The evaluation of mutagenicities of 19 structurally related aromatic amines and acetamides in Salmonella typhimurium TA98 and TA100

Connor, Thomas H.; Ramanujam, V. M. Sadagopa; Rinkus, Stephen J.; Legator, Marvin S.; Trieff, Norman M.

doi:10.1016/0165-1218(83)90115-5

Cited by 33 publications

(10 citation statements)

References 6 publications

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“…Both authors suggest that the genotoxicity could be associated with the metals discharged by the tanneries industries, especially chromium. TA98 and TA100 Salmonella strains were demonstrated in the past (Connor et al, 1983). The formation of these aromatic amines still concern the researchers worldwide nowadays, and Brüschweiler et al (2014) pointed the Acid Black 210 as a non-regulated dye that could generate aromatic amines of toxicological concern.…”

Section: Discussionmentioning

confidence: 99%

Ecotoxicological risk assessment of the “Acid Black 210” dye

et al. 2017

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The "Acid Black 210" dye is one of the most used black dyes by the leather industry. This compound contains three azo groups in its chemical structure, and has been quoted as a non-regulated dye with toxicological concern, since it could generate carcinogenic aromatic amines. The objective of this study was to perform the ecotoxicological risk assessment of this dye through testing its toxicity in vitro and in vivo with the Ames test, the Comet assay, the Daphnia similis test, and the zebrafish embryo acute toxicity test. Moreover, we evaluated the presence of this dye in environmental samples related with a tannery industry. All the tests performed were negative, with the exception of the Ames test with the Salmonella typhimurium TA98 strain, which resulted in a low mutagenic potency. Due to the low concentrations of the "Acid Black 210" dye found in tannery effluents, and the high concentrations where any toxic activity is occasionally described, we concluded that this dye is safe from the ecotoxicological point of view in the areas evaluated and in the light of the current knowledge.

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Section: Discussionmentioning

confidence: 99%

Ecotoxicological risk assessment of the “Acid Black 210” dye

et al. 2017

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“…Accordingly to experimental studies [27,[30][31], formation of N-acetyl nitrenium ions from amides was found to be a process less favorable than nitrenium ion generation from the corresponding amines [112]. This observation was ascribed to the loss of negative charge density at the oxygen atom by polarization of the carbonyl group of the amides.…”

Section: Aromatic (Ar)mentioning

confidence: 94%

“…For the N-hydroxyarylamides intermediates (hydroxamic acids) esterification is required for subsequent reactivity with DNA [27]. Although amides generally appear to be no less carcinogenic than amines [19], the acetamido derivatives were consistently less mutagenic when compared to their parent amines [30,31].…”

Section: Introductionmentioning

confidence: 99%

Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons

Borosky

2008

CMC

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Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants well known as mutagenic/carcinogenic agents. This review will discuss recent theoretical studies regarding the stability and reactivity of ultimate carcinogenic metabolites from PAHs, focusing on their diol epoxide and amine derivatives. Geometrical and electronic features will be analyzed in order to obtain structure-activity relationships. Charge delocalization modes (positive charge density distribution), substituent effects, and conformational aspects will be considered. Computed properties will be compared with the available biological activity data. Correlations between experimental mutagenic potencies reported in the literature and calculated reaction energies and electronic properties will be shown. Heteroaromatic compounds (aza-PAHs, thia-PAHs, and heteroaromatic amines) will also be examined. To model the important step of covalent adduct formation, calculation of the adducts resulting from bond formation between some of these electrophilic intermediates and nucleotide bases (guanine, cytosine) will be described.

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“…Aromatic amides follow the same metabolic pathway as aromatic amines (10-12), even though esterification of the N-hydroxyarylamides intermediates (hydroxamic acids) is required for subsequent reactivity with DNA (10). Although amides generally appear to be no less carcinogenic than amines (1), the acetamido derivatives were always less mutagenic when compared to their parent amines (61,62). In agreement with this, heterolysis of the N-O bond to give a nitrenium ion was calculated by DFT to be less favorable in the arylamides because of the loss of amide resonance in their precursors (41); but not owing to inductive destabilization of the arylnitrenium ion by the N-acetyl group, as proposed earlier according to semiempirical computations (63,64).…”

Section: Aromatic Amidesmentioning

confidence: 99%

Quantum-chemical studies on mutagenicity of aromatic and heteroaromatic amines

Borosky¹

2013

Front Biosci

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Arylamines are well-known as widespread industrial and environmental mutagens and carcinogens. Their bioactivity stems from enzymatic metabolic activation to reactive and highly electrophilic intermediates. In this work, computational investigations related to the biological activity of these compounds have been reviewed, especially focusing on studies reporting results from quantum-mechanical calculations. Correlations between relative mutagenicities and structural and electronic features of the parent amines and of their derived nitrenium ion intermediates were examined, with the aim of achieving a clearer comprehension of the main factors determining the genotoxic potential of this type of compounds.

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The evaluation of mutagenicities of 19 structurally related aromatic amines and acetamides in Salmonella typhimurium TA98 and TA100

Cited by 33 publications

References 6 publications

Ecotoxicological risk assessment of the “Acid Black 210” dye

Ecotoxicological risk assessment of the “Acid Black 210” dye

Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons

Quantum-chemical studies on mutagenicity of aromatic and heteroaromatic amines

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