Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Triazines”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,405 records · Page 78Linked to original sources
PubMed2006

Estimating constants for metabolism of atrazine in freshly isolated rat hepatocytes by kinetic modeling.

This study estimated the kinetic constants for oxidative metabolism of atrazine (ATRA) and its chlorotriazine (Cl-TRI) metabolites, 2-chloro-4-ethylamino-6-amino-1,3,5-triazine (ETHYL), 2-chloro-4-amino-6-isopropylamino-1,3,5-triazine (ISO), and diaminochlorotriazine (DACT), using freshly isolated rat hepatocytes. Hepatocytes were incubated with 1.74, 44, 98, and 266 microM ATRA. Disappearance of ATRA and formation of the Cl-TRI metabolites were quantified over 90 min. At all incubation concentrations, ATRA was preferentially metabolized to ETHYL, producing ETHYL concentrations approximately 6 times higher than those of ISO. DACT concentrations peaked at 44 microM ATRA and decreased with increasing incubation concentrations, indicating non-linear metabolic behavior of ATRA with respect to DACT formation. A series of kinetic models were developed from these data to describe the dose and time-dependent oxidative metabolism of ATRA and the Cl-TRI metabolites. An integrated model for all the chloro-triazines included multi-substrate competitive inhibition of metabolism to describe the non-linear behavior of DACT production in relation to ATRA while simultaneously simulating the time-course behavior of the Cl-TRIs at all four ATRA concentrations. The maximal metabolic rate (V(max)) of ATRA metabolism and the Michaelis-Menten constant (K(M)) for the reaction were 1.6 microM/min and 30 microM, respectively. V(max) and K(M) values for ETHYL and ISO metabolism to DACT were also estimated using this modeling approach.

Animals↗
PubMed1999

Polarographic properties and potential carcinogenicity of some natural nucleosides and their synthetic analogues.

The polarographic reduction and the index of potential carcinogenicity tg alpha determined polarographically in aprotic conditions and in the presence of alpha-lipoic acid of nine naturally occurring and synthetic pyrimidine and six synthetic 1,3,5-triazine (5-aza) nucleosides was compared to the reduction of eight synthetic 1,3,6-triazine (6-aza) nucleosides. Nucleosides are of interest because of their key role in the nucleic acid structure and because of the antimetabolite and cytotoxic/antileukemia properties of their synthetic analogues. It was shown that polarographic reduction of the studied compounds is achieved at gradually increased potentials in the order of 6-aza < 5-aza < pyrimidine nucleosides. On other hand, the potential carcinogenicity of studied compounds increases usually in the order of pyrimidine < 6-aza << 5-aza nucleoside. The only compounds with remarkable potential carcinogenicity identified at this study were those ones from the 5-aza (1,3,5-triazine) antimetabolite series-arabinosyl-5-azacytosine (0.275), 5-aza-cytidine (0.295) and 5-aza-uracil (0.400)-and 2,2'-anhydrouridine (0.260). The relation of the data obtained to biological activity of nucleosides included in the study is discussed.

Carcinogens↗
PubMed1999

Chemiluminescent multiassay of pesticides with horseradish peroxidase as a label.

Competitive chemiluminescent immunoassay based on a combination of five antibodies was used in a combination with neural network to identify and estimate amounts of three cross-reacting s-triazines (atrazine, terbythylazine and ametryn). Antibodies with different cross-reactivity towards s-triazines were immobilized in separate wells an eight-well microtiter strip. Training of neural networks was carried out with four different learning procedures. The best topology for the data measured was a net with two hidden layers with ten neurons in the first and 15 in the second layer trained with the Schmidhuber method. s-Triazine classification of environmental samples containing various analyte mixtures was correct in 70-100% of all cases depending on the type of analyte. The test developed can be proposed as an alternative field test for multianalyte environmental monitoring.

Atrazine↗
PubMed2005

Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound.

The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NDeltaHf), experimentally determined using an additive method, is shown to be the highest positive NDeltaHf compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds, for example, 2,4,6-triazido-1,3,5-triazine; 4,4',6,6'-tetra(azido)hydrazo-1,3,5-triazine; 4,4',6,6'-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3,4,6,7,9,9b-heptaazaphenalene (heptazine).

Azides↗
PubMed1985

Quantitative structure-activity relationship of antifolate inhibition of bacteria cell cultures resistant and sensitive to methotrexate.

