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PubMed2000

Enrichment and isolation of non-specific aromatic degraders from unique uncontaminated (plant and faecal material) sources and contaminated soils.

Microbial analysis of contaminated soil and uncontaminated plant and faecal material resulted in the enrichment of a number of microbial communities capable of utilizing a range of environmental pollutants. Growth was observed on polycyclic aromatic hydrocarbons, polychlorinated biphenyls, heterocyclic aromatic compounds and organochlorine pesticides. However, none of the communities could grow on pentachlorophenol. Pure cultures were isolated from microbial communities using phenanthrene and pyrene as the sole carbon and energy source. Isolates were also obtained using DDT, DOH, DBH and PCPA when peptone was supplemented to the medium. Strain AJR39,504, isolated using DDT and peptone, could not be positively identified on the basis of substrate utilization tests. However, it most closely resembled Stenotrophomonas maltophilia (0.424 similarity) using the Microlog 3 database software. Isolate AJR39, 504 could also grow on polycyclic aromatic hydrocarbons, chlorinated- and nitro-aromatic compounds. In addition, the degradation of DDT (100 mg l(-1)) by isolate AJR39,504 resulted in a 35% decrease in DDT concentration after 28 days with a concomitant increase in DDD concentration.

Biphenyl Compounds↗

PubMed1999

Synthesis and cytotoxic activity of N-(2-chloroethyl)-N-nitroureas and N-(2-chloroethyl)-N-nitrocarbamates.

As analogs of the widely used anti-tumor agents, N-(2-chloroethyl)-N-nitrosoureas, N-(2-chloroethyl)-N-nitroureas and N-(2-chloroethyl)-N-nitrocarbamates were synthesized by nitration following the reaction of the appropriate amines or alcohols with 2-chloroethyl isocyanate. All tested compounds exert cytotoxic effect with IC50 values of 10(-4) to 10(-6) M and most of them show somewhat higher cytotoxicity in nitrogen than in air.

Air↗

PubMed1975

Characterization of an inducible amidase from Pseudomonas acidovorans AE1.

The main molecular and catalytic properties of an acetanilide-hydrolyzing enzyme from Pseudomonas acidovorans AE 1, purified to a homogeneous state, were investigated. The molecular weight was 57 500 as determined by gel filtration and 55 300 as computed from the amino acid composition. By polyacrylamide gel electrophoresis in dodecylsulfate a polypeptide chain weight of 56 700 was obtained. Based on the reaction of the highly purufied enzyme with diethyl-4-nitrophenyl phosphate an equivalent weight of approximately 59 100 was found. From these results it was concluded that the enzyme consists of a single polypeptide chain and contains one active site per molecule. The enzyme hydrolyzed esters as well as certain aromatic amides. It also catalysed the transfer of acetyl groups to phenetidine yielding phenacetin. The activities towards aliphatic esters were much smaller. The enzyme was stable at pH values ranging from 7 to 9 and its pH-optimum was about 10. It was strongly inhibited by organophosphorous compounds, like diethyl-4-nitrophenyl phosphate or diisopropylphosphorofluoridate, as well as by physostigmine sulfate and -SH-blocking reagents, like HgCl-2 or 4-chloromercuribenzoic acid. o-Nitrophenol caused a competitive inhibition and phenetidine an uncompetitive inhibition.

Acetanilides↗

PubMed2003

Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).

Laboratory bioassays applying the neonicotinoid insecticides imidacloprid, acetamiprid and nitenpyram against clones of the peach-potato aphid Myzus persicae (Sulzer) demonstrated that these compounds effectively circumvent the known carboxylesterase, modified acetylcholinesterase (MACE) and knock-down (kdr) insecticide resistance mechanisms in this species. However, some clones showed cross-tolerance (up to 18-fold) of these compounds relative to susceptible standards. A survey assessing the frequency of neonicotinoid tolerance in M persicae in the UK, based on samples collected from the field and glasshouses between 1997 and 2000, showed that such tolerance is still rare. Experiments on neonicotinoid-susceptible and -tolerant populations of M persicae under simulated field conditions in the laboratory showed that, although the latter were well controlled by imidacloprid applied at recommended application rates, they were more likely to survive and reproduce when this compound was applied at lower concentrations. Such conditions are probably periodically present in imidacloprid-treated field and glasshouse crops. Selection favouring tolerant forms of M persicae could lead to increases in their frequency and the evolution of more potent resistance to neonicotinoids.

