Summary: Very toxic industrial chemicals. They are absorbed through the skin, causing lethal blood, bladder, liver, and kidney damage and are potent, broad-spectrum carcinogens in most species.

Top Publications

  1. Josephy P, Eling T, Mason R. The horseradish peroxidase-catalyzed oxidation of 3,5,3',5'-tetramethylbenzidine. Free radical and charge-transfer complex intermediates. J Biol Chem. 1982;257:3669-75 pubmed
    ..A theoretical analysis of this redox system is presented, including a determination of the extinction coefficients and equilibrium constant for the nonradical species. ..
  2. Park J, Hisanaga N, Kim Y. Transfer of occupational health problems from a developed to a developing country: lessons from the Japan-South Korea experience. Am J Ind Med. 2009;52:625-32 pubmed publisher
    ..Corporate social responsibility should be emphasized, close inter-governmental collaboration is necessary and cooperation among non-governmental organizations is helpful. ..
  3. Kim Y, Park J, Shin Y. Dye-manufacturing workers and bladder cancer in South Korea. Arch Toxicol. 2007;81:381-4 pubmed
  4. Murata M, Kawanishi S. Mechanisms of oxidative DNA damage induced by carcinogenic arylamines. Front Biosci (Landmark Ed). 2011;16:1132-43 pubmed
    ..The oxidative DNA damage induced by arylamine compounds may participate in chemical carcinogenesis, in addition to DNA adduct formation. ..
  5. Song Y, Qu K, Zhao C, Ren J, Qu X. Graphene oxide: intrinsic peroxidase catalytic activity and its application to glucose detection. Adv Mater. 2010;22:2206-10 pubmed publisher
  6. Baan R, Straif K, Grosse Y, Secretan B, El Ghissassi F, Bouvard V, et al. Carcinogenicity of some aromatic amines, organic dyes, and related exposures. Lancet Oncol. 2008;9:322-3 pubmed publisher
  7. Luan Q, Gan N, Cao Y, Li T. Mimicking an Enzyme-Based Colorimetric Aptasensor for Antibiotic Residue Detection in Milk Combining Magnetic Loop-DNA Probes and CHA-Assisted Target Recycling Amplification. J Agric Food Chem. 2017;65:5731-5740 pubmed publisher
    ..2 pg mL-1 within 30 min. The assay can be conveniently extended for on-site screening of other antibiotics in foods by simply changing the base sequence of the probes. ..
  8. Lea M, Randolph V, Lee J, Desbordes C. Induction of histone acetylation in mouse erythroleukemia cells by some organosulfur compounds including allyl isothiocyanate. Int J Cancer. 2001;92:784-9 pubmed
    ..It was concluded that treatment of mouse erythroleukemia cells with allyl isothiocyanate can cause increased acetylation of histones but the mechanism for this effect requires further elucidation. ..
  9. Di J, Wu Y, Ma Y. A novel spectrophotometric determination of trace copper based on charge transfer complex. Spectrochim Acta A Mol Biomol Spectrosc. 2005;61:937-41 pubmed
    ..003-0.1 microg mL(-1), and the molar absorptivity at 660 nm is 2.54 x 10(5) L mol(-1) cm(-1). The proposed method was simple, selective, and sensitive. It was applied to the analytic samples with satisfactory results. ..

More Information


  1. Naumchik I, Karasyova E, Metelitza D, Edimecheva I, Sorokin V, Shadyro O. Inhibition of peroxidase-catalyzed oxidation of 3,3 ,5,5 -tetramethylbenzidine by aminophenols. Biochemistry (Mosc). 2005;70:322-9 pubmed
  2. Naito S, Tanaka K, Koga H, Kotoh S, Hirohata T, Kumazawa J. Cancer occurrence among dyestuff workers exposed to aromatic amines. A long term follow-up study. Cancer. 1995;76:1445-52 pubmed
    ..Although the occupational exposure to some aromatic amines is recognized to cause bladder carcinoma, the long term effect of such exposure on the risk for disease, including other malignant tumors, remains unknown...
  3. Adris P, López Estraño C, Chung K. The metabolic activation of 2-aminofluorine, 4-aminobiphenyl, and benzidine by cytochrome P-450-107S1 of Pseudomonas aeruginosa. Toxicol In Vitro. 2007;21:1663-71 pubmed
    ..The metabolic activation of tested procarcinogens is, therefore, carried out by CYP107S1 in P. aeruginosa. ..
