In vitro metabolism and toxicity assessment of N-methylcarbazole in primary cultured rat hepatocytes

Yang, Wei; Jiang, T.; Davis, Patrick J.; Acosta, Daniel

doi:10.1016/0300-483x(91)90071-8

Cited by 10 publications

References 17 publications

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Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290

Waldau

Mikolasch

Lalk

et al. 2009

Appl Microbiol Biotechnol

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Different 9H-carbazole derivatives have been investigated within the last decades due to their broad range of pharmacological applications. While the metabolism of 9H-carbazole has previously been reported, nothing was known about the bacterial transformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole. Thus, for the first time, the bacterial biotransformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole was analyzed using biphenyl-grown cells of Ralstonia sp. strain SBUG 290 expressing biphenyl 2,3-dioxygenase. This strain accumulated 3-hydroxy-1,2,3,5,6,7,8,9-octahydrocarbazol-4-one and 6'-iminobicyclohexylidene-2',4'-dien-2-one as major products during the incubation with 2,3,4,9-tetrahydro-1H-carbazole. Carbazol-9-yl-methanol was verified as the primary oxidation product of 9-methyl-9H-carbazole. In addition, 9H-carbazol-1-ol, 9H-carbazol-3-ol, and 3-hydroxy-1,2,3,9-tetrahydrocarbazol-4-one where detected in lower concentrations during the transformation of carbazol-9-yl-methanol and 9-methyl-9H-carbazole. Products were identified by high-performance liquid chromatography, gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, as well as (1)H and (13)C nuclear magnetic resonance analyses.

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