Anabasine↗

PubMed1987

The nature of the mutagenicity and carcinogenicity of nitrated, aromatic compounds in the environment.

Gaseous substances such as nitrogen dioxide (NO2) and sulfur dioxide (SO2) stimulate the process of nitration of polycyclic aromatic hydrocarbons, and the transformation products display a broad spectrum of mutagenicity, genotoxicity, and carcinogenicity. Bacterial mutation by nitroarenes is specific. Tetracyclic nitroarenes are thought to be the most mutagenic compounds in the Salmonella test system, and some are carcinogenic in rats and mice. Furthermore, it was found that the mutational nitroarenes produced mostly DNA damage, which is subject to recombination repair in the rec assay system using Bacillus subtilis. Nitroarenes in the environment seem to be ubiquitous; the majority of the compounds are emitted directly from diesel emissions, kerosene heaters, and gas and liquefied-gas burners or heaters. In nitroarenes induced during incomplete combustion, nitropyrene and nitrofluoranthene derivatives are the most important mutagens/carcinogens for determining the chronic toxicity of nitroarenes overall.

Animals↗

PubMed2001

Insecticidal and binding activities of N3-substituted imidacloprid derivatives against the housefly Musca domestica and the alpha-bungarotoxin binding sites of nicotinic acetylcholine receptors.

N3-substituted imidacloprid congeners containing C1-C6 alkyl groups or various analogous groups, and their corresponding nitromethylene analogues, were used in this study. Their insecticidal activity against the housefly, Musca domestica, and their binding activity toward the nicotinic acetylcholine receptor were determined. The insecticidal test was conducted using the synergists piperonyl butoxide and propargyl propyl phenylphosphonate. The binding assay was performed with housefly head membrane preparations using radio-labelled alpha-bungarotoxin. Both insecticidal and binding activities were drastically lowered by the introduction of alkyl/allyl groups at the imidazolidine NH sites of both nitroimino and nitromethylene compounds. The binding activity of N3-substituted nitromethylene analogues was much higher than that of the corresponding nitroimino analogues. However, the insecticidal activity of both series of compounds with a given substituent was nearly identical. The insecticidal activity correlated positively with the binding activity after taking into account the structural difference of the nitroimino and nitromethylene moieties and a structural feature of the N3-substituents.

Animals↗

PubMed2003

Kinetics and mechanism of the exothermic first-stage decomposition reaction of 1,3-bis(2,2,2-trinitroethyl)-1,3-diazacyclopentanone-2.

The thermal behavior, mechanism and kinetic parameters of the exothermic first-stage decomposition reaction of the title compound in a temperature-programmed mode have been investigated by means of DSC, TG-DTG and IR. The reaction mechanism was proposed. The kinetic model function in differential form, apparent activation energy (E(a)) and pre-exponential factor (A) of this reaction are (1-alpha)(2), 178.41 kJ mol(-1) and 10(17.06)s(-1), respectively. The critical temperature of thermal explosion of the compound is 184.99 degrees C. The values of DeltaS( not equal ), DeltaH( not equal ) and DeltaG( not equal ) of this reaction are 91.54 J mol(-1)K(-1), 176.86 kJ mol(-1) and 135.83 kJ mol(-1), respectively.

Cyclopentanes↗

PubMed2000

Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3)H]imidacloprid binding site.

