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Xenobiotica
the fate of foreign compounds in biological systems
Volume 45, 2015 - Issue 12
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General Xenobiochemistry

S-carboxymethyl-l-cysteine and it (R/S)-S-oxides in beagle dog plasma and hepatic cytosol

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Pages 1047-1053 | Received 23 Feb 2015, Accepted 15 Apr 2015, Published online: 11 Jun 2015

References

  • Aiache JM, Borel JP, Kantelip JP. (1982). Comparative bioavailability of S-carboxymethyl-l-cysteine from two dosage forms: hard gelatin capsule and syrup. Biopharm Drug Dispos 9:275–81
  • Baines PJ, Bray HG, James SP. (1977). Mercapturic acid formation in the developing rat. Xenobiotica 7:653–63
  • Barnsley EA. (1964). The metabolism of S-methyl-l-cysteine in the rat. Biochem Biophys Acta 90:24–36
  • Barnsley EA, Grenby TH, Young L. (1966). The metabolism of 1- and 2-bromopropane in rats. Biochem J 100:282–88
  • Barnsley EA, Thompson AER, Young L. (1964). The biosynthesis of ethyl mercapturic acid sulphoxide. Biochem J 90:588–96
  • Barnsley EA, Eskin NAM, James SP, Waring RH. (1969). The acetylation of S-alkylcytseines by the rat. Biochem Pharmacol 18:2393–401
  • Bi HC, Zhong GP, Huang M, et al. (2005). Bioequivalence evaluation of two tablet formulations of carbocysteine in healthy Chinese men. J Appl Res 5:598–604
  • Boonyapiwat B. Forbes B, Steventon GB. (2004). Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. Anal Biochem 335:91–7
  • Boonyapiwat B, Panagopoulos P, Jones H, et al. (2005). Phenylanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-l-cysteine in HepG2 cells. Drug Metab Drug Interact 21:1–18
  • Boonyapiwat B, Forbes B, Mitchell SC, Steventon GB. (2008). Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-l-cysteine by human cytosolic fractions. Drug Metab Drug Interact 23:261–82
  • Boonyapiwat B, Panaretou B, Forbes B, et al. (2009). Human phenylalanine monooxygenase and thioether metabolism. J Pharm Pharmacol 61:63–7
  • Bradford MM. (1976). A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–54
  • Brandolini L, Allegeretti M, Berdini V, et al. (2003). Carbocysteine lysine salt monohydrate (SCMC-LYS) is a selective scavenger of reactive oxygen intermediates (ROIs). Eur Cytokine Netw 14:20–6
  • Brockmöller J, Staffeldt B, Root I. (1991). Evaluation of proposed sulphoxidation pathways of carbocysteine in man by HPLC quantification. Eur J Clin Pharmacol 40:387–92
  • Damani LA. (1989). Thioethers, thiols, dithioic acids and disulphides: phase I reactions. In: Damani LA, ed. Sulphur containing drugs and related organic compounds. Vol. 1A. Chichester, UK: Ellis Horwood Ltd, 135–50
  • De Person M, Chaimbault P, Elfakir C. (2008). Analysis of native amino acids by liquid chromatography/electrospray ionization mass spectrometry: comparative study between two sources and interfaces. J Mass Spectrom 43:204–15
  • Dysko RC, Nezek JA, Levin SI, et al. (2002). Biology and diseases of dogs. In: Fox JG, Anderson LC, Loew FM, Quimby FW, eds. Laboratory animal medicine. 2nd edn. Amsterdam: Academic Press, 395–458
  • Finsterer U, Prucksunand P, Brechtelsbauer H. (1973). Critical evaluation of methods for determination of blood volume in the dog. Pflügers Arch 341:63–72
  • Ford RB. (1990). Chronic lung disease in old dogs and cats. Vet Rec 126:399–402
  • Gibson JG, Keeley JL, Pijoan M. (1938). The blood volume of normal dogs. Am J Physiol 121:800–6
  • Goreish AH, Bednar S, Jones H, et al. (2004). Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-l-cysteine. Drug Metab Drug Interact 20:159–74
  • Hall BE, James SP. (1986). Mercapturic acid formation in the marmoset (Callithrix jacchus). Xenobiotica 16:609–14
  • Herbrandson HF, Dickerson Jr RT. (1959). Derivatives of aromatic sulfinic acids. III. Evidence for the hydrogen dichloride ion from epimerization reactions. J Am Chem Soc 81:4102–6
  • Hooper C, Calvert J. (2008). The role for S-carboxymethylcycteine (carbocisteine) in the management of chronic obstructive pulmonary disease. Internat J COPD 3:659–69
  • Hooper Jr J, Tabor H, Winkler AW. (1944). Simultaneous measurement of the blood volume in man and dog by means of Evans blue dye, T1824, and by means of carbon monoxide. 1. Normal subjects. J Clin Invest 23:628–35
