Mutagenicity evaluation of nitroanilines and nitroaminophenols in Salmonella typhimurium

Shahin, Majdi M.

doi:10.1111/j.1467-2494.1985.tb00422.x

Cited by 23 publications

(5 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…IACR classified benzidine and dyes metabolized to benzidine as category 1carcinogens (114). p-Phenylenediamine was reported to be non-mutagenic (126,127); but Shahin et al (128)(129)(130) reported it to be a weak mutagen. Chung et al (131) studied the mutagenicity of p-phenylenediamine and found it to be weakly mutagenic to Salmonella tester strain TA98 with metabolic activation.…”

Section: -Aminobiphenylmentioning

confidence: 99%

Occurrence uses and carcinogenicity of arylamines

Chung¹

2015

Front Biosci

View full text Add to dashboard Cite

Arylamines are chemically synthesized and contained in oxidants, epoxy polymers, explosives, fungicides, pesticides, colorants, polyurethanes, and used in rubber, pharmacology, cosmetics, and other chemical industries. Many arylamines are ubiquitously present in cigarette smoke, cooking fume hoods, foods, automobile exhaust, industrial sites, etc. Some arylamines can be generated through azo reduction by intestinal, skin, and environmental microorganisms from azo dyes that are widely used. Arylamines can also be generated by reduction of the nitro-group containing polyhydrated hydrocarbons including muntions. Some arylamines are released by burning nitrogen containing organic materials at high temperatures. Some medical drugs are also arylamines. Furthermore, many arylamines are essential constituents of normal metabolism or the result of abnormal metabolism or dietary sources. Some arylamines are mutagenic, carcinogenic or the cause of other kinds of maladies. Some arylamine are considered the major etiological agents of bladder tumors in humans and animals but may also induce other types of cancers in various organs. The organ, tissue, and species specificity of the arylamine-inducing carcinogenesis may be determined by their availability, distribution, and the presence of metabolic activation/detoxicification enzymes of each organ or tissue of different species. The ubiquitous arylamines, therefore, pose serious hazards to human health and environment. This article will address the occurrence, uses, carcinogenicity, and other arylamines-induced diseases.

show abstract

Section: -Aminobiphenylmentioning

confidence: 99%

Occurrence uses and carcinogenicity of arylamines

Chung¹

2015

Front Biosci

View full text Add to dashboard Cite

show abstract

“…We tested the three unsubstituted NAs, 2NA, 3NA, and 4NA. Previous studies showed that 2NA is inactive in strain TA98 (Shahin, ; Shimizu and Yano, ; Blakey et al, ; Assmann et al, ) whereas 3NA and 4NA are positive, albeit weakly so (Shimizu and Yano, ; Chung et al, ; Assmann et al, ). We confirmed that 2NA is negative in TA98 and found that it was also negative in YG1024, with no increase in revertant yield up to the highest dose tested (1 μmol per plate); data not shown.…”

Section: Resultsmentioning

confidence: 96%

Structure–activity investigation of the potentiating effect of cyano substitution on nitroaniline mutagenicity in the ames test

Josephy

Dhanoa

Elzawy

et al. 2017

Environ and Mol Mutagen

View full text Add to dashboard Cite

2,6-Dicyano-4-nitroaniline and 2-cyano-4-nitroaniline (CNNA; 2-amino-5-nitrobenzonitrile) are potent mutagens in the Ames test, even though unsubstituted nitroanilines (NAs) are no more than weak mutagens. These compounds are putative reduction products of many commercial azo dyes, including Disperse Blue 165, Disperse Blue 337, Disperse Red 73, Disperse Red 82, Disperse Violet 33, and Disperse Violet 63. We have examined the mutagenicity in strains TA98 and YG1024 of a series of commercially-available isomers of CNNA, and some related compounds, to probe the relationship between structure and genotoxic activity in this class of compounds. The potentiating effect of the cyano substituent is seen in many cases; e.g. 2-amino-4-nitrobenzonitrile is a much more potent mutagen than 3-NA. 2,4-Dinitrobenzonitrile is also highly mutagenic. Possible mechanisms for the "cyano effect" are considered, with respect to the likely structures of cyanonitroaniline-DNA adducts and the roles of the enzymes (nitroreductase and acetyl CoA:arylamine N-acetyltransferase) believed to be involved in the activation of nitroaromatic compounds. Environ. Mol. Mutagen. 59:114-122, 2018. © 2017 Wiley Periodicals, Inc.

show abstract

“…This compound can also be produced in the reduction of Methyl Orange, Orange II, Ponceau BS, and Ponceau S ( Table 2). p-Nitroaniline was first reported as very weakly mutagenic or non-mutagenic in the presence of S9 mix in S. Typhimurium strain TA98 (124). The mutagenicity of the compound was later confirmed in the test system of S. Typhimurium strain TA98 with or without S9 activation, but the results were negative for all other strains.…”

Section: Genotoxicity Of Metabolites Of Azo Dyesmentioning

confidence: 99%

Toxicological significance of azo dye metabolism by human intestinal microbiota

Chen¹

2012

Front Biosci

113

View full text Add to dashboard Cite

Approximately 0.7 million tons of azo dyes are synthesized each year. Azo dyes are composed of one or more R 1-N=N-R 2 linkages. Studies have shown that both mammalian and microbial azoreductases cleave the azo bonds of the dyes to form compounds that are potentially genotoxic. The human gastrointestinal tract harbors a diverse microbiota comprised of at least several thousand species. Both water-soluble and water-insoluble azo dyes can be reduced by intestinal bacteria. Some of the metabolites produced by intestinal microbiota have been shown to be carcinogenic to humans although the parent azo dyes may not be classified as being carcinogenic. Azoreductase activity is commonly found in intestinal bacteria. Three types of azoreductases have been characterized in bacteria. They are flavin dependent NADH preferred azoreductase, flavin dependent NADPH preferred azoreductase, and flavin free NADPH preferred azoreductase. This review highlights how azo dyes are metabolized by intestinal bacteria, mechanisms of azo reduction, and the potential contribution in the carcinogenesis/mutagenesis of the reduction of the azo dyes by intestinal microbiota.

show abstract

Mutagenicity evaluation of nitroanilines and nitroaminophenols in Salmonella typhimurium

Cited by 23 publications

References 27 publications

Occurrence uses and carcinogenicity of arylamines

Occurrence uses and carcinogenicity of arylamines

Structure–activity investigation of the potentiating effect of cyano substitution on nitroaniline mutagenicity in the ames test

Toxicological significance of azo dye metabolism by human intestinal microbiota

Contact Info

Product

Resources

About