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PubMed1987

Inducibility of NADPH cytochrome c (P-450) reductase in yeast: role in the bioactivation of nitroimidazo(2,1-b)thiazoles.

Nine nitroimidazo(2,1-b)thiazoles were tested for their ability to induce convertants, revertants and mitotic recombinants on growing and stationary phase cells of Saccharomyces cerevisiae D7 strain. All compounds were genetically active only on cells from the logarithmic growth phase (from a 20% glucose medium), inducing dose-related increases in conversion and reversion frequencies. The addition of S9 microsomal fraction to stationary phase cells gave positive results at levels of doses 10-100 times lower than that used with growing cells. NADPH cytochrome c (P-450) reductase activity was determined in order to compare the capability of hepatic and yeast microsomes in bioactivating the test compounds. Results showed that nitroreductive enzymes are inducible by conditions supporting growth. The greater sensitivity of the treatment with external metabolic activation could be due to the greater content (about 14-fold) of NADPH cytochrome c-reductase activity in hepatic microsomes.

Animals↗

PubMed2006

Identification of a high-affinity binding site for dinotefuran in the nerve cord of the American cockroach.

The binding of the neonicotinoid insecticide dinotefuran to insect nicotinic acetylcholine receptors (nAChRs) was examined by a centrifugation method using the nerve cord membranes of American cockroaches and [3H]dinotefuran (78 Ci mmol-1). The Kd and Bmax values of [3H]dinotefuran binding were estimated to be 13.7 nM and 14.8 fmol 40 microg-1 protein respectively by Scatchard analysis. Epibatidine, an nAChR agonist, showed a rather lower affinity to the dinotefuran binding site (IC50=991 nM) than dinotefuran (IC50=5.02 nM). Imidacloprid and nereistoxin displayed lower potencies than dinotefuran but higher potencies than epibatidine. The potencies of five dinotefuran analogues in inhibiting the specific binding of [3H]dinotefuran to nerve cord membranes were determined. A good correlation (r2=0.970) was observed between the -log IC50 values of the tested compounds and their piperonyl butoxide-synergised insecticidal activities (-log LD50 values) against German cockroaches. The results indicate that a high-affinity binding site for dinotefuran is present in the nerve cord of the American cockroach and that the binding of ligands to the site leads to the manifestation of insecticidal activity.

Animals↗

PubMed2006

A duplicated nitrotienyl derivative with antimycobacterial activity: synthesis, X-ray crystallography, biological and mutagenic activity tests.

A duplicated nitrotienyl derivative was obtained as a by-product from the synthesis of a proposed molecular hybrid of a nitrotienyl derivative and isoniazid with an expected dual antimycobacteria mechanism. The structure was shown to be the 5,5'-dinitro-2-(2,3-diaza-4-(2'-tienyl)buta-1,3-dienyl)tiophene by X-ray crystallography. The minimal inhibitory concentration (MIC) determination of this compound proved to be promising against Mycobacterium pathogenic strains such as M. avium and M. kansasii, although it had a high level of mutagenicity, as observed in mutagenic activity tests.

Antitubercular Agents↗

PubMed2002

Salmonella typhimurium mutagenicity tester strains that overexpress oxygen-insensitive nitroreductases nfsA and nfsB.

We have designed and constructed a series of plasmids that contain the major and/or minor Escherichia coli nitroreductase genes, nfsA and nfsB, in different combinations with R plasmid mucA/B genes and the Salmonella typhimurium OAT gene. The plasmid encoded gene products are necessary for both the metabolic activation of a range of structurally diverse nitrosubstituted compounds, and for mutagenic translation bypass. Introduction of these plasmids into S. typhimurium TA1538 and TA1535 has created several new tester strains which exhibit an extremely high mutagenic sensitivity and a broad substrate specificity towards a battery of nitrosubstituted test compounds that included 4-nitroquinoline-1-oxide (4-NQO), nitrofurazone (NF), 1-nitropyrene (1-NP), 2-nitronaphthalene (2-NN), 2-nitrofluorene (2-NF), and 1,6-dinitropyrene (1,6-DNP). Our studies show that the nfsA gene encodes a product that is extremely effective in the metabolic activation of a range of structurally diverse nitrosubstituted compounds. Several of the new tester strains are more than two orders of magnitude more sensitive to nitrosubstituted compounds than the Ames tester strains TA100 or TA98. In addition to enhancing mutagenic sensitivity, plasmids encoding both metabolic and mutagenesis functions on a single plasmid provide considerable flexibility for future mechanistic studies or tester strain development, in which it may be necessary to introduce additional plasmids containing different antibiotic resistance markers.

