, Schulz-Utermoehl T, et al. A quantitative high-throughput trapping assay as a measurement of potential for bioactivation. Anal Biochem 2006;351(2):266–72
- Kalgutkar AS, Dalvie DK, O’Donnell JP, et al. On the diversity of oxidative bioactivation reactions on nitrogen-containing xenobiotics. Curr Drug Metab 2002;3(4):379–424
- Johansson T, Jurva U, Gronberg G, et al. Novel metabolites of amodiaquine formed by CYP1A1 and CYP1B1: structure elucidation using electrochemistry, mass spectrometry, and NMR. Drug Metab Dispos 2009;37(3):571–9
- Ravindranath V, Burka LT, Boyd MR. Reactive metabolites from the bioactivation of toxic methylfurans. Science 1984;224(4651):884–6
- O’Donnell JP, Dalvie DK, Kalgutkar AS, et al. Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab Dispos 2003;31(11):1369–77
- Chauret N, Nicoll-Griffith D, Friesen R, et al. Microsomal metabolism of the 5-lipoxygenase inhibitors L-746,530 and L-739,010 to reactive intermediates that covalently bind to protein: the role of the 6,8-dioxabicyclo[3.2.1]octanyl moiety. Drug Metab Dispos 1995;23(12):1325–34
- Miller EC, Miller JA. Reactive metabolites as key intermediates in pharmacologic and toxicologic responses: examples from chemical carcinogenesis. Adv Exp Med Biol 1981;136(Pt A):1–21
- Li Y, Doss GA, Li Y, et al. In vitro bioactivation of a selective estrogen receptor modulator (2S,3R)-(+)-3-(3-hydroxyphenyl)-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-2,3-dihydro -1,4-benzoxathiin-6-ol (I) in liver microsomes: formation of adenine adducts. Chem Res Toxicol 2012;25(11):2368–77
- Corbett MD, Lim LO, Corbett BR, et al. Covalent binding of N-hydroxy-N-acetyl-2-aminofluorene and N-hydroxy-N-glycolyl-2-aminofluorene to rat hepatocyte DNA: in vitro and cell-suspension studies. Chem Res Toxicol 1988;1(1):41–6
- Zhang Z, Chen Q, Li Y, et al. In vitro bioactivation of dihydrobenzoxathiin selective estrogen receptor modulators by cytochrome P450 3A4 in human liver microsomes: formation of reactive iminium and quinone type metabolites. Chem Res Toxicol 2005;18(4):675–85
- Lim HK, Chen J, Sensenhauser C, et al. Overcoming the genotoxicity of a pyrrolidine substituted arylindenopyrimidine as a potent dual adenosine A(2A)/A(1) antagonist by minimizing bioactivation to an iminium ion reactive intermediate. Chem Res Toxicol 2011;24(7):1012–30
- Teffera Y, Colletti AE, Harmange JC, et al. Chemical reactivity of methoxy 4-o-aryl quinolines: identification of glutathione displacement products in vitro and in vivo. Chem Res Toxicol 2008;21(11):2216–22
- Nair SK, Matthews JJ, Cripps SJ, et al. N-(Pyridin-2-yl) arylsulfonamide inhibitors of 11beta-hydroxysteroid dehydrogenase type 1: strategies to eliminate reactive metabolites. Bioorg Med Chem Lett 2013;23(8):2344–8
- Courtney R, Stewart PM, Toh M, et al. Modulation of 11beta-hydroxysteroid dehydrogenase (11betaHSD) activity biomarkers and pharmacokinetics of PF-00915275, a selective 11betaHSD1 inhibitor. J Clin Endocrinol Metab 2008;93(2):550–6
- Park BK, Boobis A, Clarke S, et al. Managing the challenge of chemically reactive metabolites in drug development. Nat Rev Drug Discov 2011;10(4):292–306
- Testa L, Bhindi R, Agostoni P, et al. The direct thrombin inhibitor ximelagatran/melagatran: a systematic review on clinical applications and an evidence based assessment of risk benefit profile. Expert Opin Drug Saf 2007;6(4):397–406
- Kenne K, Skanberg I, Glinghammar B, et al. Prediction of drug-induced liver injury in humans by using in vitro methods: the case of ximelagatran. Toxicol In Vitro 2008;22(3):730–46
- Qiu Y, Benet LZ, Burlingame AL. Identification of the hepatic protein targets of reactive metabolites of acetaminophen in vivo in mice using two-dimensional gel electrophoresis and mass spectrometry. J Biol Chem 1998;273(28):17940–53
- Qiu Y, Benet LZ, Burlingame AL. Identification of hepatic protein targets of the reactive metabolites of the non-hepatotoxic regioisomer of acetaminophen, 3’-hydroxyacetanilide, in the mouse in vivo using two-dimensional gel electrophoresis and mass spectrometry. Adv Exp Med Biol 2001;500:663–73
- Liebler DC. Proteomic approaches to characterize protein modifications: new tools to study the effects of environmental exposures. Environ Health Perspect 2002;110(Suppl 1):3–9
- Liebler DC. Protein damage by reactive electrophiles: targets and consequences. Chem Res Toxicol 2008;21(1):117–28
- Koen YM, Gogichaeva NV, Alterman MA, et al. A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol 2007;20(3):511–19
- Fang J, Koen YM, Hanzlik RP. Bioinformatic analysis of xenobiotic reactive metabolite target proteins and their interacting partners. BMC Chem Biol 2009;9:5
- Hanzlik RP, Koen YM, Fang J. Bioinformatic analysis of 302 reactive metabolite target proteins. Which ones are important for cell death? Toxicol Sci 2013;135(2):390–401
- Leone AM, Kao LM, McMillian MK, et al. Evaluation of felbamate and other antiepileptic drug toxicity potential based on hepatic protein covalent binding and gene expression. Chem Res Toxicol 2007;20(4):600–8
- Dinkova-Kostova AT, Holtzclaw WD, Kensler TW. The role of Keap1 in cellular protective responses. Chem Res Toxicol 2005;18(12):1779–91
- Dinkova-Kostova AT. The Role of Sulfhydryl Reactivity of Small Molecules for the Activation of the KEAP1/NRF2 Pathway and the Heat Shock Response. Scientifica 2012;2012:606104
- Ohnuma T, Nakayama S, Anan E, et al. Activation of the Nrf2/ARE pathway via S-alkylation of cysteine 151 in the chemopreventive agent-sensor Keap1 protein by falcarindiol, a conjugated diacetylene compound. Toxicol Appl Pharmacol 2010;244(1):27–36
- Natsch A. The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers--functional relevance and a hypothesis on innate reactions to skin sensitizers. Toxicol Sci 2010;113(2):284–92
- Hong F, Sekhar KR, Freeman ML, et al. Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation. J Biol Chem 2005;280(36):31768–75