The biochemistry of aromatic amines. 9. Mercapturic acids as metabolites of aniline and 2-naphthylamine

Boyland, E.; Manson, D.; Nery, Rosane Maria

doi:10.1042/bj0860263

Cited by 46 publications

(25 citation statements)

References 21 publications

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“…However, in the absence of NMR spectroscopic data, the location of the mercapturate on the metabolite cannot be confirmed. This is an interesting conjugate that has been encountered in the 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8. metabolism of anilines and acetanilides in the rat and rabbit (Boyland 1963;Scarfe et al 2002a). Finally, peak 7 gave a mass spectrum consistent with the presence of N-(5-chloro-4-fluoro-2-hydroxyphenyl)acetamide (metabolite X).…”

Section: Metabolite Identificationmentioning

confidence: 98%

Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

et al. 2006

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The metabolic fate of 3-chloro-4-fluoroaniline was investigated in rat following intraperitoneal (i.p.) administration at 5 and 50 mg kg(-1) using a combination of HPLC-MS, HPLC-MS/MS, (19)F-NMR spectroscopy, HPLC-NMR spectroscopy and high-pressure liquid chromatography-inductively coupled plasma mass spectrometry (HPLC-ICPMS) with (35)Cl and (34)S detection. The metabolism of 3-chloro-4-fluoroaniline at both doses was rapid and extensive, to a large number of metabolites, with little unchanged compound excreted via the urine. Dosing at 5 mg kg(-1) with [(14)C]-labelled compound enabled the comparison of standard radioassay analysis methods with (19)F-NMR spectroscopy. (19)F-NMR resonances were only readily detectable in the 0-12 h post-dose samples. Dosing at 50 mg kg(-1) allowed the facile and specific detection and quantification of metabolites by (19)F-NMR spectroscopy. Metabolite profiling was also possible at this dose level using HPLC-ICPMS with (35)Cl-specific detection. The principal metabolites of 3-chloro-4-fluoroaniline were identified as 2-amino-4-chloro-5-fluorophenyl sulfate and 2-acetamido-4-chloro-5-fluorophenyl glucuronide. N-acetylation and hydroxylation followed by O-sulfation were the major metabolic transformations observed.

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Section: Metabolite Identificationmentioning

confidence: 98%

Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

et al. 2006

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“…Two mercapturic acids have been identified in the urine of animals dosed with 2-naphthylamine1 a compound that causes bladder tumors (Boyland, Manson, and Nery, 1963;Boyland and Manson, 1966). One is N-acetyl-S-(Zacetamido-5,6-dihydro-6-hydroxy-5-naphthyl)-~-cysteine (42) and is probably formed through an intermediate epoxide.…”

Section: A Arylaminesmentioning

confidence: 99%

“…The second mercapturic acid probably arises through the formation of an intermediate, 2-naphthylhydroxylamine (43), which, after conjugation with glutathione and rearrangement, yields the mercapturic acid (44) (Boyland, Manson, and Nery, 1963). After administration of the analgesic, acetophenetidine, 27& was metabolized in man to the cysteine derivative (45) (Jagenburg and Toczko, 1964).…”

Section: H O P~mentioning

confidence: 99%

The Role of Glutathione and Glutathione S‐Transferases in Mercapturic Acid Biosynthesis

Boyland¹,

Chasseaud²

1969

Advances in Enzymology - And Related Areas of Molecular Biology

332

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“…The Rp values are given in Tables 1 and 2. Compounds were detected on chromatograms with the reagents described by Boyland, Manson & Nery (1963). Colour reactions are given in Table 3.…”

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confidence: 99%

The biochemistry of aromatic amines. 2-Formamido-1-naphthyl hydrogen sulphate, a metabolite of 2-naphthylamine

Boyland¹,

Manson²

1966

Biochemical Journal

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1. 2-Formamido-1-naphthyl hydrogen sulphate is excreted by dogs and rats dosed with 2-naphthylamine or with 2-amino-1-naphthyl hydrogen sulphate and was isolated from dog urine. 2. 2-Formamido-1-naphthol, naphtho[2,1-d]oxazole and N-formyl-2-naphthylhydroxylamine are excreted as (2-formamido-1-naphthyl glucosid)uronic acid. 2-Formamidonaphthalene is converted into conjugates of 2-amino-6-naphthol and 2-amino-8-naphthol, but 2-methylaminonaphthalene is excreted as 2-amino-1-naphthyl hydrogen sulphate and its N-methyl and N-formyl derivatives and (2-amino-1-naphthyl glucosid)uronic acid. 3. 2-Methylamino-1-naphthyl hydrogen sulphate is converted into 2-formamido-1-naphthyl hydrogen sulphate and 2-amino-1-naphthyl hydrogen sulphate on charcoal. 2-Amino-1-naphthyl hydrogen sulphate and formaldehyde react on charcoal to yield 2-methylamino- and 2-formamido-1-naphthyl hydrogen sulphate. 4. 2-Formamido-1-naphthol, 2-formamido-1-naphthyl hydrogen sulphate, N-formyl-2-naphthylhydroxylamine and N-formyl-2-naphthylhydroxylamine-O-sulphonic acid were synthesized.

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The biochemistry of aromatic amines. 9. Mercapturic acids as metabolites of aniline and 2-naphthylamine

Cited by 46 publications

References 21 publications

Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

The Role of Glutathione and Glutathione S‐Transferases in Mercapturic Acid Biosynthesis

The biochemistry of aromatic amines. 2-Formamido-1-naphthyl hydrogen sulphate, a metabolite of 2-naphthylamine

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The biochemistry of aromatic amines. 9. Mercapturic acids as metabolites of aniline and 2-naphthylamine

Cited by 46 publications

References 21 publications

Metabolism of 3-chloro-4-fluoroaniline in rat using [14C]-radiolabelling,19F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

Metabolism of 3-chloro-4-fluoroaniline in rat using [14C]-radiolabelling,19F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

The Role of Glutathione and Glutathione S‐Transferases in Mercapturic Acid Biosynthesis

The biochemistry of aromatic amines. 2-Formamido-1-naphthyl hydrogen sulphate, a metabolite of 2-naphthylamine

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Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR

Metabolism of 3-chloro-4-fluoroaniline in rat using [¹⁴C]-radiolabelling,¹⁹F-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR