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PubMed2006

Synthesis of tetraazacalix[2]arene[2]triazines: tuning the cavity by the substituents on the bridging nitrogen atoms.

[Structure: see text] A number of tetraazacalix[2]arene[2]triazines bearing different substituents on the bridging nitrogen atoms were synthesized efficiently using a fragment coupling strategy. The N-arylation of the parent azacalix[2]arene]2]triazine afforded tetra(arylaza)calix[2]arene[2]triazine in 91% yield. The introduction of different substituents on the bridging positions led to the regulation of the cavity of the resulting macrocyclic molecules.

Crystallography, X-Ray↗

PubMed1999

Triazine dyes as inhibitors and affinity ligands of glycosyltransferases.

The triazine dyes: Cibacron Blue 3GA, Reactive Red 120, Reactive Yellow 86, Reactive Green 19, Reactive Blue 4, Reactive Brown 10 inhibited the activity of a purified preparation of alpha1,6fucosyltransferase (GDP-L-fucose: N-acetyl beta-glucosaminide 6-alpha-L-fucosyltransferase, EC 2.4.1.68) from human blood platelets. Cibacron Blue 3GA and Reactive Red 120 were examined for the nature of the inhibition and both were found to be competitive inhibitors of the enzyme, with Ki = 11 microM and 2 microM, respectively. The two dyes inhibited also serum glycosyltransferases: alpha1,2fucosyltransferase (GDP-L-fucose: beta-D-galactosyl-R2-alpha-L-fucosyltransferase, EC 2.4.1.69), beta1,4galactosyltransferase (UDP-galactose: N-acetyl-D-glucosamine 4-beta-D-galactosyltransferase, EC 2.4.1.90) and beta1,3N-acetylglucosaminyltransferase (UDP-GlcNAc: 4-beta-D-galactosyl-D-glucose). Cibacron Blue 3GA was a more effective inhibitor of the glycosyltransferases that use UDP-linked sugar donors than Reactive Red 120 while the latter was a stronger inhibitor of the fucosyltransferases that use GDP-linked donor. All four glycosyltransferases could be affinity purified on Cibacron Blue 3GA-Agarose columns. The order of elution of glycosyltransferases from the columns with solutions of 0.25-1.0 M potassium iodide also depended upon the structure of nucleotide sugar donor, i.e. whether it contained UDP or GDP. Thus, triazine dyes should interact with the sugar donor binding sites of glycosyltransferases. The main advantages of the use of triazine dyes as affinity ligands for isolation of glycosyltransferases are their universal applicability regardless of enzyme specificity, low cost, and insensitivity to high concentration of other proteins present in the solution.

Azo Compounds↗

PubMed2004

Triazine dyes are agonists of the NAADP receptor.

NAADP has been shown to be a potent calcium-releasing second messenger in a wide variety of cell types to date. However, research has been hampered by a lack of pharmacological agents, with which to investigate NAADP-induced calcium release, and by the molecular identity of its cellular target protein being unknown. In the present paper, the sea urchin egg model was used to investigate whether triazine dyes, which can act as nucleotide mimetics, can bind to the NAADP receptor, induce Ca(2+) release and be used for affinity chromatography of the receptor. Indeed, all the triazine dyes tested (Reactive Red 120 (RR120), Reactive Green 19 (RG19), Reactive Green 5 (RG5), Cibacron Blue 3GA and Reactive Yellow 86) displayed micromolar affinities, except for Reactive Orange 14. Furthermore, unlike NAADP, RR120, RG19 and RG5 did not bind in an irreversible manner. The compound that displayed the highest affinity, RR120, was tested in a (45)Ca(2+) efflux assay. This compound released Ca(2+) via the NAADP receptor, as shown by the ability of subthreshold NAADP concentrations to inhibit this release. Furthermore, heparin and ruthenium red were unable to block RR120-induced Ca(2+) release. We have also shown that RG5 and RG19, immobilised on resins, retain the ability to bind to the receptor, and that this interaction can be disrupted by high salt concentrations. As a proof of principle, we have shown that this can be used to partially purify the NAADP receptor by at least 75-fold. In conclusion, triazine dyes interact with the NAADP receptor, and this could be exploited in future to create a new generation of pharmacological tools to investigate this messenger and, in combination with other techniques, to purify the receptor.

Animals↗

PubMed2005

Synthesis and stability of exocyclic triazine nucleosides.

Synthesis and stability studies of exocyclic amino triazine nucleosides were performed. Stability of the nucleosides was found to be dependent on triazine ring electron density, solvent, and pH. The nucleosides were found to be more stable when the triazine ring was electron deficient, in high pH aqueous solutions and in aprotic solvents.

Drug Stability↗

PubMed2006

Triazine and metolachlor herbicide residues in farm areas of the Lower Fraser valley, British Columbia, Canada.

Crop soils, ditch sediments and water flowing from several Lower Fraser River (LFR) farm areas of British Columbia, Canada, to salmon tributary streams of that river were sampled in 2004-2005 to quantify for residues of triazine [atrazine, desethylatrazine (a transformation product of atrazine), propazine, and simazine] and metolachlor (a chloroacetamide) herbicides. Average concentrations [microg kg-1 dry weight (d.w.)] of triazine (10,110) and metolachlor (8,910) herbicides detected in crop soils at the start (May 2004, 2005) of the growing season were about 17 and 6 times, respectively, higher than those found for both herbicide groups during (June-Sept, 2004, 2005) the growing season. In contrast, mean concentrations (microg L-1) of triazines (0.092) and metolachlor (0.014) in permanent ditches adjacent to farms were about 7 and 28 times, respectively, lower at the start than during the growing season. Both herbicide groups in ditch sediments were detected only during the growing season at concentrations averaging about 315 microg kg-1 d.w. The risk potential of these herbicides for non-target aquatic organisms inhabiting permanent farm ditches contiguous to tributary streams of the LFR during the growing season is evaluated and discussed.

Acetamides↗

PubMed1999

Formation of s-triazines during aerial oxidation of 8-oxo-7,8-dihydro-2'-deoxyguanosine in concentrated ammonia.

After automated DNA synthesis, oligodeoxynucleotides containing 8-oxoguanine are sensitive to aerial oxidation when subjected to the basic conditions necessary for deprotection and release of the oligomer from the control pore glass support. The major oxidation products of this heterocyclic moiety have been characterized by permitting 8-oxo-7,8-dihydro-2'-deoxyguanosine to react with oxygen in the presence of 28% aqueous ammonia at room temperature. Products were isolated by reverse phase HPLC and analyzed by electrospray ionization-mass spectrometry and gas chromatography-mass spectrometry of the trimethylsilyl-derivatives. 2-Amino-4-hydroxy-s-triazine-6-carboxylic acid and 2-amino-4-hydroxy-6-carbamyl-s-triazine were identified by these techniques and standards were synthesized. In addition, GC-MS analysis revealed other oxidation products, including urea, guanidine and 2-deoxyribose, which were not observed by HPLC because these compounds are transparent in the UV region of the spectrum. Both s-triazines were also observed when a purified, synthetic oligodeoxynucleotide containing a single 8-oxoguanine moiety was exposed to the same conditions. Oxidation of 8-oxoguanine appears to parallel the uric acid oxidation pathway, and a mechanistic scheme is proposed to account for the products of degradation.

8-Hydroxy-2'-Deoxyguanosine↗

PubMed1992

Influence of the triazine ring on the mutagenicity of triazinoindoles and some congeners.

Three compounds, which could be considered as precursors or derivatives of the 3-(4'-substituted-benzylidenamino)5H- 1,2,3-triazin[5,4b]indol-4-one series, were selected from the study of their mutagenic activity. Ames tests were performed study of their mutagenic activity. Ames tests were performed using the Salmonella typhimurium strains TA97, TA98, TA100, and TA102, according to the preincubation procedure, both with and without metabolic activation. The 3-amino-5H-1,2,3-triazin[5,4b]indol-4-one has been shown to be a strong S9-independent mutagen, which reverts frameshift and substitution mutations. Nevertheless its potency increases with the addition of microsomal fraction. In contrast, the 2-benzyliden-1-(3-aminoindol)-2-carbohydrazide and the 3-aminoindol-2-carbohydrazide congeners were not mutagenic. These results suggest that the 1,2,3-triazine ring is the principle substructure responsible for the mutagenicity of the triazinoindole congeners studied.

Hydrazines↗

PubMed1997

Triazine dyes inhibit HIV-1 entry by binding to envelope glycoproteins.

