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Original Articles

Predicting azo dye toxicity

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Pages 249-324 | Published online: 09 Jan 2009

References

  • Allan , R. J. and Roxon , J. J. 1974 . Metabolism by intestinal bacteria: the effect of bile salts on tartrazine azo reduction . Xenobiotica , 4 : 637
  • Ashby , J. , Lefevre , P. A. and Callander , R. D. 1983 . The possible role of azoreduction in the bacterial mutagenicity of 4‐dimethylaminoazobenzene (DAB) and 2 of its analogues (6BT and 51) . Mutat. Res. , 116 : 271
  • Autrup , H. and Warwick , G. P. 1975 . Some characteristics of two azoreductase systems in rat liver, relevance to the activity of 2‐[4'‐di(2"‐bromopropyl)‐aminophenylazo]benzoic acid (CB10–252), a compound possessing latent cytotoxic activity . Chem.‐Biol. Interact. , 11 : 329
  • Beland , F. A. , Tullis , D. L. , Kadlubar , F. F. , Straub , K. M. and Evans , F. E. 1980 . Characterization of DNA adducts of the carcinogen N‐methyl‐4‐aminoazobenzene in vitro and in vivo . Chem.‐Biol. Interact. , 31 : 1
  • Blake , B. W. , Enslein , K. , Gombar , V. K. and Borgstedt , H. H. 1990 . Salmonella mutagenicity and rodent carcinogenicity: quantitative structure‐activity relationships . Mutat. Res. , 241 : 261
  • Boeniger , M. F. 1980 . Carcinogenicity of azo dyes, especially those derived from benzidine , (NIOSH), Publ. No. 80–119 Cincinnati, OH : Department of Health and Human Services .
  • Bos , R. P. , Van der Krieken , W. , Smeijsters , L. , Koopman , J. P. , De Jonge , H. R. , Theuws , J. L. G. and Henderson , P. T. 1986 . Internal exposure of rats to benzidine derived from orally administered benzidine‐based dyes after intestinal azo reduction . Toxicology , 40 : 207
  • Brown , J. P. and Dietrich , P. S. 1983 . Mutagenicity of selected sulfonated azo dyes in the Salmonella/microsome assay: use of aerobic and anaerobic activation procedures . Mutat. Res. , 116 : 305
  • Brown , J. P. , McGarraugh , G. V. , Parkinson , T. M. , Windgard , R. E. Jr. and Onderdonk , A. B. 1983 . A polymeric drug for treatment of inflammatory bowel disease . J. Med. Chem. , 26 : 1300
  • Brown , J. P. 1981 . Reduction of polymeric azo and nitro dyes by intestinal bacteria . Appl. Environ. Microbiol. , 41 : 1283
  • Brown , J. P. , Dietrich , P. S. and Bakner , C. M. 1979 . Mutagenicity testing of some drug and cosmetic dye lakes with the Salmonella/mammalian‐microsome assay . Mutat. Res. , 66 : 181
  • Calogero , F. , Freeman , H. S. , Esancy , J. F. , Whaley , W. M. and Dabney , B. J. 1987 . An approach to the design of non‐mutagenic azo dyes. II. Potential replacements for the benzidine moiety of some mutagenic azo dyestuffs . Dyes Pigm. , 8 : 431
  • Cartwright , R. A. 1983 . Historical and modem epidemiological studies on populations exposed to N‐substituted aryl compounds . Environ. Health Perspect. , 49 : 13
  • Case , R. A. M. , Hosker , M. E. , McDonald , D. B. and Pearson , J. T. 1954 . Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. I. The role of aniline, benzidine, alpha naphthylamine and beta naphthylamine . Br. J. Ind. Med. , 11 : 75
