Literature DB >> 22922990

Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci.

Alicja B Veselá1, Helena Pelantová, Miroslav Sulc, Martina Macková, Petra Lovecká, Markéta Thimová, Fabrizia Pasquarelli, Martina Pičmanová, Miroslav Pátek, Tek Chand Bhalla, Ludmila Martínková.   

Abstract

The aim of this work was to determine the ability of rhodococci to transform 3,5-dichloro-4-hydroxybenzonitrile (chloroxynil), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and 2,6-dichlorobenzonitrile (dichlobenil); to identify the products and determine their acute toxicities. Rhodococcus erythropolis A4 and Rhodococcus rhodochrous PA-34 converted benzonitrile herbicides into amides, but only the former strain was able to hydrolyze 2,6-dichlorobenzamide into 2,6-dichlorobenzoic acid, and produced also more of the carboxylic acids from the other herbicides compared to strain PA-34. Transformation of nitriles into amides decreased acute toxicities for chloroxynil and dichlobenil, but increased them for bromoxynil and ioxynil. The amides inhibited root growth in Lactuca sativa less than the nitriles but more than the acids. The conversion of the nitrile group may be the first step in the mineralization of benzonitrile herbicides but cannot be itself considered to be a detoxification.

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Year:  2012        PMID: 22922990     DOI: 10.1007/s10295-012-1184-z

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN: 1367-5435            Impact factor:   3.346


  26 in total

1.  Metabolism of acetonitrile and propionitrile by Nocardia rhodochrous LL100-21.

Authors:  M J DiGeronimo; A D Antoine
Journal:  Appl Environ Microbiol       Date:  1976-06       Impact factor: 4.792

2.  Bioconversion of butyronitrile to butyramide using whole cells of Rhodococcus rhodochrous PA-34.

Authors:  J Raj; A Seth; S Prasad; T C Bhalla
Journal:  Appl Microbiol Biotechnol       Date:  2007-01-11       Impact factor: 4.813

3.  The in vitro degradation of the herbicide bromoxynil.

Authors:  A E Smith; D R Cullimore
Journal:  Can J Microbiol       Date:  1974-05       Impact factor: 2.419

4.  Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS).

Authors:  Marie K K Nielsen; Maria S Holtze; Bo Svensmark; René K Juhler
Journal:  Pest Manag Sci       Date:  2007-02       Impact factor: 4.845

5.  2,6-Dichlorobenzamide (BAM) herbicide mineralisation by Aminobacter sp. MSH1 during starvation depends on a subpopulation of intact cells maintaining vital membrane functions.

Authors:  Ole R Sjøholm; Ole Nybroe; Jens Aamand; Jan Sørensen
Journal:  Environ Pollut       Date:  2010-09-09       Impact factor: 8.071

Review 6.  Biodegradation potential of the genus Rhodococcus.

Authors:  Ludmila Martínková; Bronislava Uhnáková; Miroslav Pátek; Jan Nesvera; Vladimír Kren
Journal:  Environ Int       Date:  2008-09-11       Impact factor: 9.621

7.  Acyl transfer activity of an amidase from Rhodococcus sp. strain R312: formation of a wide range of hydroxamic acids.

Authors:  D Fournand; F Bigey; A Arnaud
Journal:  Appl Environ Microbiol       Date:  1998-08       Impact factor: 4.792

8.  Transformation of the herbicide 2,6-dichlorobenzonitrile to the persistent metabolite 2,6-dichlorobenzamide (BAM) by soil bacteria known to harbour nitrile hydratase or nitrilase.

Authors:  Maria Sommer Holtze; Jan Sørensen; Hans Christian B Hansen; Jens Aamand
Journal:  Biodegradation       Date:  2006-02-22       Impact factor: 3.909

9.  Purification of a hyperactive nitrile hydratase from resting cells of Rhodococcus rhodochrous PA-34.

Authors:  S Prasad; J Raj; T C Bhalla
Journal:  Indian J Microbiol       Date:  2009-06-06       Impact factor: 2.461

10.  Diversity of nitrile hydratase and amidase enzyme genes in Rhodococcus erythropolis recovered from geographically distinct habitats.

Authors:  Pedro F B Brandão; Justin P Clapp; Alan T Bull
Journal:  Appl Environ Microbiol       Date:  2003-10       Impact factor: 4.792

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  6 in total

1.  Dichlobenil and 2,6-dichlorobenzamide (BAM) dissipation in topsoil and deposits from groundwater environment within the boreal region in southern Finland.

Authors:  Veera Pukkila; Merja H Kontro
Journal:  Environ Sci Pollut Res Int       Date:  2013-09-21       Impact factor: 4.223

2.  The Epigenetic Impact of Cruciferous Vegetables on Cancer Prevention.

Authors:  Kendra J Royston; Trygve O Tollefsbol
Journal:  Curr Pharmacol Rep       Date:  2015-02-01

3.  A comparative study of nitrilases identified by genome mining.

Authors:  Ondřej Kaplan; Alicja B Veselá; Alena Petříčková; Fabrizia Pasquarelli; Martina Pičmanová; Anna Rinágelová; Tek Chand Bhalla; Miroslav Pátek; Ludmila Martínková
Journal:  Mol Biotechnol       Date:  2013-07       Impact factor: 2.695

4.  Biodegradation potential of cyano-based ionic liquid anions in a culture of Cupriavidus spp. and their in vitro enzymatic hydrolysis by nitrile hydratase.

Authors:  Jennifer Neumann; Magdalena Pawlik; Dieter Bryniok; Jorg Thöming; Stefan Stolte
Journal:  Environ Sci Pollut Res Int       Date:  2013-12-13       Impact factor: 4.223

5.  Substrate Profiling of the Cobalt Nitrile Hydratase from Rhodococcus rhodochrous ATCC BAA 870.

Authors:  Adelaide R Mashweu; Varsha P Chhiba-Govindjee; Moira L Bode; Dean Brady
Journal:  Molecules       Date:  2020-01-06       Impact factor: 4.411

6.  A high-throughput screening assay for distinguishing nitrile hydratases from nitrilases.

Authors:  Leticia Mara Lima Angelini; Amanda Ribeiro Martins da Silva; Lucas de Freitas Coli Rocco; Cintia Duarte de Freitas Milagre
Journal:  Braz J Microbiol       Date:  2015-03-31       Impact factor: 2.476

  6 in total

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