The insect nicotinic acetylcholine receptor (nAChR) is a major target for insecticide action. The rapidly expanding use of neonicotinoid insecticides of varied structures makes it increasingly important to define similarities and differences in their action, particularly for the first-generation chloropyridinyl compounds versus the second-generation chlorothiazolyl derivatives. We have shown with Musca domestica that a convenient and relevant determination of the neonicotinoid insecticide target is a binding site assay with [(3)H]imidacloprid ([(3)H]IMI). This study uses membranes from the aphids MYZUS: persicae and Aphis craccivora and from heads of the flies Drosophila melanogaster and Musca domestica to characterize the [(3)H]IMI binding sites relative to their number and possible species variation in structure-activity relationships. With emphasis on commercial neonicotinoids, six potent chloropyridinyl compounds are compared with the corresponding six chlorothiazolyl analogues (syntheses are given for chemicals prepared differently than previously described). The preference for chloropyridinyl versus chlorothiazolyl is not dependent on the insect species examined but instead on other structural features of the molecule. The chlorothiazolyl substituent generally confers higher potency in the clothianidin and desmethylthiamethoxam series and the chloropyridinyl moiety in the imidacloprid, thiacloprid, acetamiprid, and nitenpyram series. Two chlorothiazolyl compounds compete directly with the chloropyridinyl [(3)H]IMI for the same binding sites in Myzus and Drosophila membranes. This study shows conserved neonicotinoid specificity of the [(3)H]IMI binding site in each of the four insect species examined.

Amino Acid Sequence↗

PubMed1997

Levels of amino acids and related compounds in bronchoalveolar lavage fluids of asthmatic patients.

The constituents of bronchoalveolar lavage (BAL) fluid have been shown to reflect the presence and possible etiology of several pulmonary diseases. Presently, although research studies have reported the concentrations of cytokines and compounds such as major basic protein in BAL fluids, only the cellular elements, total protein, albumin, and immunoglobulins have been well defined. We hypothesize that amino acids and related amino compounds, well known participants in physiologic and biochemical processes, are present in BAL fluid and may have involvement in asthma. Our objective was to extend knowledge of the total chemical profile and clinical value of BAL fluids in humans by measuring these amino compounds in normal control subjects and asthmatic patients. Analysis by high-pressure liquid chromatography revealed the presence of 25 compounds. A few compounds in control subjects and patients were found to have values > 1.0 nmol/ml, while the majority were present in comparatively low concentrations < 1.0 nmol/ml. Asparagine, phosphoethanolamine, and taurine were significantly increased in the asthmatic patients. We conclude that the present profile of amino acids and related amino compounds in BAL fluid serves as a potential diagnostic tool in the study of various pulmonary disorders. The significance of increased asparagine, phosphoethanolamine, and taurine in the asthmatic patients is discussed and deserves further study.

Adult↗

PubMed2003

Compounds acting at the endocannabinoid and/or endovanilloid systems reduce hyperkinesia in a rat model of Huntington's disease.

We have recently reported that the administration of AM404, an inhibitor of the endocannabinoid re-uptake process, which also has affinity for the vanilloid VR1 receptors, is able to reduce hyperkinesia, and causes recovery from neurochemical deficits, in a rat model of Huntington's disease (HD) generated by bilateral intrastriatal injections of 3-nitropropionic acid (3NP). In the present study, we wanted to explore the mechanism(s) by which AM404 produces its antihyperkinetic effect in 3NP-lesioned rats by employing several experimental approaches. First, we tried to block the effects of AM404 with selective antagonists for the CB1 or VR1 receptors, i.e. SR141716A and capsazepine, respectively. We found that the reduction caused by AM404 of the increased ambulation exhibited by 3NP-lesioned rats in the open-field test was reversed when the animals had been pre-treated with capsazepine but not with SR141716A, thus suggesting a major role of VR1 receptors in the antihyperkinetic effects of AM404. However, despite the lack of behavioral effects of the CB1 receptor antagonist, the pretreatment with this compound abolished the recovery of neurochemical [gamma-aminobutyric acid (GABA) and dopamine] deficits in the caudate- putamen caused by AM404, as also did capsazepine. In a second group of studies, we wanted to explore the potential antihyperkinetic effects of various compounds which, compared to AM404, exhibit more selectivity for either the endovanilloid or the endocannabinoid systems. First, we tested VDM11 or AM374, two selective inhibitors or the endocannabinoid re-uptake or hydrolysis, respectively. Both compounds were mostly unable to reduce hyperkinesia in 3NP-lesioned rats, although VDM11 produced a certain motor depression, and AM374 exhibited a trend to stimulate ambulation, in control rats. We also tested the effects of selective direct agonists for VR1 (capsaicin) or CB1 (CP55,940) receptors. Capsaicin exhibited a strong antihyperkinetic activity and, moreover, was able to attenuate the reductions in dopamine and GABA transmission provoked by the 3NP lesion, whereas CP55,940 had also antihyperkinetic activity but was unable to cause recovery of either dopamine or GABA deficits in the basal ganglia. In summary, our data indicate a major role for VR1 receptors, as compared to CB1 receptors, in the antihyperkinetic effects and the recovery of neurochemical deficits caused in 3NP-lesioned rats by compounds that activate both CB1 and VR1 receptors, either directly or via manipulation of the levels of endogenous agonists.

