The reduction of azo dyes by the intestinal microflora
Abstract
Azo dyes are widely used in the textile, printing, paper manufacturing, pharmaceutical, and food industries and also in research laboratories. When these compounds either inadvertently or by design enter the body through ingestion, they are metabolized to aromatic amines by intestinal microorganisms. Reductive enzymes in the liver can also catalyze the reductive cleavage of the azo linkage to produce aromatic amines. However, evidence indicates that the intestinal microbial azoreductase may be more important than the liver enzymes in azo reduction. In this article, we examine the significance of the capacity of intestinal bacteria to reduce azo dyes and the conditions of azo reduction. Many azo dyes, such as Acid Yellow, Amaranth, Azodisalicylate, Chicago Sky Blue, Congo Red, Direct Black 38, Direct Blue 6, Direct Blue 15, Direct Brown 95, Fast Yellow, Lithol Red, Methyl Orange, Methyl Red, Methyl Yellow, Naphthalene Fast Orange 2G, Neoprontosil, New Coccine, Orange II, Phenylazo-2-naphthol, Ponceau 3R, Ponceau SX, Red 2G, Red 10B, Salicylazosulphapyridine, Sunset Yellow, Tartrazine, and Trypan Blue, are included in this article. A wide variety of anaerobic bacteria isolated from caecal or fecal contents from experimental animals and humans have the ability to cleave the azo linkage(s) to produce aromatic amines. Azoreductase(s) catalyze these reactions and have been found to be oxygen sensitive and to require flavins for optimal activity. The azoreductase activity in a variety of intestinal preparations was affected by various dietary factors such as cellulose, proteins, fibers, antibiotics, or supplementation with live cultures of lactobacilli.
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Fibers, antibiotics, or supplementation with live cultures of lactobacilli can affect azoreductase enzyme activity.
“fibers, antibiotics, or supplementation with live cultures of lactobacilli were able to affect azoreductase enzyme activity (Chung et al., 1992)”
From Gut reactions: Breaking down xenobiotic–microbiome interactions (2019) · cites this paper as Chung et al., 1992
The metabolism of azo dyes to aromatic amines is carried out by azoreductases.
“The metabolism of azo dyes to aromatic amines is also carried out by azoreductases”
From Gut reactions: Breaking down xenobiotic–microbiome interactions (2019) · cites this paper as Chung et al., 1992
Cites
Mutagenicity of azo dyes: Structure-activity relationships
Chung, K., & Cerniglia, C. E. (1992) · Mutation Research/Reviews in Genetic Toxicology · doi:10.1016/0165-1110(92)90044-a · Cited by 493 · see citing works
Self-citationTHE ROLE OF INTESTINAL BACTERIA IN THE METABOLISM OF SALICYLAZOSULFAPYRIDINE
PEPPERCORN, M. A., & GOLDMAN, P. (1972) · The Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)29238-2 · Cited by 450 · see citing works
Disposition of quercetin in man after single oral and intravenous doses
Gugler, R., Leschik, M., & Dengler, H. J. (1975) · European Journal of Clinical Pharmacology · doi:10.1007/bf00614022 · Cited by 405 · see citing works
Microbial Degradation of Xenobiotics and Recalcitrant Compounds
(1983) · Food and Chemical Toxicology · doi:10.1016/0278-6915(83)90168-0 · Cited by 402 · see citing works
The Metabolic Activation of Carcinogenic Aromatic Amines and Amides1
MILLER, J. A., & Miller, E. C. (2015) · Progress in tumor research · doi:10.1159/000391399 · Cited by 342 · see citing works
Azoreductase activity of anaerobic bacteria isolated from human intestinal microflora