We have attempted to purify envelope (Env) glycoproteins of human immunodeficiency virus (HIV) from the culture supernatants of CHO-Sec cells that secreted truncated 140-kDa precursor and mature 120-kDa Env glycoproteins. The concentrated culture supernatants were applied to a column coupled with cibacron blue 3GA (CB3GA) to separate albumin from the Env proteins because CB3GA, a triazine dye, has been known to have a high affinity to albumin. Unexpectedly, Env proteins as well as albumin bound to the column, and the bound Env proteins were eluted by increasing the ionic strength using KCl. Gp120 was eluted at 0.5-0.9 M of KCl, while a higher concentration (0.9-1.5 M) was necessary for the elution of gp140. The agarose gel coupled with reactive red 120 (RR120), another triazine dye with similar characteristics, also retained both Env proteins, and the bound Env proteins could be eluted in a similar manner. In addition, these agents inhibited syncytium formation caused by HTLV-IIIB and HTLV-IIIMN. Inhibition was also seen when a virus-free fusion assay between Env protein expressed in CHO cells and fluorescent labeled SupT1 cells were used. These findings indicate that triazine dyes bind to the functional regions of Env proteins of HIV-1 that play important role(s) for HIV infection.

Albumins↗

PubMed1997

Effects of two N-arylpiperazinylmethylpyrazolo [1,5-d][1,2,4]triazine derivatives in pain and antidepressant tests in mice.

The antinociceptive and antidepressant effects of two pyrazolotriazine derivatives, 2-phenyl-3,3a-dihydro-4-oxo-5-(4-phenylpiperazin-1-yl) methyl-pyrazolo[1,5-d][1,2,4]-triazine (SM1) and 2-phenyl-3,3a-dihydro-4-oxo-5-[4-(4-fluorophenyl)piperazin-1-yl] methylpyrazolo[1,5-d][1,2,4] triazine (SM3) have been investigated in mice using classical pharmacological tests. The intraperitoneal LD50 values of SM1 and SM3 were 253.4 and 218.8 mg kg-1 respectively. SM1 and SM3 showed analgesic properties in the phenylbenzoquinone-induced abdominal constriction test (ED50 approximately 10-15 mg kg-1, i.p.) and in the hot-plate test. The antinociceptive effects of the triazines were significantly reduced by administration of naloxone (1 and 3.2 mg kg-1, s.c.) and yohimbine (1 mg kg-1, p.o.). Acute intraperitoneal administration of both compounds (1 mg kg-1 SM1 or 1.5 mg kg-1 SM3) potentiated morphine (0.15 mg kg-1, s.c.) analgesia in the phenylbenzoquinone test. Although this synergistic activity was not reversed by methysergide (0.5 mg kg-1, i.p.), the analgesic activity of both compounds was enhanced by administration of 5-hydroxytryptophan (50 mg kg-1, i.p.) in conjunction with carbidopa (25 mg kg-1, i.p.). Furthermore, neither compound (at 100 mg kg-1, i.p.) significantly reduced the duration of immobility of mice in the forced swimming test, and both (at 75 mg kg-1, i.p.) were ineffective at enhancing the toxic effects of yohimbine (30 mg kg-1, s.c.). Only SM3 (ED50 = 74.5 mg kg-1, i.p.) significantly antagonized reserpine (2.5 mg kg-1, i.p.)-induced ptosis. Thus, the results suggest that SM1 and SM3 have antinociceptive properties related to co-involvement of opioidergic and alpha 2-adrenoceptor mechanism without associated antidepressant properties.

Adrenergic alpha-Antagonists↗

PubMed2000

Characterization of metabolites during biodegradation of hexahydro-1, 3,5-trinitro-1,3,5-triazine (RDX) with municipal anaerobic sludge.

The biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) in liquid cultures with municipal anaerobic sludge showed that at least two degradation routes were involved in the disappearance of the cyclic nitramine. In one route, RDX was reduced to give the familiar nitroso derivatives hexahydro-1-nitroso-3,5-dinitro-1,3, 5-triazine (MNX) and hexahydro-1,3-dinitroso-5-nitro-1,3,5-triazine (DNX). In the second route, two novel metabolites, methylenedinitramine [(O(2)NNH)(2)CH(2)] and bis(hydroxymethyl)nitramine [(HOCH(2))(2)NNO(2)], formed and were presumed to be ring cleavage products produced by enzymatic hydrolysis of the inner C---N bonds of RDX. None of the above metabolites accumulated in the system, and they disappeared to produce nitrous oxide (N(2)O) as a nitrogen-containing end product and formaldehyde (HCHO), methanol (MeOH), and formic acid (HCOOH) that in turn disappeared to produce CH(4) and CO(2) as carbon-containing end products.

Anaerobiosis↗

PubMed2002

Arthrobacter aurescens TC1 metabolizes diverse s-triazine ring compounds.

