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PubMed2004

Biodegradation of the nitramine explosives hexahydro-1,3,5-trinitro-1,3,5-triazine and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine in cold marine sediment under anaerobic and oligotrophic conditions.

The in situ degradation of the two nitramine explosives, hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), was evaluated using a mixture of RDX and HMX, incubated anaerobically at 10 degrees C with marine sediment from a previous military dumping site of unexploded ordnance (UXO) in Halifax Harbor, Nova Scotia, Canada. The RDX concentration (14.7 mg.L-1) in the aqueous phase was reduced by half in 4 days, while reduction of HMX concentration (1.2 mg.L-1) by half required 50 days. Supplementation with the carbon sources glucose, acetate, or citrate did not affect the removal rate of RDX but improved removal of HMX. Optimal mineralization of RDX and HMX was obtained in the presence of glucose. Using universally labeled (UL)-[14C]RDX, we obtained a carbon mass balance distributed as follows: CO2, 48%-58%; water soluble products, 27%-31%; acetonitrile extractable products, 2.0%-3.4%; and products covalently bound to the sediments and biomass, 8.9% (in the presence of glucose). The disappearance of RDX was accompanied by the formation of the mononitroso derivative hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine (MNX) and formaldehyde (HCHO) that subsequently disappeared. In the case of HMX, mineralization reached only 13%-27% after 115 days of incubation in the presence or absence of the carbon sources. The disappearance of HMX was also accompanied by the formation of the mononitroso derivative. The total population of psychrotrophic anaerobes that grew at 10 degrees C was 2.6 x 10(3) colony-forming units.(g sediment dry mass)-1, and some psychrotrophic sediment isolates were capable of degrading RDX under conditions similar to those used for sediments. Based on the distribution of products, we suggest that the sediment microorganisms degrade RDX and HMX via an initial reduction to the corresponding mononitroso derivative, followed by denitration and ring cleavage.

Acetates↗
PubMed1994

Studies on anti-platelet agents. V. Synthesis and structure-activity relationship of 3-substituted 5,6-bis(4-methoxyphenyl)-1,2,4-triazines.

The syntheses and structure-activity relationships of a series of 3-substituted 5,6-bis(4-methoxyphenyl)-1,2,4-triazines as anti-platelet agents based on cyclooxygenase (CO) inhibition are described. Of these compounds, 1-[5,6-bis(4-methoxyphenyl)-1,2,4-triazin-3-yl]carbonyl-4-methylpi perazine (10) exhibited potent CO inhibition in vitro (IC50 = 2.8 x 10(-7) M) with vasodilatory activity (ED50 = 4.5 x 10(-5) M). Compound 10 also showed potent ex vivo activities, completely preventing platelet aggregation induced by arachidonic acid and collagen at 6 h after oral administration of 3.2 and 1.0 mg/kg. The ex vivo potency of 10 is more than three times that of aspirin. Moreover, 10 demonstrated no gastrointestinal side effect in rats even at 100 mg/kg in spite of its potent CO inhibition activity, while aspirin, the most widely-used anti-platelet drug, showed gastrointestinal side effects in a dose-dependent manner (32, 100, and 320 mg/kg) in our study. These results suggested that 10 is a very attractive candidate for development as an anti-platelet drug since an aspirin-like anti-platelet agent, based on CO inhibition and being free from gastrointestinal side effects, is a major goal of thromboembolic research.

Animals↗
PubMed1997

Synthesis and aromatase-inhibitory activity of imidazolyl-1,3,5-triazine derivatives.

Triamino-substituted 1,3,5-triazine derivatives were synthesized and tested for inhibitory activities against the aromatase of human placental microsomes and the cytochrome P450 side chain cleavage of cholesterol (P450SCC) of pig adrenal mitochondria. The compounds having imidazolyl and tertiary amino groups as substituents in the 1,3,5-triazine ring showed significant aromatase-inhibitory activity. Among them, compounds 17, 23, 26, 27 and 28 were more active than the reference compound, CGS 16949A. The inhibitory activities of these compounds against P450SCC were much weaker than their aromatase-inhibitory activities. These compounds may be regarded as selective aromatase inhibitors.

