Mutagenicity of 2,6-dinitrotoluene and its metabolites, and their related compounds in Salmonella typhimurium

Sayama, Michio; Mori, Masaaki; Shirokawa, Tomoko; Inoue, Masami; Miyahara, Tetsuhiro; Kono, Hiroshi

doi:10.1016/0165-7992(89)90017-1

Cited by 17 publications

(2 citation statements)

References 7 publications

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“…4À8 Since 2,4-DNBA and 2,6-DNBA are mutagenic, knowledge of their solubility will help assess their impact on the environment. 9,10 The solubility of neutral organic compounds can be altered by the presence of inorganic salts. When the solubility decreases, the process is commonly called "salting-out" (see review in Xie et al 11 ).…”

Section: ' Introductionmentioning

confidence: 99%

“…In the case of 2,4-dinitrobenzaldehyde (2,4-DNBA) and 2,6-dinitrobenzaldehyde (2,6-DNBA), the aqueous solubility has been estimated in pure water but not yet measured. These compounds are used in chemical synthesis and can also be formed by the photolysis of dinitrotoluenes (DNTs) that are leaking from UXOs or as a byproduct of the treatment of DNTs with ozone and peroxide. − Since 2,4-DNBA and 2,6-DNBA are mutagenic, knowledge of their solubility will help assess their impact on the environment. , …”

Section: Introductionmentioning

confidence: 99%

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Assessing the Salting-Out Behavior of 2,4-Dinitrobenzaldehyde and 2,6-Dinitrobenzaldehyde from Solubility Values in Pure Water and Seawater at Temperatures between (280 and 313) K

Prak¹,

O’Sullivan²

2011

J. Chem. Eng. Data

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The salting-out behavior of 2,4-dinitrobenzaldehyde (2,4-DNBA) and 2,6-dinitrobenzaldehyde (2,6-DNBA) was determined from solubility measurements in pure water and seawater with ionic strengths of (0.1662, 0.3352, 0.5071, and 0.6820) mol 3 kg À1 at temperatures between (280 and 314) K. For both compounds tested, the solubility increased with increasing temperature. As the ionic strength of the solution increased, the solubility of the organic compounds decreased. The average saltingout coefficients for 2,4-DNBA and 2,6-DNBA were (0.12 and 0.10) kg 3 mol À1 , respectively, which are consistent with measurements for other nitroaromatic compounds. Over the temperature range examined, the salting-out coefficients did not vary significantly.

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Section: ' Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Assessing the Salting-Out Behavior of 2,4-Dinitrobenzaldehyde and 2,6-Dinitrobenzaldehyde from Solubility Values in Pure Water and Seawater at Temperatures between (280 and 313) K

Prak¹,

O’Sullivan²

2011

J. Chem. Eng. Data

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Modulation of 2,6-dinitrotoluene genotoxicity by alachlor treatment of Fischer 344 rats

Brooks

et al. 1998

Environ. Mol. Mutagen.

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Due to its widespread use as a preemergent herbicide, alachlor has been detected as a groundwater contaminant. The procarcinogen, 2,6‐dinitrotoluene (DNT), a by‐product of the munitions industry and a precursor to polyurethane production, is found in the manufacturing waste stream. This study explores the effect of alachlor treatment on the bioactivation of DNT by examining urine mutagenicity, intestinal enzymes, and hepatic DNA adducts to detect changes in metabolism. Five‐week‐old male rats were treated daily by gavage with 50 mg/kg of alachlor for up to 5 weeks while control animals received an equal volume of peanut oil. At 1, 3, and 5 weeks following the initial alachlor dose, animals were administered p.o. 75 mg/kg DNT or DMSO. Urine was collected for 24 hr in metabolism cages. Following incubation with sulfatase and β‐glucuronidase, urines were individually concentrated by C‐18 solid phase extraction, dried under N2, and prepared for bioassay in Salmonella typhimurium strain TA98 with and without metabolic activation. Urine from peanut oil‐ and alachlor‐treated rats was not mutagenic. Even though calf thymus DNA–alachlor adducts formed in vitro, no hepatic DNA adducts were detected in vivo in these two treatment groups. Interestingly, a significant increase in excretion of mutagenic urine from DNT‐treated rats was observed following 3 weeks of alachlor treatment in the absence of S9 (690 ± 130 vs. 339 ± 28 revertants/ml) which corresponded to increased DNT‐related hepatic DNA adduct formation (5.90 ± 0.88 adducts/108 nucleotides vs. 10.56 × ±0.59 adducts/108 nucleotides [relative adduct level (RAL)]). Elevation in the production of mutagenic urine from control and treated animals was linked to increases in intestinal nitroreductase and β‐glucuronidase activities; however, the only significant alachlor‐related effects were an increase in small intestinal 1‐week β‐glucuronidase and 5‐week dehydrochlorinase activities. The increased urine mutagenicity and hepatic DNA adduct formation indicates that alachlor has a transient effect on DNT bioactivation that apparently is unrelated to intestinal bioactivation. Environ. Mol. Mutagen. 31:274–281, 1998. © 1998 Wiley‐Liss, Inc.

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Dinitrotoluenes (mixtures of isomers) [MAK Value Documentation, 1993]

2012

The MAK‐Collection for Occupational Health and Safety

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Published in the series Occupational Toxicants , Vol. 6 (1993) The article contains sections titled: Characterization of the isomers and the mixture Toxic Effects and Modes of Action Pharmacokinetics Enzyme induction Macromolecular binding, DNA repair Effects in Man Effects on Animals Acute toxicity Haematological studies Subchronic and chronic toxicity Genotoxicity Ames Test Dominant lethal test Other mutagenicity tests Reproductive and Developmental Toxicity Teratogenicity studies In vitro antifertility studies Carcinogenicity Long‐term studies Mouse lung adenoma test Initiation‐promotion studies Manifesto (MAK value, classification)

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Mutagenicity of 2,6-dinitrotoluene and its metabolites, and their related compounds in Salmonella typhimurium

Cited by 17 publications

References 7 publications

Assessing the Salting-Out Behavior of 2,4-Dinitrobenzaldehyde and 2,6-Dinitrobenzaldehyde from Solubility Values in Pure Water and Seawater at Temperatures between (280 and 313) K

Assessing the Salting-Out Behavior of 2,4-Dinitrobenzaldehyde and 2,6-Dinitrobenzaldehyde from Solubility Values in Pure Water and Seawater at Temperatures between (280 and 313) K

Modulation of 2,6-dinitrotoluene genotoxicity by alachlor treatment of Fischer 344 rats

Dinitrotoluenes (mixtures of isomers) [MAK Value Documentation, 1993]

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