DNADamage_GN_oxoethyl7GN_chloroethylene_oxide – DNA base alkylation (guanine ==> 7-(2'-oxoethyl)-guanine; chloroethylene oxide)

Name
WID DNADamage_GN_oxoethyl7GN_chloroethylene_oxide View in model
Name DNA base alkylation (guanine ==> 7-(2'-oxoethyl)-guanine; chloroethylene oxide) View in model
 
Classification
Type base_alkylation View in model
 
Reaction
Stoichiometry [c]: chloroethylene_oxide + GN ⇒ CL + oxoethyl7GN View in model
 
Energetics
Is spontaneous (pH 7.5, 25C, I = 0) True View in model
 
Associations
Process Process_DNADamage View in model
 
Comments
Comments 1,N6-Etheno-2'-deoxyadenosine, 3,N4-Etheno-2'-deoxycytidine, N2,3-etheno-2′-deoxyguanosine, and 7-(2'-oxoethyl)-2'-deoxyguanosine formed in vitro by vinyl chloride, chloroethylene oxide, and chloroacetaldehyde [PUB_0468, PUB_0469]; vinyl chloride ==> chloroethylene oxide ==> and chloroacetaldehyde [PUB_0469]; rate constant 0.049 s^-1 M^-1, actiavtion energy 19.5 kcal/mol [PUB_0470]
References

  1. Bren U, Zupan M, Guengerich FP, Mavri J. Chemical reactivity as a tool to study carcinogenicity: reaction between chloroethylene oxide and guanine. J Org Chem 71, 4078-84 (2006). WholeCell: PUB_0470, PubMed: 16709046

  2. Eberle G, Barbin A, Laib RJ, Ciroussel F, Thomale J, Bartsch H, Rajewsky MF. 1,N6-etheno-2'-deoxyadenosine and 3,N4-etheno-2'-deoxycytidine detected by monoclonal antibodies in lung and liver DNA of rats exposed to vinyl chloride. Carcinogenesis 10, 209-12 (1989). WholeCell: PUB_0468, PubMed: 2783395

  3. Kielhorn J, Melber C, Wahnschaffe U, Aitio A, Mangelsdorf I. Vinyl chloride: still a cause for concern. Environ Health Perspect 108, 579-88 (2000). WholeCell: PUB_0469, PubMed: 10905993
 
Metadata
Created 2012-10-01 15:08:31
Last updated 2012-10-01 15:16:22