Detoxication products of the carcinogenic azodye Sudan I (Solvent Yellow 14) bind to nucleic acids after activation by peroxidase

Stiborová, Marie; Frei, Eva; Schmeiser, Heinz H.; Wießler, Manfred; Hradec, J

doi:10.1016/0304-3835(93)90217-w

Cited by 20 publications

(12 citation statements)

References 15 publications

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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

392

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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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

392

206

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“…It is a clastogenic compound, inducing micronuclei in the bone marrow of rats (Westmoreland and Gatehouse, 1991). There is also evidence that this compound exhibits genotoxic effects, after its metabolic activation by hepatic cytochrome P450 (CYP) and peroxidase enzymes in vitro , and in the rat liver and urinary bladder in vivo (Stiborová et al ., 1988b; c; 1990a; b; 1992; 1993; 1995a; b; 1999a; b; 2002; 2006; Dixit et al ., 2008; Zhang et al ., 2008b,), and in a human hepatoma cell line, HepG2 (An et al ., 2007; Zhang et al ., 2008b). …”

Section: Toxicity Mutagenicity and Carcinogenicity Of Sudan Imentioning

confidence: 99%

“…But relatively high levels of peroxidases are expressed in this tissue (Wise et al ., 1984). We have found that in addition to microsomal CYP enzymes, Sudan I and its C-hydroxylated metabolites are also oxidized by peroxidases such as a model plant peroxidase from horseradish as well as the mammalian enzyme, prostaglandin H synthase (cyclooxygenase), as a consequence DNA, RNA and protein adducts are formed (Stiborová et al ., 1988c; 1990a;b; 1991; 1992; 1993; 1995a; 1999b) (Figure 2). In bladder, therefore, peroxidase-catalyzed activation of Sudan I has been suggested, similar to other carcinogens such as carcinogenic aromatic amines (Wise et al ., 1984; Yamazoe et al ., 1985; Eling et al ., 1990; Chen et al, 1996).…”

Section: Activation and Detoxication Metabolism Of Sudan I By Peroxidmentioning

confidence: 99%

Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study

Stiborová¹,

Martínek²,

Semanská³

et al. 2009

Interdisciplinary Toxicology

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Sudan I [1-(phenylazo)-2-hydroxynaphthalene, C.I. Solvent Yellow 14, CAS No: 842-07-9] is used as the compound employed in chemical industry and to color materials such as hydrocarbon solvents, oils, fats, waxes, plastics, printing inks, shoe and floor polishes and gasoline. Such a wide used could result in a considerable human exposure. Sudan I is known to cause developments of tumors in the liver or urinary bladder in rats, mice, and rabbits, and is considered a possible weak human carcinogen and mutagen. This carcinogen is also a potent contact allergen and sensitizer. Here, we compare the data concerning the Sudan I oxidative metabolism catalyzed by cytochrome P450 (CYP) and peroxidase enzymes, which has been investigated in our laboratory during the last two decades. These two types of enzymes are responsible both for Sudan I detoxication and activation. Among the Sudan I metabolites, C-hydroxylated derivatives and a dimer of Sudan I are suggested to be the detoxication metabolites formed by CYPs and peroxidases, respectively. Metabolic activation of Sudan I by both types of enzymes leads to formation of reactive species (the benzenediazonium ion by CYP and Sudan I radicals by peroxidase) that bind to DNA and RNA, generating covalent adducts in vitro and in vivo. Whereas the structure of the major adduct formed by the benzenediazonium ion in DNA has already been identified to be the 8-(phenylazo)guanine adduct, the structures of adducts formed by peroxidase, have not been characterized as yet. Biological significance of the DNA adducts of Sudan I activated with CYP and peroxidase enzymes and further aims of investigations in this field are discussed in this study.

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“…1,7-Naphthalenediol and 2, 3-naphthalenediol are prohibited components in cosmetics, while the addition of 2,7naphthalenediol and 1,5-naphthalenediol is strictly controlled [6]. Long-term excessive exposure to naphthalenediols can cause serious irritation to respiratory system and eyes, and may cause skin allergies [7,8]. Therefore, it is necessary to establish a simple and efficient separation method to determine the content of the four naphthalenediols.…”

Section: Introductionmentioning

confidence: 99%

Determination of four naphthalenediols in cosmetic samples by sweeping-micellar electrokinetic chromatography and a comparison with HPLC

Wang

Zheng

et al. 2022

AChrom

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A sweeping micellar electrokinetic chromatography (sweeping-MEKC) method was developed for the determination of 1,7-naphthalenediol, 2,3-naphthalenediol, 1,5-naphthalenediol and 2,7-naphthalenediol in cosmetics. Several parameters affecting sweeping-MEKC method were studied systematically and the separation conditions were optimized as 20 mM NaH2PO4–110 mM SDS and 40% (v/v) MeOH (pH 2.4), with −22 kV applied voltage and UV detection at 230 nm. The sample matrix is 60 mmol L−1 NaH2PO4 and sample introduction was performed at 3 psi for 6 s. Separation of the four naphthalenediols was completed in less than 17 min. Limit of detection (LOD) and limit of quantitation (LOQ) are 0.0045∼0.0094 μg mL−1 and 0.015∼0.031 μg mL−1. Linear relationship (r 2 > 0.999) is satisfactory at the range of 0.1–10 μg mL−1. The developed method has been successfully applied to the determination of the four naphthalenediols in real cosmetic samples, with recoveries in foundation, sun cream and lotion in the range of 92.3%∼106.8% and relative standard deviation (RSD) less than 4.15%. A HPLC method described in the National Standards of the People’s Republic of China was carried out for the comparison with the proposed method. The results showed that the proposed sweeping-MEKC method has the advantages of fast, low cost with comparative sensitivity.

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Detoxication products of the carcinogenic azodye Sudan I (Solvent Yellow 14) bind to nucleic acids after activation by peroxidase

Cited by 20 publications

References 15 publications

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study

Determination of four naphthalenediols in cosmetic samples by sweeping-micellar electrokinetic chromatography and a comparison with HPLC

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