Adrenal Glands↗
PubMed2006

Triazine adsorption by saponite and beidellite clay minerals.

We investigated the sorption of three triazine herbicides (atrazine, simazine, and metribuzin) by saponite and beidellite clay minerals saturated with K+, Cs+, Na+, and Ca2+. Saponite clay sorbed a larger fraction of each pesticide from aqueous solution than did beidellite clay. The lower cation-exchange capacity in saponite compared to that in beidellite presumably results in a less crowded interlayer, with more siloxane surface being available for adsorption. Generally, Cs-saturated clays sorbed more triazines than did clays saturated by K+, Na+, or Ca2+. We attribute this to the smaller hydrated radius of Cs+, which again increases the siloxane surface that is available for sorption. Furthermore, the relatively weak hydration of Cs+ reduces the swelling of clay interlayers, thus making sorption domains less hydrated and more receptive to hydrophobic molecules. The Cs-saponite manifested a sorption of more than 1% atrazine by weight above equilibrium concentrations of 6 mg/L, which to our knowledge is the largest sorption of neutral atrazine from water yet reported for an inorganic sorbent. Molecular dynamics simulations indicate that atrazine interacts both with clay basal planes and with multiple cations in the clay interlayer.

Adsorption↗
PubMed1999

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

Some new heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety (3-22) have been achieved by treatment of 3-amino-5,6-disubstituted-1,2,4-triazines 2a-h with some cyclic and acyclic oxygen compounds followed by heterocyclization. Structures of the products have been deduced by elemental analysis and spectral data. Significant anti-HIV and anticancer activities were observed in vitro for some members of the series, where compounds 5 and 18 showed a moderate activity.

Anti-HIV Agents↗
PubMed1999

Synthesis of some new heterobicyclic nitrogen systems bearing the 1,2,4-triazine moiety as anti-HIV and anti-cancer drugs, Part II.

Some new heterobicyclic nitrogen systems 5-18 and/or thioethers 20, 22 bearing the 1,2,4-triazine moiety have been synthesized via condensation of 3-formylamino-1,2,4-triazine 3 with nitrogen compounds followed by heterocyclization with oxygen reagents. Thioether analogs 20, 22 have been obtained from fusion of compound 19 with 4-chlorothiophenol. The structure of the products have been established by elemental analysis and spectral data. The anti-HIV and anticancer activities of some products have also been investigated where compounds 20a, c and 22b exhibited a moderate activity. The biocidal-structures activity correlation was also studied.

Anti-HIV Agents↗
PubMed2000

Antimetastatic and antitumor effects of 2,4-diamino-6-(pyridine-4-yl)-1,3,5-triazine (4PyDAT) on the high lung metastatic colon 26 tumor in mice.

The therapeutic potential of a diaminotriazine, 2,4-diamino-6-(pyridine-4-yl)-1,3,5-triazine (4PyDAT), was investigated in a metastatic model using the mouse colon 26 carcinoma variant (Co26Lu), which preferentially metastasizes to the lung of mouse. The compound had a moderate antimetastatic activity as well as antitumor activity, without toxicity to the host, when administered orally. In the cytotoxicity test in vitro, 4PyDAT showed very weak direct cytotoxicity against the Co26Lu cell line, Co26Lu(F55) (IC50 < or = 1000 microM). Less microcapiral formation on tumors were observed for the treated group with a hemorrhage than the control group under microscopy. 4PyDAT significantly inhibited the production of urokinase-type plasminogen activator (u-PA) in Co26Lu(F55) cells. These results suggest that the antimetastatic and antitumor activities of 4PyDAT are due in part to inhibition of angiogenesis, rather than direct antiproliferative action on the tumor cells. 4PyDAT may become a lead compound to develop antitumor triazine derivatives based on antiangiogenic action.

Animals↗
PubMedDate not supplied

Stability and recovery of triazine and chloroacetamide herbicides from pH adjusted water samples by using empore solid-phase extraction disks and gas chromatography with ion trap mass spectrometry.

