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Xenobiotica
the fate of foreign compounds in biological systems
Volume 44, 2014 - Issue 11
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Topics in Xenobiochemistry

Ethyl sulphate, a chemically reactive human metabolite of ethanol?

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Pages 957-960 | Received 12 Jun 2014, Accepted 30 Jun 2014, Published online: 18 Jul 2014

References

  • Asita A. (1989). A comparative study of the clastogenic activity of ethylating agents. Mutagenesis 4:432–6
  • Atwater WO, Benedict FG. (1899). Experiments on the metabolism of matter and energy in human body. US Dept Agric Bull No. 69, Washington, DC
  • Baranowski S, Annerose S, Thierauf A, et al. (2008). In vitro study of bacterial degradation of ethyl glucuronide and ethyl sulphate. Int J Legal Med 122:389–93
  • Battelli F, Stern L. (1910). Die alkoholoxydase in den tiergeweben. Biochem Z 28:145–68
  • Benkovic SJ, Benkovic PA. (1966). Studies on sulphate esters. 1. Nucleophilic reactions of amines with p-nitrophenyl sulphate. J Am Chem Soc 88:5504–11
  • Bicker W, Lammerhofer M, Keller T, et al. (2006). Validated method for the determination of the ethanol consumption markers ethyl glucuronide, ethyl phosphate, and ethyl sulphate in human urine by reversed phase/weak anion exchange liquid chromatography-tandem mass spectrometry. Anal Chem 78:5884–92
  • Bonte W, Ruedell E, Sprung R, et al. (1981). Experimentelle Untersuchungen zum Nachweis geringer Dosen hoherer aliphatischer Alkohole in Blut von Versuchsteilnehmern. Blutalkohol 18:399–411
  • Boston WF, Li TK. (1980) Alcohol dehydrogenase. In: Jakoby WB, ed. Enzymatic basis of detoxication. Vol. 1. New York: Academic Press, 231–48
  • Boström H, Vestermark A. (1960). Studies on ester sulphates. 7. On alcohols in the urine of rats. Acta Physiol Scand 48:88–94
  • Brimacombe JS, Foster AB, Hancock EB, et al. (1960). Aspects of stereochemistry. Part III. Acidic and basic hydrolysis of some diol cyclic sulphates and related compounds. J Chem Soc 201–11
  • Burwell RL. (1952). The hydrolysis of optically active secondary butyl hydrogen sulphate. J Am Chem Soc 74:1462–6
  • Burwell RL, Holmquist HE. (1948). A new Walden inversion. J Am Chem Soc 70:878
  • Day CP, Bassendine MF. (1992). Genetic predisposition to alcoholic liver disease. Gut 33:1444–7
  • Dresen S, Weinmann W, Wurst FM. (2004). Forensic confirmatory analysis of ethyl sulphate – a new marker for alcohol consumption – by liquid chromatography/electrospray ionization/tandem mass spectrometry. J Am Soc Mass Spectrom 15:1644–8
  • Dumas JB, Boullay P. (1827). Mémoire sur la formation de l’éther sulfurique. Ann Chim Phys 36:294–310. (J Pharm (1828) 14:1–16.)
  • Edwards DR, Lohman DC, Wolfenden R. (2012). Catalytic proficiency: the extreme case of S–O cleaving sulfatases. J Am Chem Soc 134:525–31
  • Evans PN, Albertson JM. (1917). The ethyl-sulfuric acid reaction. J Am Chem Soc 39:456–61
  • Frobenius SA. (1729). An account of a spiritus vini aethereus, together with several experiments tried therewith. Phil Trans R Soc 36:283–9
  • Frobenius SA, Mortimer C. (1739). Abstracts of the original papers communicated to the Royal Society by Sigismond Augustus Frobenius M.D. concerning his spiritus vini aethereus: Collected by C. Mortimer M.D. Secr. R.S. Phil Trans R Soc 41:864–70
  • Glatt H. (1997). Bioactivation of mutagens via sulfation. FASEB J 11:314–21
  • Haas SL, Ye W, Lohr JM. (2012). Alcohol consumption and digestive tract cancer. Curr Opin Clin Nutr Metabol Care 15:457–67
  • Halter CC, Laengin A, Al-Ahmad A, et al. (2009). Assessment of the stability of the ethanol metabolite ethyl sulphate in standardised degradation tests. Forensic Sci Int 186:52–5
