Mutagenicities of 2,4- and 2,6-dinitrotoluenes and their reduced products in Salmonella typhimurium nitroreductase- and O-acetyltransferase-overproducing Ames test strains

Sayama, Michio; Mori, Masaaki; Shoji, Mitsuru; Uda, Shinsuke; Kakikawa, Makiko; Kondo, Takashi; Kodaira, Ken-Ichi

doi:10.1016/s1383-5718(98)00139-9

Cited by 31 publications

(13 citation statements)

References 20 publications

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“…Similar observations were made for other energy-producing nitro-compounds [Lachance et al, 1999, George et al, 2001. Also, dinitrotoluenes and their reduced derivatives induced higher mutagenic responses in tester strains over-expressing nitroreductase [Sayama et al, 1998]. It is well documented that there are several nitroreductases involved in the mutagenic responses produced by nitro-containing chemicals [Rosenkranz et al, 1982;Rosenkranz and Mermelstein, 1982;Rosenkranz and Howard, 1986], and our findings indicate that the ''classical'' bacterial nitroreductase (which performs one-electron transfers and is lacking in TA98NR) catalyses the activation of most of the compounds that we tested.…”

Section: Discussionsupporting

confidence: 79%

“…TNT itself is a potent mutagen in the Salmonella/microsome assay [Whang et al, 1984;George et al, 2001]; the only compound that had a similar mutagenic potency in the present study was 2,4,6-TNBA. In contrast, much weaker responses or negative results were found in a study of several dinitrotoluenes and their amino-substituted derivatives that are formed as nitro-explosive degradation products [Sayama et al, 1998]. Hydroxylamino-derivatives produced relatively strong mutagenic effects (up to 150 revertants/nmol) [Padda et al, 2003]; but these compounds were only mutagenic in TA100.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Genotoxicity of nitrosulfonic acids, nitrobenzoic acids, and nitrobenzylalcohols, pollutants commonly found in ground water near ammunition facilities

Grummt

Wunderlich

Chakraborty³

et al. 2006

Environ. Mol. Mutagen.

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2-Amino-4,6-dinitrobenzoic acid (2-A-4,6-DNBA), 4-amino-2,6-dinitrobenzoic acid (4-A-2,6-DNBA), 2,4,6-trinitrobenzoic acid (2,4,6-TNBA), 2-amino-4, 6-dinitrobenzylalcohol (2-A-4,6-DNBAlc), 4-amino-2,6-dinitrobenzylalcohol (4-A-2,6-DNBAlc), 2,4-dinitrotoluol-5-sulfonic acid (2,4-DNT-5-SA), 2,4-dinitrotoluol-3-sulfonic acid (2,4-DNT-3-SA), and 2, 4-dinitrobenzoic acid (2,4-DNBA) are derivatives of nitro-explosives that have been detected in groundwater close to munitions facilities. In the present study, the genotoxicity of these compounds was evaluated in Salmonella/microsome assays (in strains TA100 and TA98, with and without S9 and in TA98NR without S9), in chromosomal aberration (CA) tests with Chinese hamster fibroblasts (V79), and in micronucleus (MN) assays with human hepatoma (HepG2) cells. All compounds except the sulfonic acids were positive in the bacterial mutagenicity tests, with 2,4,6-TNBA producing the strongest response (8023 revertants/micromol in TA98 without S9 activation). 2-A-4,6-DNBA was a direct acting mutagen in TA98, but negative in TA100. The other positive compounds were approximately 1-3 orders of magnitude less mutagenic than 2,4,6-TNBA in TA98 and in TA100; relatively strong effects ( approximately 50-400 revertants/micromol) were produced by the benzylacohols in the two indicator strains. With the exception of 2,4-DNBA, the mutagenic responses were lower in the nitroreductase-deficient strain TA98NR than in the parental strain. 2,4-DNBA produced a marginally positive response in the V79-cell CA assay; the other substances were devoid of activity. Only the benzoic acids were tested for MN induction in HepG2 cells, and all produced positive responses. As in the bacterial assays, the strongest effect was seen with 2,4,6-TNBA (significant induction at >or=1.9 microM). 4-A-2,6-DNBA was positive at 432 microM; the weakest effect was observed with 2,4,-DNBA (positive at >or=920 microM). The differences in the sensitivity of the indicator cells to these agents can be explained by differences in the activities of enzymes involved in the activation of the compounds. The strong responses produced by some of the compounds in the human-derived cells suggest that environmental exposure to these breakdown products of nitro-explosives may pose a cancer risk in man.

