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Adducts between the carcinogen 2-acetamidophenanthrene and adenine and guanine of DNA
Abstract:
The sulfate and acetate esters of the carcinogen N-hydroxy-2-acetamidophenanthrene attack calf thymus DNA in vitro to yield adducts of 2-acetamidophenanthrene with guanine and adenine in the DNA. These adducts were found to be 8-(N-2-phenanthrylacetamido)deoxyguanosine and N6-1-(2-acetamidophenanthryl)deoxyadenosine, respectively. These reactions, and the already known reactions of esters of N-hydroxy-2-acetamidofluorene, together with Hückel molecular orbital calculations, suggest that the relative tendencies of a series of N-aryl-N-acetylnitrenium ions to react with adenine and guanine may be predicted.
Insights
Carcinogen esters of N-hydroxy-2-acetamidophenanthrene form DNA adducts with guanine and adenine. This research helps predict how similar N-aryl-N-acetylnitrenium ions interact with DNA bases.
Area of Science:
- * Chemical carcinogenesis
- * Molecular toxicology
- * DNA adduct formation
Background:
- * N-hydroxy-2-acetamidophenanthrene is a known carcinogen.
- * Esters of this compound can react with DNA.
- * Understanding these reactions is crucial for assessing carcinogenic risk.
Purpose of the Study:
- * To investigate the DNA adducts formed by sulfate and acetate esters of N-hydroxy-2-acetamidophenanthrene.
- * To characterize the specific adducts with guanine and adenine.
- * To explore the predictive potential for N-aryl-N-acetylnitrenium ion reactivity.
Main Methods:
- * In vitro reaction of DNA with carcinogen esters.
- * Identification of DNA adducts using chemical and spectroscopic methods.
- * Computational analysis using Hückel molecular orbital calculations.
Main Results:
- * Formation of 8-(N-2-phenanthrylacetamido)deoxyguanosine with guanine.
- * Formation of N6-1-(2-acetamidophenanthryl)deoxyadenosine with adenine.
- * Established a correlation between experimental findings and theoretical predictions.
Conclusions:
- * The sulfate and acetate esters of N-hydroxy-2-acetamidophenanthrene are reactive towards DNA, forming specific adducts with guanine and adenine.
- * The study provides insights into the mechanism of DNA damage by these carcinogens.
- * The findings suggest that computational methods can predict the reactivity of related compounds with DNA bases.