Sets of 5-(substituted benzyl)-2,4-diaminopyrimidines and 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(3-substituted phenyl)-s-triazines as well as several other antifolates were tested as inhibitors of Escherichia coli dihydrofolate reductase and E. coli cell cultures both sensitive and resistant to methotrexate. From the results quantitative structure-activity relationships (QSAR) were formulated. The triazines were found to inhibit sensitive and resistant cell cultures to the same degree, but the benzylpyrimidines showed marked differences against the two types of cells. Increased hydrophobicity produced benzylpyrimidines more active against the resistant E. coli cell. Metroprine did not discriminate between the two types of cells cultures, but pyrimethamine and 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidin e (BW 301U) did. The results are compared with triazines and benzylpyrimidines acting on Lactobacillus casei and murine tumor cells sensitive and resistant to methotrexate. QSAR is shown to be an effective means for detecting receptor differences.

Biological Transport, Active↗
PubMed1999

In vitro metabolism of simazine, atrazine and propazine by hepatic cytochrome P450 enzymes of rat, mouse and guinea pig, and oestrogenic activity of chlorotriazines and their main metabolites.

1. The in vitro metabolism of chlorotriazines, simazine (SIZ), atrazine (ATZ) and propazine (PRZ) in liver microsomes from rat, mouse and guinea pig and the oestrogenic activity of chlorotriazines and their main metabolites have been studied. 2. The formation rates of products in chlorotriazine metabolism were determined by HPLC. The principal reactions catalysed by the cytochrome P450 (P450) system were N-monodealkylation and isopropylhydroxylation in all liver microsomes. As a result, 2-chloro-4-ethylamino-6-amino-1,3,5-triazine (M1) (SIZ-M1 for SIZ and ATZ-M1 for ATZ) and 2-chloro-4-amino-6-isopropylamino-1,3,5-triazine (M2) (ATZ-M2 for ATZ and PRZ-M2 for PRZ), and 2-chloro-4-ethylamino-6-(1-hydroxyisopropylamino)-1,3,5-triazine (M3) (ATZ-M3 for ATZ) and 2-chloro-4-isopropylamino-6-(1-hydroxyisopropylamino)-1,3,5-triazi ne (M4) (PRZ-M4 for PRZ) were detected as the metabolites. N-bidealkylation was not found in this system. 3. The formation rates of N-deethylated metabolites (SIZ-M1 and ATZ-M2) were generally higher in mouse than in rat and guinea pig. The formation rates of N-deisopropylated metabolites (ATZ-M1 and PRZ-M2) in guinea pig were the lowest among the three animal species. The formation rates of isopropylhydroxylated metabolites (ATZ-M3 and PRZ-M4) were remarkably low in mouse compared with rat and guinea pig. 4. The enzyme kinetics of chlorotriazine metabolism were examined by Eadie-Hofstee analyses. Some species differences in Michaelis-Menten parameters for each metabolite were observed, and the ranking orders were varied among the metabolites. 5. The binding affinity of chlorotriazines (SIZ, ATZ and PRZ) and their metabolites (M1-4) for recombinant human oestrogen receptor-alpha was assayed using the fluorescence polarization method. The binding affinity of M2 was significantly higher than those of parent compounds and other metabolites, although the oestrogenic activity was remarkably low compared with that of 17beta-oestradiol (E2). 6. These results suggest that the pattern of metabolism of SIZ, ATZ and PRZ by the P450 system differs extensively among rat, mouse and guinea pig, and that M2 may be an activated metabolite of chlorotriazines.

Animals↗
PubMed1987

A randomized clinical trial of combination chemotherapy in advanced colorectal cancer.

One hundred and sixty-five patients with advanced colorectal cancer were entered into a prospectively randomized trial of combination chemotherapy comparing three 5-fluorouracil plus methyl CCNU (FM)-based regimens: FM plus ICRF-159 (FMI), FM plus triazinate (FMT), and FM plus vincristine (FMV). Patients were stratified according to performance status, anatomic site of primary indicator lesion, and prior chemotherapy. Those with abnormal kidney or liver function were randomized between FMI and FMV because triazinate depends on both hepatic and renal mechanisms for elimination. There were no significant differences between the treatment regimens in objective response rate (11%-17%), interval to progression (median, 10-14 weeks), or survival (median, 5-6 months). The primary side effect observed was hematologic toxicity, which tended to increase in severity with repeated courses of therapy. Although ICRF-159 and triazinate have been shown to have limited single-agent phase II activity against colorectal cancer in previous trials, neither agent combined with 5-fluorouracil plus methyl CCNU has an improved treatment effect compared with FMV. We do not recommend the further use of these regimens in the treatment of advanced colorectal cancer.

Adult↗
PubMed2005

Consequence of herbivory for the fitness cost of herbicide resistance: photosynthetic variation in the context of plant-herbivore interactions.