Bacterial Proteins↗

PubMed2004

Soil photolysis in a moisture- and temperature-controlled environment. 2. Insecticides.

The photolytic degradations of imidacloprid, carbofuran, diazinon, chlorpyrifos, pyridaben, propoxur, and esfenvalerate were independently compared in both moist (75% field moisture capacity at 0.33 bar) and air-dry microbially viable soils at 5 microg/g. All compounds were applied to sandy soil except for propoxur, which was applied to sandy loam soil. Diazinon was applied to both sandy soil and sandy loam soil. The samples were exposed for up to 360 h, depending on the half-life of the compound. Moisture and temperature were maintained through the use of a specially designed soil photolysis apparatus. Corresponding dark control studies were performed concurrently. With the exception of esfenvalerate, the other compounds exhibited significantly shorter half-lives in moist soils, attributed to the increased hydrolysis and microbial activity of the moist soil. The esfenvalerate metabolism was not first order due to limited mobility in the soil because of its very low water solubility. The overall half-life for esfenvalerate was 740 h, as the percent remaining did not drop below 60%. The imidacloprid half-life in irradiated moist soil was 1.8 times shorter than in air-dry soils. However, on dry soil the photodegradation showed poor first-order kinetics after 24 h of exposure. The metabolism of carbofuran and diazinon was highly dependent on soil moisture. Carbofuran exhibited 2.2 times longer half-lives when less moisture was available in the soil. Diazinon in moist sandy soil degraded rapidly, but slowed significantly in irradiated and dark control air-dry sandy soil. Diazinon photolysis on sandy loam soil was not first order, as it attained a constant concentration of 54.9%, attributed to decreased mobility in this soil. Chlorpyrifos photolysis was 30% shorter on moist sand than on air-dry sand. Pyridaben photolyzed rapidly throughout the first 72 h of irradiation but maintained 48% through 168 h. Propoxur metabolism in moist sandy loam soil was not first order and did not degrade below 50% after 360 h of exposure, but the overall half-life was still nearly half of that on irradiated air-dry soil. Three of the compounds showed differences in metabolism patterns during exposure on moist or air-dry soil. Typically, the moist soils produced a more linear decline than that seen in the dry soils, corresponding to the susceptibility of the particular chemical to hydrolysis and/or biodegradation. Four of the eight experiments had shorter half-lives in dark control moist soils than in irradiated dry soils.

Carbofuran↗

PubMedDate not supplied

Application of ELISA techniques to metabolic disposition studies for 1,3-dinitrobenzene: comparison with HPLC and radiochemical methods.

An enzyme-linked immunosorbent assay (ELISA) is reported for the detection and quantitation of 1,3-dinitrobenzene, a widely used chemical intermediate in industrial syntheses and potent testicular toxicant in rats. Radiolabeled [14C]-1,3-dinitrobenzene (25 mg/kg, ip) was administered to rats, and the blood disappearance curve generated with the ELISA assay was compared with HPLC separation and quantitation by using both UV and radiochemical methods. An excellent correlation was found between the two methods. Matrix effects from the blood samples were minimal. Cross reactivity with metabolites of 1,3-dinitrobenzene occurred only at levels that were 3 orders of magnitude greater than for the parent compound. The specificity of the ELISA for 1,3-dinitrobenzene was further demonstrated with a variety of other nitroaromatic compounds, of which only 2,4-dinitrotoluene showed significant cross reactivity. The sensitivity and specificity of the 1,3-dinitrobenzene ELISA demonstrate the usefulness of an approach which, if verified with conventional analytical methods, allows rapid and inexpensive measurement of xenobiotic levels in biological samples.

Animals↗

PubMed2003

FK506 attenuates 1-methyl-4-phenylpyridinium- and 3-nitropropionic acid-evoked inhibition of kynurenic acid synthesis in rat cortical slices.

Kynurenic acid (KYNA), the only known endogenous glutamate antagonist, is produced in the brain by kynurenine aminotransferases (KATs) I and II. Mitochondrial toxins, 1-methyl-4-phenylpyridinium (MPP +) and 3-nitropropionic acid (3-NPA), were previously shown to reduce KYNA synthesis via interference with KAT I and II. Data presented here demonstrate that immunophilin ligand, FK506 (10-130 microM), but not CsA (1-50 microM), or ryanodine receptor blocker, dantrolene (1-100 microM), enhances the formation of KYNA in cortical slices. FK506, but not CsA or dantrolene, abolished the inhibition of KYNA synthesis evoked by MPP+ and 3-NPA. None of studied compounds influenced the activity of KAT I and KAT II. FK506 is the first among currently used drugs that might stimulate KYNA synthesis. This effect does not seem to arise from the interference with KATs or calcineurin activity.

