Disease relevance of Clarosan

• Several mutants of the purple bacterium Rhodopseudomonas viridis resistant to terbutryn [2-(methylthio)-4-(ethylamino)-6-(tert-butylamino)-s-triazine] have been isolated by their ability to grow photosynthetically in the presence of the herbicide [1].
• Inhibition of Staphylococcus aureus by free iodine dosages of 0.25, 0.5, 0.75, and 1.0 mg/liter was unaffected by the presence of 2.0 mg of terbutryne per liter [2].
• However, the effects on L. variegatus were an indirect effect of terbutryn as a consequence of decrease in the aufwuchs food source and occurred at three-orders-of-magnitude-lower concentrations of terbutryn than the acute toxicity effects [3].
• The uptake of the triazine herbicides, atrazine and terbutryn, was determined for two freshwater photosynthetic microorganisms, the green microalga Chlorella vulgaris and the cyanobacterium Synechococcus elongatus [4].

High impact information on Clarosan

• It has been established by X-ray crystallography that the triazine herbicide terbutryn binds to the QB site [5].
• The results obtained by the combination of these different techniques are discussed with respect to the three-dimensional structure of the wild type and the mode of binding of ubiquinone, terbutryn, and o-phenanthroline as determined by X-ray structure analysis [1].
• Finally, purified recombinant FMO3, the major FMO in human liver, exhibited no significant activity (< 0.1 nmol (nmol of FMO3)-1 min-1) in the formation of the parent sulfoxides of ametryne and terbutryne [6].
• Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes [6].
• Electron transport in reaction centers prepared from one of the mutants (M6) was neither inhibited by PPCTH and other NH-thiazoles nor terbutryn [7].

Biological context of Clarosan

• From a spontaneous mutant of R. viridis that is resistant to the herbicide terbutryn, the puf operon was cloned in pKVS1 and transferred by conjugation into R. viridis wild-type cells [8].
• A new mutation in the pufL gene responsible for the terbutryn resistance phenotype in Rubrivivax gelatinosus [9].
• The modifications of the binding site appear to diminish the affinity of the B-site for ubiquinone as well as terbutryn [10].
• This gives rise to biphasic decay kinetics from which koff for terbutryn was estimated to be 3 sec-1 [10].
• The metabolic properties of the cell line expressing both CYPOR and CYP1A2 were characterized regarding dealkylation and deethylation of 7-alkoxyresorufins and sulfoxidation of the triazine derivatives ametryne and terbutryne, in comparison with the cell line expressing only CYP1A2 [11].

Anatomical context of Clarosan

• Sixteen metabolites of terbutryn were isolated from the urine and feces of either rats or a goat given single oral doses of terbutryn-[14C](2-(t-butylamino)-4-(ethylamino)-6-(methylthio)-s-triazine) [12].
• K1F4 is a hybridoma secreting monoclonal (IgG) antibody reactive to terbutryn and prometryn, two members of the triazine family [13].
• 5. The amplitudes of chemically evoked contractions in "skinned muscle cells" of Helix PRM or Lumbricus segments were influenced neither by CIPC nor by terbutryn [14].

Associations of Clarosan with other chemical compounds

• In this study the identity of specific phase-I enzymes involved in the metabolism of s-triazine derivatives (atrazine, terbuthylazine, ametryne, and terbutryne) by human liver microsomes was determined [6].
• Four triazine herbicides: amitrole, metribuzin, prometryn and terbutryn, and the bipyridal compound diquat dibromide have been evaluated for genotoxicity in the wing somatic mutation and recombination test of Drosophila melanogaster, following standard procedures [15].
• The model compound terbutryn, an s-triazine and an inhibitor of photosynthesis, was applied once in each stream at nominal concentrations of 0.6, 6, 60, or 600 microg/L [3].
• In this study, the DNA-damaging ability of the herbicide was evaluated in the alkaline single-cell microgel-electrophoresis ("comet") assay by testing terbutryn in the presence of S9mix (rat liver homogenate containing microsomal enzymes plus cofactors) prepared with liver homogenate from both uninduced (basal) and aroclor 1254-induced rats [16].
• The effects of two herbicides used wide-spread, isoproturon (phenylurea) and terbutryn (triazine), on growth, dry weight, elemental composition, photosynthetic pigments and protein content, and cell volume assayed by flow cytometry in the freshwater microalgae Chlorella vulgaris were studied [17].

Gene context of Clarosan

• The CYP1A2-dependent metabolism of the triazine derivatives ametryne and terbutryne was moderately enhanced by increased CYPOR activity [11].
• Except MAV 3 all Rps. viridis mutants are different from those selected by their resistance towards the closely related triazine terbutryn [18].

Analytical, diagnostic and therapeutic context of Clarosan

• Two methods for estimating terbutryne residues in water using high-pressure liquid chromatography and gas-liquid chromatography with a conductivity detector [19].
• Metabolites of terbutryn in G. fossarum and A. aquaticus were analyzed by HPLC [20].
• As far as we are aware this is the most sensitive ELISA for terbutryn yet reported [21].
• 2-Aminobutylamino-4-ethylamino-6-isopropylamino-1,3,5-triazine (ABA-atrazine) has been synthesized and used as a coating hapten in an immunoassay with a monoclonal antibody against terbutryn [21].
• We determined that terbutryn was toxic to L. variegatus at 23.7 mg/L (96-h median lethal concentration [LC50]) and 16.5 mg/L (96-h median effective concentration [EC50]) in static acute toxicity tests [3].

References