Disease relevance of NSC56189

• Cloning and analysis of s-triazine catabolic genes from Pseudomonas sp. strain NRRLB-12227 [1].
• We used degenerate oligodeoxyribonucleotides derived from the N-terminal sequence of the s-triazine hydrolase from Rhodococcus corallinus NRRL B-15444R in an amplification reaction to isolate a DNA segment containing a 57-bp fragment from the trzA gene [2].
• The TrzN protein, which is involved in s-triazine herbicide catabolism by Arthrobacter aurescens TC1, was cloned and expressed in Escherichia coli as a His-tagged protein [3].
• In spite of clinical activity in heavily-pretreated ovarian cancer, the antitumour s-triazine trimelamol [TM; tris(hydroxymethyl)-tris(methyl)melamine] had to be withdrawn from further clinical studies due to formulation difficulties related to instability [4].
• The genetic toxicity of atrazine, a member of the s-triazine herbicides, was reviewed with the objective of classifying the chemical [5].

High impact information on NSC56189

• The basis for unprecedented noncovalent bonding between anions and the aryl centroid of electron-deficient aromatic rings has been demonstrated by an ab initio study of the interaction between 1,3,5-triazine and the fluoride, chloride, and azide ion at the MP2 level of theory [6].
• A series of 1,3,5-triazine-based estrogen receptor (ER) modulators that are modestly selective for the ERbeta subtype are reported [7].
• AtzF, allophanate hydrolase, is a recently discovered member of the amidase signature family that catalyzes the terminal reaction during metabolism of s-triazine ring compounds by bacteria [8].
• Pseudomonas sp. strain ADP is the model strain for studying bacterial degradation of the s-triazine herbicide atrazine [9].
• Arthrobacter aurescens TC1 metabolizes diverse s-triazine ring compounds [10].

Chemical compound and disease context of NSC56189

• The rates of degradation of cyanuric acid, a key intermediate in a metabolic pathway of s-triazine herbicides, were measured for Pseudomonas sp. NRRL B-12227 [11].
• LA 2851 (2-4-diamino-7-methyl-pyrazolo (1,5-a) 1,3,5-triazine), a bronchodilator and antiallergic compound, in type I hypersensitivity, has been tested orally for activity against carrageenan oedema and complement dependent, reverse passive Arthus (RPA) and zymosan oedema in rats [12].
• Hexamethylmelamine (HMM), a 1,3,5-triazine derivative has previously been recognized as an antitumor agent effective against lung, ovarian and breast cancer, but failed to show a significant cytotoxic activity in the present study [13].

Biological context of NSC56189

• The s-triazine hydrolase activity of the recombinant strains carrying the trzA plasmid were compared with that of the R. corallinus strain from which it was derived [2].
• AtzB had 25% amino acid identity with TrzA, a protein that catalyzes a hydrolytic deamination of the s-triazine substrate melamine [14].
• On a weight basis, the s-triazine, commonly named triazine amine (TAM), constitutes approx. half of several sulfonylurea herbicides and is formed after hydrolysis of these herbicides [15].
• This technique may be useful in determining the bioavailability of other s-triazine compounds in soils [16].
• The second and third clone originated from the molecular evolution of the s-triazine selective antibody IPR-7 [17].

Anatomical context of NSC56189

• Low central nervous system penetration of N2,N4,N6,-trihydroxymethyl-N2,N4,N6,-trimethylmelamine (Trimelamol): a cytotoxic s-triazine with reduced neurotoxicity [18].
• The in vitro metabolism of four s-triazine herbicides (atrazine, terbuthylazine, ametryne, and terbutryne) was studied using liver microsomes from rats, pigs, and humans [19].
• Adhesion of PMNs to vascular endothelial cells (ECs) is a critical step in recruitment and infiltration of leucocytes into tissues during inflammation, and the effects of 1,3,5-triazine derivatives on PMN adhesion to ECs from the human umbilical vein (HUVEC) were also investigated [20].
• The effect of 2-benzylamino-1,3,5-triazines on photosynthetic electron transport (PET) was measured with thylakoids isolated from atrazine-resistant, wild-type Chenopodium album, and spinach to find novel 1,3,5-triazine herbicides bearing a strong PET inhibition [21].

Associations of NSC56189 with other chemical compounds

• Plasmid pADP-1 was previously shown to encode AtzA, AtzB, and AtzC, which catalyze the sequential hydrolytic removal of s-triazine ring substituents from the herbicide atrazine to yield cyanuric acid [22].
• Hexamethylmelamine is an s-triazine that began clinical trials during the 1960s based on its level of antitumor activity in murine tumor models [23].
• This study is devoted to a detailed theoretical study of an inverse-electron demand Diels-Alder reaction (IDA) with 1,3,5-triazine as the diene and 2-aminopyrrole 1A(alpha) as the dienophile, which is a key step in a cascade reaction for the one-pot synthesis of purine analogues [24].
• Coupling of m-aminophenylboronic acid to s-triazine-activated Sephacryl: use in the affinity chromatography of glycated hemoglobins [25].
• Moisture-triggered 1,3,5-triazine-based Cu(II) molecular switch: a combined X-ray single-crystal and powder diffraction study [26].

Gene context of NSC56189

• Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX [27].
• Therefore, P450 1A2 alone is likely to be responsible for the hepatic oxidative phase-I metabolism of the s-triazine derivatives in exposed humans [28].
• The compounds having imidazolyl and tertiary amino groups as substituents in the 1,3,5-triazine ring showed significant aromatase-inhibitory activity [29].
• The replacement of the bound [(14)C]atrazine by 1,3,5-triazines was tested to determine whether the novel 1,3,5-triazine analogues exhibit the same binding pattern at the D1-protein as atrazine [30].
• Effects of s-triazine herbicides on hormone-receptor complex formation, 5 alpha-reductase and 3 alpha-hydroxysteroid dehydrogenase activity at the anterior pituitary level [31].

Analytical, diagnostic and therapeutic context of NSC56189

• 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 [1].
• A concept based on the Peroxidase-chip (P-chip), antibody co-immobilization, competitive and enzyme-channeling principle was exploited to develop an integrated flow-through amperometric biosensor for detection of environmental pollutants such as s-triazine herbicides [32].
• Synthesis and evaluation of a new biselector s-triazine based chiral stationary phase for enantioselective HPLC: potentiality of the approach and perspectives [33].

References