Title: Butadiene monoxide and deoxyguanosine alkylation products at the <i>N</i>7-position
Abstract: 3,4-Epoxy-l-butene, an active metabolite of 1,3-butadiene, was reacted with guanosine, deoxyguanosine and calf thymus DNA. The products were isolated and positively identified using various spectroscopic techniques. Treatment of calf thymus-DNA with 3,4-epoxy-l-butene yielded two N7-guanine adducts of equal stability. Depurination by neutral hydrolysis showed that 7-(2-hydroxy-3-buten-l-yl)guanine (compound I) was formed in greater quantities compared to its regioisomer 7-(l-hydroxy-3-buten-2-yl)-guanine (compound II); spontaneous depurination experiments showed that compound I was released in the highest proportion. The circular dichroism spectral studies with R and S 3,4-epoxy-l-butene revealed that the reaction mechanism at aqueous neutral pH media is more similar to SN2-type rather than SNl-type. The HPLC-electrochemical detection method used to carry out the DNA alkylation study provides a rapid and sensitive quantitation of N7 guanine adducts in biological fluids. This serves as a useful tool for further human bioraonitoring experiments.
Publication Year: 1995
Publication Date: 1995-01-01
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 26
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