Rafii, F., Franklin, W., & Cerniglia, C. E. (1990) · Applied and Environmental Microbiology · doi:10.1128/aem.56.7.2146-2151.1990 · Cited by 340 · see citing works
Self-citationThe Relationship Between Diet and Rat Fecal Bacterial Enzymes Implicated in Colon Cancer 2 3
Goldin, B. R., & Gorbach, S. L. (1976) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/57.2.371 · Cited by 338 · see citing works
Kinsella, J. E. (1973) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(73)85288-9 · Cited by 326 · see citing works
Combes, R. D., & Haveland-Smith, R. B. (1982) · Mutation Research/Reviews in Genetic Toxicology · doi:10.1016/0165-1110(82)90015-x · Cited by 319 · see citing works
The significance of azo-reduction in the mutagenesis and carcinogenesis of azo dyes
Chung, K. (1983) · Mutation Research/Reviews in Genetic Toxicology · doi:10.1016/0165-1110(83)90035-0 · Cited by 312 · see citing works
Self-citationEffect of Diet and Lactobacillus acidophilus Supplements on Human Fecal Bacterial Enzymes23
Goldin, B. R., Swenson, L., Dwyer, J., Sexton, M., & Gorbach, S. L. (1980) · JNCI: Journal of the National Cancer Institute · doi:10.1093/jnci/64.2.255 · Cited by 286 · see citing works
Reduction of azo dyes by intestinal anaerobes
Chung, K., Fulk, G. E., & Egan, M. (1978) · Applied and Environmental Microbiology · doi:10.1128/aem.35.3.558-562.1978 · Cited by 271 · see citing works
Self-citationMarteau, P. R., Pochart, P., Flourié, B., Pellier, P., dos Santos, L., Desjeux, J. F., & Rambaud, J. C. (1990) · American Journal of Clinical Nutrition · doi:10.1093/ajcn/52.4.685 · Cited by 259 · see citing works
Distribution Studies of Salicylazosulfapyridine and its Metabolites
Peppercorn, M. A., & Goldman, P. (1973) · Gastroenterology · doi:10.1016/s0016-5085(73)80035-6 · Cited by 246 · see citing works
Mutagenicity testing of some commonly used dyes
Chung, K., Fulk, G. E., & Andrews, A. W. (1981) · Applied and Environmental Microbiology · doi:10.1128/aem.42.4.641-648.1981 · Cited by 242 · see citing works
Self-citationThe metabolism of azo compounds: a review of the literature
Walker, R. (1970) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(70)80455-2 · Cited by 226 · see citing works
Gastrointestinal Microflora in Mammalian Nutrition
Savage, D. C. (1986) · Annual Review of Nutrition · doi:10.1146/annurev.nu.06.070186.001103 · Cited by 195 · see citing works
Haley, T. J. (1975) · Clinical Toxicology · doi:10.3109/15563657508988044 · Cited by 175 · see citing works
Mechanisms of Azo Reduction byStreptococcus faecalisII. The Role of Soluble Flavins
Gingell, R., & Walker, R. (1971) · Xenobiotica · doi:10.3109/00498257109033172 · Cited by 160 · see citing works
Ecotoxicology of dyestuffs—A joint effort by industry
Anliker, R. (1979) · Ecotoxicology and Environmental Safety · doi:10.1016/0147-6513(79)90060-5 · Cited by 156 · see citing works
Reduction of Azo Food Dyes in Cultures ofProteus vulgaris
Dubin, P. L., & Wright, K. L. (1975) · Xenobiotica · doi:10.3109/00498257509056126 · Cited by 153 · see citing works
ENZYMATIC REDUCTION OF PRONTOSIL AND OTHER AZO DYES
Fouts, J. R., Kamm, J. J., & Brodie, B. B. (1957) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)23278-5 · Cited by 142 · see citing works
Lauritsen, K., Hansen, J. P. H., Ryde, M., & Rask-Madsen, J. (1984) · Gastroenterology · doi:10.1016/s0016-5085(84)80164-x · Cited by 140 · see citing works
Reduction of Polymeric Azo and Nitro Dyes by Intestinal Bacteria
BROWN, J. P. (1981) · Applied and Environmental Microbiology · doi:10.1128/aem.41.5.1283-1286.1981 · Cited by 136 · see citing works