Empore disks were used to successfully extract herbicide residues from a difficult-to-analyze surface water source and deionized water. Herbicide recoveries were lower in surface water at 7,14, or 21 days after fortification and storage at 4 degrees C, presumably due to chemical sorption onto precipitated organic particulates. The addition of acid to the samples, as recommended in EPA Method 525.2, did not affect recoveries of alachlor and metolachlor, but reduced recoveries of atrazine, simazine, and cyanazine. Treatment of water samples with sodium hypochlorite did not affect alachlor or metolachlor recoveries, but greatly reduced the recovery of all triazine herbicides. This indicates that addition of acid or sodium hypochlorite to water samples may be detrimental to triazine analysis.

Acetamides↗
PubMed1975

Anti-inflammatory action of an s-triazine derivative in rats.

Anti-inflammatory action of an s-triazine derivate (M 1704, 2-amino-4-(p-fluoroanilino)-6-n-propyl-1,3,5-triazine) was studied in rats. M 1704 inhibited carrageenan edema, cotton-pellet granuloma and adjuvant arthritis in intact rats. M 1704 was not effective on carrageenan edema in adrenalectomized rats, but effective when administered with cortisol. The drug appeared to potentiate the anti-inflammatory effects of cortisol on cotton-pellet granuloma. The results obtained in this and a previous study suggest that M 1704 exerts the anti-inflammatory action mainly by potentiating the peripheral anti-inflammatory action of endogenous steroid and partly by stimulating the secretion of corticosteroids.

Administration, Topical↗
PubMed2001

Determination of resistant biotypes of Amaranthus retroflexus L. on triazines.

Considering the fact that since 1966 in our country the mostly produced have been triazine herbicides on the bases of ametryn, simazine, atrazine and prometryn, we have studied resistance of Amaranthus retroflexus from different sites in regard to the above mentioned herbicides. Seed of weed species for which exist-possibility of resistance have been collected from different localities in Vojvodina, such as Backa Palanka, Backi Maglic and Becej. Studies were performed during 1999 and 2000 by whole plant studies (Thurnwachter, 1998) and by petri dish assays (Clay, Underwood, 1989). Plants were treated by range of atrazine rates (Atrazin S-50) including also susceptible, referent population. Results indicate atrazine resistance of Amaranthus retroflexus at Backa Palanka and Backi Maglic sites, which have been treated by triazine herbicides in many years lasting period.

Amaranthus↗
PubMed2003

Purification of glucose-6-phosphate dehydrogenase from baker's yeast in aqueous two-phase systems with free triazine dyes as affinity ligands.

To improve the selectivity of glucose-6-phosphate dehydrogenase (G6PDH) extraction by an aqueous two-phase system, a simple and inexpensive affinity aqueous two-phase system using unbound reactive triazine dyes as ligands was introduced. In a polyethylene glycol (PEG)/hydroxypropyl starch (PES) system, the unbound free triazine dyes, Cibacron Blue F3GA and Procion Red HE3B, partitioned unevenly in the top PEG-rich phase and thus showed an affinity effect on G6PDH, but no influence on hexokinase. The various parameters investigated were pH of the system, buffers, molecular weight of PEG, and ligand type and concentration. A two-step affinity extraction process was established for the purification of G6PDH from baker's yeast. The total yield of G6PDH was 66.9% and purification factor was 2.35.

Chromatography, Affinity↗
PubMed2003

Adsorption and correlation with their thermodynamic properties of triazine herbicides on soils.

Adsorption of atrazine, prometryne and prometon was determined on six soils with different physical and chemical properties. The adsorption isotherms of three herbicides could well fit Freundlich equation. On all of six soils, adsorption of herbicides increased in the order: atrazine approximately = prometon < prometryne. This order is quite the same to the calculation result of by means of excess thermodynamic properties of triazine. The Freundlich adsorption constants, Kf, showed to have good correlation with organic matter (OM%) of soils for each of these herbicides, suggesting that OM is the main factor, which dominates in the adsorption process of these triazine herbicides.

Adsorption↗
PubMedDate not supplied

Synthesis and anticancer activity of novel 2-amino-4-(4-phenylpiperazino)- 1,3,5-triazine derivatives.

