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      • Record: found
      • Abstract: found
      • Article: found
      Is Open Access

      2-fenilbenzotriazóis (PBTA): uma nova classe de contaminantes ambientais Translated title: 2-phenylbenzotriazoles (PBTAs): a new class of environmental contaminants

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          Translated abstract

          This work is a literature review of PBTAs, the phenylbenzotriazoles generated from the reduction and chlorination of azo dyes. The PBTAs and the non- chlorinated PBTAs were isolated for the first time from river blue rayon organic extracts that showed high mutagenic activity in the Salmonella/microsome genotoxicity assay. To date, 8 PBTAs have been identified and beside their mutagenic activity in bacteria they cause genotoxic effects in fish and mammalian cell cultures. Due to the large number of textile dyeing facilities in Brazil, studies to determine them in the aquatic environment seem to be relevant.

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          Most cited references41

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          Replication inhibition and miscoding properties of DNA templates containing a site-specific cis-thymine glycol or urea residue.

          J M McNulty, B Jerkovic, P. Bolton … (1998)
          Oligodeoxynucleotides modified site-specifically with cis-thymine glycol or urea residue, two ionizing radiation/oxidation damages, were used as templates in primer extension reactions catalyzed by 3' --> 5' exonuclease-deficient Klenow fragment, human DNA polymerase beta, AMV reverse transcriptase, and a modified T7 DNA polymerase (Sequenase). Both lesions blocked DNA replication one nucleotide before and opposite the lesion site, but a significant fraction of full-length product was obtained after prolonged incubation. Hill plot analysis of the results on both thymine glycol- and urea- containing templates by 3' --> 5' exonuclease-deficient Klenow fragment for incorporation of either dATP or dGTP gave linear plots with Hill coefficients much less than 1. This suggests that the dNTP concentration influences the termination of DNA synthesis at multiple steps of the catalytic process. The specificity of nucleotide incorporation opposite these lesions and chain extension by the same polymerase was determined by a steady-state kinetic analysis. The kinetic studies established that the rate of nucleotide incorporation and chain extension was highest with deoxyadenosine opposite both these lesions. However, the efficiency of forming a G.T pair relative to an A.T pair for the control at a level of 1/10(9) was enhanced to approximately 1/160 for thymine glycol and 1/20 for urea, although the former lesion was more bypassable than the latter lesion. On the basis of these in vitro results, we conclude that both these DNA damages are impediments of DNA synthesis and that a urea residue, in particular, has the potential to miscode.
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            Environ. Health Perspect.

            M. Maddaloni, N. J. Lolacono, W. Manton … (1989)
            Article 0 comments Cited 36 times – based on 0 reviews     Review now
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              Hydrogen Exchange Equilibria in Thiols

              Dustin Hofstetter, Basil Thalmann, Thomas Nauser … (2012)
              Cysteine, cysteinyl-glycine, glutathione, phenylalanyl-cysteinyl-glycine, and histidyl-cysteinyl-glycine were dissolved in acidic and neutral D(2)O in the presence of the radical generator 2,2'-azobis(2-methylpropionamidine) dihydrochloride and radical mediator compounds (benzyl alcohol and 2-propanol). An exchange of H-atoms by D-atoms took place in these peptides due to intramolecular H-abstraction equilibria. NMR measurements allow one to follow the extent of H-D exchanges and to identify the sites where these exchanges take place. Significant exchanges occur in acidic media in GSH at positions Glu-β and Glu-γ, in Phe-Cys-Gly at positions Phe ortho, Phe-β, Cys-α, Cys-β, and Gly-α, and in His-Cys-Gly at positions His H1, His H2, His β, Cys β, and Gly α. In neutral media, exchanges occur in Cys-Gly at position Cys β and in GSH at position Cys α. Phe-Cys-Gly and His-Cys-Gly were not examined in neutral media. Sites participating in the radical exchange equilibria are highly dependent on structure and pH; the availability of electron density in the form of lone pairs appears to increase the extent of exchange. Interestingly, and unexpectedly, 2D NMR experiments show that GSH rearranges itself in acidic solution: the signals shift, but their patterns do not change. The formation of a thiolactone from Gly and Cys residues matches the changes observed.
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                Author and article information

                Contributors
                Fábio Kummrow: Role: ND
                Gisela de Aragão Umbuzeiro: Role: ND
                Journal
                Journal ID (publisher): qn
                Title: Química Nova
                Abbreviated Title: Quím. Nova
                Publisher: Sociedade Brasileira de Química (São Paulo )
                ISSN: 1678-7064
                Publication date (Print): 2008
                Volume: 31
                Issue: 2
                Pages: 401-406
                Affiliations
                [1 ] Universidade Federal de Alfenas Brazil
                [2 ] Companhia de Tecnologia de Saneamento Ambiental Brazil
                Article
                Publisher ID: S0100-40422008000200037
                DOI: 10.1590/S0100-40422008000200037
                SO-VID: 254ff516-908a-475d-b248-57881f81e0c4
                License:

                http://creativecommons.org/licenses/by/4.0/

                History
                Product

                SciELO Brazil

                Self URI (journal page): http://www.scielo.br/scielo.php?script=sci_serial&pid=0100-4042&lng=en
                Categories
                Subject: CHEMISTRY, MULTIDISCIPLINARY

                ScienceOpen disciplines: General chemistry
                Keywords: 2-phenylbenzotriazole-type mutagens,PBTAs,genotoxic environmental contaminants
                Data availability:
                ScienceOpen disciplines: General chemistry
                Keywords: 2-phenylbenzotriazole-type mutagens, PBTAs, genotoxic environmental contaminants

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