The cost of adaptations may depend on environmental conditions. We consider how the fitness cost of resistance to the herbicide triazine in Amaranthus hybridus interacts with folivory from the beetle Disonycha glabrata. Triazine-resistant (TR) genotypes suffer a fitness cost because of a pleiotropic reduction in the light reaction of photosynthesis, which in turn often leads to a reduction in photosynthetic rate. We found that the fitness cost of triazine resistance was 360% greater in the presence than absence of D. glabrata. This resulted from multiple phenotypic trade-offs, with TR plants suffering greater herbivory and displaying a diminished tolerance of damage. Our work highlights the importance of incorporating appropriate ecological variation into the assessment of fitness trade-offs. The results of this study also illustrate the potential for herbivores to impose selection on photosynthetic variation, and for variation in resource acquisition to obscure fitness costs.

Adaptation, Physiological↗
PubMed1996

Synthesis of isomelamines and isocyanurates and their biological evaluation.

The reaction of cyanogen bromide (1) with primary amines (2a-p), including arylmethylamines (2l-p), gave the corresponding cyanamides (3a-p). Trimerization of 3a-p gave 1,3,5-trisubstituted 2,4,6-triiminohexahydro-1,3,5-triazines (isomelamines) (4a-p), which were treated with hydrochloric acid to give the corresponding 1,3,5-trisubstituted 2,4,6-trioxohexahydro-1,3,5-triazines (isocyanurates) (5a-c, f) and 1,3,5-trisubstituted 2-imino-4,6-dioxohexahydro-1,3,5-triazines (5b'-e'). Biological evaluation of 4a-p, 5a-c,f, and 5b'-e' was carried out, and some of these compounds showed bronchodilator and positive inotropic activities.

Animals↗
PubMed1995

Nucleotide sequence of the variable region of the heavy and light chains of a monoclonal IgG antibody reactive to herbicides, terbutryn and prometryn.

Members of the triazine family of herbicides are reliable indicators of contamination of the ground water or soil with pesticide residues. To facilitate better detection of the chemical residues using improved immunoassay procedures, several monoclonal antibodies against triazine herbicides have been developed. K1F4 is a hybridoma secreting monoclonal (IgG) antibody reactive to terbutryn and prometryn, two members of the triazine family. We have cloned the genes encoding the variable regions of the heavy and light chains of this monoclonal antibody and report the nucleotide sequence here.

Amino Acid Sequence↗
PubMed2001

Synthesis of some new biologically active bis-(thiadiazolotriazines) and bis-(thiadiazolotriazinyl) alkanes.

4-Amino-3-mercapto-1,2,4-triazin-5(4H)-ones (1) were condensed with dicarboxylic acids 2 to yield bis-(4-oxo-4H-1,3,4-thiadiazolo[2,3-c]-1,2,4-triazin-7-yl)alkanes (3b-d,f-h,j-l,n-p) and bis-thiadiazolotriazines (3a,e,i,m). All the newly synthesised compounds were characterised by analytical, IR, NMR and mass spectral studies. Some of the newly synthesised compounds were screened for their antibacterial and antifungal properties. Among the tested compounds, compound 7,7'-(1,4-butanediyl)-his-(3-t-butyl-4-oxo-4H-1,3,4-thia-diazolo[2,3-c]-1,2,4-triazine (3p) exhibited highest degree of antifungal activity.

Alkanes↗
PubMed2004

Identification of the bound residue composition derived from 14C-labeled chlorsulfuron in soil by using LC-MS and isotope tracing method.

A new method for extracting the bound residue(BR) derived from 14C-labeled chlorsulfuron in soils was developed, and the technique of combining LC-MS with isotope tracing method was subsequently applied to identify the composition of the 14C-BR in a loamy Fluvent derived from marine deposit. The results showed that the 14C-[2-amino-4-methoxyl-6-methyl-1,3,5]-triazine, 14C-[2-amino-4-hydroxyl-6-methyl-1,3,5]-triazine and 14C-chlorsulfuron parent compound constituted the main composition of the 14C-BR derived from 14C-labeled chlorsulfuron in the soil. The radioactive ratio of three compounds accounted for 39.8%, 35.4% and 17.9% of total recovered radioactivity, respectively. However, a small amount(3.6% of total recovered radioactivity) of the complex of 14C-[2-amino-4-hydroxyl-6-methyl-1,3,5]-triazine might have existed in the 14C-BR in association with an unknown soil substrate. 2-chlorobenzenesulfonamide was also detected to be one of the components of the BR. The results could well explain the mechanism of phytotoxicity caused by the BR derived from chlorsulfuron in soil. In addition, the mechanism of BR formation in soil was also discussed in details.