1-Methyl-4-phenylpyridinium↗

PubMed1986

The effects of various substituted hydrocarbons on two heme synthesis regulatory enzymes.

Benzene and some of its derivatives have been shown to cause alterations in heme and globin synthesis. Structure/activity relationships of the effects of substituted aromatic hydrocarbons on delta-aminolevulinic acid synthetase (ALAS) and ferrochelatase (FC) activities were studied. These enzyme systems were studied because they were regulatory and represented the initial and final enzymes in the biosynthesis of heme. Normal values for rat liver ALAS were 250-350 microM ALA/g protein/30 min, mean 293 microM/g +/- 44 (SD). Normal values for FC were 12-40 microM heme/g protein/45 min, mean 18 microM/g +/- 0.7 (SD). Nitrosonaphtholics inhibited ALAS activity an average of 49%; nitrosobenzenes, 48%; chloronitrobenzoic acids, 39%; phenol, 37%; nitrophenols, 22%; aminophenols, 16% and chlorophenols, 5%. Certain compounds inhibited FC activity: nitrosonaphtholics, 99%; chlorophenols, 56% and nitrosobenzenes, 3%. Some compounds that significantly inhibited ALAS activity enhanced FC activity, e.g. phenolic compounds and chloronitrobenzoic acids. The inhibitory effect may reflect a blockage of the active site of the enzymes and/or binding of a required substrate. The enhancing effect may be due to making the binding site of the heme pocket of the porphyrin more accessible to iron. These techniques may prove useful for assessing toxicity of pollutants in animal species.

5-Aminolevulinate Synthetase↗

PubMed2000

Chemotaxis of a Ralstonia sp. SJ98 toward different nitroaromatic compounds and their degradation.

A Ralstonia sp. SJ98, isolated by a chemotactic enrichment technique, was capable of utilizing different nitroaromatic compounds (NACs). It utilized p-nitrophenol, 4-nitrocatechol, o-nitrobenzoic acid, and p-nitrobenzoic acid as the sole source of carbon and energy. It was observed that Ralstonia sp. SJ98 was chemotactic to the above-mentioned NACs as tested by the drop assay, swarm plate assay, and capillary assay. However, it failed to show chemotactic behavior toward those compounds which were not degraded by the microorganism. This is the first report which shows the chemotaxis of a microorganism toward different NACs and their subsequent degradation. Some of the intermediates of the NACs' degradative pathways have been identified using TLC, GC, and GC-MS studies. The results presented here indicate a correlation between chemotaxis and biodegradation of NACs.

Betaproteobacteria↗

PubMed2000

Synthesis and aldose reductase inhibitory activities of novel N-nitromethylsulfonanilide derivatives.

A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC50 = 0.35 M, showed uncompetitive inhibition. Subsequent in vitro culture studies of rat lenses with 11 indicated that this series of aldose reductase inhibitors are effective in either preventing or retarding sugar cataract formation associated with diabetes.

Aldehyde Reductase↗

PubMed2001

3-Methyl 5-isopropyl 2-methoxyiminomethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

The crystal structure of the title compound, C(20)H(23)N(3)O(7), consists of relatively isolated molecules. The substituted 1,4-dihydropyridine ring adopts a flattened boat conformation. Both ester groups, at positions 3 and 5, have cis,cis geometry. The phenyl ring is nearly planar and is approximately perpendicular to the 1,4-dihydropyridine ring (dihedral angle 87.70 degrees ).

Calcium Channel Agonists↗

PubMed1987

Therapeutic activities of nitrothiazoles against trichomonads.

Certain nitrothiazole derivatives, such as niridazole (Ba 32644, Ambilhar), exert pronounced activities against several trichomonad strains when tested under anaerobic conditions comparable to those of the nitroimidazole derivatives. Few compounds of the nitrothiazole group, however, are markedly less active in vitro. The in vivo activity of the nitrothiazole derivatives as determined in mice infected subcutaneously with T. foetus, is as good as that of metronidazole. A nitrothiazole derivative with a laminar side chain is inactive in vivo after oral administration, although it shows pronounced antitrichomonad activity in vitro.

Animals↗

PubMed2001

Discrepancy between acute and chronic toxicity induced by imidacloprid and its metabolites in Apis mellifera.