Mueller, G. C., & MILLER, J. A. (1949) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)51226-1 · Cited by 135 · see citing works
Studies on the mechanism of action of mammalian hepatic azoreductase—I
Hernandez, P. H., Gillette, J. R., & Mazel, P. (1967) · Biochemical Pharmacology · doi:10.1016/0006-2952(67)90297-3 · Cited by 131 · see citing works
The excretion and metabolism of edible food colors
Daniel, J. W. (1962) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(62)90085-6 · Cited by 124 · see citing works
THE CARCINOGENICITY OF CERTAIN DERIVATIVES OF p-DIMETHYLAMINOAZOBENZENE IN THE RAT
MILLER, J. A., & Miller, E. C. (1948) · The Journal of Experimental Medicine · doi:10.1084/jem.87.2.139 · Cited by 120 · see citing works
Radomski, J. L., & Mellinger, T. J. (1962) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)26290-5 · Cited by 116 · see citing works
Chemical Induction of Cancer: Structural Bases and Biological Mechanisms
Arcos, J. C., & Argus, M. F. (2013) · Cited by 114 · see citing works
Goldin, B. R., & Gorbach, S. L. (1984) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/73.3.689 · Cited by 104 · see citing works
Kadlubar, F. F., MILLER, J. A., & Miller, E. C. (1976) · PubMed · Cited by 102 · see citing works
Cerniglia, C. E., Freeman, J. P., Franklin, W., & Pack, L. D. (1982) · Carcinogenesis · doi:10.1093/carcin/3.11.1255 · Cited by 95 · see citing works
Self-citationMueller, G. C., & MILLER, J. A. (1950) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)56402-4 · Cited by 93 · see citing works
Bonser, G. M., Bradshaw, L., Clayson, D. B., et al. (1956) · British Journal of Cancer · doi:10.1038/bjc.1956.63 · Cited by 93 · see citing works
Reduction of water-soluble azo dyes by intestinal bacteria
Roxon, J. J., & Ryan, A. J. (1967) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(67)83064-5 · Cited by 91 · see citing works
Hartman, C. P., Fulk, G. E., & Andrews, A. W. (1978) · Mutation Research/Genetic Toxicology · doi:10.1016/0165-1218(78)90001-0 · Cited by 90 · see citing works
The metabolism and excretion of tartrazine in the rat, rabbit and man
Jones, R. N., Ryan, A. J., & Wright, S. E. (1964) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(64)80287-x · Cited by 88 · see citing works
Enzymatic reduction of tartrazine by Proteus vulgaris from rats
Roxon, J. J., Ryan, A. J., & Wright, S. E. (1967) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(67)83216-4 · Cited by 88 · see citing works
Rat liver cytosolic azoreductase. Purification and characterization.
Huang, M., Miwa, G. T., & Lu, A. (1979) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)50676-1 · Cited by 83 · see citing works
In Situ Bacterial Metabolism and Colon Mutagens
Goldin, B. R. (1986) · Annual Review of Microbiology · doi:10.1146/annurev.mi.40.100186.002055 · Cited by 82 · see citing works
Metabolism of the benzidine-based azo dye Direct Black 38 by human intestinal microbiota
Manning, B. W., Cerniglia, C. E., & Federle, T. W. (1985) · Applied and Environmental Microbiology · doi:10.1128/aem.50.1.10-15.1985 · Cited by 78 · see citing works
Self-citationMILLER, J. A., Miller, E. C., & FINGER, G. C. (1957) · PubMed · Cited by 77 · see citing works
The Carcinogenicity of Certain Azo Dyes Related to p-Dimethylaminoazobenzene
Miller, J. A., & Baumann, C. A. (1945) · Cancer Research · Cited by 77 · see citing works
Huang, M., Miwa, G. T., Cronheim, N., et al. (1979) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)86473-6 · Cited by 76 · see citing works
BROWN, J. P., & Lamanna, C. (1977) · C R C Critical Reviews in Food Science and Nutrition · doi:10.1080/10408397709527224 · Cited by 74 · see citing works
