Mutagenicity Studies of Benzidine and Its Analogs: Structure-Activity Relationships

Chung, Kyung Tae; Chen, Ssu Ching; Wong, Tit-Yee; Li, Ying Sing; Wei, Cheng; Chou, Ming W.

doi:10.1093/toxsci/56.2.351

Cited by 57 publications

(35 citation statements)

References 33 publications

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“…Murata et al [2001] demonstrated that the N-hydroxy derivative of 4-Ab had the ability to produce oxidative DNA adducts, including 8-OHdG. Chung et al [2000] reported on the mutagenicities of Bz and its analogues. In the presence of S9 mix, 4-Ab, Bz, 3,3 0 -dichlorbenzidine-2HCl, 3,3 0 -dimethoxybenzidine, and 4,4 0 -dinitro-2-biphenylamine were mutagenic to TA98, and 4-Ab, 3,3 0 -dichlorobenzidine-2HCl, 3,3 0 -dimethoxybenzidine, and 4,4 0 -dinitro-2-biphenylamine were mutagenic in TA100.…”

Section: Discussionmentioning

confidence: 99%

Evidence that 4‐aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species

Makena

Chung

2007

Environ and Mol Mutagen

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4-Aminobyphenyl (4-Ab), benzidine (Bz), and Bz congeners were evaluated for their ability to induce genotoxicity through an oxidative mechanism. The mutagenicity of these compounds was tested in the presence and absence of Aroclor 1254-induced rat S9 mix using Salmonella typhimurium tester strain TA102, which is sensitive to agents producing reactive oxygen species (ROS). In the presence of S9, 4-Ab, Bz, N-acetyl-benzidine, and 3,3-dimethoxybenzidine were strongly mutagenic in TA102, whereas, 3,3,5,5-tetra-methylbenzidine, 3,3-dimethylbenzidine (O-tolidine), and N,N-diacetylbenzidine were not mutagenic. In addition, 3,3-dichlorobenzidine and 4,4-dinitro-2-biphenylamine were directly mutagenic in TA102. Incorporation of the free radical and metal scavengers, catalase, superoxide dismutase (SOD), butylated hydroxytolune (BHT), and ethylenediamine tetraacetic acid (EDTA) reduced the mutagenic responses of 4-Ab and Bz, whereas heat-inactivated catalase and SOD had no effect. 4-Ab and Bz also induced lipid peroxidation in the presence of S9 mix as shown using the thiobarbituric acid reactive substances assay. The results of this study indicate that 4-Ab and Bz induce mutations through the induction of ROS.

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Section: Discussionmentioning

confidence: 99%

Evidence that 4‐aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species

Makena

Chung

2007

Environ and Mol Mutagen

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“…DCB was mutagenic in TA98, TA100, TA98/1,8-DNP6, TA1535, TA1537, and TA1538 with S9 mix, and the highest potency was detected in TA98 (20)(21)(22)(23)(24). In this study, DCB was revealed to be highly mutagenic in YG1024, Oacetyltransferase-overproducing derivative of TA98, with S9 mix, and its activity was about 50 times as high as that in TA98 with S9 mix (Table 2).…”

Section: Discussionmentioning

confidence: 54%

“…Mutagenicity of DCB: It has been revealed that DCB is mutagenic in S. typhimurium TA98, TA100, and some other strains with and/or without S9 mix (20)(21)(22)(23)(24), and that the most potent mutagenicity was detected in TA98 with S9 mix. However, there was no report on the mutagenicity of DCB in S. typhimurium YG1024, an O-acetyltransferase-overproducing deriva- tive of TA98.…”

Section: Resultsmentioning

confidence: 99%

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Detection of 3,3′-Dichlorobenzidine in Water from the Waka River in Wakayama, Japan

