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PubMed2004

Imprinted polymer layer for recognizing double-stranded DNA.

A method of preparing a thin polymer layer able to recognize double-stranded DNA (dsDNA) was developed by using 2-vinyl-4,6-diamino-1,3,5-triazine (VDAT) as a functional monomer for creating a DNA-imprinted polymer. The formation of hydrogen bonds between VDAT and A-T base pairs in dsDNA was confirmed by measuring the effects of VDAT on the melting point and the NMR and CD spectra of dsDNA. An imprinted polymer that can recognize dsDNA of the verotoxin gene was prepared by polymerizing VDAT, acrylamide, a crosslinking agent, and the template verotoxin dsDNA on a silanized glass surface. The specificity of this polymer layer for binding verotoxin dsDNA was investigated by using fluorescent-labelled dsDNAs. The fluorescence intensity of the polymer layer after binding verotoxin dsDNA was twice as high as after binding oligo(dG)-oligo(dC), indicating that verotoxin dsDNA was preferentially bound to the polymer imprinted with verotoxin dsDNA. The kinetics of verotoxin dsDNA binding to the imprinted polymer were analyzed by surface plasmon resonance measurements. The dissociation constant (KD) was low, of the order of 10(-9)M.

Acrylic Resins↗
PubMed2004

Triamino derivatives of triazolotriazine and triazolopyrimidine as adenosine A2a receptor antagonists.

Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been shown to be potent and selective adenosine A(2a) receptor antagonists. We now demonstrate that potent and selective A(2a) receptor antagonists could still be obtained when the arylpiperazines are separated from the triazolotriazine core structure by an ethylenediamine spacer. Selected analogs bearing this triazolotriazine or the related triazolopyrimidine core structure have been found to be orally active in a mouse catalepsy model of Parkinson's disease.

Adenosine A2 Receptor Antagonists↗
PubMed2005

Pyrimidine containing RSV fusion inhibitors.

The knowledge of SAR in a series of biphenyl anionic RSV inhibitors has been broadened by synthesis and testing of analogs with pyrimidine linkers. Generally, pyrimidine compounds were much harder to synthesize, and their anti-RSV activity was lower in comparison with triazine analogs.

Animals↗
PubMed2005

New dual inhibitors of EGFR and HER2 protein tyrosine kinases.

A novel series of dual EGFR and HER2 inhibitors based on the pyrrolo[2,1-f][1,2,4]triazine nucleus is described. A general route toward their synthesis, which enables functionalization at multiple sites, has been developed. Biological evaluation in enzymatic and cell-based assays has identified a series of C-6 carbamates with potent biochemical and cellular activities.

Binding Sites↗
PubMed2005

A single-cell analysis of myogenic dedifferentiation induced by small molecules.

An important direction in chemical biology is the derivation of compounds that affect cellular differentiation or its reversal. The fragmentation of multinucleate myofibers into viable mononucleates (called cellularization) occurs during limb regeneration in urodele amphibians, and the isolation of myoseverin, a trisubstituted purine that could apparently activate this pathway of myogenic dedifferentiation in mammalian cells, generated considerable interest. We have explored the mechanism and outcome of cellularization at a single-cell level, and we report findings that significantly extend the previous work with myoseverin. Using a panel of compounds, including a triazine compound with structural similarity and comparable activity to myoseverin, we have identified microtubule disruption as critical for activation of the response. Time-lapse microscopy has enabled us to analyze the fate of identified mononucleate progeny, and directly assess the extent of dedifferentiation.

Animals↗
PubMed2004

Transfer of hexazinone and glyphosate through undisturbed soil columns in soils under Christmas tree cultivation.