Mutagenicity of azo dyes following metabolism by different reductive/oxidative systems
Reid, T. M., Morton, K. C., Wang, C. Y., et al. (1984) · Environmental Mutagenesis · doi:10.1002/em.2860060508 · Cited by 73 · see citing works
Reduction of tartrazine by a proteus species isolated from rats
Roxon, J. J., Ryan, A. J., & Wright, S. E. (1966) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(66)80583-7 · Cited by 73 · see citing works
Martin, C. N., & Kennelly, J. C. (1981) · Carcinogenesis · doi:10.1093/carcin/2.4.307 · Cited by 69 · see citing works
Robens, J. F., Dill, G. S., Ward, J. M., et al. (1980) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(80)90170-2 · Cited by 68 · see citing works
Mutagenic activation of the benzidine-based dye Direct Black 38 by human intestinal microflora
Cerniglia, C. E., Zhuo, Z., Manning, B. W., Federle, T. W., & Heflich, R. H. (1986) · Mutation Research Letters · doi:10.1016/0165-7992(86)90138-7 · Cited by 68 · see citing works
Self-citationA Preliminary Study Concerning the Possibility of Dietary Carcinogenesis
Willheim, R., & Ivy, A. C. (1953) · Gastroenterology · doi:10.1016/s0016-5085(53)80082-x · Cited by 65 · see citing works
Hydrocolloid food additives and rat caecal microbial enzyme activities
Mallett, A. K., Wise, A., & Rowland, I. R. (1984) · Food and Chemical Toxicology · doi:10.1016/0278-6915(84)90322-3 · Cited by 63 · see citing works
METABOLIC FATE OF FOOD COLORANTS
Parkinson, T. M., & BROWN, J. P. (1981) · Annual Review of Nutrition · doi:10.1146/annurev.nu.01.070181.001135 · Cited by 61 · see citing works
Cerniglia, C. E., Freeman, J. P., Franklin, W., & Pack, L. D. (1982) · Biochemical and Biophysical Research Communications · doi:10.1016/s0006-291x(82)80128-9 · Cited by 60 · see citing works
Self-citationEnzyme activities of the hindgut microflora of laboratory animals and man
Rowland, I. R., Mallett, A. K., Bearne, C. A., & Farthing, M. J. G. (1986) · Xenobiotica · doi:10.3109/00498258609043540 · Cited by 57 · see citing works
Teratology studies on food colourings. Part I. Embryotoxicity of amaranth (FD & C Red No. 2) in rats
Collins, T. F. X., & McLaughlin, J. K. (1972) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(72)80142-1 · Cited by 57 · see citing works
Formation of a mutagenic drug metabolite by intestinal microorganisms.
Batzinger, R. P., Bueding, E., Reddy, B. S., et al. (1978) · PubMed · Cited by 56 · see citing works
Prival, M. J., Davis, V. M., Peiperl, M. D., et al. (1988) · Mutation Research/Genetic Toxicology · doi:10.1016/0165-1218(88)90168-1 · Cited by 55 · see citing works
Mechanisms of Azo Reduction by StreptococcusfaecalisI. Optimization of Assay Conditions
Walker, R., Gingell, R., & Murrells, D. F. (1971) · Xenobiotica · doi:10.3109/00498257109033171 · Cited by 55 · see citing works
Rowland, I., Mallett, A. K., & Wise, A. (1983) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(83)90130-8 · Cited by 52 · see citing works
Kornbrust, D. J., & Barfknecht, T. R. (1984) · Mutation Research/Genetic Toxicology · doi:10.1016/0165-1218(84)90059-4 · Cited by 52 · see citing works
Tissue and Bacterial Splitting of Sulphasalazine
Khan, A., Guthrie, G., Johnston, H. H., et al. (1983) · Clinical Science · doi:10.1042/cs0640349 · Cited by 52 · see citing works
Metabolic profile of caecal micro-organisms from rats fed indigestible plant cell-wall components
Rowland, I. R., Wise, A., & Mallett, A. K. (1983) · Food and Chemical Toxicology · doi:10.1016/0278-6915(83)90264-8 · Cited by 51 · see citing works
Activation and inactivation of chemical carcinogens and mutagens in the mammal.
