1994
DOI: 10.1016/0165-1110(94)90025-6
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Genetic toxicity of 2-acetylaminofluorene, 2-aminofluorene and some of their metabolites and model metabolites

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Cited by 226 publications
(223 citation statements)
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“…The C8-AAF adduct was shown to exist predominantly (∼70%) in the base-displaced intercalated conformation in a sequence in which the modified dGuo was flanked by dCyd, as is the case for the G 3 -position of the NarI sequence (42). Cho and Zhou utilized a C7-fluorinated AAF-derivative and 19 F NMR spectroscopy to examine the conformational heterogeneity of the C8-dGuo adduct. These studies showed that the C8-(7-fluoro-AAF) adduct adopted two distinct base-displaced intercalated conformations in a local -GGA-sequence that differed by the torsional angle of the N-acetyl group (43).…”
Section: Thermal Melting (T M ) Studies Of Iq-adducted Oligo-nucleotidesmentioning
confidence: 99%
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“…The C8-AAF adduct was shown to exist predominantly (∼70%) in the base-displaced intercalated conformation in a sequence in which the modified dGuo was flanked by dCyd, as is the case for the G 3 -position of the NarI sequence (42). Cho and Zhou utilized a C7-fluorinated AAF-derivative and 19 F NMR spectroscopy to examine the conformational heterogeneity of the C8-dGuo adduct. These studies showed that the C8-(7-fluoro-AAF) adduct adopted two distinct base-displaced intercalated conformations in a local -GGA-sequence that differed by the torsional angle of the N-acetyl group (43).…”
Section: Thermal Melting (T M ) Studies Of Iq-adducted Oligo-nucleotidesmentioning
confidence: 99%
“…Perhaps the most well studied of the aromatic amines are 2-aminofluorene (AF) and N-acetyl-2-aminofluorene (AAF) (19). Although structurally similar, these compounds elicit significantly different biological responses.…”
Section: Introductionmentioning
confidence: 99%
“…These bulky DNA lesions, if not repaired, can produce mutations during replication that initiate the process of carcinogenesis. In bacteria AF-adducts mostly induce G→T transversions, whereas AAF-adducts cause mostly deletion mutations (3). In mammalian cells, however, both adducts promote sequence dependent base substitution mutations (8).…”
Section: Introductionmentioning
confidence: 99%
“…Arylamines and their nitro derivatives are a major group of mutagens and carcinogens (3,4). The environmental carcinogen 2-nitrofluorene and its amino derivatives are the prototype arylamine carcinogens (5,6).…”
Section: Introductionmentioning
confidence: 99%
“…Although the mechanisms of mutagenesis have been studied extensively, the conformational aspects underlying replication and repair efficiencies are not well-understood (3)(4)(5). A case in point is the strong hepatocarcinogen N-acetyl-2-aminofluorene, which reacts with DNA to produce two major C8-substituted dG adducts in vivo: an aminofluorene (AF) 1 Figure 1A) and an acetylaminofluorene (AAF) adduct [N-(2′-deoxyguanosin-8-yl)-2-acetylaminofluorene] (6). The N-deacetylated AF adduct in particular has drawn special attention because of its ability to adopt uniquely different conformations depending on the location of the aminofluorene moiety (1,(7)(8)(9)(10)(11)(12).…”
Section: Introductionmentioning
confidence: 99%