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At least 649 records · Page 36Linked to original sources
PubMed2006

Bioavailability of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to the prairie vole (Microtus ochrogaster).

Concerns have been raised over potential bioavailability and biotransfer of energetic materials such as hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). The present study assessed plant-incorporated [14C]RDX and plant-derived [14C]RDX-metabolite ingestion by the prairie vole (Microtus ochrogaster). The animals were fed labeled chow (maximum, < or =10 g/d) for 5 or 7 d, followed by a 6- or 4-d chase period. More than 95% of all label presented was recovered in the summed excreta, with 74% of this in the fecal nonabsorbed bulk. Greater than 20% of the presented [14C]RDX and plant-derived [14C]RDX metabolites were absorbed by the animals' digestive tracts. These materials were either metabolized to (14)CO2 (8-10% of the total label) or removed as nitrogenous waste through the kidneys (10-14%). Both 14C-urine and (14)CO2 excretion continued after the feces cleared, indicating ongoing metabolism of the labeled material. Approximately 4% was retained within the tissues at death, with the highest total activity in the liver and the highest specific activity in the testes. Other labeled tissues included the lung, heart, brain, spleen, skeletal muscle, bone, and pancreas. All these tissues containing [14C]RDX-derived materials are available to subsequent predators, indicating a potential for transfer to a higher trophic level.

Animals↗
PubMed2001

Ecotoxicological effects of hexahydro-1,3,5-trinitro-1,3,5-triazine on soil microbial activities.

Although hexahydro-1,3,5-trinitro-1,3,5-triazine (also called RDX or hexogen) is a potentially toxic explosive compound that persists in soil, its ecotoxicological effects on soil organisms have rarely been assessed. In this study, two uncontaminated garden soils were spiked with 10 to 12,500 mg RDX/kg dry soil. Soil microbial activities, i.e., potential nitrification, nitrogen fixation, dehydrogenase, basal respiration, and substrate-induced respiration were chosen as bioindicators and were determined after 1-, 4-, and 12-weeks of exposure. Experimental results indicate that RDX showed significant inhibition (up to 36% of control) on indigenous soil microbial communities over the period of this study. All five bioindicators responded similarly to the RDX challenge. The length of exposure also affected the microbial toxicity of RDX, with 12-week exposure exerting more significant effects than the shorter exposure periods, suggesting that soil microorganisms might become more vulnerable to RDX when exposure is extended. The estimated lowest observable adverse effect concentration of RDX was 1,235 mg/kg. No biodegradation products of RDX were detected at all three sampling times. Compared with 2,4,6-trinitrotoluene (TNT), RDX is less toxic to microbes, probably because of its resistance to biodegradation under aerobic conditions, which precludes metabolic activation of nitro groups.

Soil Microbiology↗
PubMed2004

Determination of triazine pesticides and related compounds in environmental water by liquid chromatography-mass spectrometry.

A method for the determination of 5 triazine herbicides and 12 degradation products in environmental water samples using liquid chromatography-electrospray ionization mass spectrometry (LC/ESI/MS) has been developed. The pesticides in water were extracted with two types of solid phase: a styrene-divinylbenzene copolymer and a graphitized carbon black. Desorption solvents for the extracted compounds were acetone for the styrene-divinylbenzene copolymer and methanol for the graphitized carbon black. Overall recoveries from ground water and river water ranged from 73% to 111%. The limits of detection (LODs) were 0.2 to 28 ng l(-1). This method was applied to several ground water samples.

Chromatography, Liquid↗
PubMed2006

Solvent sublation and spectrometric determination of iron(II) and total iron using 3-(2-pyridyl)-5,6-bis(4-phenylsulfonic acid)-1,2,4-triazine and tetrabutylammonium bromide.