Pn, M. (1974) · PubMed · Cited by 50 · see citing works
The mutagenicity of methyl orange and metabolites produced by intestinal anaerobes
Chung, K., Fulk, G. E., & Andrews, A. W. (1978) · Mutation Research/Genetic Toxicology · doi:10.1016/0165-1218(78)90033-2 · Cited by 49 · see citing works
Self-citationAzo Reduction of Salicyl-Azo-Sulphapyridine in Germ-free and Conventional Rats
Schröder, H., & Gustafsson, B. E. (1973) · Xenobiotica · doi:10.3109/00498257309151518 · Cited by 48 · see citing works
The Absorption, Metabolism and Excretion of the Sulphonated Azo Dye, Acid Yellow, by Rats
Scheline, R. R., & Longberg, B. (1965) · Acta Pharmacologica et Toxicologica · doi:10.1111/j.1600-0773.1965.tb00344.x · Cited by 48 · see citing works
The influence of the gut microflora on food toxicity
Rowland, I. (1981) · Proceedings of The Nutrition Society · doi:10.1079/pns19810011 · Cited by 47 · see citing works
Scheline, R. R., Nygaard, R., & Longberg, B. (1970) · Food and Cosmetics Toxicology · doi:10.1016/s0015-6264(70)80223-1 · Cited by 45 · see citing works
Metabolic activity and enzyme induction in rat fecal microflora maintained in continuous culture
Mallett, A. K., Bearne, C. A., & Rowland, I. (1983) · Applied and Environmental Microbiology · doi:10.1128/aem.46.3.591-595.1983 · Cited by 44 · see citing works
Reduction of sulphonated water-soluble azo dyes by micro-organisms from human faeces
Watabe, T., Ozawa, N., Kobayashi, F., et al. (1980) · Food and Cosmetics Toxicology · doi:10.1016/0015-6264(80)90187-x · Cited by 44 · see citing works
Metabolism of Xenobiotics by Strains of Intestinal Bacteria
Soleim, H. A., & Scheline, R. R. (1972) · Acta Pharmacologica et Toxicologica · doi:10.1111/j.1600-0773.1972.tb03610.x · Cited by 43 · see citing works
Bacterial Azo Reduction: a Metabolic Reaction in Mammals
Ryan, A. J., Roxon, J. J., & SlVAYAVIROJANA, A. (1968) · Nature · doi:10.1038/219854a0 · Cited by 40 · see citing works
Metabolism of 6-nitrochrysene by intestinal microflora
Manning, B. W., Campbell, W. L., Franklin, W., Delclos, K. B., & Cerniglia, C. E. (1988) · Applied and Environmental Microbiology · doi:10.1128/aem.54.1.197-203.1988 · Cited by 37 · see citing works
Self-citationIntestinal Absorption of Polymeric Derivatives of the Food Dyes Sunset Yellow and Tartrazine in Rats
Honohan, T., Enderlin, F. E., Ryerson, B. A., et al. (1977) · Xenobiotica · doi:10.3109/00498257709038706 · Cited by 37 · see citing works
Mutagenicity of urinary metabolites of benzidine and benzidine-based azo dyes
Tanaka, K., Mii, T., Marui, S., et al. (1981) · International Archives of Occupational and Environmental Health · doi:10.1007/bf00377671 · Cited by 37 · see citing works
Diet and prevention of coronary heart disease and cancer
Zarins, C. K. (1987) · Journal of Vascular Surgery · doi:10.1016/0741-5214(87)90241-2 · Cited by 37 · see citing works
Activation of a procarcinogen to a mutagen by cell-free extracts of anaerobic bacteria
McCoy, E. C., Speck, W. T., & Rosenkranz, H. S. (1977) · Mutation Research/Environmental Mutagenesis and Related Subjects · doi:10.1016/0165-1161(77)90002-4 · Cited by 35 · see citing works
The release of 4,4′ -diaminobiphenyls from azodyes in the rat
Kennelly, J. C., Hertzog, P. J., & Martin, C. N. (1982) · Carcinogenesis · doi:10.1093/carcin/3.8.947 · Cited by 33 · see citing works
Production of a mutagen from ponceau 3R by a human intestinal anaerobe
Hartman, C. P., Andrews, A. W., & Chung, K. (1979) · Infection and Immunity · doi:10.1128/iai.23.3.686-689.1979 · Cited by 31 · see citing works
Self-citationSpecial occupational hazard review for benzidine-based dyes.