Arthrobacter aurescens strain TC1 was isolated without enrichment by plating atrazine-contaminated soil directly onto atrazine-clearing plates. A. aurescens TC1 grew in liquid medium with atrazine as the sole source of nitrogen, carbon, and energy, consuming up to 3,000 mg of atrazine per liter. A. aurescens TC1 is metabolically diverse and grew on a wider range of s-triazine compounds than any bacterium previously characterized. The 23 s-triazine substrates serving as the sole nitrogen source included the herbicides ametryn, atratone, cyanazine, prometryn, and simazine. Moreover, atrazine substrate analogs containing fluorine, mercaptan, and cyano groups in place of the chlorine substituent were also growth substrates. Analogs containing hydrogen, azido, and amino functionalities in place of chlorine were not growth substrates. A. aurescens TC1 also metabolized compounds containing chlorine plus N-ethyl, N-propyl, N-butyl, N-s-butyl, N-isobutyl, or N-t-butyl substituents on the s-triazine ring. Atrazine was metabolized to alkylamines and cyanuric acid, the latter accumulating stoichiometrically. Ethylamine and isopropylamine each served as the source of carbon and nitrogen for growth. PCR experiments identified genes with high sequence identity to atzB and atzC, but not to atzA, from Pseudomonas sp. strain ADP.

Arthrobacter↗

PubMed1991

Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227.

Pseudomonas sp. strain NRRLB-12227 degrades the s-triazine melamine by a six-step pathway which allows it to use melamine and pathway intermediates as nitrogen sources. With the plasmid pLG221, mutants defective in five of the six steps of the pathway were generated. Tn5-containing-EcoRI fragments from these mutants were cloned and identified by selection for Tn5-encoded kanamycin resistance in transformants. A restriction fragment from ammelide-negative mutant RE411 was used as a probe in colony hybridization experiments to identify cloned wild-type s-triazine catabolic genes encoding ammeline aminohydrolase, ammelide aminohydrolase, and cyanuric acid amidohydrolase. These genes were cloned from total cellular DNA on several similar, but not identical, HindIII fragments, as well as on a PstI fragment and a BglII fragment. Restriction mapping and Southern hybridization analyses of these cloned DNA fragments suggested that these s-triazine catabolic genes may be located on a transposable element, the ends of which are identical 2.2-kb insertion sequences.

Blotting, Southern↗

PubMed1986

Triazine monomers and their adhesion to dentin.

A series of 4,6-dichloro-1,3,5-triazines [e.g., 2-allylamino-(ADT), diallylamino-(DADT), 2-N-p-allyloxyphenylamino-, 2-N-allyl-N-phenylamino-, and 2-N-allyl-N-p-tolylamino-4,6-dichloro-1,3,5-triazine] was synthesized and characterized by IR, NMR, and mass spectrometry. These monomers have chlorine atoms that can react with NH2 or OH groups and double bonds capable of copolymerization. Aniline reacted readily with ADT and DADT, ethanol reacted with ADT, but acetone, H2O, and DMF did not react with either triazine. It appears that ADT or DADT will react with dentinal collagen through NH2 or OH groups in the peptide side-chains. An aprotic solvent should be used for ADT or DADT, but absolute dryness in clinical usage is not essential because of the slow hydrolysis of ADT and DADT. Stability of the N-di-substituted amino derivative (DADT) is greater than that of the mono-substituted compound (ADT), which may isomerize. ADT and methyl methacrylate were copolymerized at 37 degrees C with amine-peroxide. ADT solutions enhanced the adhesive strength of restorative resin to dentin. Thus, monomers such as ADT and DADT appear to be promising dentin-bonding agents.

Chemical Phenomena↗

PubMed2002

Tandem vicarious nucleophilic substitution of hydrogen/intramolecular Diels-Alder reaction of 1,2,4-triazines into functionalized cycloalkenopyridines.

Synthesis of 2,3- and 3,4-cyclopentenopyridines, 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines from 1,2,4-triazine derivatives is reported. Introduction of an alpha-functionalized methyl substituent (e.g. arylsulphonyl, sulphonamide, sulphonic acid ester) into position 3- or 6- of triazines by vicarious nucleophilic substitution of hydrogen and subsequent alkylation with alkyl iodides bearing an acetylenic function in terminal position afforded valuable intermediates for intramolecular Diels-Alder reaction with inverse electron demand. When heated at higher temperature, these triazine derivatives gave the Diels-Alder cycloadducts, which, after spontaneous extrusion of nitrogen moiety, led to a variety of functionalized cycloalkenopyridine derivatives.

Alkylation↗

PubMed2006

Seasonality effects on pharmaceuticals and s-triazine herbicides in wastewater effluent and surface water from the Canadian side of the upper Detroit River.

