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PubMed1986

Isolation, identification and bacterial mutagenicity of 2-nitro-9-fluorenone from diesel-exhaust particle extracts.

Organic extracts of diesel-exhaust particles show direct mutagenic activity in the Salmonella typhimurium bacterial mutagenicity assay. Nitro-aromatic compounds are believed to be responsible for part of the mutagenicity. A previously unidentified polyfunctional nitro-aromatic compound, 2-nitro-9-fluorenone (2N-Fone) was isolated from diesel-exhaust particles using a two-step fractionation scheme consisting of Sephadex LH20 chromatography and silica-gel thin-layer chromatography. Positive identification was by gas chromatography/mass spectroscopy and coelution with an authentic standard. Direct and indirect mutagenicities of 2N-Fone in several bacterial strains were also determined. The results indicated that 2N-Fone produces 60-70 rev/nmole of direct mutagenic activity, and is about 1/5 to 1/10 as mutagenic as 1-nitropyrene.

Chromatography↗
PubMed2001

Studies on energetic compounds. Part 16. Chemistry and decomposition mechanisms of 5-nitro-2,4-dihydro-3H-1,2,4-triazole-3-one (NTO).

The present review deals with the chemistry and thermolysis of NTO and plausible decomposition pathways have been described. The decomposition of 5-nitro-2,4-dihydro-3H-1,2,4-triazole-3-one (NTO) induced by X-ray, UV, laser, photochemical irradiation has also been discussed. High-speed photographic studies of the impact responses of NTO are also included. The thermal decomposition of labelled NTO has also been described here. Methods of detection as well as safe disposal of NTO have also been mentioned.

Molecular Structure↗
PubMed2000

The genotoxicity of 3-nitrobenzanthrone and the nitropyrene lactones in human lymphoblasts.

Polycyclic aromatic hydrocarbons (PAH) and nitrated polycyclic aromatic compounds (nitro-PAC) have been found to be mutagenic in bacterial and human cells as well as carcinogenic in rodents. In this investigation, the genotoxic effects of 3-nitrobenzanthrone (3NB) and a mixture of nitropyrene lactones (NPLs) were determined using forward mutation assays performed in two human B-lymphoblastoid cell lines, MCL-5 and h1A1v2, which are responsive to the nitro-PAC class of compounds. Mutagenicity of the compounds was determined at the heterozygous tk locus and the hemizygous hprt locus, thus, identifying both large-scale loss of heterozygosity (LOH) events as well as intragenic mutagenic events. Genotoxicity was also determined using the CREST modified micronucleus assay, which detects chromosomal loss and breakage events. Results indicate 3NB is an effective human cell mutagen, significantly inducing mutations at the tk and hprt loci in both cell lines, and inducing micronuclei in the h1A1v2 cell line. The NPL isomers are also mutagenic, inducing mutations at the two loci as well as micronuclei in both cell lines. Because of their mutagenic potencies and their presence in ambient air, further assessments should be made of human exposures to these nitro-PAC and the potential health risks involved.

B-Lymphocytes↗
PubMed2003

Nitroheterocyclic drugs with broad spectrum activity.

The group of biologically active nitroheterocyclic compounds includes various 5- and 2-nitroimidazoles and 5-nitrofurans, which can be used as therapeutic agents against a variety of protozoan and bacterial (anaerobic) infections of humans and animals. The current status in the the treatment of giardiasis, trichomoniasis, balantidiasis, histomoniasis, and amebiasis (including infections due to opportunistic amebas) is presented. The most relevant drugs (benznidazole, furazolidone, metronidazole, misonidazole, nifurtimox, nimorazole, nitazoxanide, ornidazole, secnidazole, and tinidazole) are characterized with regard to their chemical, chemotherapeutic, toxicological, pharmacokinetic, and pharmacological properties, including the mechanism of action and resistance in certain parasitic protozoa.

Animals↗
PubMed1990

Redox cycling of radical anion metabolites of toxic chemicals and drugs and the Marcus theory of electron transfer.

A wide variety of aromatic compounds are enzymatically reduced to form anion free radicals that generally contain one more electron than their parent compounds. In general, the electron donor is any of a wide variety of flavoenzymes. Once formed, these anion free radicals reduce molecular oxygen to superoxide and regenerate the parent compound unchanged. The net reaction is the oxidation of the flavoenzyme's coenzymes and the reduction of molecular oxygen. This catalytic behavior has been described as futile metabolism or redox cycling. Electron transfer theory is being applied to these reactions and, in some cases, has successfully correlated Vmax and Km with the reduction potentials of the aromatic compounds.

Anions↗
PubMed1981

Mutagenicity of nitro derivatives induced by exposure of aromatic compounds to nitrogen dioxide.

