N-Acetyl-2-aminofluorene

The metabolic formation of N-sulfonyloxy-N-acetyl-2-aminofluorene (N-sulfonyloxy-AAF) and its observed electrophilic reactivity, provided the first evidence for the importance of enzymatic conjugation reactions in chemical carcinogenesis (23,24). This reaction was shown to be catalyzed by PAPS-dependent sulfotrans-ferases that are located predominantly in liver cytosol and has been subsequently demonstrated for N-hydroxy arylamide metabolites of several other carcinogens, including N-acetyl-4-aminobiphenyl (AABP), benzidine, N-acetyl-2-aminophenanthrene and phenacetin. 

ACETYLAMINO-FLUOREN (GERMAN) see FDROOO 4-ACETYLAMINOFLUOREN (GERMAN) see ABYOOO 4-ACETYLAMINOFLUORENE see ABYOOO N-ACETYL-2-AMINOFLUORENE see FDROOO... 

C15H13N02 N-hydroxy-N-acetyl-2-aminofluorene 53-95-2 558.90 49.571 2 28417 C15H16N20 N -ethyl-N,N-diphenylurea 18168-01-9 623.15 55.834 2... 

Mekhovich, O., Tang, M., and Romano, LJ. (1998) Rate of incision of N-acetyl-2-aminofluorene and N-2-aminofluorene adducts by UvrABC nuclease is... 

SYNONYMS 2-acetamidofluorene, 2 acetaminofluorene, acetoaminofluorene, N-acetyl-2-aminofluorene. 

Synonyms/Trade Names AAF, 2-AAF, 2-Acetaminofluorene, N-Acetyl-2-aminofluorene, F/VA, 2-F/ A, 2-Fluorenylacetamide ... 

The characteristic fluorescence of Tb(III) ion iis enhanced on interaction with G bases, principally, when present in single-stranded conformation. AAF, N-acetyl-2-aminofluorene, reacts principally at the 8 position of purine rings. 

Synonyms AAF 2-AAF 2-Acetamidofluorene 2-Acetaminofluorene 2-Acetoaminofluorene 2-(Acetylamino)fluorene A-Acetyl-2-aminofluorene 2-Aminoacetylfluorene AI3-52433 BRN 2807677 CCRIS 1 EINECS 200-188-6 FAA 2-FAA 2-Fluorenilacetamide A-9 -Fluoren-2-ylacetamide 2-Fluorenylacetamide 7V-2-Fluorenylacetamide A-Fluoren-2-acetylacetamide N-Fluorenyl-2-acetamlde NSC 12279 RCRA waste number U005 UN 3143. 

Translesion synthesis with DNA Pol of the iV-acetyl-2-aminofluorene adduct of guanosine (88) is inefficient with templates eontaining (88). In the presence of the Revl protein, translesion synthesis occurs and dCTP is the major nucleotide incorporated opposite it," and studies with a mutant DNA Pol I gave similar results." Benzo[a]pyrene is a potent environmental carcinogen, which when metabolised leads to anii-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide anti-BPDE). With dG, the major lesion is (+)-tra w-a n-B[a]P-A -dG, (89), and is usually repaired by the nucleotide excision repair (NER) pathway. The translesion synthesis past (89) has been examined with a number of polymerases. With human RNA Pol II, (89) is a block to synthesis," whilst DNA Pol k preferentially incorporated the correct nucleotide." In yeast cells, Pol induced a large number of mutations involving Pol p, whilst Pol p alone contributed to 1-3 deletions or insertions." The NER of (89) with UvrB proteins was also studied." ... 

Bosold, F. and G. Boche. 1990. The ultimate carcinogen, 0-acetyl-N-2-(fluorenyl)hydroxylamine ( N-acetoxy-2-aminofluorene ), and its reaction in vitro to form 2-[N-(deoxyguanosin-8-yl)amino]fluorene. Angew. Chem. Int. Ed. Engl. 29 63-64. 

Boche and co-worker ° carried out detailed studies of the decomposition reactions of various A -hydroxylamine esters in the presence of DNA and deoxygua-nosine, and characterized the adducts that resulted from these reactions. Thus, the nitrenium ion derived from 0-acetyl-N-(2-aminofluorene) added to DNA to give an adduct joining the C8 position of the base with the nitrenium ion nitrogen. Similar experiments carried out with the precursor of 2-naphthylnitrenium ion gave N2-ortho 148 and C8-N adducts 149 as shown in Figure 13.72. ... 

An alternative activation mechanism for glucxironldes that may occur with hydroxamic acids is the de-acetylation of N-acetyl-N-0-glucuronldes, as has been demonstrated for 2AAF ( ). Deacetylation of the N-O-glucuronlde of N-hydroxy-2AAF yields the N-O-glucuronlde of 2-aminofluorene, which is very reactive and binds spontaneously to DNA. Whether such a mechanism operates in vivo is still unclear. 

Figure 14. Major known adducts of 2-aminofluorene to DNA. Cg-AF is the adduct to ring position 8 of a guanine base Cg-AAF is identical to Cg-AF except for an N-acetyl group.

Fucoganglioside Accumulated in Precancerous Rat Liver and in Rat Heptatoma Induced by N-2-acetyl-aminofluorene , Journal of Biological Chemistry, 257, 7698-703... 

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