Preparation, isolation, analysis, and characterization of 3-benzo[a]pyrenyl-β-d-glucopyranosiduronic acid: A metabolite of 3-hydroxybenzo[a]pyrene with potentially high carcinogenic activity

Johnson, D. Barrie; Engel, James F.; Murrill, Evelyn E.; Guire, Patrick E.; Barker, Charles W.; Bardwell, Cindy M.; Shan, Alice; Swanson, Melvin J.; Stone-Heurner, Jacqueline G.

doi:10.1016/0003-2697(78)90824-2

Analytical Biochemistry

1978

DOI: 10.1016/0003-2697(78)90824-2

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Preparation, isolation, analysis, and characterization of 3-benzo[a]pyrenyl-β-d-glucopyranosiduronic acid: A metabolite of 3-hydroxybenzo[a]pyrene with potentially high carcinogenic activity

D. Barrie Johnson¹,

James F. Engel²,

Evelyn E. Murrill³

et al.

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Cited by 4 publications

References 7 publications

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Benzo[a]pyrene glucuronide and sulfate conjugate characterization by field desorption mass spectrometry

Deutsch

Gelboin

1982

Biol. Mass Spectrom.

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The field desorption mass spectral behaviour of benzo[a]pyrene metabolites were studied. Each of the phenol, diol, quinone and diol-epoxide metabolites of benzo[a]pyrene showed a single peak corresponding to the molecular ion. The water soluble glucuronides and sulfate conjugated metabolites showed protonated and cationized molecular ions. With the glucuronides, three peaks were observed and the abundance of these peaks may be indicators for characterization of the three isomeric glucuronides.

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Benzo[a]pyrene glucuronide and sulfate conjugate characterization by field desorption mass spectrometry

Deutsch

Gelboin

1982

Biol. Mass Spectrom.

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Investigations on antipyrine metabolism: II—Analysis of conjugated metabolites of antipyrine in rat and human urine by off-line combination of liquid chromatography and field desorption mass spectrometry

Lehmann

Böttcher

Bässmann

et al. 1982

Biol. Mass Spectrom.

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The complex pattern of conjugates in the metabolism of antipyrine in man and rat has been investigated using an off-line combination of liquid chromatography and field desorption mass spectrometry. Using this approach, field desorption mass spectrometry enables the direct identification of underivatized glucuronides and sulphates in antipyrine metabolism on the basis of the corresponding protonated or cationized molecules representing the base peaks in the field desorption mass spectra. All conjugated metabolites of antipyrine established so far--four glucuronides and three sulphates--were identified in extracts of urine after stepwise purification by column chromatography and subsequent mass spectrometric analysis.

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Glucuronidation of Lipophilic Substrates: Preparation of 3-Benzo[a]pyrenyl-β-D-glucopyranosiduronic Acid in Multimilligram Quantities by Microsomal UDP-Glucuronyl Transferase

Db¹,

Mj²,

Cw³

et al. 1979

Preparative Biochemistry

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A convenient method for the enzymic conversion of multimilligram quantities of 3-hydroxybenzo[a]pyrene to 3-benzo[a]pyrenyl-beta-D-glucopyranosiduronic acid in 90% yield is described. Commercially available freeze-dried rabbit liver microsomes were incubated in the presence of UDPGA, 3-hydroxybenzo[a]pyrene, and Triton X-100 detergent (Figure 1). The course of the biosynthetic reaction was followed by fluorimetry. The glucuronide product was extracted from the acidified incubation supernate with ethyl acetate and the acid function of the glucuronide was utilized in an acid-base extraction procedure to purify the glucuronide from biological and unreacted starting material. The glucuronide precipitated from ethyl acetate and was collected by centrifugation. High pressure liquid chromatography and spectroscopic techniques were used to verify the structure and purity of 3-benzo[a]pyrenyl-beta-D-glucopyranosiduronic acid.

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Preparation, isolation, analysis, and characterization of 3-benzo[a]pyrenyl-β-d-glucopyranosiduronic acid: A metabolite of 3-hydroxybenzo[a]pyrene with potentially high carcinogenic activity

Cited by 4 publications

References 7 publications

Benzo[a]pyrene glucuronide and sulfate conjugate characterization by field desorption mass spectrometry

Benzo[a]pyrene glucuronide and sulfate conjugate characterization by field desorption mass spectrometry

Investigations on antipyrine metabolism: II—Analysis of conjugated metabolites of antipyrine in rat and human urine by off-line combination of liquid chromatography and field desorption mass spectrometry

Glucuronidation of Lipophilic Substrates: Preparation of 3-Benzo[a]pyrenyl-β-D-glucopyranosiduronic Acid in Multimilligram Quantities by Microsomal UDP-Glucuronyl Transferase

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