Metabolism of the benzidine-based azo dye Direct Black 38 by human intestinal microbiota

Manning, Bradford W.; Cerniglia, Carl E.; Federle, Thomas W.

doi:10.1128/aem.50.1.10-15.1985

Cited by 72 publications

(29 citation statements)

References 21 publications

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“…conserved regions in catalytic centers have been shown for other enzymes (AKP c t ril. 1985. HARKER ct d. 1986, KOVACS et al 1989, D I t T K I~l~s c' t o/.…”

Section: Discussionmentioning

confidence: 99%

“…Azo dyes are used in the pharmaceutical, food, textile, leather and cosmetic industries. Azoreductase enzymes of intestinal microorganisms catalyze the reductive cleavage of azo (N = N ) linkages in azo dyes to produce aromatic amines, some of which are known carcinogens that have been associated with bladder cancer in dyestuff workers ( HARTMAN et al 1978, NIOSH 1980, BROWN 1981, CERNIGLIA et al 1982a, 1982b. MANNING et a/.…”

mentioning

confidence: 99%

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Immunological homology among azoreductases from Clostridium and Eubacterium strains isolated from human intestinal microflora

Rafii

Smith

et al. 1992

J. Basic Microbiol.

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Azoreductases from several anaerobic intestinal bacteria have been shown to reduce azo dyes to carcinogenic aromatic amines. To evaluate the structural similarities of azoreductases from four species of Clostridium and one species of Eubacterium, a polyclonal antibody against purified Clostridium perfringens azoreductase was generated in rabbits. This antibody inhibited the azoreductase activity of all five bacteria tested. ELISA showed different degrees of binding of the antibody to various species of bacteria. In a Western blot, the antibody reacted with the purified azoreductases from all four Clostridium species and the Eubacterium species. These results demonstrate that the azoreductases from the bacteria tested share similar antigenic domains, which are probably located in the active site of the enzyme. Azoreductases from these intestinal bacteria are similar enough to be considered as a single group of enzymes with respect to their functions and antigenicity.

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“…conserved regions in catalytic centers have been shown for other enzymes (AKP c t ril. 1985. HARKER ct d. 1986, KOVACS et al 1989, D I t T K I~l~s c' t o/.…”

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Immunological homology among azoreductases from Clostridium and Eubacterium strains isolated from human intestinal microflora

Rafii

Smith

et al. 1992

J. Basic Microbiol.

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show abstract

“…It is also interesting to note that 4-aminobiphenyl is inhibitory to bacteria. 4-Aminobiphenyl is the deamination product of benzidine that is generated from reduction of benzidinebased azo dyes such as Direct Black 38 in the gastrointestinal tract or in the environment [30,31].…”

Section: 33ј-44ј-tetraaminobiphenyl Was Inhibitory To Only Aeromomentioning

confidence: 99%

Effects of Benzidine and Benzidine Analogues on Growth of Bacteria Including Azotobacter Vinelandii

Chung¹,

Chen²,

Wong³

et al. 1998

Environ Toxicol Chem

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Abstract-Benzidine and benzidine analogues are mutagenic and carcinogenic metabolites of azo dyes that are widely found in the environment. The toxicities of benzidine and nine of its analogues against 18 bacterial strains including nitrogen-fixing Azotobacter vinelandii were tested using the well diffusion assay technique. 2-Aminobiphenyl and 3-aminobiphenyl were the most inhibitory to all bacterial species tested except A. vinelandii. 4-Aminobiphenyl was inhibitory to the growth of A. vinelandii using a plate count assay, although it failed to show an inhibitory effect in the well diffusion assay. 3,3Ј-4,4Ј-Tetraaminobiphenyl was inhibitory to both A. vinelandii and Aeromonas hydrophila, whereas benzidine, 3,3Ј-dimethoxybenzidine, 4,4Ј-dinitro-2-biphenylamine, 3,3Ј-5,5Ј-tetramethylbenzidine, N,N-NЈ,NЈ-tetramethylbenzidine, and o-tolidine were not inhibitory to any of the bacterial species tested. Of all these compounds tested, only 3,3Ј-4,4Ј-tetraaminobiphenyl and 4-aminobiphenyl inhibited the nitrogenase activity of A. vinelandii.

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“…Some azo dyes are not normally toxic but the amines resulting from the anaerobic digestion of these substances may possess these characteristics . Some authors have found that the cleavage of azo bonds in benzidine based azo dyes or direct dyes produce benzidine and 4‐aminobiphenyl which are classified as carcinogenic and mutagenic . Table presents studies of the degradation of different direct dyes and their by‐products in reactors with different configurations.…”

Section: Introductionmentioning

confidence: 99%

Influence of the organic loading rate on the hydraulic behaviour and the azo‐dye removal in an anaerobic filter

Cobos‐Becerra

González‐Martínez

2014

J of Chemical Tech & Biotech

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BACKGROUND: Biofilm processes have proven to more efficiently remove xenobiotics than suspended growth systems. They offer higher solid retention times to prevent washout of adapted microorganisms. The main problem with anaerobic filters is clogging when the biofilm develops rapidly or after long operating periods. In this work, an anaerobic filter was operated for 466 days to evaluate the degradation of Direct Blue 2 (DB2) azo dye and the influence of organic loading rate on the hydraulic behaviour and on azo dye removal. Axial Dispersion and Wolf and Resnick models were used for the analysis of tracer curves. RESULTS:Tracer tests showed that the anaerobic filter behaves predominantly as a plug flow reactor and as the biofilm grows thicker with increasing organic load, the void volume and the hydraulic retention time decrease. In addition, with increasing organic loading rate, the dispersion coefficient increases. The anaerobic biofilm removed up to 60% of the Direct Blue 2 azo dye. CONCLUSION: The higher the organic load, the better the azo dye was removed. Both the dye Direct Blue 2 and its degradation products (benzidine and 4-aminobiphenyl) can be removed by an anaerobic biofilm. The anaerobic biofilm did not only break the azo bonds but also decomposed benzidine to 4-aminobiphenyl.

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Metabolism of the benzidine-based azo dye Direct Black 38 by human intestinal microbiota

Cited by 72 publications

References 21 publications

Immunological homology among azoreductases from Clostridium and Eubacterium strains isolated from human intestinal microflora

Immunological homology among azoreductases from Clostridium and Eubacterium strains isolated from human intestinal microflora

Effects of Benzidine and Benzidine Analogues on Growth of Bacteria Including Azotobacter Vinelandii

Influence of the organic loading rate on the hydraulic behaviour and the azo‐dye removal in an anaerobic filter

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