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Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate

Cited 59 time in Web of Science Cited 55 time in Scopus
Authors
Park, Kwang-Kyun; Surh, Young-Joon; Stewart, Bradley C.; Miller, James A.
Issue Date
1990-06
Citation
Biochemical and Biophysical Research Communications, Vol.169 No.3, pp.1094-1098
Abstract
Vinyl carbamate reacted with dimethyldioxirane in dry acetone to give a high yield of pure crystalline vinyl carbamate epoxide. This epoxide was characterized by its NMR and MS spectra and elementary analysis. It is unstable at room temperature and has a half-life in water solution of approximately 32 minutes. It reacts with adenosine to form 1,N6-ethenoadenosine and more of this etheno nucleoside was found in hydrolysates of hepatic RNA of male mice injected i.p. with the epoxide than with vinyl carbamate. Tests with Salmonella typhimurium TA1535 showed that this epoxide is a strong direct mutagen. It is also more toxic in the mouse than vinyl carbamate. Studies on the carcinogenicity of this epoxide are in progress. © 1990.
ISSN
0006-291X
URI
https://hdl.handle.net/10371/172686
DOI
https://doi.org/10.1016/0006-291X(90)92007-M
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Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
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