Pesticide-Derived Aromatic Amines and Their Biotransformation

Dupret, Jean‐Marie; Dairou, Julien; Busi, Florent; Silar, Philippe; Martins, Marta; Mougin, Christian; Rodrigues‐Lima, Fernando; Cocaign, Angélique

doi:10.5772/18279

Cited by 12 publications

(11 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mutagens entering freshwaters due to incomplete removal in wastewater treatment systems and occurring in drinking water abstracted from polluted lakes and rivers result in adverse effects on aquatic , and human life . Although several studies tried to identify the chemicals that cause the mutagenicity in the rivers, in only few cases individual chemicals could be identified as the cause of the observed effect, − whereas in other studies the origin of mutagenicity was inconclusive and could not be explained by identified compounds. − Along with polycyclic aromatic hydrocarbons (PAHs) and nitro-aromatic compounds, aromatic amines are an important compound class with many suspected or known environmental mutagens. − Aromatic amines are used as industrial chemicals and may be formed by transformation of pesticides, dyes and nitroaromatic compounds. − Compounds like naphthylamines, substituted anilines , or benzidine analogues are well-studied for their mutagenic/carcinogenic potentials. Furthermore, it was shown that heterocyclic aromatic amines such as 2-amino-3,8-dimethylimidazo[4,5- f ]quinoxaline (MeIQx), 2-amino-3-methylimidazo[4,5- f ]quinoline (IQ), 2-amino-alpha-carboline (AαC) or 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP) originating from grilled/fried meat and fish are discharged by sewage effluents and contribute significantly to the mutagenicity of surface waters. , All of these compound groups require metabolic activation by the N -oxidation to aryl- N -hydroxylamines, which in turn form nitrenium ions, the reactive electrophilic metabolite which covalently binds to DNA .…”

Section: Introductionmentioning

confidence: 99%

Mutagenicity in Surface Waters: Synergistic Effects of Carboline Alkaloids and Aromatic Amines

Muz

Krauß

Kutsarova

et al. 2017

Environ. Sci. Technol.

View full text Add to dashboard Cite

For decades, mutagenicity has been observed in many surface waters with a possible link to the presence of aromatic amines. River Rhine is a well-known example of this phenomenon but responsible compound(s) are still unknown. To identify the mutagenic compounds, we applied effect-directed analysis (EDA) utilizing novel analytical and biological approaches to a water sample extract from the lower Rhine. We could identify 21 environmental contaminants including two weakly mutagenic aromatic amines, and the known alkaloid comutagen norharman along with two related β-carboline alkaloids, carboline, and 5-carboline, which were reported the first time in surface waters. Results of mixture tests showed a strong synergism of the identified aromatic amines not only with norharman, but also with carboline and 5-carboline. Additionally, other nitrogen-containing compounds also contributed to the mutagenicity when aromatic amines were present. Thus, comutagenicity of β-carboline alkaloids with aromatic amines is shown to occur in surface waters. These results strongly suggest that surface water mutagenicity is highly complex and driven by synergistic mechanisms of a complex compound mixture (of which many are yet unidentified) rather than by single compounds. Therefore, mixture effects should be considered not only from mutagens alone, but also including possible comutagens and nonmutagenic compounds.

show abstract

Section: Introductionmentioning

confidence: 99%

Mutagenicity in Surface Waters: Synergistic Effects of Carboline Alkaloids and Aromatic Amines

Muz

Krauß

Kutsarova

et al. 2017

Environ. Sci. Technol.

View full text Add to dashboard Cite

show abstract

“…Elimination of aromatic amines, particularly chloroanilines like 3,4-DCA, has been very challenging, as those compounds can be toxic and resistant to microbial biodegradation [ 60 , 61 ]. Understanding the microbial metabolic pathways associated with arylamine detoxification and/or degradation has attracted interest [ 62 ], and NAT-mediated conjugation has been investigated as a route to reducing toxicity of 3,4-DCA in soil [ 63 , 64 ]. We became interested in T .…”