(1980) · doi:10.26616/nioshpub80109 · Cited by 30 · see citing works
Mallett, A. K., King, L. J., & Walker, R. (1982) · Biochemical Journal · doi:10.1042/bj2010589 · Cited by 29 · see citing works
Effect of dietary cellulose on the metabolic activity of the rat caecal microflora
Mallett, A. K., Wise, A., & Rowland, I. R. (1983) · Archives of Toxicology · doi:10.1007/bf00316499 · Cited by 28 · see citing works
(1974) · Elsevier eBooks · doi:10.1016/c2013-0-10298-x · Cited by 27 · see citing works
Collins, T. F. X., McLaughlin, J. K., & Gray, G. C. (1973) · Food and Cosmetics Toxicology · doi:10.1016/0015-6264(73)90001-1 · Cited by 24 · see citing works
Mallett, A. K., Rowland, I. R., Bearne, C. A., & Nicklin, S. (1985) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(85)90243-1 · Cited by 24 · see citing works
Trypan blue: Identification and teratogenic and oncogenic activities of its coloured constituents
Field, F. E., Roberts, G., Hallowes, R. C., et al. (1977) · Chemico-Biological Interactions · doi:10.1016/0009-2797(77)90154-5 · Cited by 24 · see citing works
Reduction of Sulphonated Water‐soluble Azo Dyes by Caecal Microorganisms from the Rat
Larsen, J. C., Meyer, T., & Scheline, R. R. (1976) · Acta Pharmacologica et Toxicologica · doi:10.1111/j.1600-0773.1976.tb03130.x · Cited by 24 · see citing works
Ishidate, M., Tamura, Z., & Samejima, K. (1963) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.11.1014 · Cited by 24 · see citing works
Metabolism by Intestinal Bacteria : The Effect of Bile Salts on Tartrazine Azo Reduction
Allan, R., & Roxon, J. J. (1974) · Xenobiotica · doi:10.1080/00498257409169766 · Cited by 23 · see citing works
A deficiency of dietary fiber may be one cause of certain colonic and venous disorders
Burkitt, D. P. (1976) · Digestive Diseases and Sciences · doi:10.1007/bf01072052 · Cited by 22 · see citing works
Role of isozymes of cytochrome P-450 in the metabolism of N,N-dimethyl-4-aminoazobenzene in the rat.
Levine, W. G., & Lu, A. (1982) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)07845-6 · Cited by 21 · see citing works
N-Hydroxylation enzymes of carcinogenic aminoazo dyes: possible involvement of cytochrome P-448.
Kimura, T., Kodama, M., & Nagata, C. (1982) · PubMed · Cited by 21 · see citing works
Manning, B. W., Federle, T. W., & Cerniglia, C. E. (1987) · Journal of Microbiological Methods · doi:10.1016/0167-7012(87)90056-x · Cited by 20 · see citing works
Self-citationComparative mutagenicity studies of AZO dyes and their reduction products insalmonella typhimurium
Krishna, G., Xu, J., & Nath, J. (1986) · Journal of Toxicology and Environmental Health · doi:10.1080/15287398609530852 · Cited by 20 · see citing works
Raza, H., & Levine, W. G. (1986) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)08269-8 · Cited by 20 · see citing works
Studies on microsomal azoreduction
Levine, W. G. (1985) · Biochemical Pharmacology · doi:10.1016/0006-2952(85)90343-0 · Cited by 19 · see citing works
Long-term effects of dietary amaranth in rats I. Effects on reproduction
Collins, T. F. X., Keeler, H. V., Black, T. N., et al. (1975) · Toxicology · doi:10.1016/0300-483x(75)90013-x · Cited by 19 · see citing works
The Potency of 20-Methylcholanthrene Relative to Other Carcinogens on Bladder Implantation
Bonser, G. M., Clayson, D. B., & Jull, J. W. (1963) · British Journal of Cancer · doi:10.1038/bjc.1963.33 · Cited by 19 · see citing works
Long-term effects of dietary amaranth rats II. Effects on fetal development
Collins, T. F. X., Black, T. N., & Ruggles, D. I. (1975) · Toxicology · doi:10.1016/0300-483x(75)90014-1 · Cited by 18 · see citing works
Dietary protein and cecal microbial metabolism in the rat
Wise, A., Mallett, A. K., & Rowland, I. (1982) · Nutrition and Cancer · doi:10.1080/01635588209513767 · Cited by 16 · see citing works
Dietary Effects on the Composition of Fecal Flora of Rats
Chung, K., Fulk, G. E., & Silverman, S. J. (1977) · Applied and Environmental Microbiology · doi:10.1128/aem.33.3.654-659.1977 · Cited by 15 · see citing works
Self-citationMori, Y., Niwa, T., Toyoshi, K., et al. (1983) · Mutation Research Letters · doi:10.1016/0165-7992(83)90106-9 · Cited by 14 · see citing works
Pieniaszek, H. J., & Bates, T. R. (1976) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(25)30587-2 · Cited by 13 · see citing works
Metabolism of 1‐, 3‐, and 6‐nitrobenzo[a]pyrene by intestinal microflora
Richardson, K. E., Fu, P. P., & Cerniglia, C. E. (1988) · Journal of Toxicology and Environmental Health · doi:10.1080/15287398809531134 · Cited by 13 · see citing works
Self-citationRelationship Between Azo Dye Structure and Rat Hepatic Azoreductase Activity
Shargel, L., Banijamali, A. R., & Kuttab, S. H. (1984) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600730206 · Cited by 11 · see citing works
Shargel, L., & Mazel, P. (1972) · Biochemical Pharmacology · doi:10.1016/0006-2952(72)90251-1 · Cited by 11 · see citing works
A case‐sar study of mammalian hepatic azoreduction
Nesnow, S., Bergman, H. B., Bryant, B. J., et al. (1988) · Journal of Toxicology and Environmental Health · doi:10.1080/15287398809531180 · Cited by 11 · see citing works
Protection from mutagenic effects of antischistosomal and other drugs.