  4. Choi J. Cytochemical demonstration of methanol-resistant peroxidase in eosinophils using a combined method of wright stain and benzidine base. Int J Hematol. 2002;76:379-80 pubmed
  5. Chen S, Nyman M. Influence of pH on sediment-associated sorption reactions of benzidine. Environ Toxicol Chem. 2009;28:1834-41 pubmed publisher
    ..g., from pH 3 to 7). This model strategy could provide an alternative way to predict the complex sorption processes of aromatic amines containing one or two amino groups in the aqueous-sediment environment. ..
  6. Krewinkel M, Dworeck T, Fioroni M. Engineering of an E. coli outer membrane protein FhuA with increased channel diameter. J Nanobiotechnology. 2011;9:33 pubmed publisher
    ..As large scale protein production is possible our approach can give a contribution to nanochannel industrial applications. ..
  7. Rahsepar A, Mirzaee A, Moodi F, Moohebati M, Tavallaie S, Khorashadizadeh F, et al. Prooxidant-antioxidant balance and cardiac function in patients with cardiovascular disease following cardiac surgery. J Heart Valve Dis. 2013;22:408-17 pubmed
    ..Levels of oxidative stress, as assessed by the PAB assay, were not significantly different for patients undergoing surgery with or without CPB. ..
  8. Ahn H, Moon H, Kodell R. Estimation of lag time between onset of and death from an occult tumor. J Biopharm Stat. 2008;18:901-14 pubmed publisher
    ..The proposed method is illustrated using a real data set. The accuracy of the estimation of lag time is evaluated via a Monte Carlo simulation study. This study shows that the estimated lag time is quite reliable. ..
  9. Heitzler C, Asbury L, Kusner S. Bringing "play" to life: the use of experiential marketing in the VERB campaign. Am J Prev Med. 2008;34:S188-93 pubmed publisher
  10. Cao Z, Jiang X, Meng W, Xie Q, Yang Q, Ma M, et al. An EQCM study on the interaction of heparin with the charge-transfer complex generated during o-tolidine electrooxidation: a biosensing mode with a dynamically renewed surface. Biosens Bioelectron. 2007;23:348-54 pubmed
  11. Tian J, Shen W. Printing enzymatic reactions. Chem Commun (Camb). 2011;47:1583-5 pubmed publisher
    ..These methods can create novel printing effects on commodity surfaces for advanced applications. ..
  12. Li H, Wang L, Zhai J, Zhang Y, Tian J, Sun X. Coordination polymer nanobelts as an effective sensing platform for fluorescence-enhanced nucleic acid detection. Macromol Rapid Commun. 2011;32:899-904 pubmed publisher
    ..The duplex cannot be adsorbed by CPN due to its rigid conformation and the absence of unpaired DNA bases, leading to an obvious fluorescence enhancement. ..
  13. Sills R, Hailey J, Neal J, Boorman G, Haseman J, Melnick R. Examination of low-incidence brain tumor responses in F344 rats following chemical exposures in National Toxicology Program carcinogenicity studies. Toxicol Pathol. 1999;27:589-99 pubmed
  14. Chroni S, Ghanotakis D. Accessibility of tyrosine Y(.)(Z) to exogenous reductants and Mn(2+) in various Photosystem II preparations. Biochim Biophys Acta. 2001;1504:432-7 pubmed
    ..Z) to exogenous reductants, such as benzidine. In addition, it was shown that in the presence of the native Mn complex exogenous Mn(2+) does not reduce Y(.)(Z). ..
  15. Matsunaga I, Sumimoto T, Ayata M, Ogura H. Functional modulation of a peroxygenase cytochrome P450: novel insight into the mechanisms of peroxygenase and peroxidase enzymes. FEBS Lett. 2002;528:90-4 pubmed
    ..These results suggest that there are critical structural elements at the distal active site which determine whether this enzyme acts as a peroxygenase or a peroxidase. ..
  16. Muneer M, Singh H, Bahnemann D. Semiconductor-mediated photocatalysed degradation of two selected priority organic pollutants, benzidine and 1,2-diphenylhydrazine, in aqueous suspension. Chemosphere. 2002;49:193-203 pubmed
    ..4-amino-biphenyl (7) and hydroquinone (13) were identified as intermediate products by GC/MS technique and probable pathways for the formation of the products are proposed. ..
  17. Bamberger C, Else T, Bamberger A, Frilling A, Beil F, Allolio B, et al. Telomerase activity in benign and malignant adrenal tumors. Exp Clin Endocrinol Diabetes. 1999;107:272-5 pubmed
    ..These data indicate that telomerase activity may not be a suitable marker for malignancy in the adrenal gland. Our results also challenge the current dogma of close correlation between cell dedifferentiation and telomerase activity. ..