Mutagenic nitro derivatives were readily induced when 6 kinds of chemicals were exposed to 10 ppm of nitrogen dioxide (NO2). Single nitro derivatives were formed from pyrene, phenanthrene, fluorene or chrysene. Carbazole and fluoranthene each produced 2 derivatives substituted with nitro groups at different positions. The formation of nitro derivatives was enhanced by exposure of pyrene to NO2 containing nitric acid (HNO3, less than 100-fold enhancement) or sulphur dioxide (SO2, less than 15-fold enhancement). After 24 h of exposure the yields of the nitro derivative were 0.02% with 1 ppm of NO2 in air and 2.85% with NO2 (1 ppm) containing traces of HNO3. The nitro derivatives from all but phenanthrene and carbazole were chemically identified by means of gas chromatography (GC) and mass spectrometry (MS), and the mutagenicity of the 4 kinds of authentic nitro derivatives was tested by using Salmonella strains TA98 and TA1538 with or without the S9 fraction from rat liver treated with Aroclor 1254. The nitro derivative induced from pyrene was determined to be 1-nitropyrene; that of chrysene was 6-nitrochrysene; that of fluorene was 2-nitrofluorene; and those of fluoranthene were 3-nitrofluoranthene, and 8-nitrofluoranthene. Tested with strain TA98 in the absence of the S9 fraction, the first 4 of these derivatives yielded, respectively, 3050, 269, 433 and 13 400 revertants per nmole. Thus, each nitro derivative formed was potentially a direct-acting frameshift-type mutagen. Each compound exposed to NO2 showed a decreased mutagenic activity when tested in the presence of S9 mix. A possible explanation comes from experiments in which 1-nitropyrene was incubated with the S9 mix at 37 degree C for 10 min, and 1-aminopyrene was formed. The mutagenic activity of 1-aminopyrene was appreciable, but only about one-tenth of that of 1-nitropyrene in the Ames test.

Heterocyclic Compounds↗
PubMed1973

New synthetic antibacterial compound, 1-(2-hydroxyethyl)-3-nitro-4-pyrazole carboxamide.

A series of 3-nitropyrazole compounds represent a new class of synthetic antibacterial agents. One member of this series, 1-(2-hydroxyethyl)-3-nitro-4-pyrazolecarboxamide, exhibited an antibacterial spectrum similar to that of nitrofurantoin. The inhibitory concentrations of this nitropyrazole were lower than those required for nitrofurantoin. Single oral doses of 20 mg/kg resulted in peak nitropyrazole concentrations of 5.8 and >1,000 mug/ml in mouse blood and urine, respectively. In dogs, 87% of a 10 mg/kg oral dose was recovered in urine during a 24-h period with a peak serum concentration of 13.6 mug/ml. This nitropyrazole was highly effective against experimental bacterial infections in mice. The low acute toxicity in mice, rats, or dogs and significant antibacterial activity lead to the conclusion that further evaluation of this compound is warranted.

Amides↗
PubMed1995

Potential radioprotective agents--VI. Chalcones, benzophenones, acid hydrazides, nitro amines and chloro compounds. Radioprotection of murine intestinal stem cells.

There is an interest and need for new compounds that protect tissues from radiation injury. In cancer therapy, the protection of normal tissue without protecting tumors is one way to increase the therapeutic gain. Thiol compounds are currently in clinical trials, but are limited to some extent by their human toxicities including hypotension, nausea, and emesis. Several new aminochalcones and aminobenzophenones were synthesized and tested for radioprotective activity in mice. All were less active than p-aminobenzophenone itself. Several acid hydrazides were synthesized and tested similarly, but none exhibited significant activity. The high radioprotective activity of 4-nitroaniline was confirmed, but other nitro amines were substantially less active. 4-Chloro-N-methylaniline is as active as 4-chloroaniline, but other chloro aromatics are devoid of significant activity. When compared with the phosphorothioate amyfostine (WR-2721) using the intestinal clonogenic cell survival assay, 1-(p-aminophenyl)-1-propanol (15), p-aminopropiophenone (16), its ethylene ketal (14), and a mixture of the two (17) protected to a great extent, though slightly less than WR-2721. These results suggest that there is direct cellular radioprotection by these non-thiol compounds. The studies further suggest that preclinical toxicity testing of the most protective agents is warranted.

Amines↗
PubMed1998

Oxygen-insensitive nitroreductases: analysis of the roles of nfsA and nfsB in development of resistance to 5-nitrofuran derivatives in Escherichia coli.

Nitroheterocyclic and nitroaromatic compounds constitute an enormous range of chemicals whose potent biological activity has significant human health and environmental implications. The biological activity of nitro-substituted compounds is derived from reductive metabolism of the nitro moiety, a process catalyzed by a variety of nitroreductase activities. Resistance of bacteria to nitro-substituted compounds is believed to result primarily from mutations in genes encoding oxygen-insensitive nitroreductases. We have characterized the nfsA and nfsB genes of a large number of nitrofuran-resistant mutants of Escherichia coli and have correlated mutation with cell extract nitroreductase activity. Our studies demonstrate that first-step resistance to furazolidone or nitrofurazone results from an nfsA mutation, while the increased resistance associated with second-step mutants is a consequence of an nfsB mutation. Inferences made from mutation about the structure-function relationships of NfsA and NfsB are discussed, especially with regard to the identification of flavin mononucleotide binding sites. We show that expression of plasmid-carried nfsA and nfsB genes in resistant mutants restores sensitivity to nitrofurans. Among the 20 first-step and 53 second-step mutants isolated in this study, 65 and 49%, respectively, contained insertion sequence elements in nfsA and nfsB. IS1 integrated in both genes, while IS30 and IS186 were found only in nfsA and IS2 and IS5 were observed only in nfsB. Insertion hot spots for IS30 and IS186 are indicated in nfsA, and a hot spot for IS5 insertion is evident in nfsB. We discuss potential regional and sequence-specific determinants for insertion sequence element integration in nfsA and nfsB.

Amino Acid Sequence↗