Bueding, E., Batzinger, R. P., Cha, Y. N., et al. (1978) · Pharmacological Reviews · doi:10.1016/s0031-6997(25)06775-4 · Cited by 10 · see citing works
Metabolism of 1,8‐dinitropyrene by human, rhesus monkey, and rat intestinal microflora
Cerniglia, C. E., Lambert, K. J., White, G. L., et al. (1988) · Environmental Toxicology and Water Quality · doi:10.1002/tox.2540030206 · Cited by 8 · see citing works
Self-citationThe Effect of Dioctyl Sodium Sulphosuccinate on Tartrazine Azo reduction by Intestinal Bacteria
Allan, R., & Roxon, J. J. (1977) · Xenobiotica · doi:10.3109/00498257709036249 · Cited by 4 · see citing works
Gorelova, N. D., Dikun, P. P., Dmitročenko, A. P., et al. (1970) · Voprosy Pitaniya · Cited by 2 · see citing works
Kt, C., Ct, K., & Fj, C. (1989) · PubMed · Cited by 2 · see citing works
Allen, J. G. (1974) · Xenobiotica · doi:10.3109/00498257409052081 · Cited by 1 · see citing works
Goldin (1977) · doi:10.1002/1097-0142(197711)40:5+
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Tlaskalová-Hogenová, H., Štěpánková, R., Kozáková, H., Hudcovic, T., Vannucci, L., Tučková, L., Rossmann, P., Hrnčíř, T., Kverka, M., Zákostelská, Z., et al. (2011) · Cellular & Molecular Immunology · doi:10.1038/cmi.2010.67 · Cited by 693 · see citing works
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Crews, H., Alink, G., Andersen, R., Braesco, V., Holst, B., Maiani, G., Ovesen, L., Scotter, M., Solfrizzo, M., van den Berg, R., et al. (2001) · British Journal Of Nutrition · doi:10.1079/bjn2001337 · Cited by 99 · see citing works
Identification, Isolation and characterization of a novel azoreductase from Clostridium perfringens
Morrison, J. M., Wright, C. M., & John, G. H. (2012) · Anaerobe · doi:10.1016/j.anaerobe.2011.12.006 · Cited by 72 · see citing works
- Authors
- Chung, K.-T., Stevens, S. E., & Cerniglia, C. E.
- Affiliations
- University of Memphis (US)
- National Center for Toxicological Research (US)
- Venue
- Critical Reviews in Microbiology
- Publisher
- Informa UK Limited
- Published
- 1992-01
- Volume
- 18
- Issue
- 3
- Pages
- 175-190
- ISSN
- 1040-841X (ISSN-L)
- 1549-7828
- OpenAlex
- W2038991343
- Cited by
- 538
- References
- 116
- Citations by year
- 2026: 6 · 2025: 11 · 2024: 12 · 2023: 19 · 2022: 26 · 2021: 14 · 2020: 18 · 2019: 21 · 2018: 23 · 2017: 16 · 2016: 14 · 2015: 20 · 2014: 25 · 2013: 31 · 2012: 19
- FWCI
- 9.40
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Critical Reviews in Microbiology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Analytical Chemistry › Dye analysis and toxicity
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Keywords
- azo dyes, gut microbiota, azoreductase, aromatic amines, anaerobic bacteria, cecal microbiota, dietary factors, flavin cofactor, food dyes
- MeSH terms
- Animals, Azo Compounds, Bacteria, Diet, Coloring Agents, Humans, Intestines, Oxidation-Reduction, Molecular Structure
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
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