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Section: Discussionsupporting

confidence: 79%

Section: Discussionmentioning

confidence: 99%

Genotoxicity of nitrosulfonic acids, nitrobenzoic acids, and nitrobenzylalcohols, pollutants commonly found in ground water near ammunition facilities

Grummt

Wunderlich

Chakraborty³

et al. 2006

Environ. Mol. Mutagen.

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“…Additionally, Sayama et al. (15) have shown that 2,5‐MNA and some dinitrotoluenes are mutagenic in Salmonella typhimurium YG. 1,4‐DCB induced kidney tumors in male rats and liver tumors in male and female mice (16), whereas 2,5‐DCA was nephrotoxic in rats (17).…”

Section: Introductionmentioning

confidence: 99%

Tattooing of skin results in transportation and light‐induced decomposition of tattoo pigments – a first quantification in vivo using a mouse model

Engel

Vasold

Santarelli

et al. 2009

Experimental Dermatology

100

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Millions of people are tattooed with inks that contain azo pigments. The pigments contained in tattoo inks are manufactured for other uses with no established history of safe use in humans and are injected into the skin at high densities (2.5 mg/cm(2)). Tattoo pigments disseminate after tattooing throughout the human body and although some may photodecompose at the injection site by solar or laser light exposure, the extent of transport or photodecomposition under in vivo conditions remains currently unknown. We investigated the transport and photodecomposition of the widely used tattoo Pigment Red 22 (PR 22) following tattooing into SKH-1 mice. The pigment was extracted quantitatively at different times after tattooing. One day after tattooing, the pigment concentration was 186 microg/cm(2) skin. After 42 days, the amount of PR 22 in the skin has decreased by about 32% of the initial value. Exposure of the tattooed skin, 42 days after tattooing, to laser light reduced the amount of PR 22 by about 51% as compared to skin not exposed to laser light. A part of this reduction is as a result of photodecomposition of PR 22 as shown by the detection of corresponding hazardous aromatic amines. Irradiation with solar radiation simulator for 32 days caused a pigment reduction of about 60% and we again assume pigment decomposition in the skin. This study is the first quantitative estimate of the amount of tattoo pigments transported from the skin into the body or decomposed by solar or laser radiation.

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“…In Stämmen mit entweder erhöhter Nitroreduktase-Aktivität (YG1021, YG1026) oder erhöhter O-Acetyltransferase-Aktivität (YG1024, YG1029) waren einige der getesteten Verbindungen positiv. In den Stäm-men, in denen jedoch beide Aktivitäten erhöht waren (YG1041, YG1042), waren praktisch alle, zum Teil stark mutagen (Sayama et al 1998). Es muss also die Nitroreduktase und insbesondere die O-Acetyltransferase-Aktivität ausreichend hoch sein, um die Nitrogruppe zur Hydroxylamino-Stufe zu reduzieren, die dann durch O-Acetylierung zum ultimalen Mutagen aktiviert wird.…”

Section: In Vitrounclassified

Monozyklische aromatische Amino‐ und Nitroverbindungen [MAK Value Documentation in German language, 2003]

2012

The MAK‐Collection for Occupational Health and Safety

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Veröffentlicht in der Reihe Gesundheitsschädliche Arbeitsstoffe , 37. Lieferung, Ausgabe 2003 Der Artikel enthält folgende Kapitel: Einleitung Einstufung Toxizität Hinweise auf nicht‐genotoxische Effekte Genotoxizität In vitro In vivo Tumorentstehung Wirksamkeit Diskussion Wirkungsmechanismus Struktur‐Wirkungs‐Beziehungen Der Einfluss der Stellungsisomerie Analogien zwischen Arylaminen und Nitroverbindungen Die Gemeinsamkeiten Die Unterschiede Folgerungen für die Einstufung Schlussfolgerungen Ausblick

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Mutagenicities of 2,4- and 2,6-dinitrotoluenes and their reduced products in Salmonella typhimurium nitroreductase- and O-acetyltransferase-overproducing Ames test strains

Cited by 31 publications

References 20 publications

Genotoxicity of nitrosulfonic acids, nitrobenzoic acids, and nitrobenzylalcohols, pollutants commonly found in ground water near ammunition facilities

Genotoxicity of nitrosulfonic acids, nitrobenzoic acids, and nitrobenzylalcohols, pollutants commonly found in ground water near ammunition facilities

Tattooing of skin results in transportation and light‐induced decomposition of tattoo pigments – a first quantification in vivo using a mouse model

Monozyklische aromatische Amino‐ und Nitroverbindungen [MAK Value Documentation in German language, 2003]

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