3,4-Dihydroxyphenylacetic Acid↗

PubMed2002

In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis.

The activities of the N-(nitrothiazolyl) salicylamide nitazoxanide and its metabolite tizoxanide were compared with metronidazole in vitro in microplates against six axenic isolates of Giardia intestinalis. Tizoxanide was eight times more active than metronidazole against metronidazole-susceptible isolates and twice as active against a resistant isolate. In 10 axenic isolates of Entamoeba histolytica, while tizoxanide was almost twice as active as metronidazole against more susceptible isolates, it was more than twice as active against less susceptible isolates. Fourteen metronidazole-susceptible isolates of Trichomonas vaginalis were 1.5 times more susceptible to tizoxanide, which was nearly five times as active against resistant isolates. Two highly metronidazole-resistant isolates retained complete susceptibility to tizoxanide, and one moderately resistant isolate showed reduced susceptibility. In all three organisms, nitazoxanide results paralleled those of tizoxanide. Analogues lacking the reducible nitro-group had similar low activities against susceptible G. intestinalis, E. histolytica and T. vaginalis, indicating that nitro-reduction and free radical production was a probable mode of action. Nitazoxanide and its metabolite tizoxanide are more active in vitro than metronidazole against G. intestinalis, E. histolytica and T. vaginalis. Although, like metronidazole, they depend on the presence of a nitro-group for activity, they retain some activity against metronidazole-resistant strains, particularly of T. vaginalis. The results suggest that resistance mechanisms for metronidazole can be bypassed by nitazoxanide and tizoxanide.

Amebicides↗

PubMedDate not supplied

Standardized HPLC/DAD system, based on retention indices and spectral library, applicable for systematic toxicological screening.

An HPLC gradient elution system is applied for general toxicological screening. The use of a diode array detector with library software allows storage of retention parameters, UV spectra, and peak quality parameters of examined substances. The developed library is used for automatic identification of compounds. The retention indices of 225 substances are measured in the 1-nitroalkane scale. These data may be of interlaboratory use because of an appropriate correction procedure. Long-term reproducibilities of retention behavior of 1-nitroalkanes and correction standards are satisfactory. The conditions of interlaboratory use are discussed.

Chromatography, High Pressure Liquid↗

PubMed1990

LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium.

Quantitative structure-activity relationships have been derived for the mutagenic activity of 47 nitroaromatic compounds acting on Salmonella typhimurium (TA100) and 66 acting on TA98. The mutagenicity is linearly dependent on the energy of the lowest occupied molecular orbital and bilinearly dependent on the hydrophobicity (octanol/water log P) of the mutagens. The mechanism of action is considered in the light of these findings.

Biotransformation↗

PubMed1994

Toxicity of monocyclic and polycyclic nitroaromatic compounds in a panel of mammalian test cell lines.

The cytotoxicity of polycyclic and monocyclic nitroarenes was tested in cell lines V79/NH, H4IIEC3/G-, 5L and BWI-J, which are distinguished by their specific expression of xenobiotic metabolizing enzymes. The results show that polycyclic nitroarenes differentially affect the test cell lines suggesting that some compounds, such as 1,3-dinitropyrene, are activated by cytochrome P4501A1, others, such as 1,6-dinitropyrene, by reductase(s) and acetyltransferase. No such cell specific responses were seen for 13 monocyclic nitroarenes tested. This group of chemicals apparently is activated by an enzyme(s) other than the polycyclic nitroarenes tested.