Solvent sublation has been studied for the separation and determination of trace iron(II) in various kinds of water samples. A strongly magenta-colored anionic [Fe(FZ)3](4-) complex was formed at pH 5.0 upon adding 3-(2-pyridyl)-5,6-bis(4-phenylsulfonic acid)-1,2,4-triazine (ferrozine, FZ) to the sample solution. Tetrabutylammonium bromide (TBAB) was added in the solution to form the (TBA)4[Fe(FZ)3)] ion pair, and an oleic acid (HOL) surfactant was added. Then, the (TBA)4[Fe(FZ)3] ion pairs were floated by vigorous shaking in the flotation cell and extracted into methyl isobutyl ketone (MIBK) on the surface of the aqueous solution. The iron collected in the MIBK layer was measured directly by spectrophotometry and/or flame atomic-absorption spectrophotometry. Different experimental variables that may affect the sublation efficiency were thoroughly investigated. The molar absorptivity of the (TBA)4[Fe(FZ)3] ion pair was 2.8 x 10(4) l mol(-1) cm(-1) in the aqueous layer. Beer's law held up to 1.0 mg L(-1) Fe(II) in the aqueous as well as in the organic layers. The adopted solvent sublation method was successfully applied for the determination of Fe(II) in natural water samples with a preconcentration factor of 200. The application was extended to determine iron in pharmaceutical samples.

Dose-Response Relationship, Drug↗
PubMed2007

6-Chloro-N,N-diethyl-1,3,5-triazine-2,4-diamine (CAT) sensor based on biomimetic recognition utilizing a molecularly imprinted artificial receptor.

We aimed to develop a 6-chloro-N,N-diethyl-1,3,5-triazine-2,4-diamine (CAT)-sensing system based on a biomimetic receptor of a molecularly imprinted polymer for CAT and electrochemical determination of CAT. A molecularly imprinted polymer for CAT was prepared by the polymerization of methacrylic acid (MAA) as a functional monomer and ethylene glycol dimethacrylate (EDMA) as a cross-linker with a template molecule (CAT) in dimethyl formamide (DMF). The polymer prepared with the ratio of these monomers (CAT:MAA:EDMA = 1:7.5:20) showed the most selective rebinding to CAT, and the obtained polymer was recognized as a CAT-imprinted polymer (CAT-MIP). The effect of the specific imprinting sites of CAT-MIP was demonstrated by Scatchard analysis. In an aqueous solution of CAT, CAT-MIP showed the maximum binding of CAT in a 0.05 M phosphate buffer (PB), pH 5.0. The binding amount of CAT to CAT-MIP was 24% more than atrazine and 72% more than propazine. The CAT-sensing system was composed of a column of CAT-MIP particles and a voltammetry analyzer. The reductive current of CAT depended on the concentration of CAT up to 30 microM with the system.

Biomimetic Materials↗
PubMedDate not supplied

Acute and subacute toxicology and safety evaluation of hexahydro-1,3,5-triethyl-S-triazine.

Acute and subacute toxicology and safety evaluation was determined for hexahydro-1,3,5-triethyl-s-triazine (Vancide-TH), a bacteriostatic and fungiastatic agent proposed for industrial use by R. T. Vanderbilt and Co., Inc. Single dose oral toxicity, subacute 14 day dermal toxicity and eye irritation studies were conducted on either the rat or the rabbit. The data obtained indicate that Vancide-TH should be classified as a "toxic, corrosive and an eye-irritating" substance as defined under the "Regulations" of the Federal Hazardous Substances Act. Since the acute dermal LD50 closely approximated the acute oral LD50 in rats, this route might constitute the most serious hazard involved with V-TH and special precautions should be exercised when handling or using this substance. Because of the severe eye-irritating action, precautions should be taken to protect the eyes when handling or using the compound; the ocular damage produced may be irreversible. The "in use" concentrations (1,000 to 10,000 ppm) produced a much lesser toxocity in animals and could be without hazard if precautions are taken.

Animals↗
PubMed1999

The antimalarial triazine WR99210 and the prodrug PS-15: folate reversal of in vitro activity against Plasmodium falciparum and a non-antifolate mode of action of the prodrug.

We have studied the reversal of activity against Plasmodium falciparum of WR99210, a triazine antimalarial drug, and of the pro-drug PS-15 by folic acid (FA) and folinic acid (FNA). Folic acid and FNA inhibit the growth of P. falciparum in vitro at concentrations > 10(-4.5) and 10(-3.5) mol/L, respectively. The activity of pyrimethamine against Kenyan strains M24 and K39 is reduced 10-12-fold by 10(-5) mol/L of FA, and virtually eliminated by 10(-5) mol/L of FNA. Folates do not antagonise the action of WR99210 against Kenyan strains, and only partially antagonize the action of WR99210 action against the Southeast Asian strains V1/S and W282. Similarly, FA and FNA exerted weak or no antagonism of the action of PS-15. The inability of folates to antagonize the action of WR99210 can be explained in terms of high drug-enzyme affinity, but this does not account for the inability of FA and FNA to antagonize PS-15. These results suggest that action of PS-15 against P. falciparum is primarily due to a non-folate mechanism.

