Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats

H. M. Bolt; G. Schmiedel; J. G. Filser; H. P. Rolzhäuser; K. Lieser; D. Wistuba; V. Schurig

doi:10.1007/BF00395388

Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats

H. M. Bolt, G. Schmiedel, J. G. Filser, H. P. Rolzhäuser, K. Lieser, D. Wistuba, V. Schurig

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

When 1,3-butadiene is incubated with rat liver microsomes and NADPH both enantiomers of vinyl oxirane are formed, the amount of epoxide being dependent on incubation time, microsomal protein, and substrate concentration. Inhibition by SKF 525 A or dithiocarb as well as induction by pretreatment with phenobarbital or 20-methylcholanthrene suggest participation of cytochrome P-450 in this reaction. The amount of epoxide is enhanced by addition of 1,1,1-trichloropropene oxide and reduced by glutathione, especially in the presence of hepatic cytosol. When rats are exposed to 1,3-butadiene in a closed chamber (conditions of maximal metabolism) vinyl oxirane is exhaled and can be quantitatively determined from the gas phase. The concurrent exhalation of acetone is consistent with the idea of biologic action of a reactive metabolite.

Original language	English
Pages (from-to)	112-116
Number of pages	5
Journal	Journal of Cancer Research and Clinical Oncology
Volume	106
Issue number	2
DOIs	https://doi.org/10.1007/BF00395388
State	Published - Oct 1983
Externally published	Yes

Keywords

1,3-butadiene
Epoxide enantiomers
Vinyl oxirane

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/BF00395388

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title = "Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats",

abstract = "When 1,3-butadiene is incubated with rat liver microsomes and NADPH both enantiomers of vinyl oxirane are formed, the amount of epoxide being dependent on incubation time, microsomal protein, and substrate concentration. Inhibition by SKF 525 A or dithiocarb as well as induction by pretreatment with phenobarbital or 20-methylcholanthrene suggest participation of cytochrome P-450 in this reaction. The amount of epoxide is enhanced by addition of 1,1,1-trichloropropene oxide and reduced by glutathione, especially in the presence of hepatic cytosol. When rats are exposed to 1,3-butadiene in a closed chamber (conditions of maximal metabolism) vinyl oxirane is exhaled and can be quantitatively determined from the gas phase. The concurrent exhalation of acetone is consistent with the idea of biologic action of a reactive metabolite.",

keywords = "1,3-butadiene, Epoxide enantiomers, Vinyl oxirane",

author = "Bolt, \{H. M.\} and G. Schmiedel and Filser, \{J. G.\} and Rolzh{\"a}user, \{H. P.\} and K. Lieser and D. Wistuba and V. Schurig",

year = "1983",

month = oct,

doi = "10.1007/BF00395388",

language = "English",

volume = "106",

pages = "112--116",

journal = "Journal of Cancer Research and Clinical Oncology",

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T1 - Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats

AU - Bolt, H. M.

AU - Schmiedel, G.

AU - Filser, J. G.

AU - Rolzhäuser, H. P.

AU - Lieser, K.

AU - Wistuba, D.

AU - Schurig, V.

PY - 1983/10

Y1 - 1983/10

N2 - When 1,3-butadiene is incubated with rat liver microsomes and NADPH both enantiomers of vinyl oxirane are formed, the amount of epoxide being dependent on incubation time, microsomal protein, and substrate concentration. Inhibition by SKF 525 A or dithiocarb as well as induction by pretreatment with phenobarbital or 20-methylcholanthrene suggest participation of cytochrome P-450 in this reaction. The amount of epoxide is enhanced by addition of 1,1,1-trichloropropene oxide and reduced by glutathione, especially in the presence of hepatic cytosol. When rats are exposed to 1,3-butadiene in a closed chamber (conditions of maximal metabolism) vinyl oxirane is exhaled and can be quantitatively determined from the gas phase. The concurrent exhalation of acetone is consistent with the idea of biologic action of a reactive metabolite.

AB - When 1,3-butadiene is incubated with rat liver microsomes and NADPH both enantiomers of vinyl oxirane are formed, the amount of epoxide being dependent on incubation time, microsomal protein, and substrate concentration. Inhibition by SKF 525 A or dithiocarb as well as induction by pretreatment with phenobarbital or 20-methylcholanthrene suggest participation of cytochrome P-450 in this reaction. The amount of epoxide is enhanced by addition of 1,1,1-trichloropropene oxide and reduced by glutathione, especially in the presence of hepatic cytosol. When rats are exposed to 1,3-butadiene in a closed chamber (conditions of maximal metabolism) vinyl oxirane is exhaled and can be quantitatively determined from the gas phase. The concurrent exhalation of acetone is consistent with the idea of biologic action of a reactive metabolite.

KW - 1,3-butadiene

KW - Epoxide enantiomers

KW - Vinyl oxirane

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DO - 10.1007/BF00395388

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AN - SCOPUS:0021056672

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VL - 106

SP - 112

EP - 116

JO - Journal of Cancer Research and Clinical Oncology

JF - Journal of Cancer Research and Clinical Oncology

IS - 2

ER -

Biological activation of 1,3-butadiene to vinyl oxirane by rat liver microsomes and expiration of the reactive metabolite by exposed rats

Abstract

Keywords

UN SDGs

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