title: Identification of 7-(2-hydroxyethyl)guanine as a product of alkylation of calf thymus DNA with clomesone.
abstract: Evidence at the molecular level is presented in support of alkylation of O6-guanine moieties of DNA as the mechanism of cytotoxicity of Clomesone to HT-29 cells and consists in the isolation and identification of a product resulting from alkylation of calf thymus DNA with Clomesone, followed by depurination to yield 7-(2-hydroxyethyl)guanine, whose formation is reasonably explained by O6-guanine chloroethylation followed by intramolecular alkylation at N7 of guanine and subsequent hydrolysis to the hydroxyethylguanine.
authors.affiliation: Southern Research Institute, Birmingham, AL 35255.
authors.forename: R F
authors.initials: RF
authors.lastname: Struck
authors.forename: J A
authors.initials: JA
authors.lastname: Alexander
authors.forename: D M
authors.initials: DM
authors.lastname: McCain
authors.forename: Y F
authors.initials: YF
authors.lastname: Shealy
authors.forename: L M
authors.initials: LM
authors.lastname: Rose
mesh_terms: D000478:Alkylation; D000818:Animals; D000970:Antineoplastic Agents; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000378:metabolism*; D006147:Guanine / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification; D006868:Hydrolysis; D008698:Mesylates / Q000494:pharmacology*; D008745:Methylation; D013950:Thymus Gland / Q000187:drug effects / Q000378:metabolism*
chemical_list: D000970:Antineoplastic Agents; D008698:Mesylates; C041189:clomesone; C035018:N(7)-hydroxyethylguanine; D006147:Guanine; C030920:6-hydroxyethylguanine; D004247:DNA