The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers

Stiborová, Marie; Asfaw, Befekadu; Anzenbacher, Pavel; Lešetický, L.; Hodek, Petr

doi:10.1016/0304-3835(88)90091-2

Cited by 43 publications

(31 citation statements)

References 10 publications

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“…This unexpected observation could not be explained at that time. Stiborova et al (44) observed the transformation of Sudan I (1-phenylazo-2-hydroxynaphthalene) by microsomal enzymes (P-450-type heme-containing oxygenases) to a variety of products. One product was benzenediazonium ion, which could be produced only by asymmetric cleavage, probably by an oxidative mechanism similar to that proposed by us for heme-containing peroxidases.…”

Section: Discussionmentioning

confidence: 99%

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New pathway for degradation of sulfonated azo dyes by microbial peroxidases of Phanerochaete chrysosporium and Streptomyces chromofuscus

et al. 1994

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Pathways for the degradation of 3,5-dimethyl-4-hydroxy-azobenzene-4'-sulfonic acid (I) and 3-methoxy-4-hydroxyazobenzene-4'-sulfonamide (II) by the manganese peroxidase and ligninase of Phanerochaete chrysosporium and by the peroxidase of Streptomyces chromofuscus have been proposed. Twelve metabolic products were found, and their mechanisms of formation were explained. Preliminary oxidative activation of the dyes resulted in the formation of cationic species, making the molecules vulnerable to the nucleophilic attack of water. Two types of hydrolytic cleavage were observed. Asymmetric splitting gave rise to quinone and diazene derivatives, while symmetric splitting resulted in the formation of quinone monoimine and nitroso derivatives. These unstable intermediates underwent further redox, oxidation, and hydrolytic transformation, eventually furnishing 11 organic products and ammonia.

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Section: Discussionmentioning

confidence: 99%

“…2-Methoxy-4-aminophenol was prepared from guaiacol (2-methoxyphenol) by nitrosation and reduction as described previously for aminothymol (44).…”

mentioning

confidence: 99%

New pathway for degradation of sulfonated azo dyes by microbial peroxidases of Phanerochaete chrysosporium and Streptomyces chromofuscus

et al. 1994

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“…The major DNA adduct which is formed in this reaction was identified as the 8-(phenylazo) guanine adduct. In addition to microsomal enzymes, Sudan I and its C-hydroxylated metabolites are also oxidized by peroxidases and as a consequence DNA, RNA, and protein adducts are formed [271,[275][276][277][278][279][280][281][282][283][284][285][286][287].…”

Section: Sudan Dyes Are Potential Carcinogens and Mutagens For Humansmentioning

confidence: 99%

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

Przybylski¹,

Huczyński²,

Pyta³

et al. 2009

COC

382

206

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Aza-derivatives of phenols such as Schiff bases and hydrazones are an important and interesting group of chemical compounds. They exhibit a number of biological activities and play an important role in the regulation of many biochemical processes. Due to these properties, these compounds are potentialy useful for the design and production of novel anticancer, antimalaria, antivirus and antimicrobial drugs.The primary aim of the present review is to compare selected groups of phenol-derivatives containing azo-, heterocyclic, aromatic, alkyl and sugar moieties in view of their potential use and undesired effects, since some of them are widely used as dyes in the industry.Despite the vast number of azo derivatives of phenols which were synthesized and tested with respect to their biological activities, there is a continuous search for compounds of this group which might exhibit interesting, new biological effects.The main contribution to the development of Schiff base chemistry undoubtedly came from pharmaceutical research that began with the early studies of Hugo Schiff in the 19th century. Indeed, a vast number of publications on this matter underline the relevance of Schiff bases and related compounds in chemistry, pharmacy, biochemistry and industry. GOSSYPOLGossypol (Scheme 1) is a bisesquiterpene with interesting physico-chemical properties and pronounced biological activities. Despite many useful biological and physiological characteristics the main obstacle in using this compound as a drug is its relatively high toxicity and some other side effects [1][2][3][4][5]. The toxicity of gossypol is directed mainly towards the reproductive system, liver, heart and lipid membranes [6,7]. In the last thirty years biological and medical applications of gossypol and its derivatives mainly of its Schiff bases were on the focus of research. More than two thousand publications about gossypol and its derivates in medical therapy show the importance of this compound today. Scheme 1.

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“…An interesting alternative mechanism is the activation to carcinogens without metabolic reduction of azo bonds 56,57 . The azo dye Sudan I (20) was oxidized in the liver to a reactive diazonium intermediate as the proximate electrophilic carcinogen and further bound to calf thymus DNA in vivo ( Figure 5).…”

Section: Toxicitymentioning

confidence: 99%