  • Cerniglia , C. E. , Freeman , J. P. , Franklin , W. and Pack , L. D. 1982 . Metabolism of azo dyes derived from benzidine, 3,3'‐dimethylbenzidine and 3,3'‐dimethoxybenzidine to potentially carcinogenic aromatic amines by intestinal bacteria . Carcinogenesis , 3 : 1255
  • Chi , Z. and Bai , Y. 1988 . Microbial degradation of azo dyes and their reduction products . Shandong Daxue Xuebao, Ziran Kexueban , 23 : 94
  • Chung , K.‐T. 1983 . The significance of azo‐rcduction in the mutagenesis and carcinogenesis of azo dyes . Mutat. Res. , 114 : 269
  • Chung , K.‐T. , Fulk , G. E. and Andrews , A. W. 1978a . The mutagenicity of methyl orange and metabolites produced by intestinal anaerobes . Mutat. Res. , 58 : 375
  • Chung , K. T. , Fulk , G. E. and Egan , M. 1978b . Appl. Environ. Microbiol. , 35 : 558
  • Collins , T. F. X. , McLaughlin , J. and Gray , G. C. 1973 . Teratology studies on food colourings. II. Embryotoxiciry of R salt and metabolites of amaranth (FD&C Red No. 2) in rats . Food Cosmet. Toxicol. , 11 : 355
  • Daniel , J. W. 1967 . Enzymatic reduction of azo food colourings . Food Cosmet. Toxicol. , 5 : 533
  • Daniel , J. W. 1962 . The excretion and metabolism of edible food colours . Toxic. Appl. Pharmacol. , 4 : 572
  • Dashwood , R. H. , Combes , R. D. and Ashby , J. 1986 . Limitation of in vitro assays for distinguishing between a carcinogen/non‐carcinogen pair of monoazo dyes . Food Chem. Toxicol. , 24 : 707
  • De Lemos , M. L. and Sugden , J. K. 1988 . Some aspects of the photochemical degradation of azo food dyes . Pharm. Acta Helv. , 63 : 176
  • Decad , G. M. and Snyder , C. D. 1983 . Fate of water‐insoluble and water‐soluble dichlorobenzidine‐based pigments in Fischer 344 rats . J. Toxicol. Environ. Health , 11 : 455
  • Dieckhues , B. 1960 . Untersuchungen zur reduktiven Spaltung der Azofarbstoffe durch Bakterien . Zen‐ tralbl. Bakteriol. Parasitenk, Infektionskr. Abt. 1 Orig. , 180 : 244
  • Dubin , P. and Wright , K. L. 1975 . Reduction of azo food dyes in cultures of . Proteus vulgaris, Xeno‐biotica , 5 : 563
  • Enslein , K. and Borgstedt , H. H. 1989 . A QSAR model for the estimation of carcinogenicity: example application to an azo‐dye . Toxicol. Lett. , 49 : 107
  • Field , F. E. , Roberts , G. , Hallowes , R. C. , Palmer , A. K. , Williams , K. E. and Lloyd , J. B. 1977 . Trypan Blue: identification and teratogenic and oncogenic activities of its coloured constituents . Chem.‐Biol. Interact. , 16 : 69
  • Flaminio , L. M. , Tragni , E. , De Giorgi , A. , Brusa , T. and Galli , C. L. 1988 . Reduction rate of 14C‐carmoisine by resting cell bacterial suspension from human and rat faeces . Pharmacol. Res. Common. , 20 : 907
  • Fore , H. , Walker , R. and Goldberg , L. 1967 . Studies on brown FK. II. Degradative changes undergone in vitro and in vivo . Food Cosmet. Toxicol. , 5 : 459
  • Fouts , J. R. , Kamm , J. J. and Brodie , B. B. 1957 . Enzymatic reduction of prontosil and other azo dyes . J. Pharm. Exp. Ther. , 120 : 291
  • Fuller , A. T. 1937 . Is p‐aminobenzenesulphonamide the active agent in prontosil therapy? . Lancet , 1 : 194
  • Garner , R. C. and Nutman , C. A. 1977 . Testing of some azo dyes and their reduction products for mutagenicity using Salmonella typhimurium TA 1538 . Mutat. Res. , 44 : 9