Field studies monitoring pesticide pollution in the Morvan region (France) have revealed surface water contamination by some herbicides. The purpose of this study was to investigate in greater detail the transport of two herbicides, used in Christmas tree production in the Morvan, under controlled laboratory conditions. Thus, the leaching of hexazinone (3-cyclohexyl-6-dimethyl-amino-1-methyl-1,3,5-triazine-2,4 (1H,3H) dione) and glyphosate (N-(phosphono-methyl-glycine)) through structured soil columns was studied using one loamy sand and two sandy loams from sites currently under Christmas tree cultivation in the Morvan. The three soils were cultivated sandy brunisol [Sound reference base for soils, D. Baize, M.C. Girard (Coord.), INRA, Versailles, 1998, 322 p] or, according to the FAO [FAO, World reference base for soil resources, ISSS-ISRIC-FAO, FAO, Rome, Italy, 1998], the La Garenne was an arenosol and the two other soils were cambisols. The clay contents of the soils ranged from 86 to 156 g kg(-1) and the organic carbon ranged from 98 to 347 g kg(-1). After 160 mm of simulated rainfall applied over 12 days, 2-11% of the applied hexazinone was recovered in the leachate. The recovery was much higher than that of glyphosate, which was less than 0.01%. The greater mobility of hexazinone might be related to its much lower adsorption coefficient, K(oc), 19-300 l kg(-1), compared with 8.5-10231 l kg(-1) for glyphosate (literature values). Another factor that may explain the higher amounts of hexazinone recovered in the leachates of the three soil columns is its greater persistence (19.7-91 days) relative to that of glyphosate (7.9-14.4 days). The mobility of both herbicides was greater in the soils with higher gravel contents, coarser textures, and lower organic carbon contents. Moreover, glyphosate migration seems negatively correlated not only to soil organic carbon, but also to aluminium and iron contents of soils. This soil column study suggests that at the watershed scale, surface water contamination by hexazinone could occur via the horizontal subsurface flow in upper centimeters of soil. In contrast, the surface water contamination with glyphosate by this mechanism appears unlikely.

Carbon↗
PubMed2004

Photosensitized degradation of Irgarol 1051 in water.

Irgarol 1051 (2-methylthio-4-tert-butylamino-6-cyclopropylamino-s-triazine) is a herbicide analogue that is added to antifouling agents used on ships. Our former study on its degradation in sunlight suggested that unknown photosensitizers in natural waters accelerated the photodegradation to the degradation product, M1. In this study, the photodegradation of Irgarol in water was investigated in the presence of some photosensitizers. Test water containing Irgarol or M1, with or without photosensitizers, was irradiated with light from a UV-A fluorescent lamp for 48h. The concentrations of Irgarol and M1 in the test water were determined by HPLC after solid-phase extraction. M1 was more stable than Irgarol when irradiated in the presence of photosensitizers such as acetone, benzophenone, tryptophan, and rose bengal. Hydrogen peroxide (HP) accelerated the photodegradation of Irgarol, and the product M1 was degraded in the presence of more than 100mgl(-1) HP after 10h. Natural humic substances (NHS) also accelerated the photodegradation of Irgarol, but in this case, the product M1 persisted even when Irgarol was completely degraded. Photosensitized degradation of Irgarol by NHS may result in the accumulation of M1 in aquatic environments.

Acetone↗
PubMed2005

Electrolytic transformation of ordinance related compounds (ORCs) in groundwater: laboratory mass balance studies.

Electrolytic reactive barriers (e(-) barriers) consist of closely spaced permeable electrodes installed across a groundwater contaminant plume in a permeable reactive barrier format. Application of sufficient potential to the electrodes results in sequential oxidation and reduction of the target contaminant. The objective of this study was to quantify the mass distribution of compounds produced during sequential electrolytic oxidation and reduction of ordinance related compounds (ORCs) in a laboratory analog to an e(-) barrier. In this study, a series of column tests were conducted using RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) and TNT (2,4,6-trinitrotoluene) as representative ORCs. The experimental setup consisted of a plexiglass column packed with quartz-feldspar sand to simulate aquifer conditions. A single set of porous electrodes consisting of expanded titanium-mixed metal oxide mesh was placed at the midpoint of the sand column as a one-dimensional analog to an e(-) barrier. Constant current of 20mA (variable voltage) was applied to the electrode set. Initial studies involved quantification of reaction products using unlabeled RDX and TNT. Approximately 70% of the influent concentration was transformed, in one pass, through sequential oxidation-reduction for both contaminants. Following the unlabeled studies, (14)C labeled RDX and TNT were introduced to determine the mass balance. An activity balance of up to 96% was achieved for both (14)C-RDX and (14)C-TNT. For both contaminants, approximately 21% of the influent activity was mineralized to (14)CO(2). The proportion of the initial activity in the dissolved fraction was different for the two test contaminants. Approximately 30% of the initial (14)C-RDX was recovered as unreacted in the dissolved phase. The balance of the (14)C-RDX was recovered as non-volatile, non-nitroso transformation products. None of the (14)C-RDX was sorbed to the column sand packing. For (14)C-TNT approximately 51% of the initial activity was recovered in the dissolved phase, the majority was unreacted TNT. The balance of the (14)C-TNT was either sorbed to the sand packing (approximately 24%) or dissolved/mineralized as unidentified ring cleavage products ( approximately 4%).

