Toxicity of explosives and related compounds to the luminescent bacterium Vibrio fischeri NRRL-B-11177

Drzyzga, Oliver; Gorontzy, Thomas; Schmidt, Arndt W.; Blotevogel, Karl-Heinz

doi:10.1007/bf00217621

Cited by 90 publications

(67 citation statements)

References 8 publications

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“…However, a comparison of corresponding EC values of the presented study indicates the long-term version to be more sensitive than the short-term assay. These "ndings are in agreement with observations of Drzyzga et al (1995) describing increasing toxicity of these compounds with increasing exposure time from 30 up to 90 min. The increased sensitivity of the long-term assay for all three compounds tested is only by a factor of 3}10, suggesting that elevated luminescence inhibition is not caused by speci"c adverse impact of the nitroaromatics on biosynthetic pathways of growing bacteria in the long-term assay, as observed for several speci"-cally acting chemicals by Backhaus et al (1997).…”

Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dsupporting

confidence: 93%

“…,scheri as determined in this study by the established short-term assay are generally concordant with those published by other authors (Drzyzga et al, 1995;Sunahara et al, 1998). In addition, the described order of decreasing toxicity with the parent molecule TNT as most toxic compound and both primary reduced metabolites 4A-DNT and 2A-DNT showing lower inhibition of bacterial luminescence was con"rmed by the results of the long-term assay with 24 h of incubation.…”

Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dsupporting

confidence: 88%

“…and EC values of the short-term assay reveal a typical sequence of decreasing toxicity, which has been described by other authors (Drzyzga et al, 1995;Sunahara et al, 1998). EC values from this study identify TNT (1.99 mg/L) to be the most toxic compound, followed by 4A-DNT (10.2 mg/L) and 2A-DNT (21 mg/L).…”

Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dmentioning

confidence: 58%

“…In the study presented here, luminescent bacteria have been chosen for toxicity screening, because sensitivity of <. ,scheri toward TNT and its derivatives has been reported (Drzyzga et al, 1995;Dodard et al, 1999). Moreover, as proposed by Sunahara et al (1998), the analogous appearance of reduced metabolites in the well-described anaerobic and aerobic reductive (bio)transformation pathway of TNT (Blotevogel and Gorontzy, 2000) would re#ect a process of detoxi"cation of the TNT molecule, which is detectable by luminescent bacteria.…”

Section: Introductionmentioning

confidence: 95%

See 3 more Smart Citations

Screening for Soil Toxicity and Mutagenicity Using Luminescent Bacteria—A Case Study of the Explosive 2,4,6-Trinitrotoluene (TNT)

Frische

2002

Ecotoxicology and Environmental Safety

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Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dsupporting

confidence: 93%

Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dsupporting

confidence: 88%

Section: Toxicity and Mutagenicity Of The Single Substances Tnt 2a-dmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 95%

See 2 more Smart Citations

Screening for Soil Toxicity and Mutagenicity Using Luminescent Bacteria—A Case Study of the Explosive 2,4,6-Trinitrotoluene (TNT)

Frische

2002

Ecotoxicology and Environmental Safety

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“…Nitroaromatic compounds including nitrofurans, nitropyrenes, and nitrobenzenes have been used as antimicrobial agents, food additives and raw materials in several industrial processes (1)(2)(3)(4)(5), and as a result are distributed widely around the environment. Many of these compounds are toxic, mutagenic, or carcinogenic (6 -8).…”

mentioning

confidence: 99%

Structure and Site-directed Mutagenesis of a Flavoprotein fromEscherichia coli That Reduces Nitrocompounds

Kobori

Sasaki

Lee

et al. 2001

Journal of Biological Chemistry

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The crystal structure of a major oxygen-insensitive nitroreductase (NfsA) from Escherichia coli has been solved by the molecular replacement method at 1.7-Å resolution. This enzyme is a homodimeric flavoprotein with one FMN cofactor per monomer and catalyzes reduction of nitrocompounds using NADPH. The structure exhibits an ␣ ؉ ␤-fold, and is comprised of a central domain and an excursion domain. The overall structure of NfsA is similar to the NADPH-dependent flavin reductase of Vibrio harveyi, despite definite difference in the spatial arrangement of residues around the putative substrate-binding site. Nitroaromatic compounds including nitrofurans, nitropyrenes, and nitrobenzenes have been used as antimicrobial agents, food additives and raw materials in several industrial processes (1-5), and as a result are distributed widely around the environment. Many of these compounds are toxic, mutagenic, or carcinogenic (6 -8). It is believed that enzymatic transformation is needed for nitroaromatic compounds to show these serious effects (9, 10). The reduction of a nitro group of a parent nitrocompound is a key step of this process (11,12). Enzymes, which catalyze the reduction of nitrocompounds using a reduced pyridine nucleotide, are termed nitroreductases and are distinguished by their sensitivity of activity to oxygen (9, 10).The oxygen-sensitive enzymes can catalyze nitroreduction only under anaerobic conditions. A nitro-anion radical formed by a one-electron transfer is immediately reoxidized in the presence of oxygen to a parent nitrocompound and superoxide (13,14). In this futile cycle, reducing equivalents are consumed without the progress of nitroreduction and nitrocompounds perform as a catalyst to reduce oxygen. On the other hand, the oxygen-insensitive enzymes catalyze an obligatory two-electron reduction. A nitro group of a parent nitrocompound is reduced by a series of two-electron transfers, through nitroso and hydroxylamine intermediates, and finally to an amino group (13). The hydroxylamine intermediate arising from the four-electron transfer in total is found to be toxic, carcinogenic, or mutagenic.Three proteins with oxygen-insensitive nitroreductase activity in Escherichia coli have been identified (15). NfsA 1 is the major component, while NfsB and NfsC are minor components. NfsA and NfsB have been well studied relative to NfsC. NfsA and NfsB have similar enzymatic property, although NfsA has only 7% identity with NfsB on the amino acid sequence alignment. Both NfsA and NfsB are flavoenzymes with FMN as the prosthetic group and catalyze the reduction of nitrocompounds by Ping Pong Bi Bi kinetics (16,17). Counterparts of NfsA and NfsB, found in luminescent bacteria (16,17), are flavin reductase (FRP) of Vibrio harveyi (18) and flavin reductase (FRase I) of Vibrio fischeri (19), respectively. Enzyme that resembles FRP in the amino acid sequence alignment is also found in Bacillus subtilus and is called NfrA1 (20). A comparison of * This work was supported in part by grants-in-aid for Scientific Res...

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Microbial Degradation of Compounds with Nitro Functions

Blotevogel¹,

Gorontzy²

2000

Biotechnology

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Toxicity of explosives and related compounds to the luminescent bacterium Vibrio fischeri NRRL-B-11177

Cited by 90 publications

References 8 publications

Screening for Soil Toxicity and Mutagenicity Using Luminescent Bacteria—A Case Study of the Explosive 2,4,6-Trinitrotoluene (TNT)

Screening for Soil Toxicity and Mutagenicity Using Luminescent Bacteria—A Case Study of the Explosive 2,4,6-Trinitrotoluene (TNT)

Structure and Site-directed Mutagenesis of a Flavoprotein fromEscherichia coli That Reduces Nitrocompounds

Microbial Degradation of Compounds with Nitro Functions

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