Imidacloprid is a systemic nitroguanidine insecticide that belongs to the neonicotinoid family. As an agonist of the acetylcholine receptor, it attacks the insect nervous system and is extremely effective against various sucking and mining pests. Oral acute and chronic toxicity of imidacloprid and its main metabolites (5-hydroxyimidacloprid, 4,5-dihydroxyimidacloprid, desnitroimidacloprid, 6-chloronicotinic acid, olefin, and urea derivative) were investigated in Apis mellifera. Acute intoxication by imidacloprid or its metabolites resulted in the rapid appearance of neurotoxicity symptoms, such as hyperresponsiveness, hyperactivity, and trembling and led to hyporesponsiveness and hypoactivity. For acute toxicity tests, bees were treated with doses of toxic compounds ranging from 1 to 1,000 ng/bee (10-10,000 microg/kg). Acute toxicity (LD50) values of imidacloprid were about 60 ng/bee (600 microg/kg) at 48 h and about 40 ng/bee (400 microg/kg) at 72 and 96 h. Out of the six imidacloprid metabolites tested, only two (5-hydroxyimidacloprid and olefin) exhibited a toxicity close to that of imidacloprid. Olefin LD50 values were lower than those of imidacloprid. The 5-hydroxyimidacloprid showed a lower toxicity than imidacloprid with a LD50 four to six times higher than that of imidacloprid. Urea also appeared as a compound of nonnegligible toxicity by eliciting close to 40% mortality at 1,000 ng/bee (10,000 microg/kg). However, no significant toxicity was observed with 4,5-dihydroxyimidacloprid, 6-chloronicotinic acid, and desnitroimidacloprid in the range of doses tested. To test chronic toxicity, worker bees were fed sucrose solutions containing 0.1, 1, and 10 microg/L of imidacloprid and its metabolites for 10 d. Fifty percent mortality was reached at approximately 8 d. Hence, considering that sucrose syrup was consumed at the mean rate of 12 microl/d and per bee, after an 8-d period the cumulated doses were approximately 0.01, 0.1, and 1 ng/bee (0.1, 1, and 10 microg/kg). Thus, all tested compounds were toxic at doses 30 to 3,000 (olefin), 60 to 6,000 (imidacloprid), 200 to 20,000 (5-OH-imidacloprid), and >1,000 to 100,000 (remaining metabolites) times lower than those required to produce the same effect in acute intoxication studies. For all products tested, bee mortality was induced only 72 h after the onset of intoxication.

Administration, Oral↗

PubMed2002

Unexpected fragmentation of beta-substituted meso-tetraphenylporphyrins induced by high-energy collisional activation.

The protonated molecules and radical cations of meso-tetraphenylporphyrins with beta-pyrrolic substituents, when formed by fast atom bombardment (FAB) and subjected to high-energy collisions, give rise to unexpected fragment ions. The reaction involves hydrogen migration from the ortho position of the phenyl ring to the a atom of the substituent, with formation of an intramolecular, six-membered ring. The process is analogous to condensed-phase cyclizations described for the same type of compounds. The fragmentation requires the presence of a double bond in the substituent group attached to the pyrrolic ring. A rearrangement process involving anchimeric assistance by the phenyl group (analogous to an ortho effect) is proposed for the formation of these ions.

Acrylates↗

PubMed2001

The discovery of thiamethoxam: a second-generation neonicotinoid.

Neonicotinoids represent a novel and distinct chemical class of insecticides with remarkable chemical and biological properties. In 1985, a research programme was started in this field, in which novel nitroimino heterocycles were designed, prepared and assayed for insecticidal activity. The methodology for the synthesis of 2-nitroimino-hexahydro-1,3,5-triazines, 4-nitroimino-1,3,5-oxadiazinanes and 4-nitroimino-1,3,5-thiadiazinanes is outlined. Bioassays demonstrated that 3-(6-chloropyridin-3-ylmethyl)-4-nitroimino-1,3,5-oxadiazinane exhibited better insecticidal activity than the corresponding 2-nitroimino-hexahydro-1,3,5-triazine and 4-nitroimino-1,3,5-thiadiazinane. In most tests, this compound was equally or only slightly less active than imidacloprid. A series of structural modifications on this lead structure revealed that replacement of the 6-chloro-3-pyridyl group by a 2-chloro-5-thiazolyl moiety resulted in a strong increase of activity against chewing insects, whereas the introduction of a methyl group as pharmacophore substituent increased activity against sucking pests. The combination of these two favourable modifications led to thiamethoxam (CGA 293 343). Thiamethoxam is the first commercially available second-generation neonicotinoid and belongs to the thianicotinyl sub-class. It is marketed under the trademarks Actara for foliar and soil treatment and Cruiser for seed treatment. The compound has broad-spectrum insecticidal activity and offers excellent control of a wide variety of commercially important pests in many crops. Low use rates, flexible application methods, excellent efficacy and the favourable safety profile make this new insecticide well-suited for modern integrated pest management programmes in many cropping systems.