Carbon Radioisotopes↗
PubMed2006

Melamine-based organoclay to sequester atrazine.

Sequestration of aqueous atrazine by organoclays prepared from the surfactant 6-piperazin-1-yl-N,N'-bis-(1,1,3,3-tetramethyl-butyl)-(1,3,5)triazine-2,4-diamine and Gonzales bentonite was assessed using 14C-labeled atrazine. Organoclays with varying ratios of surfactant to clay were evaluated with respect to their ability to sequester atrazine from an aqueous solution. Organoclays containing 100-200 g kg-1 surfactant on a total weight basis provided the most efficient adsorption of atrazine, with apparent KOC values exceeding 5000 l kg-1 at these loading fractions. Less than 12% of sequestered atrazine was released during four sequential day long washings, supporting our expectation that the majority of the reaction of atrazine with the surfactant lead to irreversible chemical bond formation through nucleophilic aromatic substitution.

Adsorption↗
PubMed2006

Transport of organic contaminants through salinity stratified water masses. A microcosm experiment.

A salt-wedge stratified microcosm, spiked with 31 target analytes, including PCBs, organochlorine and organophosphorous pesticides, triazines, organophosphate flame retardants and caffeine (an urban wastewater molecular marker), was setup. Compound behaviour was monitored during a four week period, by sampling at six different levels of the water column, in order to understand the transport and loss processes of the different classes of chemical substances. Compound transport from one water body to the other has been positively correlated with diffusion via their molar volume. Target analytes loss has been positively correlated with evaporation via their K(H) and with degradation via their halve-lives. From these two processes, evaporation was found to be predominant using a multiparametric regression.

Diffusion↗
PubMed2006

Effect of soil amendments on sorption and mobility of metribuzin in soils.

Metribuzin (4-amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one), is weakly sorbed to soil therefore, leaches easily to lower soil profiles. Soil amendments play a significant role in the management of leaching losses of pesticides. Therefore, present study reports the effect of organic manure and fly ash amendments on metribuzin downward mobility in sandy loam soil columns. Application of animal manure [T-1(OM) and T-2(OM)] and fly ash [T-1(FA) and T-2(FA)] at 2.5% and 5.0% levels increased the metribuzin retention in the soil. Freundlich constant [K(f)(1/n)] values of metribuzin for treatments T-1(OM) and T-2(OM) were 0.70 and 1.11, respectively, which were significantly higher than the value (0.27) in natural soil (T-0). The respective values for treatments T-1(FA) and T-2(FA) were 1.80 and 4.61. Downward mobility of metribuzin was studied in packed soil columns [300 mm (l)x59 mm (i.d.)]. Both the amendments significantly reduced the downward mobility of metribuzin and affected breakthrough time and maximum concentration of metribuzin in the leachate. Leaching losses of metribuzin were decreased from 97% in natural soil (T-0) column to 64% [T-1(OM)] and 42% [T-2(OM)] for animal manure-amended columns and 26% [T-1(FA)] to 100% [T-2(FA)] for fly ash-amended columns, as metribuzin did not leach out of 5% fly ash-amended column. Study indicates that both animal manure and fly ash were quite effective in reducing the downward mobility of metribuzin in packed soil columns of a sandy loam soil.

Adsorption↗
PubMed2006

Anaerobic biotransformation of explosives in aquifer slurries amended with ethanol and propylene glycol.

Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), and 2,4,6-trinitrotoluene (TNT) are explosives that are frequently found as environmental contaminants on military installations. Hydrogen has been shown to support the anaerobic transformation of these explosives. We investigated ethanol and propylene glycol as electron donors for providing syntrophically produced H2 for stimulating the anaerobic biodegradation of explosives in contaminated soil. The study was conducted using anoxic microcosms constructed with slurries of the contaminated soil and groundwater. The addition of 5mM ethanol and propylene glycol enhanced the biodegradation of RDX and HMX relative to the control bottles. Ethanol was depleted within about 20 days, resulting in the transient formation of hydrogen, acetate, and methane. The hydrogen headspace concentration increased from 8 ppm to 1838 ppm before decreasing to background concentrations. Propylene glycol was completely degraded after 15 days, forming hydrogen, propionate, and acetate as end-products. The hydrogen headspace concentrations increased from 56 ppm to 628 ppm before decreasing to background concentrations. No methane formation was observed during the incubation period of 48 days. Our findings indicate the addition of ethanol and propylene to the aquifer slurries increased the hydrogen concentrations and enhanced the biotransformation of RDX and HMX in the explosive-contaminated soil.