Carbon Radioisotopes↗
PubMedDate not supplied

Isolation and characterization of a novel quaternary ammonium-linked glucuronide of lamotrigine.

Lamotrigine (LTG) is a novel triazine anticonvulsant currently undergoing clinical trials. LTG N-glucuronide, the major human metabolite of LTG, was isolated from human urine by means of XAD-2 column chromatography and semi-preparative HPLC. The structure of the suspected lamotrigine 2-N-glucuronide was proven by mass spectroscopy and NMR spectroscopy, along with chemical and enzymatic hydrolysis studies. High resolution fast atom bombardment mass spectrometry and Electrospray tandem mass spectrometry of the glucuronide gave an M+ ion at 432.0 amu and a fragment ion at 256.0 (M - 176)+ amu. The proton NMR of the glucuronide indicated the presence of a glucuronic acid moiety. A downfield anomeric proton (5.35-5.60 ppm) implied direct attachment to the aromatic triazine ring. Carbon-13 NMR of the glucuronide revealed an upfield shift (delta = -7.0 ppm) of the C-3 carbon of the triazine ring compared to LTG, indicating attachment of the glucuronide to the N-2 position. Chemical degradation or rearrangement of the glucuronide occurs at neutral pH to produce an unknown product (RP-1), while at basic pH a different unknown product (RP-2) is formed. The glucuronide is unusually stable at acidic pH. Treatment of the glucuronide with beta-glucuronidase resulted in hydrolysis to LTG, and enzymatic hydrolysis was inhibited by saccharo-1,4-lactone.

Ammonia↗
PubMed1987

[Study of alkaline hydrolysis of reumycin using NMR spectroscopy].

The transformation sequence of reumycin in aqueous (D2O) solutions with various pD was studied by NMR spectroscopy and the structures of the yielding products were determined. It was shown that formation of 6-(3-methylureido)-1,2,4-triazine-5-carboxylic acid was the first stage of reumycin alkaline hydrolysis. The subsequent cyclization of this compound resulted in obtaining 5-methyl-5H-imidazo [4,5-e]-1,2,4-triazin-6 (7H) one-4a-carboxylic acid in mono-,di- or trianionic form which depended on the medium pH and was due to dissociation of the carboxylic group, N(4)H group of the triazine ring and N(7)H group of the imidazolidinone ring.

Antibiotics, Antineoplastic↗
PubMedDate not supplied

Design, synthesis and evaluation of biomimetic affinity ligands for elastases.

A low-molecular-weight biomimetic affinity ligand selective for binding elastase has been designed and synthesized. The ligand was based on mimicking part of the interaction between a natural inhibitor, turkey ovomucoid inhibitor and elastase, and modelled from the X-ray crystallographic structure of the enzyme-inhibitor complex. Limited solid-phase combinatorial chemistry was used to synthesize 12 variants of the lead ligand using the triazine moiety as the scaffold for assembly. The ligand library was screened for its ability to bind elastase and trypsin, and two ligands were studied further. Ligand C4/6 [2-alanyl-alanyl-4-tryptamino-6-(alpha-lysyl)-s-triazine] was found to bind porcine pancreatic elastase, but not trypsin, with a dissociation constant of 6 x 10(-5) M and a binding capacity of 21 mg elastase per ml gel. The adsorbent was used to purify elastase from a crude extract of porcine pancreas. Immobilized ligand C4/5 6 [2-alanyl-alanyl-4-tyramino-6-(alpha-lysyl)-s-triazine] was similarly chosen for optimal binding of elastase from cod and used to purify the enzyme from a crude extract of cod pyloric caeca. Ligand C4/6 was subsequently synthesized in solution and its structure verified by 1H-NMR.

Animals↗
PubMed2002

Activity of mesotrione on resistant weeds in maize.

Mesotrione is a new callistemone herbicide that inhibits the HPPD enzyme (p-hydroxyphenylpyruvate dioxygenase) and introduces a new naturally selective tool into weed-management programmes for use in maize. Mesotrione provides control of the major broad-leaved weeds, and it can be used in integrated weed-management programmes depending on the grower's preferred weed-control strategy. At post-emergence rates of 150 g AI ha-1 or less, mesotrione provides naturally selective control of key species that may show triazine resistance (TR), e.g. Chenopodium album L, Amaranthus species, Solanum nigrum L, as well as species of weed that show resistance to acetolactase synthase (ALS) inhibitors e.g. Xanthium strumarium L, Amaranthus spp and Sonchus spp. The data presented show that resistant and susceptible biotypes of these species with resistance to triazine herbicides, such as atrazine, simazine, terbutylazine and metribuzin, or ALS-inhibitor herbicides, such as imazethepyr, remain susceptible to mesotrione. These results confirm that there is no cross-resistance in biotypes with target site resistance to triazine or ALS-inhibiting herbicides. It is important that herbicide choice and rotation becomes an integral part of planning weed management, so as to minimise the risks of crop losses from weed competition, build-up of weed seed in the soil and the further development of weed resistance across a range of herbicide modes of action.