Anabasine↗

PubMed1994

Redox conversions of methemoglobin during redox cycling of quinones and aromatic nitrocompounds.

The study focused on the effects on various redox states of hemoglobin during NADPH: cytochrome P-450 reductase-catalyzed redox cycling of quinones and nitrocompounds. The following reactions involving quinone/semiquinone and methemoglobin/oxyhemoglobin redox couples were observed: (i) the direct oxidation of oxyhemoglobin by quinones, (ii) the reduction of methemoglobin by quinones, (ii) the reduction of methemoglobin during redox cycling of quinones and nitrocompounds was partially inhibited by superoxide dismutase, and (iii) the reoxidation of oxyhemoglobin by hydrogen peroxide, formed during redox cycling was accompanied by the formation of choleglobin. Hydrogen peroxide was produced during redox cycling, and upon depletion of hydrogen peroxide by catalase, the reduction of methemoglobin significantly prevailed over oxidation of oxyhemoglobin. Furthermore, the reduction of ferrylhemoglobin to oxyhemoglobin during redox cycling was about twice as slow as the reduction of methemoglobin. For a series of compounds possessing a single-electron reduction potential (E1(7)) between 0.01 and -0.355 V, the rate constants for methemoglobin reduction by their corresponding radicals was estimated to range from 4.1 x 10(5) to 7.6 x 10(7) M-1 S-1. Radicals of the nitrocompounds were approximately 10 times less reactive as compared to quinones possessing similar E1(7) values.

Acetophenones↗

PubMed2003

Determination of imidacloprid and its metabolite 6-chloronicotinic acid in greenhouse air by application of micellar electrokinetic capillary chromatography with solid-phase extraction.

A method is described for the analysis of the insecticide imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine] and its metabolite 6-chloronicotinic acid by micellar electrokinetic chromatography with diode-array detection at 270 and 227 nm, respectively. The best results were obtained using sodium dodecyl sulphate at a concentration of 60 mM and a running buffer of NH4Cl/NH3 at 15 mM (pH 8.5). The selection of instrumental parameters such as voltage at 30 kV with an injection time of 20 s gave the best resolution with an analysis time of less than 6 min. The method yields similar sensitivity for the parent compound and for the metabolite, with detection limits of 0.71 and 1.18 microg/ml for imidacloprid and 6-chloronicotinic acid, respectively. The sampling and analysis of these two pesticides in greenhouse air was carried out using personal samplers connected to XAD-2 cartridges as sampling media, investigating the dissipation of analytes in a 24-h period after their application.

Agriculture↗

PubMed2003

Comparison of the activity of selamectin, fipronil, and imidacloprid against flea larvae (Ctenocephalides felis felis) in vitro.

The activity of selamectin, fipronil and imidacloprid against larval cat fleas (Ctenocephalides felis felis) was evaluated in an in vitro potency assay system. One hundred microliters of each compound at various concentrations in acetone were added to glass vials (1.5 by 3 cm) to which had been previously added 20 mg of sand and 10 mg of flea feces. Vials were then ball milled to allow the acetone to evaporate. Selamectin and fipronil were tested at 0.001, 0.003, 0.005, 0.01, 0.03, 0.05, 0.11, 0.3, and 0.5 microg of active compound per tube. Imidacloprid was tested at 0.01, 0.03, 0.05, 0.1, 0.3, 0.5, 1.0, 3.0, and 5.0 microg of active compound per tube. Thirty first instar C. felis larvae were added to each vial. The number of larvae remaining alive in each vial was determined once daily for 72 h. With selamectin, reductions of >/=93.5% were achieved at 24 h after exposure at doses of >/=0.3 microg. In contrast, at 24 h neither fipronil nor imidacloprid reached 90% reduction, even at the highest doses tested (0.5 microg for fipronil and 5.0 microg for imidacloprid). Selamectin was significantly (P</=0.05) more potent than imidacloprid and fipronil at levels >/=0.03 microg. A similar pattern of activity was observed at both 48 and 72 h, but higher percentages of larvae were killed for each of the compounds as the incubation time increased. At 72 h selamectin was significantly (P</=0.05) more potent than imidacloprid at levels of 0.01-0.1 microg and significantly (P</=0.05) more potent than fipronil at levels of 0.003-0.01 microg. Therefore, selamectin was more potent than either fipronil or imidacloprid in killing flea larvae in this in vitro assay system.

Animals↗