  • James SP, Needham D. (1973). Some metabolites of S-pentyl-l-cysteine in the rabbit and other species. Xenobiotica 3:207–18
  • Jones AR, Walsh DA. (1980). The fate of S-propylcysteine in the rat. Xenobiotica 10:827–834
  • Kaufman S, Mason K. (1982). Specificity of amino acids as activators and substrates for phenylalanine hydroxylase. J Biol Chem 257:14667–78
  • Kodama H, Ohmori M, Suzuki M, Mizuhara S. (1970). New sulphur containing amino acids in the urine of cystathioninuric patients: supplementary data. Physiol Chem Phys 2:287–92
  • Krause RJ, Glocke SC, Elfarra AA. (2002). Sulfoxides as urinary metabolites of S-allyl-l-cysteine in rats: Evidence for the involvement of flavin-containing monooxygenases. Drug Metab Dispos 30:1137–42
  • Kukanich B, Coetzee JF, Gehring R, Hubin M. (2007). Comparative disposition of pharmacological markers for cytochrome P-450 mediated metabolism, glomerular filtration rate, and extracellular and total body fluid volume of Greyhound and Beagle dogs. J Vet Pharmacol Ther 30:314–19
  • Kunugiyama I, Ito N, Furukawa Y. (1989). Determination of blood volume in dogs using an enriched stable isotope 50Cr. Nihon Juigaku Zasshi 51:855–60
  • Macció A, Madeddu C, Panzone F, Mantovani G. (2009). Carbocysteine: clinical experience and new perspectives in the treatment of chronic inflammatory diseases. Expert Opin Pharmacother 10:693–703
  • Meese CD. (1987). S-carboxymethyl-l-cystein-(R)- un (S)-Sulphoxid. Arch Pharm (Weinheim) 320:473–74
  • Meese CO, Specht D, Hofmann U. (1990). Syntheses of metabolites of S-carboxymethyl-l-cysteine and S-methyl-l-cysteine and of some isotopically labelled (2H, 13C) analogues. Arch Pharm (Weinheim) 323:957–65
  • Meese CO, Specht D, Ratge D, et al. (1993). High-performance liquid chromatographic and carbon-13 nuclear magnetic resonance spectrometric determination of S-carboxymethyl-l-cysteine and its metabolites in human urine. Fresenius J Anal Chem 346:837–40
  • Mikolajczk M, Drabowicz J, Kielbasiński P. (1997). Chiral sulfoxides. Chiral sulfur reagents: applications in asymmetric and stereoselective synthesis. New York: CRC Press
  • Mislow K, Simmons T, Melillo JT, Ternay AL. (1964). The hydrogen chloride-catalysed racemization of sulfoxides. J Am Chem Soc 86:1452–3
  • Mitchell SC, Steventon GB. (2006). Drug metabolism and toxicity: hijacking enzymes of intermediary metabolism. Curr Top Toxicol 3:57–63
  • Mitchell SC, Steventon GB. (2012). S-Carboxymethyl-l-cysteine. Drug Metab Rev 14:129–47
  • Mitchell SC, Nickson RM. (1993). Metabolism of sulphur-containing xenobiotics. Sulfur Rep (J Sulfur Chem) 13:161–95
  • Mitchell SC, Waring RH. (1985–86). The early history of xenobiotic sulfoxidation. Drug Metab Rev 16:255–84
  • Mitchell SC, Smith RL, Waring RH, Aldington GF. (1984). The metabolism of S-methyl-l-cysteine in man. Xenobiotica 14:767–79
  • Oae S, Kitao T, Kitaoka Y. (1961). Oxygen exchange reaction of sulfoxides in sulphuric acid. Chem Ind (London) 291–2
  • Padrid P. (1992). Chronic lower airway disease in the dog and cat. Probl Vet Med 4:320–44
  • Panagopoulos P. (2008). The metabolism and pharmacokinetics of S-carboxymethyl-l-cysteine in large mammalian species [dissertation]. King’s College London, UK
  • Panagopoulos P, Forbes B, Mitchell SC, Steventon GB. (2010). The pharmacokinetics of orally administered S-carboxymethyl-l-cysteine in the dog, calf and sheep. Eur J Pharm Sci 39:219–23
  • Patel GL, Illoudi C, Boonyapiwat B, et al. (2008). Enzyme kinetic and molecular modelling studies of sulphur containing substrates of phenylalanine 4-monooxygenase. J Enzyme Inhib Med Chem 23:958–63
  • Pears J, Jung RT, Burchell A. (1989). Amiloride activation of hepatic microsomal glucose-6-phosphatase; activation of T1? Biochim Biophys Acta 993:224–27
  • Phillips H. (1925). Investigations on the dependence of rotatory power on chemical constitution. Part XXVII. The optical properties of n-alkyl-p-toluenesulphinates. J Chem Soc Trans 127:2552–87
  • Piraud M, Viany-Saban C, Petritis K, et al. (2003). ESI-MS/MS analysis of underivatised amino acids: a new tool for the diagnosis of inherited disorders of amino acid metabolism. Fragmentation study of 79 molecules of biological interest in positive and negative ionisation mode. Rapid Commun Mass Spectrom 17:1297–311