Animals↗
PubMedDate not supplied

Synthesis, anti-HIV and anticancer activities of new 4-(2-mercaptobenzenesulfonyl)perhydro-1,2,4-triazin-3-ones.

Syntheses of N-(6-chloro-1,1-dioxo-7-R1-1,4,2-benzodithiazyn-3-yl)-N'-(2- hydroxyethyl)hydrazines (IIa-d], N-(6-chloro-1,1-dioxo-7-methyl-1,4,2-benzodithiazyn-3-yl)-N'-(2- chloroethyl)hydrazine [IV], 4-(4-chloro-5-R1-2-mercaptobenzenesulfonyl)perhydro-1,2,4-triaz in-3-ones [IIIa-d] and 5-chloro-4-methyl-2-(3-oxoperhydro-1,2,4-triazin-4- ylsulfonyl)phenylthioacetic acid [V] have been described. Preliminary screening data have indicated that compounds [IIIa-d] exhibit either a moderate or a high anti-HIV activity and a moderate anticancer activity in some human tumor cell lines.

Anti-HIV Agents↗
PubMed1999

Affinity labeling of annexin VI with a triazine dye, Cibacron blue 3GA. Probable interaction of the dye with C-terminal nucleotide-binding site within the annexin molecule.

Annexin VI (AnxVI) from porcine liver, a member of the annexin family of Ca(2+)- and membrane-binding proteins, has been shown to bind ATP in vitro with a K(d) in the low micromolar concentration range. However, this protein does not contain within its primary structure any ATP-binding consensus motifs found in other nucleotide-binding proteins. In addition, binding of ATP to AnxVI resulted in modulation of AnxVI function, which was accompanied by changes in AnxVI affinity to Ca2+ in the presence of ATP. Using limited proteolytic digestion, purification of protein fragments by affinity chromatography on ATP-agarose, and direct sequencing, the ATP-binding site of AnxVI was located in a C-terminal half of the AnxVI molecule. To further study AnxVI-nucleotide interaction we have employed a functional nucleotide analog, Cibacron blue 3GA (CB3GA), a triazine dye which is commonly used to purify multiple ATP-binding proteins and has been described to modulate their activities. We have observed that AnxVI binds to CB3GA immobilized on agarose in a Ca(2+)-dependent manner. Binding is reversed by EGTA and by ATP and, to a lower extent, by other adenine nucleotides. CB3GA binds to AnxVI also in solution, evoking reversible aggregation of protein molecules, which resembles self-association of AnxVI molecules either in solution or on a membrane surface. Our observations support earlier findings that AnxVI is an ATP-binding protein.

Adenosine Triphosphate↗
PubMed1999

Potential carcinogenicity of the synthetic 1,3,6-triazine (6-azapyrimidine) nucleic acid analogues determined by DC polarography. II. Nucleosides of 6-azauracil.

The polarographic reduction of six synthetic 1,3,6-triazine (6-aza) nucleosides with 6-azauracil as the nucleoside base in the strictly anhydrous solutions was studied in the absence and presence of alpha-lipoic acid. The values of the half-wave potentials E1/2 and the parameter of potential carcinogenicity tg alpha were compared for six nucleosides of 6-azauracil and two nucleosides of 4-thio-6-azauracil. The current value of the first diffuse polarographic wave or a new diffuse polarographic wave belonging to the nucleoside-alpha-lipoic acid complex increased with the increase of the alpha-lipoic acid concentration for the all compounds only marginally. Although this diffuse current increase was linear and dependent on the alpha-lipoic acid concentration in anhydrous solutions, the determined index tg alpha values ranged between 0.027 and 0.114. This is an indication of a very low potential carcinogenicity of the all nucleoside analogues investigated.

Azauridine↗
PubMed2001

Synthesis of heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anticancer drugs, part III.

Some new fused heterobicyclic nitrogen systems such as 1,2,4-triazino[3,4-b] [1,3,4] thiadiazolones/thiadiazinones 4-15 and the related compounds 16-21 have been synthesized from treatment of 4-amino-3-mercapto-6-substituted-1,2,4-triazin-5-ones 1 with bifunctional oxygen and halogen compounds via heterocyclization reactions. Structures of the products have been deduced from their elemental analysis and spectral data. Significant anti-HIV and anticancer activities were observed in vitro for some members of the series, compounds 1e, 4e, 4f, 5, 6 and 16 showing a significant activity in Leukemia, Lung, Breast and CNS anticancer evaluation.