Anaerobiosis↗
PubMed2006

Photodegradation of organophosphorus insecticides - investigations of products and their toxicity using gas chromatography-mass spectrometry and AChE-thermal lens spectrometric bioassay.

Four organophosphorus compounds: azinphos-methyl, chlorpyrifos, malathion and malaoxon in aqueous solution were degraded by using a 125 W xenon parabolic lamp. Gas chromatography-mass spectrometry (GC-MS) was used to monitor the disappearance of starting compounds and formation of degradation products as a function of time. AChE-thermal lens spectrometric bioassay was employed to assess the toxicity of photoproducts. The photodegradation kinetics can be described by a first-order degradation curve C=C0e(-kt), resulting in the following half lives: 2.5min for azinphos-methyl, 11.6 min for malathion, 13.3 min for chlorpyrifos and 45.5 min for malaoxon, under given experimental conditions. During the photoprocess several intermediates were identified by GC-MS suggesting the pathway of OP degradation. The oxidation of chlorpyrifos results in the formation of chlorpyrifos-oxon as the main identified photoproduct. In case of malathion and azinphos-methyl the corresponding oxon analogues were not detected. The formation of diethyl (dimethoxy-phosphoryl) succinate in traces was observed during photodegradation of malaoxon and malathion. Several other photoproducts including trimethyl phosphate esters, which are known to be AChE inhibitors and 1,2,3-benzotriazin-4(3H)-one as a member of triazine compounds were identified in photodegraded samples of malathion, malaoxon, and azinphos-methyl. Based on this, two main degradation pathways can be proposed, both result of the (P-S-C) bond cleavage taking place at the side of leaving group. The enhanced inhibition of AChE observed with the TLS bioassay during the initial 30 min of photodegradation in case of all four OPs, confirmed the formation of toxic intermediates. With the continuation of irradiation, the AChE inhibition decreased, indicating that the formed toxic compounds were further degraded to AChE non-inhibiting products. The presented results demonstrate the importance of toxicity monitoring during the degradation of OPs in processes of waste water remediation, before releasing it into the environment.

Acetylcholinesterase↗
PubMed2006

Degradation of explosives-related compounds using nickel catalysts.

We report the ability of nickel-based catalysts to degrade explosives compounds in aqueous solution. Several nickel catalysts completely degraded the explosives, although rates varied. Nearly all of the organic explosive compounds tested, including 2,4,6-trinitrotoluene (TNT), hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), were rapidly degraded to below detection limits by a powdered nickel on an alumina-silicate support (Aldrich nickel catalyst). Perchlorate degradation was minimal (<25%). Degradation of TNT by Aldrich nickel catalyst resulted in apparent first-order kinetics. Significant gaseous 14C was released and collected in an alkaline solution (most likely carbon dioxide) from [14C]RDX and [14C]HMX, indicating heterocyclic ring cleavage. Significant gaseous 14C was not produced from [14C]TNT, but spectrophotometric evidence indicated loss of aromaticity. Degradation occurred in low ionic strength solutions, groundwater, and from pH 3 to pH 9. Degradation of TNT, RDX, and HMX was maintained in flow-through columns of Aldrich nickel catalyst mixed with sand down to a hydraulic retention time of 4h. These data indicate that nickel-based catalysts may be an effective means for remediation of energetics-contaminated groundwater.

Azocines↗
PubMed2006

Decomposition pathways and reaction intermediate formation of the purified, hydrolyzed azo reactive dye C.I. Reactive Red 120 during ozonation.

In this study, an aqueous solution of purified, hydrolyzed C.I. Reactive Red 120 (RR 120, Color Index), was selected as a model to investigate the degradation pathways and to obtain additional information on the reaction intermediate formation. The dye was purified to avoid the influence of the impurities on the ozonation process and on the formation of oxidation by-products. To simulate the dye-bath effluents from dyeing processes with azo reactive dyes, a hydrolyzed form of the dye was chosen as a representative compound. High performance liquid chromatography/mass spectrometry and its tandem mass spectrometry was chosen to identify the decomposition pathways and reaction intermediate formation during the ozonation process. In addition total organic carbon and high performance ion chromatography analysis were employed to obtain further information on the reaction processes during ozonation. Purified, hydrolyzed RR 120 was decomposed under the direct nucleophilic attack by ozone resulting in oxidation and cleavage of azo group and aromatic ring, while the triazine group still remained in the solution even after prolonged oxidation time (120 min) due to its high resistance to ozonation. Phenol, 1,2-dihydroxysulfobezene, 1-hydroxysulfonbezene were detected as the degradation intermediates, which were further oxidized by O(3) and *OH to other open-ring products and then eventually led to simple oxalic and formic acid identified by HPIC.