  • Gingell , R. and Bridges , J. W. 1973 . Intestinal azo‐reduction and glucuronide conjugation of prontosil . Xenobiotica , 3 : 599
  • Gingell , R. and Walker , R. 1971 . Mechanisms of azo reduction by Streptococcus faecalis. II. The role of soluble flavines . Xenobiotica , 1 : 231
  • Gingell , R. , Bridges , J. W. and Williams , R. T. 1969 . Gut flora and the metabolism of prontosils in the rat . Proc. Biochem. Soc. , 114 : 5
  • Haley , T. J. 1975 . Benzidine revisited: a review of the literature and problems associated with the use of benzidine and its congeners . Clin. Toxicol. , 8 : 13
  • Hartman , C. P. , Fulk , G. E. and Andrews , A. W. 1978 . Azo reduction of trypan blue to a known carcinogen by a cell‐free extract of a human intestinal anaerobe . Mutat. Res. , 58 : 125
  • Haveland‐Smith , R. B. and Combes , R. D. 1980 . Genotoxicity of the food colours Red 2G and Brown FK in bacterial systems; use of structurally‐related dyes and azo‐reduction . Food Cosmet. Toxicol. , 18 : 223
  • IARC, World Health Organization International Agency for Research on Cancer . 1982 . Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans , “Some Industrial Chemicals and Dyestuffs,” Vol. 29 , Lyon, , France
  • IARC, World Health Organization International Agency for Research on Cancer . 1975 . Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans Vol. 8 , Lyon, , France “Some Aromatic Azo Compounds,”
  • Idaka , E. , Horitsu , H. and Ogawa , T. 1987a . Some properties of azoreductases produced by Pseudomonas cepacia . Bull. Environ. Contam. Toxicol. , 39 : 982
  • Idaka , E. , Ogawa , T. and Horitsu , H. 1987b . Oxidative pathway after reduction of p‐aminoazobenzene by Pseudomonas cepacia . Bull. Environ. Contam. Toxicol. , 39 : 108
  • Idaka , E. , Ogawa , T. and Horitsu , H. 1987c . Reductive metabolism of aminoazobenzenes by Pseudomonas cepacia . Bull. Environ. Contam. Toxicol. , 39 : 100
  • Jones , R. , Ryan , A. J. and Wright , S. E. 1966 . The metabolism of some fat‐soluble phenylazopyra‐zolones in the rat . Food Cosmet. Toxicol. , 4 : 411
  • Jones , R. , Ryan , A. J. and Wright , S. E. 1964 . The metabolism and excretion of tartrazine in the rat, rabbit and man . Food. Cosmet. Toxicol. , 2 : 447
  • Kennelly , J. C. , Shaw , A. and Martin , C. N. 1984 . Reduction of benzidine is not necessary for the covalent binding of a benzidine azodye to rat liver DNA . Toxicology , 32 : 315
  • Kennelly , J. C. , Hertzog , P. J. and Martin , C. N. 1982 . The release of 4,4'‐diaminobiphenyls from azodyes in the rat . Carcinogenesis , 3 : 947
  • Khan , A. K. A. , Guthrie , G. , Johnston , H. H. , Truelove , S. C. and Williamson , D. H. 1983 . Tissue and bacterial splitting of sulfasalazine . Clin. Sci. , 64 : 349
  • Levine , W. G. and Raza , H. 1988 . Mechanism of azoreduction of dimethylaminoazobenzene by rat liver NADPH‐cytochrome P‐450 reductase and partially purified cytochrome P‐450. Oxygen and carbon monoxide sensitivity and stimulation by FAD and FMN . Drug Metab. Dispos. , 16 : 441
  • Levine , W. G. 1985 . Studies on microsomal azoreduction: N,N‐dimethyl‐4‐aminoazobenzene (DAB) and its derivatives . Biochem. Pharmacol. , 34 : 3259
