Microbial toxicity of the insensitive munitions compound, 2,4-dinitroanisole (DNAN), and its aromatic amine metabolites

Jidong Liang, Christopher Olivares, James A Field, Maria Reye Sierra Alvarez

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

2,4-Dinitroanisole (DNAN) is an insensitive munitions compound considered to replace conventional explosives such as 2,4,6-trinitrotoluene (TNT). DNAN undergoes facile microbial reduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN). This study investigated the inhibitory effect of DNAN, MENA, and DAAN toward various microbial targets in anaerobic (acetoclastic methanogens) and aerobic (heterotrophs and nitrifiers) sludge, and the bioluminescent bacterium, Aliivibrio fischeri, used in the Microtox assay. Aerobic heterotrophic and nitrifying batch experiments with DAAN could not be performed because the compound underwent extensive autooxidation in these assays. DNAN severely inhibited methanogens, nitrifying bacteria, and A. fischeri (50% inhibitory concentrations (IC50) ranging 41-57μM), but was notably less inhibitory to aerobic heterotrophs (IC50>390μM). Reduction of DNAN to MENA and DAAN lead to a marked decrease in methanogenic inhibition (i.e., DNAN>MENA≈DAAN). Reduction of all nitro groups in DNAN also resulted in partial detoxification in assays with A. fischeri. In contrast, reduction of a single nitro group did not alter the inhibitory impact of DNAN toward A. fischeri and nitrifying bacteria given the similar IC50 values determined for MENA and DNAN in these assays. These results indicate that reductive biotransformation could reduce the inhibitory potential of DNAN.

Original languageEnglish (US)
Pages (from-to)281-287
Number of pages7
JournalJournal of Hazardous Materials
Volume262
DOIs
StatePublished - Nov 15 2013

Fingerprint

Metabolites
Amines
Toxicity
Assays
metabolite
assay
Methanogens
toxicity
Bacteria
nitrifying bacterium
Aliivibrio fischeri
Inhibitory Concentration 50
trinitrotoluene
Detoxification
biotransformation
detoxification
explosive
sludge
bacterium
amine

Keywords

  • 2,4-Diaminoanisole
  • 2,4-Dinitroanisole
  • 2-Methoxy-5-nitroaniline
  • Microbial toxicity
  • Microtox

ASJC Scopus subject areas

  • Health, Toxicology and Mutagenesis
  • Pollution
  • Waste Management and Disposal
  • Environmental Chemistry
  • Environmental Engineering
  • Medicine(all)

Cite this

Microbial toxicity of the insensitive munitions compound, 2,4-dinitroanisole (DNAN), and its aromatic amine metabolites. / Liang, Jidong; Olivares, Christopher; Field, James A; Sierra Alvarez, Maria Reye.

In: Journal of Hazardous Materials, Vol. 262, 15.11.2013, p. 281-287.

Research output: Contribution to journalArticle

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abstract = "2,4-Dinitroanisole (DNAN) is an insensitive munitions compound considered to replace conventional explosives such as 2,4,6-trinitrotoluene (TNT). DNAN undergoes facile microbial reduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN). This study investigated the inhibitory effect of DNAN, MENA, and DAAN toward various microbial targets in anaerobic (acetoclastic methanogens) and aerobic (heterotrophs and nitrifiers) sludge, and the bioluminescent bacterium, Aliivibrio fischeri, used in the Microtox assay. Aerobic heterotrophic and nitrifying batch experiments with DAAN could not be performed because the compound underwent extensive autooxidation in these assays. DNAN severely inhibited methanogens, nitrifying bacteria, and A. fischeri (50{\%} inhibitory concentrations (IC50) ranging 41-57μM), but was notably less inhibitory to aerobic heterotrophs (IC50>390μM). Reduction of DNAN to MENA and DAAN lead to a marked decrease in methanogenic inhibition (i.e., DNAN>MENA≈DAAN). Reduction of all nitro groups in DNAN also resulted in partial detoxification in assays with A. fischeri. In contrast, reduction of a single nitro group did not alter the inhibitory impact of DNAN toward A. fischeri and nitrifying bacteria given the similar IC50 values determined for MENA and DNAN in these assays. These results indicate that reductive biotransformation could reduce the inhibitory potential of DNAN.",
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