Azo Compounds↗
PubMed2004

Protein separation with surfactant-coated polystyrene involving Cibacron Blue 3GA-conjugated triton X-100.

Through mixing of porous polystyrene particles (Amberlite XAD-4), non-ionic surfactants, and surfactant-conjugated substrates (affinity ligand) in an aqueous solution led to the formation of a novel medium (affinity admicelle) for protein separation. The ligand (CB-Triton) was synthesized by mixing a triazine dye (Cibacron Blue 3GA (CB)) and a polyoxyethylene-type non-ionic surfactant (Triton X-100) in weakly alkaline solutions. Triton X-100 and CB-Triton were competitively sorbed onto XAD-4. Albumin (bovine serum), alcohol dehydrogenase (yeast), and lysozyme (chicken egg) having specific interaction to CB were collected onto the affinity admicelle. On the other hand, the collection of ovalubmin (chicken egg white), having no binding ability to CB, was negligibly small. Lysozyme in 100 microl of chicken egg white, diluted with 900 microl of 10 mM Tris-HCl (pH 7.4), was successfully collected on 18 mg of CB-Triton admicelles and, then, it was eluted with 1 ml of aqueous solution of 100 mM phosphate (pH 7.4). The recovery based on the activity for the lysis of micrococcus and the concentration factor were 60% and 40 (n = 3), respectively.

Micelles↗
PubMed2004

Protein separation with surfactant-coated octadecylsilyl silica involving Cibacron blue 3GA-conjugated nonionic surfactant.

A novel medium for protein separation, namely affinity admicelle, was prepared by mixing of octadecylsilyl (ODS) silica gels, a polyoxyethylene-type nonionic surfactant (Triton X-100), and a surfactant-conjugated substrate (affinity ligand) in an aqueous solution. The ligand was synthesized by mixing a triazine dye (Cibacron Blue 3GA, CB) and a polyethylene glycol monooleyl ether (C18EO7, C18EO10, or C18EO20) having different length of polyoxyethylene moiety in weakly alkaline solutions. The amount of Triton X-100 sorbed on 1 g of ODS silica was 0.2 mmol. Affinity ligands having highly hydrophobic oleyl group were predominantly sorbed on ODS silica. The losses of Triton X-100 and affinity ligand were within 0.3% and negligible by washing the admicelles were with a 25-fold volume of 1 mM Tris-HCl solution (pH 7.4). The coating ODS silica with Triton X-100 was effective to prevent the irreversible sorption of albumin (bovine, serum). An NADH-dependent enzyme, alcohol dehydrogenase (ADH, yeast), was successfully collected on the admicelles involving CB-conjugated ligands (CB-C18EO20). The maximum collection of ADH to 90 mg/ml of affinity admicelles was 68+/-4%. However, CB-C18EO7 and CB-C18EO10 having shorter polyoxyethylene unit were not available, suggesting the requirement of the spacer moiety in the affinity ligand. The recovery and purification factor based on the ratio of activity (unit)/protein (mg) from Whatman DE52-treated yeast extract was 27% and 12, respectively.

Affinity Labels↗
PubMed2005

Detection of nitroaromatic and cyclic nitramine compounds by cyclodextrin assisted capillary electrophoresis quadrupole ion trap mass spectrometry.

An Agilent 3DCE capillary electrophoresis system using sulfobutylether-beta-cyclodextrin (SB-beta-CD)-ammonium acetate separation buffer pH 6.9 was coupled to a Bruker Esquire 3000+ quadrupole ion trap mass detector via a commercially available electrospray ionization interface with acetonitrile sheath flow. The CE-MS system was applied in negative ionization mode for the resolution and detection of nitroaromatic and polar cyclic or caged nitramine energetic materials including TNT [2,4,6-trinitrotoluene, formula mass (FW) 227.13], TNB (1,3,5-trinitrobenzene, FW 213.12), RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine, FW 222.26) HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine, FW 296.16), and CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, FW 438.19). The CE-MS system conformed to the high-performance liquid chromatography with ultraviolet absorbance detection (HPLC-UV) and HPLC-MS reference methods for the identification of energetic contaminants and their degradation products in soil and marine sediment samples.

Aza Compounds↗