  • Levine , W. G. and Lu , A. Y. H. 1982 . Role of isozymes of cytochrome p‐450 in the metabolism of N,N‐dimethyl‐4‐aminoazobenzene in the rat . Drug Metab. Dispos. , 10 : 102
  • Lindmark , D. G. and Muller , M. 1976 . Antitrichomonad action, mutagenicity and reduction of me‐troimidazole and other nitroimidazoles . Antimicrob. Agent. Chemother. , 10 : 476
  • Lynn , R. K. , Donielson , D. W. , Ilias , A. M. , Kennish , J. M. , Wong , K. and Matthews , H. B. 1980 . Metabolism of bisazobiphenyl dyes derived from benzidine, 3,3'‐dimethylbenzidine or 3,3'‐dimethoxybenzidine to carcinogenic aromatic amines in the dog and rat . Toxicol. Appl. Pharmacol. , 56 : 248
  • Mallett , A. K. , Bearne , C. A. and Rowland , I. R. 1986 . The use of continuous flow systems for studying the metabolic activity of the hindgut microflora in vitro . Food Chem. Toxicol. , 24 : 743
  • Mallett , A. K. , King , L. J. and Walker , R. 1985 . Solubilization, purification and reconstitution of hepatic microsomal azoreductase activity . Biochem. Pharmacol. , 2A : 337
  • Mallett , A. K. , King , L. J. and Walker , R. 1982 . A continuous spectrophotometric determination of hepatic microsomal azo reductase activity and its dependence on cytochrome P‐450 . Biochem. J. , 201 : 589
  • Martin , C. N. and Kennelly , J. C. 1981 . Rat liver microsomal azoreductase activity on four azo dyes derived from benzidine, 3,3'‐dimethylbenzidine or 3,3'‐dimethoxybenzidine . Carcinogenesis , 2 : 307
  • Martin , C. N. and Kennelly , J. C. 1985 . Metabolism, mutagenicity, and DNA binding of biphenyl‐ based azodyes . Drug Metab. Rev. , 16 : 89
  • Martin , C. N. , Beland , F. A. , Kennelly , J. C. and Kadlubar , F. F. 1983 . Binding of benzidine, N‐acetylbenzidine, N,N'‐diacetylbenzidine and direct blue 6 to rat liver DNA . Environ. Health Perspect. , 49 : 101
  • Martin , C. N. , Beland , F. A. , Roth , R. W. and Kadlubar , F. F. 1982 . Covalent binding of benzidine and N‐acetylbenzidine to DNA at the C‐8 atom of deoxyguanosine in vivo and in vitro . Cancer Res. , 42 : 2678
  • McCoy , G. D. , Rosenkranz , H. S. and Klopman , G. 1990 . Non‐mutagenic carcinogens are primarily hydrophobic . Carcinogenesis , 11 : 1111
  • Mori , Y. , Hori , T. and Toyoshi , K. 1978 . Analysis of biliary and urinary metabolites of 3'‐methyl‐4‐ (dimethylamino)azobenzene in rats . Gann , 69 : 757
  • Mueller , G. C. and Miller , J. A. 1950 . The reductive cleavage of 4‐dimethylaminoazobenzene by rat liver, reactivation of carbon dioxide‐treated homogenates by riboflavin‐adenine dinucleotide . J. Biol. Chem. , 185 : 145
  • Naik , M. S. and Nicholas , D. J. D. 1967 . Reduction of viologen dyes and a nonheme iron protein by NADH in particles from . Azotobacter vinelandii, Biochim. Biophys. Acta , 131 : 204
  • Nambara , S. and Yamaha , T. 1975 . Comparison of bacterial and microsomal azo‐ and nitro‐reductases . Yakugaku Zasshi , 95 : 1302
  • NIOSH‐NCI, National Institute for Occupational Safety and Health and National Cancer Institute . 1978 . “ Direct Black 38, Direct Blue 6 and Direct Brown 95 benzidine derived dyes ” . In Curr. Intelligence Bull. No. 24 , Cincinnati, OH : NIOSH .