Watanabe

Hasei

Ohe

et al. 2006

Genes and Environment

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In a previous study, we found that water concentrate from the Waka River, which ‰ows through an industrial area in Wakayama, Japan, showed signiˆcant mutagenicity in Salmonella typhimurium YG1024 without a mammalian metabolic system (S9 mix), and 4-amino-3,3?-dichloro-5,4?-dinitrobiphenyl (ADDB) was identiˆed as a major direct-acting mutagenic constituent in the water concentrate. ADDB induced 428,000 revertants/mg in YG1024 without S9 mix, and this activity was 48 times as high as that with S9 mix. In this study, to clarify whether other mutagenic contaminants were present in the river, water concentrates were collected at three sites along the Waka River and examined for mutagenicity by the Ames test using YG1024 and YG1029 with and without S9 mix. All water concentrates showed potent mutagenicity in YG1024 with and/or without S9 mix. ADDB was detected in water concentrate that was extremely mutagenic without S9 mix. An indirect-acting mutagen, which accounted for more than 30% of the total mutagenicity of the water concentrates in YG1024 with S9 mix, was isolated from two extremely mutagenic water concentrates by HPLC separation. On the basis of spectral data and co-chromatography using authentic chemicals, this mutagen was identiˆed as 3,3?-dichlorobenzidine (DCB). DCB showed strong mutagenicity in YG1024 with S9 mix, inducing 5,186 revertants/mg. DCB was detected in water concentrates collected on the other three sampling dates in the range from 15.8 to 28.5 mg/g of blue rayon. These results suggest that Waka River water might be continually contaminated with mutagens, and DCB was thought to be the major mutagenic constituent of the river water.

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“…It has been confirmed that DCB is mutagenic in Salmonella typhimurium TA98, TA100, TA1535, TA1537, and TA1538 with the presence of the S9 metabolic enzyme activation system [Garner, 1975;Lazear and Louie, 1978;Lazear et al, 1979;Booth et al, 1980;Vithayathil et al, 1983;Prival et al, 1984;Reid et al, 1984;Gentile et al, 1985;Iba, 1987;Lang and Iba, 1987;Messerly et al, 1987;Chung et al, 2000]. Among all dihalogenated benzidines, it is shown that DCB is the most mutagenic [Savard and Josephy, 1986].…”

Section: Introductionmentioning

confidence: 92%

Light-induced mutagenicity in Salmonella TA102 and genotoxicity/cytotoxicity in human T-cells by 3,3′-dichlorobenzidine: a chemical used in the manufacture of dyes and pigments and in tattoo inks

et al. 2005

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Abstract3,3'-Dichlorobenzidine (DCB) is used primarily as an intermediate in the manufacture of diarylide yellow or azo red pigments for printing inks, textiles, paints, and plastics. It is also used in tattoo inks. In this article, we investigate light-induced toxicity of DCB in both bacteria and human Jurkat T-cells. DCB itself is not toxic or mutagenic to Salmonella typhimurium TA102, but is photomutagenic at concentrations as low as 2 µM and phototoxic at concentrations >100 µM when the bacteria is exposed to DCB and light at the same time (1.2 J/cm 2 of UVA and 2.1 J/cm 2 of visible light). Furthermore, DCB is both photocytotoxic and photogenotoxic to human Jurkat Tcells. Under a constant light irradiation dose of 2.3 J/cm 2 of UVA and 4.2 J/cm 2 of visible light, it causes the Jurkat T-cells to become non-viable in a DCB dose-dependent manner and only 40% viable cells remaining at DCB concentrations higher than 50 µM. At the same time, DNA fragmentation is observed for the cells exposed to both DCB and light, determined by single cell gel electrophoresis (Comet assay). As much as 8 % of the cellular DNA is fragmented when exposed to 200 µM DCB and light irradiation. This suggests that DCB can penetrate the cell membrane and enter the cell. Upon light activation, DCB in the cells can cause various cellular damages, including DNA fragmentation, leading to non-viable Jurkat T-cells. It appears, though, non-viable cells may not be caused solely by fragmentation of cellular DNA, but other damages such as to proteins and cell membranes, or other forms of DNA damage such as alkylation that does not cause DNA to fragment, may also be involved. Therefore, persons exposed to DCB through environmental contamination or through tattoo piercing using DCB-contaminated inks must not only concern about its toxicity without exposing to light, but also about its phototoxicity.

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Mutagenicity Studies of Benzidine and Its Analogs: Structure-Activity Relationships

Cited by 57 publications

References 33 publications

Evidence that 4‐aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species

Evidence that 4‐aminobiphenyl, benzidine, and benzidine congeners produce genotoxicity through reactive oxygen species

Detection of 3,3′-Dichlorobenzidine in Water from the Waka River in Wakayama, Japan

Light-induced mutagenicity in Salmonella TA102 and genotoxicity/cytotoxicity in human T-cells by 3,3′-dichlorobenzidine: a chemical used in the manufacture of dyes and pigments and in tattoo inks

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