  • Hammond RB, Rumack BH, Rodgerson DD. (1973). Blood ethanol: a report of unusually high levels in a living patient. J Am Med Assoc 226:63–4
  • Helander A, Beck O. (2004). Mass spectrometric identification of ethyl sulphate as an ethanol metabolite in humans. Clin Chem 50:936–7
  • Hennell H. (1826). On the mutual action of sulphuric acid and alcohol, with observations on the composition and properties of the resulting compound. Phil Trans R Soc 116:240–9
  • IARC. (1992). Diethyl sulphate. In: Occupational exposures to mists and vapours from strong inorganic acids and other industrial chemicals: IARC Monographs on the evaluation of carcinogenic risk to humans. Vol. 54. Lyon: World Health Organisation, 213–28
  • Ingleman-Sundberg M, Johansson I. (1984). Mechanism of hydroxyl radical formation and ethanol oxidation by ethanol-inducible and other forms of rabbit liver microsomal cytochromes P-450. J Biol Chem 259:6447–58
  • Jaakonmaki PI, Knox KL, Horning EC, Horning MG. (1967). The characterization by gas-liquid chromatography of ethyl β-D-glucurosiduronic acid as a metabolite of ethanol in rat and man. Eur J Pharmacol 1:63–70
  • Kaiser ET, Panar M, Westheimer FH. (1963). The hydrolysis of some cyclic esters of sulphuric acid. J Am Chem Soc 85:602–7
  • Kamil IA, Smith JN, Williams RT. (1952). A new aspect of ethanol metabolism: isolation of ethyl glucuronide. Biochem J 51:32–3
  • Kaye S, Haag HB. (1957). Terminal blood alcohol concentrations in ninety-four fatal cases of acute alcoholism. J Am Med Assoc 165:451–2
  • Krijgsheld KR, Mulder GJ. (1982). The availability of inorganic sulfate as a rate-limiting factor in the sulfation of xenobiotics in mammals in vivo. In: Mulder GJ, Caldwell J, Van Kempen GMJ, Vonk RJ, eds. Sulfate metabolism and sulfate conjugation. London: Taylor and Francis, 59–66
  • Kurz JL. (1962). Effects of micellization on the kinetics of the hydrolysis of monoalkyl sulfates. J Phys Chem 66:2239–46
  • Kuragi K, Davidson G, Mohammed YI, et al. (2012). Ethanol sulfation by the human cytosolic sulfotransferases: a systematic analysis. Biol Pharm Bull 35:2180–5
  • Laposata M. (1998). Fatty acid ethyl esters: ethanol metabolites which mediate ethanol-induced organ damage and serve as markers of ethanol intake. Prog Lipid Res 37:307–16
  • Laposata M, Lange LG. (1986). Presence of nonoxidative ethanol metabolism in human organs commonly damaged by ethanol abuse. Science 231:497–9
  • Levy G. (1986). Sulfate conjugation in drug metabolism: role of inorganic sulfate. Fed Proc 45:2235–40
  • Lyon ES, Jakoby WB. (1980). The identity of alcohol sulfotransferases with hydroxysteroid sulfotransferases. Arch Biochem Biophys 202:474–81
  • Manautou JE, Carlson GP. (1992). Comparison of pulmonary and hepatic glucuronidation and sulphation of ethanol in rat and rabbit in vitro. Xenobiotica 22:1309–19
  • Moreno A, Cardini CE. (1964). Ethyl β-D-fructofuranoside from wheat germ. Arch Biochem Biophys 108:361–2
  • Mulder GJ, Knoese ED, Meerman JHN. (1988). The generation of reactive intermediates from xenobiotics by sulphate conjugation, and their role in drug toxicity. In: Gorrod JW, Oelschläger H, Caldwell J, eds. Metabolism of xenobiotics. London: Taylor and Francis, 243–50
  • Mulder GJ, Meerman JHN, van der Goorbergh AM. (1986). Bioactivation of xenobiotics by conjugation. In: Paulson GD, Caldwell J, Hutson DH, Menn JJ, eds. Xenobiotic conjugation chemistry. Washington: American Chemical Society, Symposium Series 299:282–300
  • Neubauer O. (1901). Glucuronsäurepaarung bei stiffen der fettreihe. Arch Exp Path Pharmak 46:133–54
  • NTP. (2011). Diethyl sulphate. In: Report on carcinogens. Washington: National Toxicology Program, US Department of Health and Human Services, Public Health Service. 12th edn., vol. 12, 161–3
