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Chemical Compound Review:

Acetoxyacetamidofluorene (ethanoyl-(9H-fluoren-2- yl)amino) ethanoate

Synonyms: NAAAF, NA-AAF, Acetoxy AAF, CCRIS 729, CHEMBL85327, ...

Dresler, S.L. et al., Abanobi, S.E. et al., Vousden, K.H. et al., Langenbach, R. et al., Aust, A.E. et al., et al.

Andrew, Burgess, Meza, Demidenko, Waugh, Hamilton, Karagas,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of ACETOXYACETYLAMINOFLUORENE

Stimulation of recombination between homologous sequences on plasmid DNA and chromosomal DNA in Escherichia coli by N-acetoxy-2-acetylaminofluorene [1].
Surprisingly mouse cells, which remove few dimers, were about as competent as control human fibroblasts at removing acetylaminofluorene lesions; however, xeroderma pigmentosum cells (group D) removed fewer N-acetoxy-2-acetylaminofluorene-induced lesions than control human cells [2].
Tobacco mosaic virus (TMV) RNA was treated with radioactive N-acetoxy-2-acetylaminofluorene (N-acetoxy-AAF) and (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BaP diol epoxide) to obtain 3-25 adducts per molecule [3].
Using a filter binding assay, we have detected and partially purified a protein from human placenta that has a high affinity for N-acetoxy-2-acetylaminofluorene-modified double-stranded DNA (AAF-[3H]DNA) of bacteriophage T7 [4].
The mononuclear leukocytes from peripheral blood samples of individuals with (n = 30) and without (n = 48) colonic polyps were examined for their abilities to carry out unscheduled DNA synthesis (UDS) induced by N-acetoxy-N-2-fluorenylacetamide (N-AcO-2-FAA) [5].

High impact information on ACETOXYACETYLAMINOFLUORENE

Irradiation of DNA with UV light or alkylation with N-acetoxyacetylaminofluorene (AAAF) shifts the transition to lower salt concentrations [6].
Neither 2-AAF nor its metabolites N-hydroxy-2-AAF (CAS: 53-95-2; N-fluoren-2-yl-acetohydroxamic acid) and N-acetoxy-2-AAF (CAS: 6098-44-8; N,O-diacetyl-N-fluoren-2-yl-hydroxylamine) influenced the insulin binding to the microsomes when added to the reaction mixture in vitro [7].
Paraoxon inhibited the induction of UDS in HCV 29 by N-OH-AAF and N-acetoxy-2-acetylaminofluorene (CAS: 6098-44-8), but not by N-OH-AF [8].
Peripheral resting mononuclear leukocytes were compared for their capacities to repair DNA lesions induced by a 1-hour exposure to a standardized 10-microM dose of N-acetoxy-N-2-fluorenylacetamide (N-AcO-2-FAA) [9].
Female F344 rats did not develop mammary tumors after topical application of N-hydroxy-N-2-fluorenylacetamide, N-acetoxy-N-2-fluorenylacetamide, or N-acetoxy-N-3-fluorenylacetamide [10].

Chemical compound and disease context of ACETOXYACETYLAMINOFLUORENE

The effect of modifying phi chi 174 viral DNA by the chemical carcinogens beta-propiolactone, N-acetoxyacetylaminofluorene and anti-benzo[a]pyrene diol-epoxide was investigated by transfecting the modified DNA into Escherichia coli spheroplasts [11].
DNA repair synthesis in fibroblast strains from patients with actinic keratosis, squamous cell carcinoma, basal cell carcinoma, or malignant melanoma after treatment with ultraviolet light, N-acetoxy-2-acetyl-aminofluorene, methyl methanesulfonate, and N-methyl-N-nitrosourea [12].
The mutagenic specificities of ethylnitrosourea (ENU), X-rays (+/-)7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7, 8,9,10-tetrahydrobenzo[a]pyrene (BPDE), ICR-191, and N-acetoxy-2-acetylaminofluorene (N-AcO-AAF) were analyzed and compared in diploid human fibroblasts and Salmonella typhimurium [13].

Biological context of ACETOXYACETYLAMINOFLUORENE

The effects of the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) and its nonpromoting structural analogue, 4-O-methyl-12-O-tetradecanoylphorbol-13-acetate (Me-TPA), on N-acetoxy-2-acetylaminofluorene-elicited DNA repair and replicative DNA synthesis was measured in normal human fibroblasts [14].
In contrast, DEDTC did not inhibit the fragmentation of liver DNA caused by several other chemical carcinogens (N-hydroxy-2-acetylaminofluorene, 3-hydroxyxanthine, aflatoxin B1, N-acetoxy-2-acetylaminofluorene, methyl methanesulfonate, methylnitrosourea, and methylazoxy-methanol acetate), whether or not they required metabolic activation [15].
We consider this mechanism of mutagenesis in the light of our other findings that the carcinogens benzo[a]pyrene diol epoxide and N-acetoxyacetylaminofluorene also specifically induce GxC leads to TxA transversions [16].
Survival and mutagenesis of the plasmid were measured as a function of the N-acetoxy-2-acetylaminofluorene concentration [1].
Here we report that interindividual variations in N-acetoxy-2-acetyl-aminofluorene-induced unscheduled DNA synthesis values parallel the actual in vivo levels of chromosome damage and, therefore, may be a rapid useful supplement in genetic risk assessment for humans [17].