  18. Metelitza D, Arapova G, Eryomin A, Losev Y. Intramolecular synergism of the inhibiting action of polydisulfide antioxidants in the system ferritin--H2O2--tetramethylbenzidine. Biochemistry (Mosc). 1999;64:1200-9 pubmed
  19. Fischer U, Ototake M, Nakanishi T. In vitro cell-mediated cytotoxicity against allogeneic erythrocytes in ginbuna crucian carp and goldfish using a non-radioactive assay. Dev Comp Immunol. 1998;22:195-206 pubmed
    ..These studies support the hypothesis that fish are capable of a genetically restricted specific cell-mediated cytotoxicity. ..
  20. Ching Chen S, Hseu Y, Sung J, Chen C, Chen L, Chung K. Induction of DNA damage signaling genes in benzidine-treated HepG2 cells. Environ Mol Mutagen. 2011;52:664-72 pubmed publisher
    ..Collectively, DNA damage response genes induced by benzidine indicate recruitment complex molecular machinery involved in DNA repair, cell-cycle arrest, and potentially, activation of the apoptosis. ..
  21. Karaseva E, Losev I, Metelitsa D. [Inhibition of peroxidase oxidation of 3,3',5,5'-tetramethylbenzidine and o-phenylenediamine by 1-amino-2-naphthol-4-sulfonic acid and its polysulfide]. Prikl Biokhim Mikrobiol. 2001;37:713-21 pubmed
    ..The degree of PhDA inhibition was maximal in acid media, reached minimum at pH 5 to 6, and than again increased at pH above 6. Tentative mechanism of coupled aromatic amine phenol bi-substrate system peroxidation is discussed. ..
  22. Zhang L, Zhu J, Li T, Wang E. Bifunctional colorimetric oligonucleotide probe based on a G-quadruplex DNAzyme molecular beacon. Anal Chem. 2011;83:8871-6 pubmed publisher
    ..This results in a decrease of catalytic activity, enabling the separate analysis of DNA and thrombin. ..
  23. Li D, Zhang Z, Liu L. [Fluorescence development of blood fingerprint]. Guang Pu Xue Yu Guang Pu Fen Xi. 2001;21:676-9 pubmed
    ..The method, main characteristics and developing effect of blood stain activation and protein decoration for developing blood fingerprint were explained. ..
  24. Refat M, Saad H, Adam A. Intermolecular hydrogen bond complexes by in situ charge transfer complexation of o-tolidine with picric and chloranilic acids. Spectrochim Acta A Mol Biomol Spectrosc. 2011;79:672-9 pubmed publisher
    ..The thermodynamic parameters were estimated from the differential thermogravimetric curves. The results indicated that the formation of molecular charge transfer complexes is spontaneous and endothermic. ..
  25. Long Y, Li Y, Liu Y, Zheng J, Tang J, Huang C. Visual observation of the mercury-stimulated peroxidase mimetic activity of gold nanoparticles. Chem Commun (Camb). 2011;47:11939-41 pubmed publisher
    ..Mercury-stimulated peroxidase mimetic activity of gold nanoparticles was presented, with which a sensitive label-free colorimetric method for Hg(2+) was developed. ..
  26. Huy N, Xuan Trang D, Uyen D, Sasai M, Harada S, Kamei K. An improved colorimetric method for quantitation of heme using tetramethylbenzidine as substrate. Anal Biochem. 2005;344:289-91 pubmed
  27. Harigae H, Suwabe N, Weinstock P, Nagai M, Fujita H, Yamamoto M, et al. Deficient heme and globin synthesis in embryonic stem cells lacking the erythroid-specific delta-aminolevulinate synthase gene. Blood. 1998;91:798-805 pubmed
    ..These results were confirmed using another ES differentiation system in vitro and suggest that ALAS-E expression, hence heme supply, is critical for the late stage of erythroid cell differentiation, which involves hemoglobin synthesis. ..
  28. Lin G, Guo W, Chen J, Qin Y, Golka K, Xiang C, et al. An association of UDP-glucuronosyltransferase 2B7 C802T (His268Tyr) polymorphism with bladder cancer in benzidine-exposed workers in China. Toxicol Sci. 2005;85:502-6 pubmed
  29. El Sayed R, Ye F, Asem H, Ashour R, Zheng W, Muhammed M, et al. Importance of the surface chemistry of nanoparticles on peroxidase-like activity. Biochem Biophys Res Commun. 2017;491:15-18 pubmed publisher
    ..The great impact of nanoparticle surface properties on catalytic reactions makes a paradigm in constructing nanozymes as peroxidase mimic for sensing application. ..
