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PubMed1989

Structural basis of the mutagenicity of phenylazoaniline dyes.

The CASE (Computer-Automated Structure Evaluation) methodology was used to gain an understanding of the basis of mutagenicity of phenylazoanilines. It was found that the activity of these molecules is dependent upon an intact moiety that spans the azo linkage, i.e., the azo bond must remain intact for mutagenicity. The study also addressed the effect of sulfonation on the activity of these azo dyes. It was revealed that sulfonation at only certain sites resulted in loss of mutagenicity. Sulfonation of the structural moiety responsible for the activity of phenylazoaniline dyes did not necessarily result in complete elimination of activity as this substitution could generate new structural moieties which contribute to the activity of the molecules.

Aniline Compounds↗
PubMed1992

Identification of metabolites of 4,4'-diaminodiphenylmethane (methylene dianiline) using liquid chromatographic and mass spectrometric techniques.

The in vitro metabolism of 4,4'-diaminodiphenylmethane (methylene dianiline, MDA) was investigated using rabbit liver microsomes. Minimal clean-up of the microsomal incubations was carried out using zinc sulphate precipitation followed by solid-phase extraction on Sep-Pak C18 cartridges. Three metabolites were detected in hepatic microsomal incubations, namely the azodiphenylmethane (azo) azoxydiphenylmethane (azoxy) and 4-nitroso-4'-aminodiphenylmethane (nitroso) compounds. The azo and azoxy metabolites were produced enzymatically whereas the nitroso compound may have been formed via a non-enzymatic process. Reversed-phase high-performance liquid chromatography-plasma spray mass spectrometry was used to initially detect these metabolites. Fast atom bombardment mass spectrometry and fast atom bombardment tandem mass spectrometry were utilized to further structurally characterise these compounds. Comparison of mass spectral data obtained from synthesised standards with data obtained on the putative metabolites substantiated the characterisation of these compounds.

Aniline Compounds↗
PubMed1985

Metabolism of the benzidine-based azo dye Direct Black 38 by human intestinal microbiota.

Benzidine-based azo dyes are proven mutagens and have been linked to bladder cancer. Previous studies have indicated that their initial reduction is the result of the azo reductase activity of the intestinal microbiota. Metabolism of the benzidine-based dye Direct Black 38 was examined by using a semicontinuous culture system that simulates the lumen of the human large intestine. The system was inoculated with freshly voided feces, and an active flora was maintained as evidenced by volatile fatty acid and gas production. Within 7 days after exposure to the dye, the following metabolites were isolated and identified by gas chromatography-mass spectrometry:benzidine, 4-aminobiphenyl, monoacetylbenzidine, and acetylaminobiphenyl. Benzidine reached its peak level after 24 h, accounting for 39.1% of the added dye. Its level began to decline, and by day 7 the predominant metabolite was acetylaminobiphenyl, which accounted for 51.1% of the parent compound. Formation of the deaminated and N-acetylated analogs of benzidine, which have enhanced mutagenicity and lipophilicity, previously has not been attributed to the intestinal microbiota.

Aminobiphenyl Compounds↗
PubMed1990

Redox cycling of radical anion metabolites of toxic chemicals and drugs and the Marcus theory of electron transfer.

A wide variety of aromatic compounds are enzymatically reduced to form anion free radicals that generally contain one more electron than their parent compounds. In general, the electron donor is any of a wide variety of flavoenzymes. Once formed, these anion free radicals reduce molecular oxygen to superoxide and regenerate the parent compound unchanged. The net reaction is the oxidation of the flavoenzyme's coenzymes and the reduction of molecular oxygen. This catalytic behavior has been described as futile metabolism or redox cycling. Electron transfer theory is being applied to these reactions and, in some cases, has successfully correlated Vmax and Km with the reduction potentials of the aromatic compounds.

Anions↗
PubMedDate not supplied

The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities.

We compared the abilities of trans-resveratrol and seven analogs to inhibit an azo compound-induced peroxidation of linoleic acid in vitro and to induce apoptosis in cultured human leukemia cells. The results showed that both the antioxidant and apoptotic activities of the analogs containing 3,4-dihydroxyl groups were significantly higher than those of the trans-resveratrol and the other analogs. Hence, the 3,4-dihydroxyl groups were important for trans-resveratrol analogs to exhibit concurrent high antioxidant and apoptotic activities.

Antineoplastic Agents, Phytogenic↗
PubMed1994

Biomonitoring of aromatic amines. IV: Use of hemoglobin adducts to demonstrate the bioavailability of cleavage products from diarylide azo pigments in vivo.

The release and availability of the carcinogenic component of the soluble azo dye Direct Red 46 and the insoluble azo pigment Pigment Yellow 17 were analyzed in Wistar rats using hemoglobin adducts as a dosimeter. The levels of hemoglobin adducts were found to be very low. Intestinal cleavage and release of 3,3'-dichlorobenzidine (3,3'-DCB) from Direct Red 46 and Pigment Yellow 17 was calculated to be 3% and 0.6% of the dose, respectively, in a 4-week feeding study. It is proposed to measure blood samples from exposed humans in order to test the applicability of the method and eventually to use it for controlling human exposure to the carcinogenic colorant components.

3,3'-Dichlorobenzidine↗