  • Peppercorn , M. A. and Goldman , P. 1972 . The role of intestinal bacteria in the metabolism of salicy‐lazosulfapyridine . J. Pharmacol. Exp. Ther. , 181 : 555
  • Peterson , F. J. , Holtzman , J. L. , Crankshaw , D. and Mason , R. P. 1988 . Two sites of azo reduction in the monooxygenase system . Mol. Pharmacol. , 34 : 597
  • Radomski , J. L. and Harrow , L. S. 1966 . The metabolism of l‐(o‐tolylazo)‐2‐naphthylamine (Yellow OB) in rats . Ind. Med. Surg. , 35 : 882
  • Radomski , J. L. and Mellinger , T. J. 1962 . The absorption, fate and excretion in rats of the water soluble azo dyes, FD&C Red No. 2, FD&C Red No. 4 and FD&C Yellow No. 6 . J. Pharmacol. Exp. Ther. , 136 : 259
  • Rakmi , A. R. , Terashima , Y. and Ozaki , H. 1990 . Biodegradation of azo dye by an acclimated culture in a continuous process . Inst. Chem. Eng. Symp. Ser. , 116 : 301
  • Reid , T. M. , Wang , C. Y. , King , C. M. and Morton , K. C. 1984a . Mutagenicity of some benzidine congeners and their N‐acetylated and N,N'‐diacetylated derivatives in different strains of Sal‐monella typhimurium . Environ. Mutagen. , 6 : 145
  • Reid , T. M. , Morton , K. C. , Wang , C. Y. and King , C. M. 1984b . Mutagenicity of azo dyes following metabolism by different reductive/oxidative systems . Environ. Mutagen. , 6 : 705
  • Reid , T. M. , Morton , K. C. , Wang , C. Y. and King , C. M. 1983 . Conversion of Congo red and 2‐azoxyfluorene to mutagens following in vitro reduction by whole‐cell rat cecal bacteria . Mutat. Res. , 117 : 105
  • Rehn , L. 1895 . Blasengeschwulste bei Fuchsin Arbeitern . Arch. Klin. Chir. , 50 : 588
  • Renton , K. W. 1980 . Methyl red azo‐reductase and its induction by 3‐methylcholanthrene in the liver by different species . Xenobiotica , 10 : 243
  • Rinde , E. and Troll , W. 1975 . Metabolic reduction of benzidine azo dyes to benzidine in the rhesus monkey . J. Natl. Cancer Inst. , 55 : 181
  • Robens , J. F. , Dill , G. S. , Ward , J. M. , Joiner , J. R. , Griesemer , R. A. and Douglas , J. F. 1980 . Thirteen‐week subchronic toxicity studies of direct blue 6, direct black 38, direct brown 95 dyes . Toxicol. Appl. Pharmacol. , 54 : 431
  • Rosenkranz , H. S. and Klopman , G. 1990 . Structural alerts to genotoxicity: the interaction of human and artificial intelligence . Mutagenesis , 5 : 333
  • Roxon , J. J. , Ryan , A. J. and Wright , S. E. 1967a . Enzymatic reduction of tartrazine by Proteus vulgaris from rats . Food Cosmet. Toxicol. , 5 : 645
  • Roxon , J. J. , Ryan , A. J. and Wright , S. E. 1967b . Reduction of water‐soluble azo dyes by intestinal bacteria . Food Cosmet. Toxicol. , 5 : 367
  • Roxon , J. J. , Ryan , A. J. and Wright , S. E. 1966 . Reduction of tartrazine by a Proteus species isolated from rats . Food Cosmet. Toxicol. , 4 : 419
  • Ryan , A. J. and Wright , S. E. 1962 . Biliary excretion of some azo dyes related to tartrazine . Nature , 195 : 1009
  • Ryan , A. J. , Roxon , J. J. and Sivayavirojana , A. 1968 . Bacterial azo reduction: a metabolic reaction in mammals . Nature , 219 : 854
  • Scheline , R. R. , Nygaard , R. T. and Longberg , R. 1970 . Enzymatic reduction of the azo dye, acid yellow, by extracts of Streptococcus faecalis isolated from rat intestine . Food Cosmet. Toxicol. , 8 : 55
  • Scheline , R. R. and Longberg , B. 1965 . The absorption, metabolism and excretion of the sulphonated azo dye, acid yellow, by rats . Acta Pharmacol. Toxicol. , 23 : 1
  • Schroder , H. and Gustafsson , B. E. 1973 . Azo reduction of salicyl‐azo‐sulphapyridine in germ‐free and conventional rats . Xenobiotica , 3 : 225