The synthesis and anticancer activity of novel 2-amino-4-(4-phenylpiperazino)-1,3,5-triazine derivatives 4a-b and 5a-f are described. Compounds 4a, 5a,c and 5f were evaluated by in vitro assays of growth inhibition against several human tumor cell lines. The vitro cytotoxic activity was found for 2-{2-amino-4-[4-(2-chlorophenyl)piperazino]- 1,3,5-triazin-6-yl}-3-(4-nitrophenyl)acrylonitrile (5f) (IC50 = 0.45 microM - 1.66 microM), whilst other tested compounds were inactive. Some of the molecular orbital calculations for the tested derivatives were also presented.

Antineoplastic Agents↗
PubMed2004

Exclusion of antimicrobial activity of some analgesic active imidazo[2,1-c]triazines.

The purpose of this study was to exclude the potential antimicrobial activity of certain analgesic active imidazo[2,1-c]triazines. These compounds contain in their chemical structure potential pharmacophore formations and features similar to those present in morphine - like analgesics and opioid receptor agonists containing no basic nitrogen atom. These compounds showed significant antinociceptive activity on the central nervous system of the tested animals, correlated with very low toxicity value (LD50 value of above 2000 mg kg(-1) b.w. via i. p.). Microbiological tests were conducted on 106 strains of bacteria, 6 strains of yeast-like fungi and 3 strains of moulds. The examined imidazo[2,1-c]triazines in concentrations of 100 microg ml(-1) and 200 microg ml(-1) had no influence on the growth of the microorganisms tested. Lack of this influence can be profitable in the case of analgesic active compounds.

Analgesics↗
PubMed2004

Exclusion of antimicrobial activity of some analgesic active imidazo[2,1-c][1,2,4]triazines.

The purpose of this study was to exclude the potential antimicrobial activity of certain analgesic active imidazo[2,1-c][1,2,4]triazines. These compounds contain in their chemical structure potential pharmacophore formations and features similar to those present in morphine-like analgesics and opioid receptor agonists containing no basic nitrogen atom. These compounds showed significant antinociceptive activity on central nervous system of tested animals, correlated with relatively low acute toxicity values (LD50 in range from 1100 to above 2000 mg kg(-1) b.w. via i. p.). Microbiological tests were conducted on 106 strains of bacteria, 6 strains of yeast-like fungi and 3 strains of moulds. The examined imidazo[2,1-c][1,2,4]triazines in concentrations of 100 microg ml(-1) and 200 microg ml(-1) had no influence on the growth of microorganisms tested. Lack of this influence can be profitable in the case of analgesic active compounds.

Analgesics↗
PubMedDate not supplied

Determination of organophosphorus and triazine pesticides in olive oil by on-line coupling reversed-phase liquid chromatography/gas chromatography with nitrogen-phosphorus detection and an automated through-oven transfer adsorption-desorption interface.

A method is described for the simultaneous determination of organophosphorus and triazine pesticides in olive oil, whereby reversed-phase liquid chromatography (LC) is coupled to gas chromatography by means of an automated through-oven transfer adsorption-desorption (TOTAD) interface. The olive oil needs to be filtered only before it is loaded into the liquid chromatograph, where preseparation of the pesticide residues from the other olive oil components is carried out by using methanol-water as the eluant. The LC fraction containing the pesticides is automatically transferred to the gas chromatograph by using the TOTAD interface, which almost totally eliminates the solvent, so that water-sensitive detectors such as the nitrogen-phosphorus detector can be used. Detection limits range from 0.07 to 0.38 microg/L for organophosphorus pesticides and from 6.0 to 7.0 microg/L for triazines. The results were compared with those obtained by flame ionization detection.

Adsorption↗
PubMed1990

Purification of rat liver mitochondrial anion carriers by triazine dye affinity chromatography.

Mitochondria were prepared from rat liver, solubilized with Triton X-100 and submitted to chromatography on dry hydroxylapatite. The pass-through from the column, containing a mixture of mitochondrial carriers, was processed further by triazine dye affinity chromatography and optimal conditions for binding and elution of mitochondrial carriers were established. Activities of the mono-, di-, tricarboxylate and 2-oxoglutarate carriers were measured after reconstitution of various chromatographic fractions into asolectin vesicles, and a good resolution of different carriers was obtained. Thus the triazine dye affinity chromatography appears to be a potent new tool for purification of mitochondrial anion carriers.

Animals↗