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PubMed1972

Nitrate reductase of rice seedlings and its induction by organic nitro-compounds.

Nitrate simultaneously induced NADH- and NADPH-nitrate reductase activities in rice seedlings. Chloramphenicol, other organic nitro-compounds such as o-nitroaniline and 2,4-dinitrophenol and nitrite also induced nitrate reductase in rice seedlings. The nitrate- or nitrite-induced nitrate reductase could accept electrons more efficiently from NADH than NADPH. However, when this enzyme was induced by organic nitro-compounds, it could accept electrons more efficiently from NADPH than NADH.

Journal Article↗
PubMed2005

Investigation of correlation between impact sensitivities and nitro group charges in nitro compounds.

A new method of calculating the Mulliken net charges of the nitro group, Q(NO)()2, to assess impact sensitivities for nitro compounds is established. All calculations including optimizations and Mulliken population and frequency analyses are performed by density functional theory (DFT) and the general gradient approximation (GGA) method in Acceryls' code Dmol(3) with the Beck-LYP hybrid functional and the DNP basis set. As a result, the charges on nitro group can be regarded as a structural parameter to estimate the impact sensitivity on the bond strength, oxygen balance, and molecular electrostatic potential. The compound with more -Q(NO)()2 will be insensitive and gives a large value of impact sensitivity H(50)(). This method considering the molecular structure is applicable for almost all nitro compounds when the C-NO(2), N-NO(2), or O-NO(2) bond is the weakest in the molecule. According to the results in this paper, the compounds with -Q(NO)()2 >0.23e show H(50)() </= 0.4 m.

Journal Article↗
PubMed1975

Microbial assimilation of alkyl nitro compounds and formation of nitrite.

66 representative strains of bacteria, yeasts and fungi were tested for their ability to grow in a semidefined medium containing 0.5% nitroethane as a nitrogen source. About half of them were found capable of growing in the medium. Hansenula beijerinckii, Candida utilis, and Penicillium chrysogenum were most active in assimilating nitroethane. 2-Nitropropane inhibited growth of most of the microorganisms tested in a medium containing 0.2% peptone and 0.2% glycerol. Hansenula mrakii was found to grow rapidly in the nitroethane-peptone medium after a lag phase. Nitrite was accumulated in the culture fluid after the phase of logarithmic multiplication, and increased with increase of the growth, followed by a decline after the maximum growth. The alkyl nitro compounds were oxidatively denitrified to form nitrite by the crude enzyme from Hansenula mrakii. Nitroethane was generally a poor substrate, but was the best inducer to produce the nitro compounds oxidizing enzyme. 2-Nitro-propane and nitroethane were enzymatically oxidized to nitrite, and acetone and acetaldehyde, respectively, which were isolated as 2,4-dinitrophenylhydrazones and identified. Nitrite formed was found to be reduced into ammonia by the intact cells and also the crude enzyme.

Acetaldehyde↗
PubMed2002

N-hydroxyarylamine O-acetyltransferase-deficient Escherichia coli strains are resistant to the mutagenicity of nitro compounds.

In Salmonella typhimurium, a single enzyme catalyzes both the acetyl CoA-dependent O-acetylation of hydroxylamines (a key step in the activation of mutagenic nitroaromatic compounds and related aromatic and heterocyclic amines) and the N-acetylation of aromatic amines. S. typhimurium Ames test mutants lacking this activity are highly resistant to the genotoxic effects of nitro compounds. However, such mutants have not yet been obtained in Escherichia coli. We used a PCR-based method to engineer a null mutation (deletion) of the nhoA gene encoding the enzyme in E. coli and we transduced this mutation into a lacZ strain background suitable for use in mutation assays. In E. coli, as in S. typhimurium, nhoA mutants show marked resistance to nitro compound mutagenicity. The new strains provide a clean background for expression of recombinant N-acetyltransferases.

Acetyltransferases↗
PubMed2000

Antifungal nitro compounds from skunk cabbage (Lysichitum americanum) leaves treated with cupric chloride.