  • Schroder , H. and Johansson , A. K. 1973 . Redox potential in caecal contents of the rat and azo reduction of salicyl‐azo‐sulphapyridine . Xenobiotica , 3 : 233
  • Shargel , L. , Banijamali , A. R. and Kuttab , S. H. 1984 . Relationship between azo dye structure and rat hepatic azoreductase activity . J. Pharm. Sci. , 73 : 161
  • Shargel , L. , Akov , S. and Mazel , P. 1972 . The reduction of nitro and azo compounds by housefly microsome . J. Agric. Food Chem. , 201 : 589
  • Sisley , P. and Porscher , C. 1911 . Du sort des matieres colorantes dans l'organisme animal, C. . R. Acad. Sci. Paris , 152 : 1062
  • Srinivasan , K. , Levine , W. G. and Bhargava , M. M. 1987 . Noncovalent binding of 3'‐methyl‐N,N‐ dimethyl‐4‐aminoazobenzene and its metabolites to liver cytosolic proteins and its role in their nuclear translocation . Drug Metab. Dispos. , 15 : 504
  • Stiborova , M. , Asfaw , B. , Anzenbacher , P. and Hodek , P. 1988a . A new way to carcinogenicity of azo dyes: the benzenediazonium ion formed from a non‐aminoazo dye, l‐phenylazo‐2‐hydroxy‐naphthalene (Sudan I) by microsomal enzymes binds to deoxyguanosine residues of DNA . Cancer Lett. , 40 : 327
  • Stiborova , M. , Asfaw , B. , Anzenbacher , P. , Leseticky , L. and Hodek , P. 1988b . The first identification of the benzenediazonium ion formation from a non‐aminoazo dye, l‐phenylazo‐2‐hydroxy‐naphthalene (Sudan I) by microsomes of rat livers . Cancer Lett. , 40 : 319
  • Trefouel , J. , Trefouel , J. , Nitti , F. and Bovet , D. 1935 . Activate du p‐aminophenylsulfamide sur les infections streptococciques. Experimentales de la souris et du lapin, C. . R. Seanc. Soc. Biol. , 120 : 756
  • Walker , R. 1970 . The metabolism of azo compounds: a review of the literature. . Food Cosmet. Toxicol. , 8 : 659
  • Walker , R. , Gingell , R. and Murrells , D. F. 1971 . Mechanisms of azo reduction by Streptococcus faecalis. I. Optimization of assay conditions . Xenobiotica , 1 : 221
  • Watabe , T. , Ozawa , N. and Kobayashi , F. 1980 . Reduction of sulphonated water‐soluble azo dyes by microorganisms from human faeces . Food Cosmet. Toxicol. , 18 : 349
  • Winton , D. J. , Flaks , B. and Flaks , A. 1988 . Quantitative electron microscopy of carcinogen‐induced alterations in hepatocyte rough endoplasmic reticulum. I. Chronic effect of 3'‐MeDAB and short‐term effects of azo dyes of different carcinogenic potentials . Carcinogenesis , 9 : 987
  • Yatome , C. , Ogawa , T. , Hayashi , H. and Ogawa , T. 1991 . Microbial reduction of azo dyes by several strains . J. Environ. Sci. Health , A26 : 471
  • Yoshida , O. and Miyakawa , M. 1973 . “ Etiology of bladder cancen metabolic aspects ” . In Analytical and Experimental Epidemiology of Cancer , Edited by: Nakahara , W. , Hirayoma , T. and Nishioka , K. 31 Baltimore : University Park Press .
  • Zbaida , S. and Levine , W. G. 1990 . Characteristics of two classes of azo dye reductase activity associated with rat liver microsomal cytochrome P‐450 . Biochem. Pharmacol. , 40 : 2415
  • Zbaida , S. , Stoddart , A. M. and Levine , W. G. 1989 . Studies on the mechanisms of reduction of azo dye carcinogens by rat liver microsomal cytochrome p‐450 . Chem.‐Biol. Interact. , 69 : 61
  • Zimmerman , T. , Gasser , F. , Kulla , H. G. and Leisinger , T. 1984 . Comparison of two bacterial azo‐reductases acquired during adaptation to growth on azo dyes . Zurich Arch. Microbiol. , 138 : 37
  • Zimmermann , T. , Kulla , H. G. and Leisinger , T. 1982 . Properties of purified orange II azoreductase, the enzyme initiating azo dye degradation by Pseudomonas KF46 . Eur. J. Biochem. , 129 : 197

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