Protein Information

Name nitrilase (protein family or complex)
Synonyms Nitrilase; Nitrilases

Compound Information

Name bromoxynil
CAS 3,5-dibromo-4-hydroxybenzonitrile

Reference List

PubMed Abstract RScore(About this table)
17789813 Stalker DM, McBride KE, Malyj LD: Herbicide Resistance in Transgenic Plants Expressing a Bacterial Detoxification Gene. Science. 1988 Oct 21;242(4877):419-423.

A gene, bxn, encoding a specific nitrilase that converts bromoxynil to its primary metabolite 3,5-dibromo-4-hydroxybenzoic acid, was cloned from the natural soil bacterium Klebsiella ozaenae.
62(0,2,2,2) Details
1390687 Kobayashi M, Yanaka N, Nagasawa T, Yamada H: Primary structure of an aliphatic nitrile-degrading enzyme, aliphatic nitrilase, from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue. Biochemistry. 1992 Sep 22;31(37):9000-7.

The amino acid sequence homology between the Rhodococcus nitrilase and the Klebsiella ozaenae bromoxynil nitrilase [Stalker et al. (1988) J.
15(0,0,1,10) Details
1400390 Kobayashi M, Komeda H, Yanaka N, Nagasawa T, Yamada H: Nitrilase from Rhodococcus rhodochrous J1. J Biol Chem. 1992 Oct 15;267(29):20746-51.

The predicted amino acid sequence of the nitrilase gene showed similarity to that of the bromoxynil nitrilase from Klebsiella ozaenae.
12(0,0,1,7) Details
1555601 Bartling D, Seedorf M, Mithofer A, Weiler EW: Cloning and expression of an Arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid. Eur J Biochem. 1992 Apr 1;205(1):417-24.

From an Arabidopsis thaliana cDNA expression library, a cDNA clone was isolated, characterized and sequenced which, at the amino acid level, resembled the Klebsiella ozaenae bromoxynil nitrilase encoded by the bxn gene.
8(0,0,1,3) Details
3530133 McBride KE, Kenny JW, Stalker DM: Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae. Appl Environ Microbiol. 1986 Aug;52(2):325-30.

Assays of cell extracts of this organism for the ability to produce ammonia from bromoxynil revealed the presence of a nitrilase (EC 3.5.51) activity.
6(0,0,1,1) Details
8798929 Gabriel J, Vekova J, Vosahlo J: High-performance liquid chromatographic study of the aromatic nitrile metabolism in soil bacteria. J Chromatogr B Biomed Appl. 1996 May 31;681(1):191-5.

Simultaneous HPLC determination of bromoxynil, ioxynil and dichlobenil, three arylnitrile herbicides, and their metabolic products in soil extracts and microbiological media is described.
Assay of aromatic nitrile hydratase, amidase or nitrilase activities is possible by the method developed.
1(0,0,0,1) Details
17125153 Nielsen MK, Holtze MS, Svensmark B, Juhler RK: Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Pest Manag Sci. 2007 Feb;63(2):141-9.

A similar process to the formation of BAM (2,6-dichlorobenzamide) from the herbicide dichlobenil (2,6-dichlorobenzonitrile) can be anticipated as bromoxynil and ioxynil are analogues of dichlobenil and they are degraded by the enzymes nitrilase, nitrile hydratase and amidase.
81(1,1,1,1) Details
3029038 Stalker DM, McBride KE: Cloning and expression in Escherichia coli of a Klebsiella ozaenae plasmid-borne gene encoding a nitrilase specific for the herbicide bromoxynil. J Bacteriol. 1987 Mar;169(3):955-60.

An enzyme (nitrilase) that converts the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) to its metabolite 3,5-dibromo-4-hydroxybenzoic acid was shown to be plasmid encoded in the natural soil isolate Klebsiella ozaenae.
80(0,2,5,5) Details
2834373 Stalker DM, Malyj LD, McBride KE: Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene. J Biol Chem. 1988 May 5;263(13):6310-4.

A Klebsiella ozaenae nitrilase which converts the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) to 3,5-dibromo-4-hydroxybenzoic acid has been expressed at 5-10% of the total protein in Escherichia coli from a cloned K. ozaenae DNA segment and purified 10.3-fold to homogeneity.
74(0,2,4,4) Details
20204468 Vesela AB, Franc M, Pelantova H, Kubac D, Vejvoda V, Sulc M, Bhalla TC, Mackova M, Lovecka P, Janu P, Demnerova K, Martinkova L: Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity. Biodegradation. 2010 Mar 4.

None of the nitrilase-producing strains hydrolyzed dichlobenil (2,6-dichlorobenzonitrile). 3,5-Dibromo-4-hydroxybenzoic acid exhibited less inhibitory effect than bromoxynil both on luminescent bacteria and germinating seeds of Lactuca sativa. 3,5-Diiodo-4-hydroxybenzoic acid only exhibited lower toxicity than ioxynil in the latter test.
32(0,1,1,2) Details