Metabolic Activation of Aromatic Amines and Amides and Interactions with Nucleic Acids
Philip L. Grover in Chemical Carcinogens and DNA, 2019
This compound represents one of the best studied examples of the group of carcinogenic azo dyes. Its reaction products with nucleic acids and proteins in vivo have been characterized by Miller and associates. Interaction products with nucleic acids have been elusive for a long time, because suitable, activated derivatives of this dye were not available. The synthetic ester N-benzoyloxy-MAB was used by Lin et al.111 as a reactive derivative to prepare products of reaction with guanosine and deoxyguanosine (Figure 7). A similar type of substitution to that observed with N-acetoxy-AAF occurred at carbon-8 of guanine. The presence of these products was established by Lin et al.112 in hydrolysates of RNA and DNA obtained from the livers of rats that had been given MAB. Lin and Fok113 showed that in an oxidative medium, employing iodine or persulfate as oxidants, MAB becomes covalently bound to DNA or to polynucleotides. In a recent study, Kadlubar et al.63 showed that N-hydroxy-MAB is activated by rat-liver microsomes, in a similar manner to N-hydroxy-AAF, by formation of the sulfate. When guanosine was used as reactant, N-guanosin-8-yl-MAB was isolated from the reaction mixture.
Ethnobotany of Useful Plants in Indo-Gangetic Plain and Central India
T. Pullaiah, K. V. Krishnamurthy, Bir Bahadur in Ethnobotany of India, 2017
Earliest evidence for the use of natural dyes dates back to more than 5000 years, with Madder (Rubia cordifolia) dyed cloth found in the Indus river valley at Mohenjodaro. India is endowed with a wealth of natural flora and fauna, which provide the basic resources for a rainbow of natural dyes. Natural dyes are environment friendly; for example, turmeric, the brightest of naturally occurring yellow dyes is a powerful antiseptic and revitalizes the skin, while indigo yields a cooling sensation. Research has shown that synthetic dyes are suspected to release harmful chemicals that are allergic, carcinogenic and detrimental to human health. Ironically, Germany that discovered azo dyes, became the first country to ban certain azo dyes in 1996 (Singh and Singh, 2002).
The Role of Fecal Microflora in Colon Carcinogenesis
Herman Autrup, Gary M. Williams in Experimental Colon Carcinogenesis, 2019
Azo dyes are commonly used as food colorants and have been shown to be toxic to animals under certain conditions.28 Many intestinal organisms including bacteroides, fusobacteria, bifidobacteria, and eubacteria reduce azo dyes to amino derivatives. Thus, the common dye trypan blue is reduced to o-tolidine by whole cell cultures of Fusobacteria29 or cell extracts of this organism. Similarly Poinceau 3P is reduced to 2,4,5-trimethyl aniline, a known mutagen, plus a number of inactive dimethyl derivatives.30 While exposure to dyes of this type is no longer widespread, it is clear that they can be degraded by the fecal flora to aromatic amines, some of which have a carcinogenic potential.
Application of crosslinked chitosan-nanoclay composite beads for efficient removal of Ponceau S azo dye from aqueous medium
Published in Toxin Reviews, 2023
Seda Çınar, Ayşe Dinçer, Ahmet Eser, Tülin Aydemir
Azo dyes, which constitute an important class of synthetic dyes, are characterized by the -N = N- bond in the chromophore group. One of the carbon atoms attached to the azo group may be aromatic (benzene, naphthalene. and derivatives) or heterocyclic ring and the other may be a group attached to the aliphatic chain. N Any azo group is not found in the natural dyestuffs structure. All of these class dyes are synthetically obtained. The strong electronegativity of the azo group balances the aromatic substances against to conversion of oxygenates (Benkhaya et al.2020). Since azo dyes are stable, their discharge into the environment causes groundwater and soil pollution. Many of the biodegradation products of synthetic azo dyes are sulfonated and non-sulfonated aromatic amines (Srinivasan and Sadasivam 2021). Decomposition products can be toxic to aquatic organisms, as well as carcinogenic and mutagenic to humans. Therefore, these dyes should be removed properly before being discharged.
Adverse effects of textile dyes on antioxidant enzymes and cholinesterase activities in Drosophila melanogaster (Oregon R+)
Published in Drug and Chemical Toxicology, 2022
Shaista Rahimi, Mahendra P. Singh, Jeena Gupta
Azo dyes are chemically stable, easy to synthesize and versatile for which they are used not only for textile dyeing but also for printing, industrial and clinical purposes (treating inflammatory bowel diseases). However, when they are environmentally released as effluent, they cause pollution not only because of their persistence but also for the toxic (Milani et al.2018) and mutagenic effects of their by-products (Chequer et al.2011; Franco et al.2018). The present study was designed to evaluate the toxic effects of two textile dyes Disperse blue 124 and Disperse black on important enzymes of living organisms. The previous studies have shown that dependent on different dyes and the used analytical methods, the concentration of dye in waste water range from traces (µg/L) to around 500 mg/L (Nojavan et al.2013). The industrial effluent may contain the dye concentration upto 7000 mg/L (Koprivanac et al.1993). Therefore we have taken a broad range of dye concentrations to evaluate their toxic effects on important enzymes of living organisms. The results from the present work confirmed that these dyes dysregulate the activity of acetyl choline esterase, xanthine oxidase and different anti-oxidant enzymes in Drosophila larvae. These results are in consistence with previous report where the red disperse dyes alter the anti-oxidant enzymes in zebrafish (Meireles et al.2018).
Protective role of Vernonia Cinerea against the Carmoisine induced brain injury and anxiogenic effect in mice
Published in Egyptian Journal of Basic and Applied Sciences, 2023
Navaneetha Krishnan Subramaniyan, Karthikeyan Elumalai, Jayaraman Rajangam, Narahari N Palei, Divya Talari, Anna Balaji, Vijayaraj Surendran
Azo dyes have been used extensively in the cosmetics, leather, food, textile, paper, and pharmaceuticals. Carmoisine is one of the most important food additives among the all-azo dyes, and it is widely used in a variety of food beverages [1,2]. To increase the aesthetic content of food preparations, a number of artificial food colors are often incorporated. Some of the permitted organic synthetic dyes in synthetic food additives include sunset yellow, orange GGN, carmoisine, dazzling blue, tartrazine, erythrosine, ponceau 4 R, scarlet GN, allure red and quick red E. Because of their coloring properties, stability, low cost, and uniformity, artificial dyes are generally used. Long-term use of this synthetic food dyes often induces anemia, indigestion, and anomalies in offspring, allergic reactions such as asthma and urticaria, tumors and cancer paralysis, inflammatory lesions in the kidney, brain, spleen, and liver, and eye disorders in the majority of individuals, resulting in blindness, growth retardation, and mental retardation [3,4]. Between the biochemical pathways that are likely to be damaged by the oxidant effect, including cellular damage induced by the ingestion of these food dyes [5].
Related Knowledge Centers
- Azo Compound
- Dye
- Functional Group
- Methyl Orange
- Organic Compound
- Reactive Dye
- Metal-Complex Dyes
- Substantive Dye
- Disperse Orange 1
- Ph Indicator