Animals↗

PubMed2005

Efficacy of a combination of imidacloprid and moxidectin against parasites of reptiles and rodents: case reports.

A new compound containing imidacloprid 10% (w/v) and moxidectin 2.5% (w/v) (Advantage multi, Advocate) was applied as a spot-on treatment to mice experimentally infected with Trichuris muris. Case reports of reptiles found positive for nematode and mite infections following parasitological examination and treated with this compound are also discussed. The results demonstrated that the registered, recommended 2.5% moxidectin concentration for use in dogs was sufficient to eliminate nematodes and mites in reptiles. Infections with nematodes were successfully treated with a single application. Mite infestations in reptiles were eliminated using a treatment repeated on 3 consecutive days.

Animals↗

PubMed1988

Mutagenic potential of binary mixtures of nitro-polychlorinated dibenzo-p-dioxins and related compounds.

The mutagenic potential of binary mixtures of nitro-polychlorinated dibenzo-p-dioxins and other environmentally related compounds was determined using Salmonella typhimurium strain TA98 in the standard plate incorporation assay. Samples tested included binary mixtures of 4-nitro-4'-chlorobiphenyl with 6-nitro-4,2',3',4',5'-pentachlorobiphenyl, 4-nitrobenzo-p-dioxin with 4-nitro-2,3,8-trichlorodibenzo-p-dioxin, and benzo[a]pyrene with either nitropentachlorobiphenyl or nitrotrichlorodibenzo-p-dioxin. Inhibition was the primary interaction observed for the mixtures of polyhalogenated dioxins or biphenyls with the direct-acting mutagens nitrodibenzo-p-dioxin or nitrochlorobiphenyl. At the highest dose tested, nitrotrichlorodibenzo-p-dioxin inhibited the bacterial mutagenicity of nitrodibenzo-p-dioxin by almost 50%, while pentachlorobiphenyl inhibited the mutagenicity of nitrobiphenyl by 34%. Conversely, synergism was the primary interaction observed for mixtures of halogenated aromatics with the promutagen benzo[a]pyrene. The addition of nitrotrichlorodioxin to benzo[a]pyrene enhanced the mutagenicity of the latter compound by as much as 70%, while the mutagenic potential of a mixture of benzo[a]pyrene and nitropentachlorobiphenyl was approximately 50% greater than the mutagenicity of benzo[a]pyrene alone. In summary, mixtures of nonmutagenic nitropolyhalogenated biphenyls or dibenzo-p-dioxins appear to inhibit the mutagenicity of direct-acting mutagens, while these same compounds seem to enhance the mutagenic potential of the promutagen benzo[a]pyrene.

Animals↗

PubMed1981

Metabolism of 1-nitropyrene and formation of DNA adducts in Salmonella typhimurium.

1-Nitropyrene is slowly reduced by intact cells of Salmonella typhimurium to yield 1-aminopyrene and N-acetyl-1-aminopyrene plus six unidentified minor products. When the bacteria are exposed to tritiated 1-nitropyrene, increasing amounts of radioactivity become bound to DNA as the nitropyrene is metabolized. Enzymatic hydrolysis of the labelled DNA yields low molecular weight labelled compounds which probably represent nucleoside adducts formed by the reaction of nitropyrene metabolites with DNA. Results with appropriate mutant strains indicate that bacterial nitroreductases are involved in activating nitropyrene to a reactive intermediate that binds to DNA and that nitropyrene adducts in DNA are subject to excision repair.

Biotransformation↗

PubMedDate not supplied

Analysis of the transformation of nitroaromatic compounds in wastewater by bacteria using micellar electrokinetic capillary chromatography.

A rapid micellar electrokinetic capillary chromatographic method is described for the analysis of nitroaromatic and nitramine explosives using sodium dodecyl sulfate-borate buffer with application to analyze specifically the biodegradation products of trinitrotoluene. The method is fast, in expensive, offers better resolution, and saves on the consumption of organic solvents used in a comparable reversed-phase HPLC method.

Bacteria↗