Section: Discussionmentioning

confidence: 99%

A taxonomically representative strain collection to explore xenobiotic and secondary metabolism in bacteria

et al. 2022

View full text Add to dashboard Cite

Bacteria employ secondary metabolism to combat competitors, and xenobiotic metabolism to survive their chemical environment. This project has aimed to introduce a bacterial collection enabling comprehensive comparative investigations of those functions. The collection comprises 120 strains (Proteobacteria, Actinobacteria and Firmicutes), and was compiled on the basis of the broad taxonomic range of isolates and their postulated biosynthetic and/or xenobiotic detoxification capabilities. The utility of the collection was demonstrated in two ways: first, by performing 5144 co-cultures, recording inhibition between isolates and employing bioinformatics to predict biosynthetic gene clusters in sequenced genomes of species; second, by screening for xenobiotic sensitivity of isolates against 2-benzoxazolinone and 2-aminophenol. The co-culture medium of Bacillus siamensis D9 and Lysinibacillus sphaericus DSM 28T was further analysed for possible antimicrobial compounds, using liquid chromatography-mass spectrometry (LC-MS), and guided by computational predictions and the literature. Finally, LC-MS analysis demonstrated N-acetylation of 3,4-dichloroaniline (a toxic pesticide residue of concern) by the actinobacterium Tsukamurella paurometabola DSM 20162T which is highly tolerant of the xenobiotic. Microbial collections enable "pipeline" comparative screening of strains: on the one hand, bacterial co-culture is a promising approach for antibiotic discovery; on the other hand, bioremediation is effective in combating pollution, but requires knowledge of microbial xenobiotic metabolism. The presented outcomes are anticipated to pave the way for studies that may identify bacterial strains and/or metabolites of merit in biotechnological applications.

show abstract

“…Knowledge of stability constant of binary/ ternary complexation between amine, metals and oxidants can be useful for controlling the action of carcinogenic and/ or toxic aromatic amines which can cause genotoxicity and cytotoxicity 1,2 . Aromatic amines can come in contact with living organisms by inhalation, ingestion and skin contact and most of these are enlisted as carcinogenic and/ or toxic due to their genotoxic or cytotoxic properties 1,2 .…”

Section: Introductionmentioning

confidence: 99%

“…Aromatic amines can come in contact with living organisms by inhalation, ingestion and skin contact and most of these are enlisted as carcinogenic and/ or toxic due to their genotoxic or cytotoxic properties 1,2 . Being used as intermediates for plastics, drugs, rubber, explosives, polymers, pesticides etc, and anilines can affect the living organisms by inhalation, skin contact and ingestion 3 .…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Stability Constant of Ternary Intermediate Complex Formation in Mnii Catalysed Periodate Oxidation Of2, 5-Xylidine by Stopped Flow Method

2017

Rasayan J Chem

View full text Add to dashboard Cite

Although proposed in many cases, the ternary complexation during periodate oxidation of majority of anilines catalyzed by metals like Mn II , has not been thoroughly subjected to investigations particularly from point of view of evaluation of stability constant of the ternary complex formed and collecting the supporting evidences. In this paper, the formation of ternary intermediate unstable complex 2,5-XYL -Mn II -IO4 -during Mn II catalyzed reduction of periodate by 2,5-xylidine(2,5-XYL) has been explored and its stability constant has been evaluated. Its value of (2.0 ± 0.66) × 10 6 has been found to be in good agreement with that calculated from rate equation derived by us on the basis of kinetic studies made by using stopped flow method. As evidenced from the stopped flow trace, the formation of complex is comparatively faster than its decomposition into other reaction products. The kinetics of ternary complexation is given by the Eqn.

show abstract

Pesticide-Derived Aromatic Amines and Their Biotransformation

Cited by 12 publications

References 64 publications

Mutagenicity in Surface Waters: Synergistic Effects of Carboline Alkaloids and Aromatic Amines

Mutagenicity in Surface Waters: Synergistic Effects of Carboline Alkaloids and Aromatic Amines

A taxonomically representative strain collection to explore xenobiotic and secondary metabolism in bacteria

Evaluation of Stability Constant of Ternary Intermediate Complex Formation in Mnii Catalysed Periodate Oxidation Of2, 5-Xylidine by Stopped Flow Method

Contact Info

Product

Resources

About