Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. II. Ortho-aminonitro derivatives of 9H-carbazole

André, Véronique; Boissart, C.; Sichel, François; Gauduchon, Pascal; Talaer, J. Y. Le; Lancelot, Jean‐Charles; Robba, M.; Mercier, Christiane; Chemtob, S.; Raoult, E.; Tallec, A.

doi:10.1016/0165-1218(95)90066-7

Cited by 14 publications

(5 citation statements)

References 46 publications

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“…As alrcady postulated, it is conceivable that formation of hydroxylamine intermediates, studied in this article in an acellular system, could be catalyzed in bacteria by nitroreductase enzymes. However, in this series of closely related derivatives, nitroreduction potential does not appear as the major parameter that condition the variations of mutagenicity [7], a result which contrasts with previous studies realized on a series of various nitroarenes [5]. On the other hand, for some of the isomers, the comparison of the stability of the hydroxylamines could, at least partly, justify the modulation of the mutagenic response.…”

Section: Discussioncontrasting

confidence: 58%

“…All derivatives were synthesized in our laboratory according to the procedures described: 3-nitrocarbazole (3NC), 2-aminocarbazole (2AC) and 3-aminocarbazole (3AC), -in [7] for 1 -nitro-2-aminocarbazole (IN2AC), 2-nitro-3-aminocarbazole (2N3AC) and 3-nitro-2-aminocarbazole (3N2AC) -in [8] for 9-methyl-2-nitrocarbazole (YMe2NC), 9-methyl-3-aminocarbazole (9Me3AC), 1,4,6-trimethyl-3-nitrocarbazole (1,4,6triMe3NC) and 1,4-dimethyl-3-aminocarbazole (1,4diMe3AC).…”

Section: Chemicalsmentioning

confidence: 99%

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Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole

Carlier¹,

Raoult²,

Tallec³

et al. 1997

Electroanalysis

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The electrochemical behavior of nitro and amino carbazole derivatives has been investigated. In aprotic medium, both in reduction and oxidation, the electrochemical process is complicated by "father-son" protonation reactions. In protic medium, the hydroxylamines resulting from 4-electron reduction of nitrocarbazoles are unstable in very acidic medium, but relatively stable in acetic or ammoniacal buffer, except for 3-hydroxylaminocarbazole; reduction of amino-nilrocarbazoles leads to unstable hydroxylamines. Oxidation of aminocarbazoles is a 2-electron process, the 2-amino compounds being more difficult to oxidize than the 3-amino derivatives. The relationships between these electrochemical behaviors and mutagenic properties of the studied compounds are also discussed.

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Section: Discussioncontrasting

confidence: 58%

Section: Chemicalsmentioning

confidence: 99%

Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole

Carlier¹,

Raoult²,

Tallec³

et al. 1997

Electroanalysis

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“…Similar results were observed for carbazole derivatives () and other PAHs such as pyrene and fluorene ( − ), and the mutagenic activity was increased with the extent of nitration. Generally, nitroarenes require metabolic reduction of the nitro functional group for expression of mutagenicity and carcinogenicity ( 10 , 16 , − . Therefore, the ease of reduction of the nitro compounds should be an important factor responsible for their genotoxic activities.…”

Section: Resultsmentioning

confidence: 99%

“…Similar results were observed for carbazole derivatives (23) and other PAHs such as pyrene and fluorene (36)(37)(38), and the mutagenic activity was increased with the extent of nitration. Generally, nitroarenes require metabolic reduction of the nitro functional group for expression of mutagenicity and carcinogenicity (10,16,(39)(40)(41).…”

Section: Table 1 Physicochemical Data Of Nitrated Dbc Derivativesmentioning

confidence: 99%

“…However, the higher activity of 2-OH-5-nitro-DBC would be contrary to this expectation. There are other factors that may affect mutagenicity, such as the lifetimes of the active intermediates and the steric effects, that need to be taken into account (41). Steric hindrance of the molecule may restrain the access of the nitro and/or hydroxy groups (i.e., at position 1 in DBC) to the active sites of the relevant enzymatic systems in the metabolic activation process.…”

Section: Table 1 Physicochemical Data Of Nitrated Dbc Derivativesmentioning

confidence: 99%

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Synthesis, Characterization, and Mutagenicity of Nitrated 7H-Dibenzo[c,g]carbazole and Its Phenolic Derivatives

Xue

LaDow

Warshawsky

1997

Chem. Res. Toxicol.

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The nitrated N-heterocyclic aromatic hydrocarbons (NAHs) are found in a variety of environmental sources; many of them have been determined to be mutagenic in short-term assays and/or carcinogenic in animal tests. In this laboratory, we synthesized and characterized nitrated 7H-dibenzo[c,g]carbazole (DBC) and the nitrophenolic metabolites of DBC as potential mutagenic and carcinogenic xenobiotics. The nitro group was formed exclusively at the 5 and/or the symmetric 9 position of DBC, 2-hydroxy-DBC, 3-hydroxy-DBC, and 4-hydroxy-DBC. Ames plate incorporation mutagenicity assays were conducted using Salmonella typhimurium strains TA98 and TA100, with or without rat liver homogenates (S9). Mutagenicities of the nitrated DBCs were higher than the parent DBC in strain TA98, 5,9-Dinitro-DBC had stronger mutagenic responses than 5-nitro-DBC in all assays, particularly in strain TA98 with S9. 5,9-Dinitro-DBC had a higher reduction potential relative to 5-nitro-DBC (-1.09 V and -1.37 V, respectively). Hydroxyl derivatives of 5-nitro-DBC at the 2, 3, 4, 10, or 12 position, synthesized through nitration of the corresponding hydroxy-DBC, possessed greater mutagenicity than the parent 5-nitro-DBC, especially in strain TA100 with or without S9. Our data suggest that nitrated DBC undergoes both nitroreduction and ring oxidation as the primary pathways for the metabolic activation leading to mutagenesis. The relative mutagenicities of the nitrohydroxy-DBC isomers are generally consistent with the resonance stabilization of the positive charge at the arylnitrenium ion, formed from the nitro functional group, as the proposed active electrophile responsible for genotoxic effects.

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(Q)SAR Models for Genotoxicity Assessment

Kulkarni

Zhu

2009

Ecotoxicology Modeling

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Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. II. Ortho-aminonitro derivatives of 9H-carbazole

Cited by 14 publications

References 46 publications

Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole

Electrochemical behavior of mutagenic nitro and amino derivatives of carbazole

Synthesis, Characterization, and Mutagenicity of Nitrated 7H-Dibenzo[c,g]carbazole and Its Phenolic Derivatives

(Q)SAR Models for Genotoxicity Assessment

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