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Reactivity of partially reduced arylhydroxylamine and nitrosoarene metabolites of 2,4,6-trinitrotoluene (TNT) toward biomass and humic acids.

TNT部分還元代謝物(アリールヒドロキシルアミンおよびニトロソアレーン)のバイオマスおよびフミン酸との反応性

in vitro study in vitro not assessed

Abstract

This study examined the binding mechanisms of partially reduced TNT metabolites to biomass and humic acids during sequential anaerobic/aerobic remediation. Using cell-free extracts of Clostridium acetobutylicum with molecular hydrogen as a reductant, approximately 10% of total 14C became associated with an organic-solvent-insoluble, protein-containing precipitate. Model reactions with 1-thioglycerol demonstrated that DHA6NT formed a novel polar product exclusively under aerobic conditions, confirming that nitroso functionality drives biomass binding. Among humic acid interactions, 4HADNT showed negligible reactivity, whereas nitrosobenzene achieved 50% removal from peat humic acid within 48 hours. Experiments with humic acids of varying protein content and selective thiol-blocking agents indicated that proteinaceous and thiol-containing fractions mediate nitrosoarene removal. Molecular modeling further revealed that more extensively reduced nitroso-bearing TNT derivatives possess greater electrophilicity and are therefore more prone to react with nucleophilic sites in humic substances.

Mechanism

Nitroso groups in partially reduced TNT metabolites react with nucleophilic thiol and proteinaceous sites in biomass and humic acids, leading to covalent incorporation into insoluble organic matter fractions.

Bibliographic

Authors
Ahmad F, Hughes JB
Journal
Environ Sci Technol
Year
2002 (2002-10-15)
PMID
12387411
DOI
10.1021/es011397p

Tags

Mechanism:酸化ストレス 活性酸素種

Delivery context

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

Safety notes

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

See also:

Cite as: H2 Papers — PMID 12387411. https://h2-papers.org/en/papers/12387411
Source: PubMed PMID 12387411