The influence of seasonal changes in water conditions and parameters on several major pharmacologically active compounds (PhACs) and s-triazine herbicides was assessed in the wastewater and sewage treatment plant (WSTP) effluent as well as the downstream surface water from sites on the Canadian side of the upper Detroit River, between the Little River WSTP and near the water intake of a major drinking water treatment facility for the City of Windsor (ON, Canada). The assessed PhACs were of neutral (carbamazepine, cotinine, caffeine, cyclophosphamide, fluoxetine, norfluoxetine, pentoxifylline, and trimethoprim) and acidic (ibuprofen, bezafibrate, clofibric acid, diclofenac, fenoprofen, gemfibrozil, indomethacin, naproxen, and ketoprofen) varieties. The major assessed s-triazine herbicides were atrazine, simazine, propazine, prometon, ametryn, prometryn, and terbutryn. At sampling times from September 2002 to June 2003, 15 PhACs were detected in the WSTP effluent at concentrations ranging from 1.7 to 1244 ng/L. The PhAC concentrations decreased by as much 92 to 100% at the Little River/Detroit River confluence because of the river dilution effect, with further continual decreases at sites downstream from the WSTP. The only quantifiable s-triazine in WSTP effluent, atrazine, ranged from 6.7 to 200 ng/L and was higher in Detroit River surface waters than in WSTP effluent. Only carbamazepine, cotinine, and atrazine were detectable at the low-nanogram and subnanogram levels in surface waters near a drinking water intake site. Unlike the PhACs, atrazine in the Detroit River is not attributable to point sources, and it is heavily influenced by seasonal agricultural usage and runoff. Detroit River surface water concentrations of carbamazepine, cotinine, and atrazine may present a health concern to aquatic wildlife and to humans via the consumption of drinking water.

Canada↗

PubMed1989

Triazine herbicides and ovarian epithelial neoplasms.

The possible role of a class of herbicides, triazines, in ovarian carcinogenesis has been evaluated in a population-based case-referent study. The trade names reported by the study subjects, and the type of cultivation in which they worked, were used for the assessment of exposure. Women previously exposed to triazines showed a significant relative risk of 2.7 for ovarian neoplasms. Although none of the doses could be quantified for the study subjects, two risk trends in favor of the plausibility of the association were found: the first by duration and the second by probability of exposure. The population representativity of the study and the comparability of information between the cases and referents suggest the lack of any major bias in the results. Triazine-related risk remained consistent when the analysis was restricted to farmers and when the exposure to other herbicides and to other types of cultivation were considered. Unexposed farmers had the same risk as unexposed nonfarmers.

Adult↗

PubMed1985

Acanthosis nigricans-like hyperpigmentation secondary to triazinate therapy.

Cutaneous hyperpigmentation resembling acanthosis nigricans developed in two patients with malignant brain tumors following chemotherapy with triazinate (Baker's Antifol), a folic acid antagonist. In both cases, the eruption resolved after the cessation of drug administration and reappeared after the reinstitution of triazinate therapy. A skin biopsy specimen from one patient showed microscopic changes consistent with those found in acanthosis nigricans. The other patient had a decreased serum folate level that returned to normal as the hyperpigmentation resolved. Folate may have a role in triazinate-induced acanthosislike hyperpigmentation.

Acanthosis Nigricans↗

PubMed1979

Triazine herbicide residues in central European streams.

Triazine herbicide residues were monitored in the rivers Adour, Danube, Garonne, Herault, Loire, Marne, Oise, Rhine, and Rhône from spring 1976 to fall 1977 to determine whether the continued use of the compounds resulted in accumulations of undesirable residues in the streams. Samples were generally collected monthly or bimonthly and analyzed for the parent compounds atrazine, simazine, terbumeton, terbuthylazine, and dealkylated metabolites GS 26571 (2-amino-4-etert-butylamino-6-methoxy-1,3,5-triazine) and G 30033 (2-amino-4-chloro-6-ethylamino-1,3,5-triazine). The compounds were extracted into dichloromethane and quantitated by gas chromatography (GC) with nitrogen-specific detection. Selected results were verified by GC with mass fragmentographic detection. Limit of detection was usually 0.4 mg/m3; 80 percent of all results were below 0.4 mg/m3, 14 percent were 0.4-1 mg/m3, 6 percent were 1-10 mg/m3, and 0.3 percent were higher than 10 mg/m3. Detectable residues were mainly atrazine from the downstream sampling sites. Residues usually peaked during June.

Europe↗