  30. Arapova G, Eryomin A, Metelitza D. Peroxidase activity of ferritin in aerosol OT reversed micelles in heptane. Biochemistry (Mosc). 1998;63:1191-9 pubmed
    ..A method of purification of iron-containing crystallite from the ferritin molecule was developed using reversed AOT micelles in heptane and heating the mixture on a water bath. ..
  31. Forbes L, Furtmüller P, Khalilova I, Turner R, Obinger C, Kettle A. Isoniazid as a substrate and inhibitor of myeloperoxidase: identification of amine adducts and the influence of superoxide dismutase on their formation. Biochem Pharmacol. 2012;84:949-60 pubmed publisher
  32. Carreon T, LeMasters G, Ruder A, Schulte P. The genetic and environmental factors involved in benzidine metabolism and bladder carcinogenesis in exposed workers. Front Biosci. 2006;11:2889-902 pubmed
    ..Additional studies and pooled analyses of existing data are needed to establish if individuals are at higher risk of bladder cancer given the presence of certain alleles that make them more susceptible to this disease. ..
  33. Zenser T, Lakshmi V, Hsu F, Davis B. Peroxygenase metabolism of N-acetylbenzidine by prostaglandin H synthase. Formation of an N-hydroxylamine. J Biol Chem. 1999;274:14850-6 pubmed
    ..Results demonstrate a peroxygenase oxidation of ABZ and N'HA by PHS and suggest a stepwise oxidation of ABZ to N'-hydroxy, 4'-nitroso, and 4'-nitro products. ..
  34. Le Goff G, Blum L, Marquette C. Enhanced colorimetric detection on porous microarrays using in situ substrate production. Anal Chem. 2011;83:3610-5 pubmed publisher
    ..The background lowering was impacted here positively on the SNPs' detection by increasing the complementary/noncomplementary signal ratio. ..
  35. Kawarai S, Masuda K, Ohmori K, Matsuura S, Yasuda N, Nagata M, et al. Cultivation and characterization of canine skin-derived mast cells. J Vet Med Sci. 2010;72:131-40 pubmed
    ..The culture system for canine SMCs developed in this study would be useful in understanding the pathophysiology and developing anti-allergic therapeutics in canine allergic dermatitis. ..
  36. Zheng A, Cong Z, Wang J, Li J, Yang H, Chen G. Highly-efficient peroxidase-like catalytic activity of graphene dots for biosensing. Biosens Bioelectron. 2013;49:519-24 pubmed publisher
    ..Due to their high catalytic activity, high diffusion and excellent biocompatibility, GDs can be expected to be applied in various fields, such as biotechnology, medical diagnostics and environmental monitoring. ..
  37. Xue Z, Wang X, Rao H, Liu X, Lu X. A colorimetric sensor of cysteine based on self-assembly nanostructures of Fe3+-H2O2/Tetramethylbenzidine system with "On-Off" switching function. Anal Biochem. 2017;534:1-9 pubmed publisher
  38. Körzdörfer T, Tretiak S, Kummel S. Fluorescence quenching in an organic donor-acceptor dyad: a first principles study. J Chem Phys. 2009;131:034310 pubmed publisher
    ..The conformational dynamics of the bridged system leads to a charge transfer process between donor and acceptor that causes the acceptor fluorescence quenching. ..
  39. Tontarski K, Hoskins K, Watkins T, Brun Conti L, Michaud A. Chemical enhancement techniques of bloodstain patterns and DNA recovery after fire exposure. J Forensic Sci. 2009;54:37-48 pubmed publisher
    ..Therefore, it is recommended that both methods be used. For the most part, the recovered DNA seemed to be unaffected by the heat, until the temperature was 800 degrees C or greater. At this temperature, no DNA profiles were obtained. ..
  40. El Shafei A, Boyle P, Hinks D, Freeman H. Non-mutagenic organic pigment intermediates. I. 3,3'-dipropoxybenzidine. Acta Crystallogr C. 2003;59:o71-3 pubmed
    ..The molecule resides on a crystallographic inversion center and the biphenyl moiety is essentially planar. The structure forms an infinite two-dimensional array of N-H.pi(arene) interactions parallel to the (101) direction. ..
  41. Ju Y, Plewa M. Mutant spectra analysis at hisG46 in Salmonella typhimurium strain YG1029 induced by mammalian S9- and plant-activated aromatic amines. Teratog Carcinog Mutagen. 2003;Suppl 1:47-60 pubmed
    ..These data show that the plant-activated and mammalian-activated aromatic amine products inflicted different types or distributions of DNA lesions that were reflected in the resulting induced mutant spectra. ..
