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Review Article

The contributions of Sidney D. Nelson to drug metabolism research

Pages 4-11 | Received 26 Aug 2014, Accepted 05 Nov 2014, Published online: 20 Nov 2014

References

  • Albano E, Rundgren M, Harvison PJ, et al. (1985). Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity. Mol Pharmacol 28:306–311
  • Axworthy DB, Hoffmann KJ, Streeter AJ, et al. (1988). Covalent binding of acetaminophen to mouse hemoglobin. Identification of major and minor adducts formed in vivo and implications for the nature of the arylating metabolites. Chem-Biol Interact 68:99–116
  • Baillie TA. (2012). Sidney D. Nelson (1945–2012). Chem Res Toxicol 25:2–3
  • Chen W, Shockcor JP, Tonge R, et al. (1999). Protein and nonprotein cysteinyl thiol modification by N-acetyl-p-benzoquinone imine via a novel ipso adduct. Biochemistry 38:8159–8166
  • Coe KJ, Nelson SD, Ulrich RG, et al. (2006). Profiling the hepatic effects of flutamide in rats: A microarray comparison with classical aryl hydrocarbon receptor ligands and atypical CYP1A inducers. Drug Metab Dispos 34:1266–1275
  • Dahlin DC, Miwa GT, Lu AYH, Nelson SD. (1984). N-Acetyl-p-benzoquinone imine: A cytochrome P-450-mediated oxidation product of acetaminophen. Proc Natl Acad Sci USA 81:1327–1331
  • Dahlin DC, Nelson SD. (1982). Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. J Med Chem 25:885–886
  • Dietz EC, Schäfer A, Omichinski JG, Nelson SD. (1997). Inactivation of glyceraldehyde-3-phosphate dehydrogenase by a reactive metabolite of acetaminophen and mass spectral characterization of an arylated active site peptide. Chem Res Toxicol 10:1097–1103
  • Gao Q, Doneanu CE, Shaffer SA, et al. (2006). Identification of the interactions between cytochrome P450 2E1 and cutochrome b5 by mass spectrometry and site-directed mutagenesis. J Biol Chem 281:20404–20417
  • Gordon WP, Forte AJ, McMurty RJ, et al. (1982). Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicol Appl Pharmacol 65:413–424
  • Gordon WP, Huitric AC, Seth CL, et al. (1987). The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran. Drug Metab Dispos 15:589–594
  • Harrelson JP, Atkins WM, Nelson SD. (2008). Multiple ligand binding in CYP2A6: Probing mechanisms of cytochrome P450 cooperativity by assessing substrate dynamics. Biochemistry 47:2978–2988
  • Harvison PJ, Nelson SD, Baillie TA. (1988). Unpublished observations
  • Hinson JA, Nelson SD, Gillette JR. (1979). Metabolism of 18O-phenacetin and 18O-acetaminophen. Mol Pharmacol 15:419–427
  • Hinson JA, Nelson SD, Mitchell JR. (1977). Differences in the microsomal activation of the arylating metabolites formed from p-hydroxyacetanilide and p-ethoxyacetanilide. Mol Pharmacol 13:625–633
  • Hoffmann KJ, Streeter AJ, Axworthy DB, Baillie TA. (1985). Identification of the major covalent adduct formed in vitro and in vivo between acetaminophen and mouse liver proteins. Mol Pharmacol 27:566–573
  • Holme JA, Søderlund EJ, Brunborg G, et al. (1989). Different mechanisms are involved in DNA damage, bacterial mutagenicity and cytotoxicity induced by 1,2-bibromo-3-chloropropane in suspensions of rat liver cells. Carcinogenesis 10:49–54
  • Khojasteh-Bakht SC, Koenigs LL, Peter RM, et al. (1998). (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos 26:701–704
  • Miller EC, Miller JA. (1947). The presence and significance of bound aminoazo dyes in the livers of rats fed p-dimethylaminoazobenzene. Cancer Res 7:468–480
  • Mitchell JR, Jollow DJ, Potter WZ, et al. (1973). Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J Pharmacol Exp Ther 187:185–194
  • Moore M, Thor H, Nelson S, et al. (1985). The toxicity of acetaminophen and N-acetyl-p-benzoquinone imine in isolated hepatocytes is associated with thiol depletion and increased cytosolic Ca2+. J Biol Chem 260:13035–13040
  • Myers TG, Dietz EC, Anderson NL, et al. (1995). A comparative study of mouse liver proteins arylated by reactive metabolites of acetaminophen and its nonhepatotoxic regioisomer, 3′hydroxyacetanilide. Chem Res Toxicol 8:403–413
  • Nelson SD, Garland WA, Mitchell JR, et al. (1978). Deuterium isotope effects on the metabolism and toxicity of phenacetin in hamsters. Drug Metab Dispos 6:363–367
  • Nelson SD, Mitchell JR, Dybing E, Sasame HA. (1976a). Cytochrome P-450 mediated oxidation of 2-hydroxyestrogens to reactive intermediates. Biochem Biophys Res Commun 70:1157–1165
  • Nelson SD, Mitchell JR, Snodgrass WR, et al. (1976b). Isoniazid and iproniazid: Activation of metabolites to toxic intermediates in man and rat. Science 193:901–903
  • Nelson SD, Omichinski JG, Iyer L, et al. (1984). Activation mechanism of tris(2,3-dibromopropyl)phosphate to the potent mutagen, 2-bromoacrolein. Biochem Biophys Res Commun 121:213–219
  • Omichinski JG, Brunborg G, Søderlund EJ, et al. (1987). Renal necrosis and DNA damage caused by selectively deuterated and methylated analogs of 1,2-bibromo-3-chloropropane in the rat. Toxicol Appl Pharmacol 91:358–370
  • Pohl LR, Nelson SD, Garland WA, Trager WF. (1975). The rapid identification of a new metabolite of warfarin via a chemical ionization mass spectrometry ion doublet technique. Biomed Mass Spectrom 2:23–30
  • Pohl LR, Nelson SD, Krishna G. (1978). Investigation of the mechanism of the metabolic activation of chloramphenicol by rat liver microsomes. Biochem Pharmacol 27:491–496
  • Pohl LR, Nelson SD, Porter WR, et al. (1976). Warfarin – Stereochemical aspects of its metabolism by rat liver microsomes. Biochem Pharmacol 25:2153–2162
  • Proubek DJ, Rundgren M, Harvison PJ, et al. (1987). Investigation of mechanisms of acetaminophen toxicity in isolated rat hepatocytes with the acetaminophen analogues 3,5-dimethylacetaminophen and 2,6-dimethylacetaminophen. Mol Pharmacol 31:647–653
  • Smith CV, Mitchell JR. (1985). Acetaminophen hepatotoxicity in vivo is not accompanied by oxidant stress. Biochem Biophys Res Commun 133:329–336
  • Stepan AF, Walker DP, Bauman J, et al. (2011). Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: A perspective based on the critical examination of trends in the top 200 drugs marketed in the United States. Chem Res Toxicol 24:1345–1410
  • Streeter AJ, Baillie TA. (1985). 2-Acetamido-p-benzoquinone: A reactive arylating metabolite of 3′-hydroxyacetanilide. Biochem Pharmacol 34:2871–2876
  • Streeter AJ, Bjorge SM, Axworthy DB, et al. (1984a). The microsomal metabolism and site of covalent binding to protein of 3′-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen. Drug Metab Dispos 12:565–576
  • Streeter AJ, Dahlin DC, Nelson SD, Baillie TA. (1984b). The covalent binding of acetaminophen to protein – Evidence for cysteine residues as major sites of arylation in vitro. Chem-Biol Interact 48:349–366
  • Søderlund EJ, Gordon WP, Nelson SD, et al. (1984). Metabolism in vitro of tris(2,3-dibromopropyl)phosphate: Oxidative bebromination and bis(2,3-dibromopropyl)phosphate formation as correlates of mutagenicity and covalent protein binding. Biochem Pharmacol 33:4017–4023
  • Søderlund EJ, Nelson SD, Dybing E. (1981). In vitro and in vivo covalent binding of the kidney carcinogen tris(2,3-dibromopropyl)phosphate. Toxicology 21:291–304
  • Søderlund EJ, Omichinske JG, Dahl JE, et al. (1988). Nephrotoxicity of selectively deuterated and methylated analogues of Tris-BP and Bis-BP in the rat. Pharmacol Toxicol 62:142–149
  • Takakusa H, Wahlin MD, Zhao C, et al. (2011). Metabolic intermediate complex formation of human cytochrome P450 3A4 by lapatinib. Drug Metab Dispos 39:1022–1030
  • Teng WC, Oh JW, New LS, et al. (2010). Mechanism-based inactivation of cytochrome P450 3A4 by lapatinib. Mol Pharmacol 78:693–703
  • Thomassen D, Knebel N, Slattery JT, et al. (1992). Reactive intermediates in the oxidation of menthofuran by cytochromes P-450. Chem Res Toxicol 5:123–130
  • Tirmenstein MA, Nelson SD. (1989). Homeostasis produced by acetaminophen and a non-hepatotoxic regioisomer, 3′-hydroxyacetanilide, in mouse liver. J Biol Chem 264:9814–9819
  • Wen B, Coe KJ, Rademacher P, et al. (2008). Comparison of in vitro bioactivation of flutamide and its cyano analogue: Evidence for reductive activation by human NADPH: Cytochrome P450 reductase. Chem Res Toxicol 21:2393–2406
  • Wen B, Doneanu CE, Lampe JN, et al. (2005). Probing the CYP3A4 active site by cysteine scanning mutagenesis and photoaffinity labeling. Arch Biochem Biophys 444:100–111

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