Agriculture↗
PubMed2003

Aqueous-phase disappearance of atrazine, metolachlor, and chlorpyrifos in laboratory aquaria and outdoor macrocosms.

Dissipation processes are described for a combination of commonly used pesticides-atrazine (6-chloro-4-ethylamino-6-isopropylamino- s-triazine), metolachlor (2-chloro- N-[2-ethyl-6-methyl-phenyl]- N-[2-methoxy-1-methylethyl] acetamide), and chlorpyrifos ( O-O diethyl O-[3,5,6-trichloro-2-pyridinyl] phosphorothioate)-in a laboratory and outdoor pond systems. Dosing rates and timing were designed to duplicate those common in the mid-Atlantic Coastal Plain, USA. Treatments ranged from 2 and 2.5 mg/L to 0.2 and 0.25 mg/L respectively for atrazine and metolachlor, and chlorpyrifos was added at 1.0 and 0.1 mg/L in the aquaria and at 0.1 mg/L in the outdoor macrocosms. Chlorpyrifos disappearance was rapid in all of the systems and followed a two-phase sequence. Initial half-lives varied from 0.16 day to 0.38 day and showed similar rates in the aquaria and the outdoor systems. The second phase of the chlorpyrifis loss pattern was slower (18-20 days) in all the treatments except for the low herbicide treatment in the outdoor test, where it was 3.4 days. Compared to the outdoor system, herbicide losses were much slower in the aquaria, e.g., 150 days for atrazine and 55 days for metolachlor, and no appreciable loss of herbicide was apparent in the high-treated aquaria. In the outdoor systems, the half-lives for the low herbicide treatment were 27 days and 12 days, respectively, for atrazine and metolachlor, and 48 and 20 days, respectively for the high herbicide-treated pond. Very low levels of CIAT (6-amino-2-chloro-4-iso-propylamino- s-triazine) and CEAT (2-chloro-4-ethylamino-6-ethylamino- s-triazine), degradation products of atrazine, were observed in the outdoor studies.

Acetamides↗
PubMed1997

Comparative sensitivity of Selenastrum capricornutum and Lemna minor to sixteen herbicides.

Aquatic plant toxicity tests are frequently conducted in environmental risk assessments to determine the potential impacts of contaminants on primary producers. An examination of published plant toxicity data demonstrates that wide differences in sensitivity can occur across phylogenetic groups of plants. Yet relatively few studies have been conducted with the specific intent to compare the relative sensitivity of various aquatic plant species to contaminants. We compared the relative sensitivity of the algae Selenastrum capricornutum and the floating vascular plant Lemna minor to 16 herbicides (atrazine, metribuzin, simazine, cyanazine, alachlor, metolachlor, chlorsulfuron, metsulfuron, triallate, EPTC, trifluralin, diquat, paraquat, dicamba, bromoxynil, and 2,4-D). The herbicides studied represented nine chemical classes and several modes of action and were chosen to represent major current uses in the United States. Both plant species were generally sensitive to the triazines (atrazine, metribuzin, simazine, and cyanazine), sulfonureas (metsulfuron and chlorsulfuron), pyridines (diquat and paraquat), dinitroaniline (trifluralin), and acetanilide (alachlor and metolachlor) herbicides. Neither plant species was uniformly more sensitive than the other across the broad range of herbicides tested. Lemna was more sensitive to the sulfonureas (metsulfuron and chlorsulfuron) and the pyridines (diquat and paraquat) than Selenastrum. However Selenastrum was more sensitive than Lemna to one of two thiocarbamates (triallate) and one of the triazines (cyanazine). Neither species was sensitive to selective broadleaf herbicides including bromoxynil, EPTC, dicamba, or 2,4-D. Results were not always predictable in spite of obvious differences in herbicide modes of action and plant phylogeny. Major departures in sensitivity ofSelenastrum occurred between chemicals within individual classes of the triazine, acetanilide, and thiocarbamate herbicides. Results indicate that neither species is predictively most sensitive, and that a number of species including a dicot species such as Myriophyllum are needed to perform accurate risk assessments of herbicides.

Chlorophyta↗