  • Ripp SL, Overby LH, Philpot RM, Elfarra AA. (1997). Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin-containing mono-oxygenases: studies with S-(1,2-dichlorovinyl)-l-cysteine, S-(1,2,2-trichlorovinyl)-l-cysteine, S-allyl-l-cysteine, and S-benzyl-l-cysteine. Mol Pharmacol 51:507–15
  • Ruff F, Jalsovszky I, Szabó D, et al. (2012). Mechanism for the reactions of sulphides and sulfoxides with hypochlorites: racemization and oxygen exchange of oxysulfonium salts and sulfoxides. J Phys Org Chem 25:1086–96
  • Sausen PJ, Elfarra AA. (1990). Cysteine conjugate S-oxidase. Characterization of a novel enzymatic activity in rat hepatic and renal microsomes. J Biol Chem 265:6139–45
  • Schon HJ, Grgurin M, Klune G, et al. (1994). Effects of hypolipidaemics ceteban and clofibrate on mitochondrial and peroxisomal enzymes of rat liver. J Pharm Pharmacol 46:144–7
  • Servin A. (1977). Demonstration of an enterohepatic cycle for S-carboxymethylcysteine. C R Séanc Soc Biol 171:39–42
  • Sklan NM, Barnsley EA. (1968). The metabolism S-methyl-l-cysteine. Biochem J 107:217–23
  • Slauson DO, Han FF. (1980). Criteria for development of animal models of disease of the respiratory system: the comparative approach in respiratory disease model development. Am J Pathol 101:S103–22
  • Staffeldt B, Brockmöller I, Roots I. (1991). Determination of S-carboxymethyl-l-cysteine and some of its metabolites in urine and serum by high-performance liquid chromatography using fluorescence pre-column labelling. J Chromatogr Biomed Appl 571:133–47
  • Steventon GB, Mitchell SC. (2009a). Measurement of phenylalanine monooxygenase (PAH) activities. Curr Protoc Toxicol 4.29:1–11
  • Steventon GB, Mitchell SC. (2009b). Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates. J Biochem Mol Toxicol 23:119–124
  • Steventon GB, Mitchell SC, Pérez B, et al. (2009). The activity of wild type and mutant phenylalanine hydroxylase with respect to the C-oxidation of phenylalanine and the S-oxidation of S-carboxymethyl-l-cysteine. Mol Gen Metab 96:27–31
  • Taylor KL, Ziegler DM. (1987). Studies on substrate specificity of the hog liver flavin-containing monooxygenases: anionic organic sulphur compounds. Biochem Pharmacol 36:141–6
  • Turnbull LB, Teng L, Kinzie JM, et al. (1978). Excretion and biotransformation of carboxymethyl-cysteine in rat, dog, monkey and man. Xenobiotica 8:621–8
  • Ubuka T, Kodama H, Mizuhara S. (1967). Isolation of S-(carboxymethyl)cysteine from urine. Biochim Biophys Acta 141:266–9
  • Wamberg S, Sandgaard NCF, Bie P. (2002). Simultaneous determination of total body water and plasma volume in conscious dogs by the indicator dilution principle. J Nutr 132:17115–35
  • Waring RH. (1978). The metabolism of S-carboxymethylcysteine in rodents, marmosets and man. Xenobiotica 8:265–70
  • Waring RH, Mitchell SC, O’Gorman J, Fraser M. (1986). Cytosolic sulphoxidation of S-carboxymethyl-l-cysteine in mammals. Biochem Pharmacol 35:2999–3002
  • Wolf AV. (1950). Osmometric analysis of thirst in man and dog. Am J Physiol 161:75–86
  • Wróbel JT, Bielawska H, Iwanow A, Ruszkowska J. (1980). Sulfur containing nuphar alkaloids. In: Cavallini D, Gaull GE, Zappia V, eds. Natural sulfur compounds: novel biochemical and structural aspects. New York: Plenum Press, 353–60
  • Zeng J, Davies MJ. (2005). Evidence for the formation of adducts and S-(carboxymethyl) cysteine on reaction of α-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. Chem Res Toxicol 18:1232–41
  • Zeng J, Dunlop RA, Rodgers KJ, Davies MJ. (2006). Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols. Biochem J 398:197–206
  • Ziegle K, Wenz A. (1934). Stereochemische studien: 1. Die Racemisation optisch aktiver Sulfinsäureester. JL Ann Chem 511:109–20
  • Ziegler DM. (1980). Microsomal flavin-containing monooxygenases: oxygenation of nucleophilic nitrogen and sulphur compounds. In: Jakoby WB, ed. Enzymatic basis of detoxication. Vol. I. New York: Academic Press, 201–27
  • Ziegler DM. (1989). S-Oxygenases I. Chemistry and biochemistry. In: Damani LA, ed. Sulphur containing drugs and related organic compounds. Vol. 2A, Chichester UK: Ellis Horwood Ltd, 53–66

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