Anatomical context of ACETOXYACETYLAMINOFLUORENE

Unscheduled DNA synthesis (excision-repair) of N-acetoxy-2-acetylaminofluorene (NA-AAF) damage to the DNA of human lymphocytes was determined quantitatively for 92 individuals with diastolic blood pressures ranging from 65 to 120 mm of Hg (8,7 to 16 kPa) [18].
In vitro modification of plasmids containing the human c-Ha-ras1 protooncogene (HRAS1) with the ultimate carcinogens N-acetoxy-2-acetylaminofluorene and r-7, t-8-dihydroxy-t-9, 10-epoxy-7,8,9,10-tetrahydrobenzo[alpha]pyrene (anti-BPDE) generated a transforming oncogene when the modified DNA was transfected into NIH 3T3 cells [19].
The inner cell mass of cultured Rev3(-/-) blastocysts dies of a delayed apoptotic response after exposure to a low dose of N-acetoxy-2-acetylaminofluorene [20].
The W8 cell line is a N-acetoxy-2-acetylaminofluorene-treated, weakly tumorigenic rat liver cell derived from the parent K16 cell line [21].
High performance liquid chromatography analysis shows that the only DNA adduct formed in NAAAF-treated CHO cells is N-(deoxyguanosine-C8-yl)-2-aminofluorene (dG-C8-AF) [22].

Associations of ACETOXYACETYLAMINOFLUORENE with other chemical compounds

Mutagenesis of Chinese hamster cells in vitro by combination treatments with methyl methanesulfonate and N-acetoxy-2-acetylaminofluorene [23].
DNA excision repair was measured in cultured human fibroblasts after single or dual treatments with ultraviolet radiation, 4-nitroquinoline 1-oxide, or N-acetoxy-2-acetylaminofluorene [24].
Cysteine at equimolar concentrations inhibited to a larger degree the mutagenesis induced by N-hydroxy-2-acetylaminofluorene than it inhibited that elicited by N-acetoxy-2-acetylaminofluorene [25].
At high doses of damage, the fraction of repair synthesis mediated by DNA polymerase alpha reaches a maximal level which is dependent on the damaging agent; the maximal level of polymerase alpha involvement is about 80% for UV radiation and N-acetoxy-2-acetylaminofluorene, about 70% for N-methyl-N-nitrosourea, and about 40% for bleomycin [26].
The direct-acting carcinogens acetoxyacetylaminofluorene, methylnitrosourea, and N-methyl-N'-nitro-N-nitrosoguanidine were tested for their ability to inhibit rat liver DNA polymerase-alpha, -beta, and -gamma activity in vitro [27].

Gene context of ACETOXYACETYLAMINOFLUORENE

Using this method, we investigated the recruitment of DNA damage checkpoint proteins RPA, Rad9, and ATR to base damage induced by UV and acetoxyacetylaminofluorene in transcribed and nontranscribed regions in wild-type and excision repair-deficient human cells in G1 and S phases of the cell cycle [28].
N-acetoxy-N-acetyl-2-aminofluorene-induced mutagenesis in the lacI gene of Escherichia coli [29].
Immediately after N-acetoxy-2-acetylaminofluorene treatment which introduced 20 to 38 mumol adducts per mol DNA-P, the adduct concentration was 4 to 5 times higher in linker DNA than in core DNA [30].
N-acetoxy-N-acetyl-2-aminofluorene-induced mutation spectrum in a human hprt cDNA shuttle vector integrated into mammalian cells [31].
S-phase block and cell death in human lymphoblasts exposed to benzo[a]pyrene diol epoxide or N-acetoxy-2-acetylaminofluorene [32].

Analytical, diagnostic and therapeutic context of ACETOXYACETYLAMINOFLUORENE

After treatment with UV light or N-acetoxy-2-acetylaminofluorene, cell strains in which DNA-incising capacity was reduced also showed a similar reduction in both colony-forming ability and DNA repair synthesis [33].
Detection of DNA adducts in N-acetoxy-2-acetylaminofluorene-treated human fibroblasts by means of immunofluorescence microscopy and quantitative immunoautoradiography [34].
These antibodies were used in competition radioimmunoassays (RIA) with [3H]DNA-AF as radioactive antigen and different N-acetoxy-2-acetylaminofluorene (N-AcO-AAF) and N-hydroxy-2aminofluorene (N-OH-AF) reacted DNAs, deoxyguanosine, dGMP, dGpA and dApG as inhibitors [35].
In addition, lymphocytes from As-exposed individuals showed higher levels of DNA damage, as measured by a comet assay, both at baseline and after a 2-acetoxyacetylaminofluorene (2-AAAF) challenge [36].
Capillary liquid chromatography-continuous-flow fast atom bombardment mass spectrometry is applied to the detection of deoxynucleoside adducts of N-acetoxy-N-acetyl-2-aminofluorene [37].

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