Disease relevance of HSDB 7091

• The mutagenic potency of 3,6-DNBeP in the Ames/Salmonella assay was extremely high, in that it induced 285,000 revertants/nmol in TA98 and 955,000 revertants/nmol in YG1024 without S9 mix and was comparable to those of DNP isomers, which are some the most potent bacterial mutagens reported so far [1].

High impact information on HSDB 7091

• Thus, distinct human cytochrome P-450 enzymes are involved in the detoxication of different dinitropyrene congeners, and the situation appears to contrast with that in rat liver [2].
• Several chemicals that are found in cigarette smoke or diesel oil engine exhausts, such as benzo[a]pyrene (B[a]P) and 1,6-dinitropyrene (DNP) are carcinogenic in experimental animal models [3].
• In the present study, we have exposed in vivo the xenotransplanted immortalized human bronchial epithelial cell line BEAS-2B to the ultimate carcinogen of B[a]P, benzo[a]pyrene diolepoxide (BPDE), to DNP or to the benzo[e]pyrene, a less active compound that has tumor-promoting abilities in mouse skin carcinogenesis bioassays [3].
• 1,6-Dinitropyrene (DNP) (0.05 microM) and dimethylnitrosamine (DMN) (1 mM) were also positive in vitro demonstrating that TE cells have the capacity to metabolically activate these compounds [4].
• Comparison of electrospray ionization, atmospheric pressure chemical ionization, and atmospheric pressure photoionization for the analysis of dinitropyrene and aminonitropyrene LC-MS/MS [5].

Biological context of HSDB 7091

• Acetylated diaminopyrene was detected in urine and after hydrolysis of the corresponding hemoglobin adducts followed by acetylation in blood samples of rats after administration of dinitropyrene but not in controls [6].
• Our studies provide detailed insight into the DNA sequence alterations and mutational mechanisms associated with dinitropyrene mutagenesis [7].
• Among the positive chemicals, the DNA-repair level of the 3 dinitropyrene isomers was much higher than other nitroarenes [8].
• The coincidence of dinitropyrene resistance and acetyltransferase deficiency implicates acetylation as an important process in the metabolic activation of dinitropyrene to a mutagenic intermediate [9].

Anatomical context of HSDB 7091

• Dinitropyrene metabolism, DNA adduct formation, and DNA amplification in an SV40-transformed Chinese hamster embryo cell line [10].
• The material extracted from the flesh walls was able to maintain DNP in solution, when added to the incubation medium in the absence of cell walls [11].
• The fact that a positive result was obtained using human lymphocytes shows that, in the presence of the appropriate activation system, dinitropyrene is genotoxic in human cells [12].
• Distribution of DNP in various tissues (blood, liver, spleen, lungs, kidneys, stomach, small and large intestine) was studied over 9 days [13].
• In studies with ligated sections of the gastrointestinal tract, DNP absorption was from the small and large intestine and there was none from the stomach [13].

Associations of HSDB 7091 with other chemical compounds

• The amount of radiolabel covalently bound to mouse lung DNA following intratracheal administration of radiolabeled benzo[a]pyrene (BaP), 1-nitropyrene, 1,3,6-trinitropyrene, or a mixture of dinitropyrene was determined following pretreatment with benzo[a]pyrene, 1-nitropyrene, and diesel exhaust extract [14].
• The abilities of brans from the cereals barley, oats, maize, rice, and wheat to adsorb in vitro the hydrophobic, environmental mutagen 1,8-dinitropyrene (DNP) were investigated using a mutagenicity assay [15].
• Modulation of the mutagenicity of three dinitropyrene isomers in vitro by rat-liver S9, cytosolic, and microsomal fractions following chronic ethanol ingestion [16].
• In order to quantify 1,3-dinitropyrene (DNP), 1,6-DNP and 1,8-DNP in soil, we developed an efficient clean-up procedure and a sensitive determination method using fluorescence detection [17].

Gene context of HSDB 7091

• Dinitropyrene-resistant Salmonella typhimurium are deficient in an acetyl-CoA acetyltransferase [9].

Analytical, diagnostic and therapeutic context of HSDB 7091

• Normal phase HPLC coupled to APPI-MS/MS gave the highest precision and sensitivity for aminonitropyrene (6%/0.2 pg on column) and dinitropyrene (9%/0.5 pg on column) [5].
• To our knowledge, this is the first time that aminonitropyrene was observed in plasma after intratracheal or oral administration directly demonstrating the reductive metabolism of dinitropyrene in vivo [5].
• DNP isomers were efficiently cleaned by three stages of fractionation, i.e., a silica gel open column chromatography using stepwise elution and two further purification steps by high-performance liquid chromatography (PPLC) using a monomeric-type octadecylsilyl (ODS) column and a polymeric-type ODS column [17].
• This paper reports the detection of dinitropyrene (DNP) as a direct-acting mutagen using nitrogen selective gas chromatography [18].

References