Identification of new sulfur-containing metabolites of naphthalene in mouse urine
Stillwell, WG; Horning, MG; Griffin, GW; Tsang, WS
HERO ID
32865
Reference Type
Journal Article
Year
1982
Language
English
PMID
| HERO ID | 32865 |
|---|---|
| In Press | No |
| Year | 1982 |
| Title | Identification of new sulfur-containing metabolites of naphthalene in mouse urine |
| Authors | Stillwell, WG; Horning, MG; Griffin, GW; Tsang, WS |
| Journal | Drug Metabolism and Disposition |
| Volume | 10 |
| Issue | 6 |
| Page Numbers | 624-631 |
| Abstract | Seven acidic sulfur-containing metabolites were isolated from mouse urine following administration of naphthalene. The metabolites have been identified as (1-hydroxy-1,2-dihydro-2-naphthalenylthio)acetic acid (I), 2-hydroxy-3-(1-hydroxy-1,2-dihydro-2-naphthalenylthio)propanoic acid (II), (1,2,3-trihydroxy-1,2,3,4-tetrahydro-4-naphthalenylthio)acetic acid (III), and N-acetyl-S-(1-hydroxy-1,2-dihydro-2-naphthalenyl)-L-cysteine (IV). The dehydration products of I, II, and IV, namely 1-(naphthalenylthio)acetic acid (V), 2-hydroxy-3-(1-naphthalenylthio)propanoic acid (VI), and N-acetyl-S-(1-naphthalenyl)-L-cysteine (VII), respectively, were also present in several urinary extracts. Nine methylthio derivatives were identified in the neutral extract of urine. These metabolites were the following: 1-methylthionaphthalene, trans-1-hydroxy-2-methylthio-1,2-dihydronaphthalene, two stereoisomeric 1,2,3-trihydroxy-4-methylthio-1,2,3,4-tetrahydronaphthalenes, 1,3-di(methylthio)-2,4-dihydroxy-1,2,3,4-tetrahydronaphthalene, 1,4-di(methylthio)-2,3-dihydroxy-1,2,3,4-tetrahydronaphthalene, two methylthiohydroxy-naphthalenes, and a methylthiodihydroxydihydronaphthalene. Following intraperitoneal administration of N-acetyl-S-(1-hydroxy-1,2-dihydro-2-naphthalenyl)-L-cysteine to mice, the acidic metabolites I, II, and unchanged IV were found. The gas-chromatographic and gas chromatographic-mass spectral properties of the methyl ester-trimethylsilyl derivatives of the acidic sulfur metabolites of naphthalene are presented. |
| Pmid | 6130911 |
| Wosid | WOS:A1982PT97300012 |
| Url | <Go to ISI>://WOS:A1982PT97300012 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Drug Metab. Dispos. 10: 624-631. |
| Is Public | Yes |
| Language Text | English |
| Keyword | naphthalene; Toxicology Abstracts; metabolism; X 24190:Polycyclic hydrocarbons |
| Is Qa | No |