  • Pelecanos M, Alderson T. (1964). The mutagenic activity of diethyl sulphate in Drosophila melanogaster. 1. The dose-mutagenic response to larval and adult feeding. Mutat Res 106:173–81
  • Perper JA, Twerski A, Wienand JW. (1986). Tolerance at high blood alcohol concentrations: A study of 110 cases and review of the literature. J Forensic Sci 31:212–21
  • Politi I, Morini L, Mari F, Groppi A, Bertol E. (2008). Ethyl glucuronide and ethyl sulphate in autopsy samples 27 years after death. Int J Legal Med 122:507–9
  • Pringsheim J. (1908). Chemisch Untersuchungen über das Wesen der Alkoholtoleranz. Biochem Z 12:143–92
  • Purohit V, Rapaka R, Kwan OS, Song BJ. (2013). Roles of alcohol and tobacco exposure in the development of hepatocellular carcinoma. Life Sci 92:3–9
  • Riches Z, Stanley EL, Bloomer JC, Coughtrie MW. (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
  • Ronis MJJ, Lindross KO, Ingleman-Sundberg M. (1996). The CYP2E subfamily. In: Ioannides C, ed. Cytochromes P450, metabolism and toxicological aspects. Florida: CRC Press, 211–39
  • Schmitt G, Aderjan R, Keller T, Wu M. (1995). Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine. J Anal Toxicol 19:91–4
  • Schneider H, Glatt H. (2004). Sulpho-conjugation of ethanol in humans in vivo and by individual sulphotransferase forms in vitro. Biochem J 383:543–9
  • Schorlemmer C. (1894). The rise and development of organic chemistry. London: Macmillan and Co
  • Sérullas M. (1828). De l’action de l’acide sulfurique sur l’alcool, et des produits qui en résultant. Ann Chim Phys 39:152–86
  • Shammi T, Sai PST. (2001). Esterification of ethanol with sulphuric acid: a kinetic study. Can J Chem Eng 79:54–64
  • Stempnevsky N. (1882). Normal ethyl sulphate. J Chem Soc 42:487–8
  • Stockwell T, Murphy D, Hodgson R. (1983). The severity of alcohol dependence questionnaire; its use, reliability and validity. Brit J Addict 78:145–55
  • Teague C, Holmes E, Maibaum E, et al. (2004). Ethyl glucoside in human urine following dietary exposure: detection by 1H NMR spectroscopy as a result of metabonomic screening of humans. Analyst 129:259–64
  • Teubner W, Meinl W, Florian S, et al. (2007). Identification and localization of soluble sulfotransferases in the human gastrointestinal tract. Biochem J 404:207–15
  • Thierauf A, Serr A, Halter CC, et al. (2008). Influence of preservatives on the stability of ethyl glucuronide and ethyl sulphate in urine. Forensic Sci Int 182:41–5
  • Tomaszewski M, Buchowicz J. (1972). Alcoholysis of the endogenous phosphate esters in rats treated with large doses of ethanol. Biochem J 129:183–6
  • Vestermark A, Boström H. (1959). Studies on ester sulfates. V. On the enzymatic formation of ester sulfates of primary aliphatic alcohols. Exp Cell Res 18:174–7
  • Villiers A. (1880). Sur l’éthérification de l’acide sulfurique. C R Hebd Séanc Acad Sci (Paris) 91:124–7
  • Weitering JG, Krijgsheld KR, Mulder GJ. (1979). The availability of inorganic sulphate as a rate limiting factor in the sulphate conjugation of xenobiotics in the rat? Sulphation and glucuronidation of phenol. Biochem Pharmacol 28:757–62
  • Wetherill CM. (1848). On neutral sulphate of ethyl and its products of decomposition with water. Ann Chem Pharm 66:117–21. (Q J Chem Soc (1849) 1:397–8)
  • Wolfenden R, Yuan Y. (2007). Monoalkyl sulfates as alkylating agents in water, alkylsulfatase rate enhancements, and the ‘energy-rich’ nature of sulphate half-esters. PNAS 104:83–6
  • Woodman J, Young L. (1971). Mercapturic acid formation from sodium alkyl sulphates in the rat. Biochem J 125:78P
  • Zaitschek A. (1897). Chemical equilibrium between ethylic alcohol and sulphuric acid. Z Phys Chem 24:1–12. (J Chem Soc (1898) 74(pt2): 19–20, Abstr.)

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