Anti-HIV Agents↗
PubMedDate not supplied

Synthesis of 1,2,4-triazino[5,6-b] indoles bearing 1,2,4-triazine moiety.

Some new 3-(5,6-Diphenyl-1,2,4-triazin-3-yl)-5-substituted- 1,2,4-triazino[5,6-b]indole derivatives (6-12) have been obtained via treatment of both (4 and 5) with p-nitro-benzoyl chloride, ammonium thiocyante, formaldehyde-methanol, acrylonitrile and thiosemi-carbazide. The former structure of the new products was established by the help of elemental analyses, as well as spectral data. Some of their showed pronounced effect on the Cellobiase produced by Thermomyces lanuginosus and Chaetomium thermophilum.

Enzyme Inhibitors↗
PubMed2002

Effect of adsorption to elemental iron on the transformation of 2,4,6-trinitrotoluene and hexahydro-1,3,5-trinitro-1,3,5-triazine in solution.

The effect of adsorption to elemental iron on the reductive transformation of 2,4,6-trinitrotoluene (TNT) and hexahydro-1,3,5-trinitro-1,3,5-triazine (royal demolition explosive [RDX]) in aqueous solution was studied with scrap iron and high-purity iron. In batch experiments with the same total iron surface area and a mixing rate of 100 rpm, TNT and RDX were removed from the solution within 30 min. With high-purity iron, adsorbed TNT was reduced to 2,4,6-triaminotoluene (TAT) rapidly, with little accumulation of intermediates at the surface. With scrap iron, the extent of adsorption of TNT and its daughter products was more significant and reduction of these adsorbed molecules to TAT was slower. Distribution of the intermediates indicated that the reaction with scrap iron occurred primarily through reduction of the ortho nitro group. Kinetic analysis suggests that mass transfer or adsorption of TNT controlled the overall rate of TNT reduction to TAT with pure iron, whereas with scrap iron, the rate of TAT formation was probably limited by other processes. Compared to TNT, transformation of adsorbed RDX was more rapid and less affected by iron type. The RDX was reduced to an unidentified, water-soluble intermediate and NH4+, which accounted for approximately 50% of the RDX nitrogen. No total organic carbon reduction was observed before and after RDX transformation with scrap iron.

Adsorption↗
PubMed2002

Toxicity of the explosives 2,4,6-trinitrotoluene, hexahydro-1,3,5-trinitro-1,3,5-triazine, and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine in sediments to Chironomus tentans and Hyalella azteca: low-dose hormesis and high-dose mortality.

The toxicity of the explosives 2,4,6-trinitrotoluene (TNT); hexahydro-1,3,5-trinitro-1,3,5-triazine (royal demolition explosive [RDX]); and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (high-melting explosive [HMX]), was evaluated in spiked sediment with two freshwater invertebrates. The midge Chironomus tentans and the amphipod Hyalella azteca demonstrated significant toxic effects after exposure to TNT and its degradation products, 1,3,5-trinitrobenzene (TNB) and 2,4-diamino-6-nitrotoluene (2,4-DANT). Significant reductions in survival of C. tentans exposed to TNT, TNB, and 2,4-DANT were observed at nominal sediment concentrations as low as 200 mg/kg. Hyalella azteca was more sensitive to TNT, TNB, and 2,4-DANT than the midge, where significant reductions in survival were observed at nominal concentrations of 50, 100, and 200 mg/kg, respectively. Survival of the midge and the amphipod was unaffected after exposure to RDX or HMX at the highest concentrations of 1,000 and 400 mg/kg, respectively. Growth of the midge, measured as total weight, was significantly reduced by 2,4-DANT. However, significantly increased growth was observed after exposure to sublethal concentrations of RDX and HMX. Although significant reductions in amphipod survival were observed at high concentrations of TNB, growth was significantly increased at sublethal concentrations. The results of the current investigation suggest that organisms exposed to explosives at contaminated sites may be affected at concentrations less than 25 mg/kg through hormetic growth enhancement and at higher concentrations through increased mortality.

Amphipoda↗