Two nitro compounds, 2-(4-methoxyphenyl)-1-nitroethane named as lysichitalexin and 2-(4-hydroxyphenyl)-1-nitroethane were isolated as stress metabolites from the leaves of Lysichitum americanum Hultén and St. John treated with cupric chloride. Their structures were determined by spectroscopic methods and chemical reactions. The former compound showed antifungal activities against Fusarium oxysporum and Cladosporium herbarum. Both compounds were isolated for the first time from this species and the former was isolated from natural sources for the first time. This is the first report on stress metabolites from a member of the Araceae.

Anti-Bacterial Agents↗
PubMed1992

Quantitative structure-activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella Typhimurium TA100.

A quantitative structure-activity relationship (QSAR) has been derived for the mutagenic activity of 117 aromatic and heteroaromatic nitro compounds acting on Salmonella typhimurium TA100. Relative mutagenic activity is bilin-early dependent on hydrophobicity, with an optimal log P of 5.44, and is linearly dependent on the energy of the lowest unoccupied molecular orbital of the nitro compound. The dependence of mutagenic activity on hydrophobicity and electronic effects is very similar for TA98 and TA100. Mutagenic activity in TA100 does not depend on the size of the aromatic ring system, as its does in TA9. The effect of the choice of assay organism, TA98 versus TA100, on nitroarene QSAR is seen to be similar to the effect previously found for aminoarenes. Lateral verification of QSARs is presented as a tool for establishing the significance of a new QSAR.

Amines↗
PubMed1982

[Bacterial reductive transformation of aromatic nitro compounds].

The transformation of 2,4,6-trinitrotoluene (TNT) and other aromatic nitro compounds by bacteria was studied in the course of their growth in a medium containing glucose. Various bacteria were found, for the first time, to be capable of growth in the presence of 200 mg/l of TNT and of transformation of the compound with a higher or lesser activity. The results indicate that Gram-negative bacteria play a key role in TNT transformation under natural conditions. The nitro group reduction is the principal step in the bacterial action on the studied compounds. It is noteworthy that there is no correlation between the degree of nitro reduction and the susceptibility of the bacteria to the toxic effect of benzoic acid, phenol and benzene nitro derivatives.

Alcaligenes↗
PubMed2006

The in vitro antiviral activity of an aliphatic nitro compound from Heteropteris aphrodisiaca.

We investigated the antiviral activity of an aliphatic nitro compound (NC) isolated from Heteropteris aphrodisiaca O. Mach. (Malpighiaceae), a Brazilian medicinal plant. The NC was tested for its antiviral activity against poliovirus type 1 (PV-1) and bovine herpes virus type 1 (BHV-1) by plaque reduction assay in cell culture. The NC showed a moderate antiviral activity against PV-1 and BHV-1 in HEp-2 cells, and the 50% inhibitory concentration (IC50) were 22.01 microg/ml (selectivity index (SI)=2.83) and 21.10 microg/ml (SI=2.95), respectively. At the highest concentration of the drug (40 microg/ml) a reduction of approximately 80% in plaque assay was observed for both viruses. The treatment of cells or virus prior to infection did not inhibit the replication of virus strains.

Animals↗
PubMed1987

Genotoxicity of a variety of nitroarenes and other nitro compounds in DNA-repair tests with rat and mouse hepatocytes.

Genotoxicity of a variety of nitroarenes and other compounds was examined in DNA-repair tests with rat or mouse hepatocytes. Out of 15 nitroarenes tested, 9 compounds, i.e., 1-nitropyrene, 1,3-dinitropyrene, 1,6-dinitropyrene, 1,8-dinitropyrene, 1-nitro-3-acetoxypyrene, 3-nitrofluoranthene, 2-nitrofluorene, 2,7-di-nitrofluorene and 5-nitroacenaphthene elicited positive response of DNA repair in the tests with rat and mouse hepatocytes. Among the positive chemicals, the DNA-repair level of the 3 dinitropyrene isomers was much higher than other nitroarenes. The results indicate that a number of nitroarenes are metabolically activated in the primary culture of rodent hepatocytes, and suggest potential carcinogenicity of 1-nitropyrene and 1-nitro-3-acetoxypyrene the carcinogenicity of which is either not clear or unknown. Of the other nitro compounds, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide as well as 4-nitroquinoline 1-oxide were clearly genotoxic in the assays with hepatocytes of both species. However, 5-nitro-2-furaldehyde semicarbazone was negative in both assays with hepatocytes of 2 species.

