nitrophenols and 2-amino-4-nitrophenol

Topics: Animals; Carcinogens; Female; Hair Dyes; Humans; Male; Mice; Mice, Inbred Strains; Nitrophenols; Rats; Rats, Inbred F344

Fungicidal effect of 2-amino-4-nitrophenol and its derivates, prepared by replacing the hydrogen atom in its amino group by different organic radicals was studied. Evaluation of the biological activity of studied substances by сomputational chemistry methods was performed. Toxicity of 2-amino-4-nitrophenol and synthesized N-(2-hydroxy-5-nitrophenyl)formamide and N-(2-hydroxy-5-nitrophenyl)acetamide to six species of phytophatogen fungi were tested in the experiment. The results of the study demonstrate that replacement of the hydrogen atom in the amino group by a aldehyde group leads to an increase in fungicidal activity with respect to Rhizoctonia solani and Bipolaris sorokiniana. A replacement of the hydrogen atom by a ketone group increases the inhibitory effect on Sclerotinia sclerotiorum and Venturia inaequalis. The paper contains comparative data on the fungicide effect of commercial preparation for studied fungi also.

Topics: Acetamides; Ascomycota; Formamides; Fungicides, Industrial; Ketones; Nitrophenols; Rhizoctonia; Structure-Activity Relationship

Some new Schiff bases (H

Topics: Aldehydes; Aminophenols; Anti-Bacterial Agents; Antioxidants; Bacteria; Bacterial Infections; Cresols; Crystallography, X-Ray; Drug Discovery; Humans; Microbial Sensitivity Tests; Models, Molecular; Nitrophenols; Pyrroles; Schiff Bases; Thiophenes

Visible matrix-assisted laser desorption/ionization (VIS-MALDI) was performed using 2-amino-3-nitrophenol as matrix. The matrix is of near-neutral pH, and has an optical absorption band in the near-UV and visible region. A frequency-doubled Nd:YAG laser operated at 532 nm wavelength was used for matrix excitation and comparisons were made with a frequency-tripled Nd:YAG laser (355 nm). Visible and ultraviolet (UV)-MALDI produce similar mass spectra for peptides, polymers, and small proteins with comparable sensitivities. Due to the smaller optical absorption coefficient of the matrix at 532 nm wavelength, the optical penetration depth is larger, and the sample consumption per laser shot in VIS-MALDI is higher than that of UV-MALDI. Nevertheless, VIS-MALDI using 2-amino-3-nitrophenol as matrix may offer a complementary technique to the conventional UV-MALDI method in applications where deeper laser penetration is required.

Topics: Adrenocorticotropic Hormone; Angiotensin I; Nitrophenols; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

The steady-state kinetics of the horseradish peroxidase (HRP)-catalyzed oxidation of 3,3',5,5'-tetramethylbenzidine (TMB) has been studied in the presence of 2-amino-4-nitrophenol (ANP), gallic acid (GA) or 4,4'-dihydroxydiphenylsulfone (DDS) and their polydisulfides poly(ADSNP), poly(DSGA), poly(DSDDS) at 20 degrees C in 10 mM phosphate buffer, pH 6.4, supplemented with 5-10% dimethylformamide. The second-order rate constants for the reactions of ANP, GA, poly(DSGA) and poly(DSDDS) with HRP-Compound I (k2) and Compound II (k3) have been determined at 25 degrees C in 10 mM phosphate buffer, pH 6.0 by stopped-flow spectrophotometry. ANP, GA and their polydisulfides strongly inhibited HRP-catalyzed TMB oxidation. Inhibition constants (Ki) and stoichiometric coefficients of inhibition (f) have been determined for these reactions. The most effective inhibitor was poly(DSGA) (Ki=1.3 microM, f=35.6). The oxidation of substrate pairs by HRP, i.e., TMB-DDS and TMB-poly(DSDDS) at pH 7.2 resulted in a approximately 8- and approximately 12-fold stimulation of TMB oxidation rates, respectively. The mechanisms of the HRP-catalyzed co-oxidation of TMB-phenol pairs are discussed.

Topics: Antioxidants; Benzidines; Catalysis; Disulfides; Enzyme Inhibitors; Gallic Acid; Horseradish Peroxidase; Hydrogen-Ion Concentration; Kinetics; Nitrophenols; Oxidation-Reduction

The effects of different concentrations of 2-amino-4-nitrophenol (ANP) and of its polydisulfide (poly(ADSNP)) on peroxidase-catalyzed oxidation of 3,3',5,5'-tetramethylbenzidine (TMB) were studied at 20 degrees C in reversed micelles of AOT (0.2 M) in heptane and in mixed reversed micelles of AOT (0.1 M)-Triton X-100 (0.1 M) in isooctane supplemented with 15% hexanol. The oxidation of TMB was activated nearly twofold in the presence of ANP and nearly fourfold in the presence of poly(ADSNP) in reversed micelles of AOT, whereas in the mixed micelles oxidation of the TMB-ANP pair was associated with inhibition of TMB conversion and poly(ADSNP) activated oxidation of TMB. The co-oxidation of TMB with 4,4'-dihydroxydiphenylsulfone (DDS) and with its polydisulfide (poly(DSDDS)) at different concentrations of phenol components was accompanied by activation of TMB conversion in 0.01 M phosphate buffer (pH 6.4) supplemented with 5% DMF and in reversed micelles of AOT in heptane. The effect of pH of the aqueous solution on the initial oxidation rate of the TMB-DDS and TMB-poly(DSDDS) pairs and also the effect of hydration degree of reversed micelles of AOT on conversion of the same pairs by peroxidase were studied. A scheme of peroxidase-dependent co-oxidation of "aromatic amine-phenol" pairs is proposed and discussed. A significant part of this scheme is a nonenzymatic exchange of phenoxyl radicals with amines and of aminyl radicals with phenols.

