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Acrylamide is metabolized to glycidamide in the rat: evidence from hemoglobin adduct formation
Abstract
Acrylamide is an important industrial chemical which is neurotoxic to experimental animals as well as humans and recently has been shown to be mutagenic and carcinogenic. Despite much research it is still unclear whether the parent compound or a metabolite is responsible for the observed toxic effects. Contradictory results as to the role of cytochrome P-450 mediated metabolism of acrylamide in the induction of neurotoxic effects prompted us to investigate the possible formation of glycidamide, a reactive epoxide metabolite. The formation of this epoxide was strongly indicated by the identification by means of gas chromatography-mass spectrometry of derivatized S-(2-carboxy-2-hydroxyethyl)cysteine in hydrolyzed hemoglobin samples from rats treated with acrylamide in vivo and in microsomal suspensions of acrylamide with cysteine in vitro. This amino acid was found to be present in uninduced and phenobarbital-induced Sprague-Dawley rats and absent in controls, but occurred in lower amounts than the adduct derived from the parent compound, S-(2-carboxyethyl)cysteine. This finding suggests that the possible role of glycidamide in the neurotoxicity and carcinogenicity of acrylamide should be evaluated further.
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Cited by
Scientific Opinion on acrylamide in food
(CONTAM), E. P. O. C. I. T. F. C. (2015) · EFSA Journal · doi:10.2903/j.efsa.2015.4104 · Cited by 828
Human exposure and internal dose assessments of acrylamide in food
Dybing, E., Farmer, P. B., Andersen, M., Fennell, T. R., Lalljie, S. P. D., Müller, D. J. G., Olin, S., Petersen, B. J., Schlatter, J., Scholz, G., et al. (2005) · Food and Chemical Toxicology · doi:10.1016/j.fct.2004.11.004 · Cited by 395
The Carcinogenicity of Acrylamide
Rice, J. M. (2005) · Mutation Research/Genetic Toxicology and Environmental Mutagenesis · doi:10.1016/j.mrgentox.2004.09.008 · Cited by 329
Acrylamide: Review of Toxicity Data and Dose-Response Analyses for Cancer and Noncancer Effects
Shipp, A., Lawrence, G., Gentry, R., McDonald, T., Bartow, H., Bounds, J., Macdonald, N., Clewell, H., Allen, B., & Van Landingham, C. (2006) · Critical Reviews in Toxicology · doi:10.1080/10408440600851377 · Cited by 305
Acrylamide: a review of its genotoxicity and an assessment of heritable genetic risk
Dearfield, K. L., Douglas, G. R., Ehling, U. H., Moore, M. M., Sega, G. A., & Brusick, D. J. (1995) · Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis · doi:10.1016/0027-5107(95)00037-j · Cited by 303
Metadata
- Authors
- Calleman, C. J., Bergmark, E., & Costa, L. G.
- Venue
- Chemical Research in Toxicology
- Publisher
- American Chemical Society (ACS)
- Published
- 1990-09
- Volume
- 3
- Issue
- 5
- Pages
- 406-412
- ISSN
- 0893-228X (ISSN-L)
- 1520-5010
- OpenAlex
- W1980655248
- Cited by
- 165
- References
- 0
- FWCI
- 10.06
- Type
- journal article
- Language
- en
- Open access
- closed
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