Literature DB >> 9143119

In vivo levels of chlorinated hydroquinones in a pentachlorophenol-degrading bacterium.

D L McCarthy1, A A Claude, S D Copley.   

Abstract

Sphingomonas chlorophenolica RA-2 is a soil microorganism that can grow on pentachlorophenol (PCP) as a sole carbon source. In this microorganism, PCP is converted to tetrachlorohydroquinone (TCHQ), trichlorohydroquinone, and 2,6-dichlorohydroquinone. The remainder of the pathway has not yet been defined. The ability to grow on PCP as a sole carbon source is remarkable because of the toxicity of PCP and its chlorinated hydroquinone metabolites. Experiments in which the levels of PCP and chlorinated hydroquinones were measured in cells metabolizing [U-14C]PCP revealed that the levels of chlorinated hydroquinones in the cytoplasm are in the low micromolar range. The toxicity of chlorinated hydroquinones was evaluated by exposure of Escherichia coli cells that had been treated with EDTA (to remove the outer membrane) to TCHQ. Significant toxicity due to TCHQ was not apparent until concentrations of 500 microM and higher. Thus, an important part of the explanation for why S. chlorophenolica RA-2 is able to grow on PCP as a sole carbon source is undoubtedly that it can process sufficient carbon for growth without accumulating high levels of toxic intermediates.

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Year:  1997        PMID: 9143119      PMCID: PMC168479          DOI: 10.1128/aem.63.5.1883-1888.1997

Source DB:  PubMed          Journal:  Appl Environ Microbiol        ISSN: 0099-2240            Impact factor:   4.792


  30 in total

1.  Purification and properties of pentachlorophenol hydroxylase, a flavoprotein from Flavobacterium sp. strain ATCC 39723.

Authors:  L Xun; C S Orser
Journal:  J Bacteriol       Date:  1991-07       Impact factor: 3.490

2.  The induction of DNA strand breaks and formation of semiquinone radicals by metabolites of 2,4,5-trichlorophenol.

Authors:  U Juhl; J K Blum; W Butte; I Witte
Journal:  Free Radic Res Commun       Date:  1991

3.  Effects of ring substituents on the activity of phenols as inhibitors and uncouplers of mitochondrial respiration.

Authors:  M Stockdale; M J Selwyn
Journal:  Eur J Biochem       Date:  1971-08-25

4.  Azotobacter vinelandii flavodoxin: purification and properties of the recombinant, dephospho form expressed in Escherichia coli.

Authors:  M F Taylor; M H Boylan; D E Edmondson
Journal:  Biochemistry       Date:  1990-07-24       Impact factor: 3.162

5.  PCP degradation is mediated by closely related strains of the genus Sphingomonas.

Authors:  M M Ederer; R L Crawford; R P Herwig; C S Orser
Journal:  Mol Ecol       Date:  1997-01       Impact factor: 6.185

6.  Exploration of the relationship between tetrachlorohydroquinone dehalogenase and the glutathione S-transferase superfamily.

Authors:  D L McCarthy; S Navarrete; W S Willett; P C Babbitt; S D Copley
Journal:  Biochemistry       Date:  1996-11-19       Impact factor: 3.162

7.  Benzene and its phenolic metabolites produce oxidative DNA damage in HL60 cells in vitro and in the bone marrow in vivo.

Authors:  P Kolachana; V V Subrahmanyam; K B Meyer; L Zhang; M T Smith
Journal:  Cancer Res       Date:  1993-03-01       Impact factor: 12.701

8.  Characterization of a Flavobacterium glutathione S-transferase gene involved reductive dechlorination.

Authors:  C S Orser; J Dutton; C Lange; P Jablonski; L Xun; M Hargis
Journal:  J Bacteriol       Date:  1993-05       Impact factor: 3.490

9.  Low-molecular-weight thiols in streptomycetes and their potential role as antioxidants.

Authors:  G L Newton; R C Fahey; G Cohen; Y Aharonowitz
Journal:  J Bacteriol       Date:  1993-05       Impact factor: 3.490

10.  The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA.

Authors:  B van Ommen; A Adang; F Müller; P J van Bladeren
Journal:  Chem Biol Interact       Date:  1986-10-15       Impact factor: 5.192

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  16 in total

1.  Evidence for natural horizontal transfer of the pcpB gene in the evolution of polychlorophenol-degrading sphingomonads.

Authors:  Marja A Tiirola; Hong Wang; Lars Paulin; Markku S Kulomaa
Journal:  Appl Environ Microbiol       Date:  2002-09       Impact factor: 4.792

2.  A previously unrecognized step in pentachlorophenol degradation in Sphingobium chlorophenolicum is catalyzed by tetrachlorobenzoquinone reductase (PcpD).

Authors:  MingHua Dai; Julie Bull Rogers; Joseph R Warner; Shelley D Copley
Journal:  J Bacteriol       Date:  2003-01       Impact factor: 3.490

3.  Degradation of a nonylphenol single isomer by Sphingomonas sp. strain TTNP3 leads to a hydroxylation-induced migration product.

Authors:  P F X Corvini; R J W Meesters; A Schäffer; H F Schröder; R Vinken; J Hollender
Journal:  Appl Environ Microbiol       Date:  2004-11       Impact factor: 4.792

4.  Pentachlorophenol hydroxylase, a poorly functioning enzyme required for degradation of pentachlorophenol by Sphingobium chlorophenolicum.

Authors:  Klara Hlouchova; Johannes Rudolph; Jaana M H Pietari; Linda S Behlen; Shelley D Copley
Journal:  Biochemistry       Date:  2012-04-27       Impact factor: 3.162

Review 5.  Evolution of efficient pathways for degradation of anthropogenic chemicals.

Authors:  Shelley D Copley
Journal:  Nat Chem Biol       Date:  2009-08       Impact factor: 15.040

6.  Sequestration of a highly reactive intermediate in an evolving pathway for degradation of pentachlorophenol.

Authors:  Itamar Yadid; Johannes Rudolph; Klara Hlouchova; Shelley D Copley
Journal:  Proc Natl Acad Sci U S A       Date:  2013-05-15       Impact factor: 11.205

7.  Identification and characterization of genes encoding a putative ABC-type transporter essential for utilization of gamma-hexachlorocyclohexane in Sphingobium japonicum UT26.

Authors:  Ryo Endo; Yoshiyuki Ohtsubo; Masataka Tsuda; Yuji Nagata
Journal:  J Bacteriol       Date:  2007-03-16       Impact factor: 3.490

8.  Genome shuffling improves degradation of the anthropogenic pesticide pentachlorophenol by Sphingobium chlorophenolicum ATCC 39723.

Authors:  MingHua Dai; Shelley D Copley
Journal:  Appl Environ Microbiol       Date:  2004-04       Impact factor: 4.792

9.  Cloning, overexpression, purification, and characterization of the maleylacetate reductase from Sphingobium chlorophenolicum strain ATCC 53874.

Authors:  Lifeng Chen; Katharine Maloney; Ed Krol; Bin Zhu; Jian Yang
Journal:  Curr Microbiol       Date:  2009-02-26       Impact factor: 2.188

10.  Sphingobium chlorophenolicum dichlorohydroquinone dioxygenase (PcpA) is alkaline resistant and thermally stable.

Authors:  Wanpeng Sun; Ramaswami Sammynaiken; Lifeng Chen; Jason Maley; Gabriele Schatte; Yijiang Zhou; Jian Yang
Journal:  Int J Biol Sci       Date:  2011-10-25       Impact factor: 6.580

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