Topics: Benzidines; Chromogenic Compounds; Disulfides; Kinetics; Micelles; Nitrophenols; Oxidation-Reduction; Peroxidase

The phototrophic bacterium Rhodobacter capsulatus photoreduces 2,4-dinitrophenol to 2-amino-4-nitrophenol, which is further metabolized by an aerobic pathway that is also light-dependent. The catabolism of 2-amino-4-nitrophenol requires O2 and the presence of alternative carbon (C) and nitrogen (N) sources, preferably acetate and ammonium. Rhodobacter capsulatus B10, a bacterium unable to assimilate nitrate, releases negligible amounts of nitrite when growing with 2-amino-4-nitrophenol, thus suggesting that an oxygenase, nitrite-producing activity is not involved in the metabolization of the compound. The diazotrophic growth of R. capsulatus increases in the presence of 2-amino-4-nitrophenol, but growth with ammonium is clearly inhibited by the compound. Mutant strains of R. capsulatus B10, which are affected in nifHDK, nifR1, or nifR4 genes, unable to fix dinitrogen, do not grow with 2-amino-4-nitrophenol as the sole N source. This indicates that the compound cannot be used as a N source. The nif mutants degrade 2-amino-4-nitrophenol to the same extent as the wild-type in the presence of ammonium. The compound is not used as a C source by the bacterium, either. Aromatic stable intermediates, such as 2,4-diaminophenol or 4-nitrocatechol, are not detectable in microaerobic cultures of R. capsulatus growing with 2,4-dinitrophenol or 2-amino-4-nitrophenol.

Topics: Aerobiosis; Biodegradation, Environmental; Environmental Pollutants; Genes, Bacterial; Light; Mutagens; Mutation; Nitrogen Fixation; Nitrophenols; Photochemistry; Rhodobacter capsulatus

Eleven groups of six ICR mice were dosed orally with 22.5 mg/kg 2,4-dinitrophenol. Groups were sacrificed at 0, 0.5, 1, 2, 4, 6, 9, 12, 24, 48, and 96 h post-treatment and plasma was collected for analysis of dinitrophenol, 2-amino-4-nitrophenol, and 4-amino-2-nitrophenol content. Analyses were performed by capillary gas chromatography--mass spectrometry after liquid--liquid extraction of plasma specimens spiked with two internal standards. Quantification was based upon peak-area ratios of base peaks obtained from the three analytes and the trideuterated internal standards 2,4-dinitrophenol and 2-amino-4-nitrophenol. Plasma concentrations for each analyte versus their respective time periods were subjected to pharmacokinetic analysis. Of the two monoamine metabolites, 2-amino-4-nitrophenol was present in the greater amount and had an elimination half-life of 46 h from plasma while that of 4-amino-2-nitrophenol was 26 h.

Topics: 2,4-Dinitrophenol; Animals; Computers; Dinitrophenols; Kinetics; Mice; Mice, Inbred ICR; Models, Biological; Nitrophenols

The absorption of 14C-labelled 2-amino-4-nitrophenol (ANP) in two hair dyeing formulations was investigated after application to the skin of rats. After 1 and 5 days, 0.21 and 0.36%, respectively, of the administered radioactivity was absorbed from formulation 1 which contained carboxymethylcellulose as a thickening agent. Absorption was greater (1.12% after 1 day, 1.67% after 5 days) from formulation 2 which contained oleic acid and isopropanol. Complementary studies of absorption after administration of [14C]ANP by sc injection or oral gavage were also carried out. The radioactivity was rapidly excreted, predominantly in the urine, in both cases. Biliary excretion was also detected in an oral study.

Topics: Administration, Oral; Administration, Topical; Animals; Feces; Female; Hair Dyes; Hair Preparations; Injections, Subcutaneous; Male; Nitrophenols; Rats; Rats, Inbred Strains; Skin Absorption

The effect of the mono- and di-nitrophenols and certain related compounds has been determined on the rate of oxygen consumption, the rate of carbon dioxide output and the rectal temperature of the Wistar albino rat.Of the compounds examined, only 2:4-dinitrophenol and its derivative, 3:5-dinitro-o-cresol, stimulated metabolic rate. 2-Nitrophenol and 2:3-, 2:6-, and 3:5-dinitrophenol produced no change in metabolic rate; 3-nitrophenol and 2:5-dinitrophenol had no action on carbon dioxide production although they caused a decrease in oxygen consumption. 4-Nitrophenol and 3:4-dinitrophenol increased only the rate of carbon dioxide output; 2-amino-4-nitrophenol increased the rate of carbon dioxide output and decreased the rate of oxygen consumption; 4-amino-2-nitrophenol caused depression of metabolic rate.It was confirmed that neither rectal temperature nor carbon dioxide output could replace rate of oxygen consumption as a reliable index of metabolic stimulant action. An apparatus is described which facilitates measurement of the oxygen consumption of small mammals.

Topics: Animals; Carbon Dioxide; Cresols; Dinitrophenols; Metabolism; Nitrophenols; Oxygen Consumption; Rats; Rats, Wistar