Animals↗
PubMed1987

Effects of nitro compounds, isosorbide dinitrate, 5-isosorbide mononitrate and glyceryl trinitrate on Ca-uptake into Ca-stores and Ca-release from Ca-stores in rabbit isolated femoral veins and femoral arteries.

In organ bath studies, effects of isosorbide dinitrate (ISDN), 5-isosorbide mononitrate (ISMN), a major metabolite of ISDN, and glyceryl trinitrate (GTN) on Ca-uptake into Ca-stores and Ca-release from Ca-stores were tested in the rabbit isolated femoral veins and femoral arteries. ISDN (10(-4) M) and GTN (10(-4) M) inhibited Ca-uptake in the femoral veins but not in the femoral arteries. The selectivity to the femoral veins was not observed in ISMN (10(-3) M) and GTN (3 X 10(-6) M). All the nitro compounds inhibited Ca-release from Ca-stores more effectively in the femoral veins than in the femoral arteries. The present results may explain the selectivity of the nitro compounds to the femoral veins.

Animals↗
PubMed1988

Application of difference spectroscopy to the determination of some pharmaceutically important nitro compounds.

A simple and selective spectrophotometric method for the determination of some pharmaceutically important nitro compounds has been developed. The suggested method depends upon the spectral changes induced by reduction using either Zn/HCl or Zn/NH4Cl. The different experimental parameters were studied and incorporated into the procedure. The mean percentage recovery ranged from 99 to 101. The proposed method was applied to the determination of the studied compounds in dosage forms, and the results obtained were compared favourably with those given with the compendial ones.

Indicators and Reagents↗
PubMed2001

Novel transformations of gamma-silyl nitro compounds.

Introduction of a gamma-silyl group into nitro compounds of dihydrobenzofuran, dihydrobenzo[b]thiophene, and dihydrofuran allowed new transformations to take place in the presence of a Lewis acid to give the corresponding alpha,beta-unsaturated oximes or multisubstituted dihydrofurans, respectively, in good to excellent yields.[reaction: see text]

Journal Article↗
PubMed1983

Effect of dietary carrageenan and pectin on the reduction of nitro-compounds by the rat caecal microflora.

Rats were fed either a basal purified diet, or that diet supplemented with 50 g/kg pectin or iota carrageenan for 50 days, and caecal microbial nitroreductase activity determined using p-nitrobenzoic acid, p-nitrophenol, 2,4-dinitrotoluene, nitrofurantoin and metronidazole as substrates. Both pectin and carrageenan increased the weight of caecal contents, and pectin also increased the number of bacteria per caecum. In contrast, carrageenan decreased the caecal bacterial population. Pectin significantly increased the rate of reduction of metronidazole and the rate of conversion of p-nitrobenzoic acid to p-aminobenzoic acid, while carrageenan significantly decreased the rate of reduction of every compound studied. The results demonstrate that microbial reduction of the nitro-group may be altered by diet, although the response found with one nitro-compound may differ from that seen with another substrate.

Animals↗
PubMed1991

Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.

A review of the literature yielded data on over 200 aromatic and heteroaromatic nitro compounds tested for mutagenicity in the Ames test using S. typhimurium TA98. From the data, a quantitative structure-activity relationship (QSAR) has been derived for 188 congeners. The main determinants of mutagenicity are the hydrophobicity (modeled by octanol/water partition coefficients) and the energies of the lowest unoccupied molecular orbitals calculated using the AM1 method. It is also shown that chemicals possessing three or more fused rings possess much greater mutagenic potency than compounds with one or two fused rings. Since the QSAR is based on a very wide range in structural variation, aromatic rings from benzene to coronene are included as well as many different types of heterocycles, it is a significant step toward a predictive toxicology of value in the design of less mutagenic bioactive compounds.

Animals↗