  42. Adris P, Chung K. Metabolic activation of bladder procarcinogens, 2-aminofluorene, 4-aminobiphenyl, and benzidine by Pseudomonas aeruginosa and other human endogenous bacteria. Toxicol In Vitro. 2006;20:367-74 pubmed
    ..For those organisms that induced metabolic activation but did not show a P450 absorption peak with the cell-free extracts, other oxidative enzymes may be involved. ..
  43. Chen X, Chen Y, Shen Z. A competitive ELISA for albumin in rat urine. J Immunoassay Immunochem. 2004;25:81-9 pubmed
    ..Since quantifying urinary albumin was very important in the experimental study of diabetic nephropathy, the results from our experiments indicated that this competitive ELISA could be used for quantification of rat urinary albumin. ..
  44. de Almeida J, Glesse N, Bonorino C. Effect of presumptive tests reagents on human blood confirmatory tests and DNA analysis using real time polymerase chain reaction. Forensic Sci Int. 2011;206:58-61 pubmed publisher
    ..Luminol 16(®) caused DNA degradation already at 30 days post-application. At 120 days post treatment, all samples treated with any of the agents but not untreated samples had DNA degradation. ..
  45. Hu J, Kulkarni A. Metabolic fate of chemical mixtures. I. "Shuttle Oxidant" effect of lipoxygenase-generated radical of chlorpromazine and related phenothiazines on the oxidation of benzidine and other xenobiotics. Teratog Carcinog Mutagen. 2000;20:195-208 pubmed
    ..Although the toxicological significance of these in vitro findings remains to be established, it is worth pondering whether such a synergistic interaction occurs in humans in vivo. Teratogenesis Carcinog. Mutagen. 20:195-208, 2000...
  46. Saha S, Mistri R, Ray B. Rapid and sensitive method for simultaneous determination of six carcinogenic aromatic amines in mainstream cigarette smoke by liquid chromatography/electrospray ionization tandem mass spectrometry. J Chromatogr A. 2009;1216:3059-63 pubmed publisher
    ..The method showed excellent reproducibility and was also rapid, selective and robust for aromatic amine determination from cigarette smoke. ..
  47. Shi W, Wang Q, Long Y, Cheng Z, Chen S, Zheng H, et al. Carbon nanodots as peroxidase mimetics and their applications to glucose detection. Chem Commun (Camb). 2011;47:6695-7 pubmed publisher
    ..This offers a simple, sensitive and selective colorimetric method for glucose determination in serum. ..
  48. Bafana A, Chakrabarti T, Muthal P, Kanade G. Detoxification of benzidine-based azo dye by E. gallinarum: time-course study. Ecotoxicol Environ Saf. 2009;72:960-4 pubmed publisher
    ..Further degradation of benzidine and 4-ABP was found to result in the decrease in toxicity and mutagenicity. ..
  49. Ulland B, Maronpot R, Lemen J, Mennear J. Transplantation studies of preputial gland and epithelial skin neoplasms derived from benzidine-based dye carcinogenicity assays in Fischer 344 male rats. Toxicol Pathol. 1989;17:50-6 pubmed
    ..Metastases from transplants were observed with both preputial gland and skin tumor lines in serial passages. The transplantation results confirm the malignant nature of these neoplasms. ..
  50. Su L, Feng J, Zhou X, Ren C, Li H, Chen X. Colorimetric detection of urine glucose based ZnFe2O4 magnetic nanoparticles. Anal Chem. 2012;84:5753-8 pubmed publisher
    ..0 × 10(-7) mol L(-1). The color change observable by the naked eyes based on the oxidation of 3,3',5,5'-tetramethylbenzidine (TMB) is the principle for the sensing of urine glucose level. ..
  51. Chung K, Adris P. Growth inhibition of intestinal bacteria and mutagenicity of 2-, 3-, 4-aminobiphenyls, benzidine, and biphenyl. Toxicol In Vitro. 2003;17:145-52 pubmed
    ..Evidence suggested that the mechanism of growth inhibition is not involved with the interaction of DNA that causes mutations, but rather on the electron transport system of these organisms. ..
  52. Puvaneswari N, Muthukrishnan J, Gunasekaran P. Biodegradation of benzidine based azodyes Direct red and Direct blue by the immobilized cells of Pseudomonas fluorescens D41. Indian J Exp Biol. 2002;40:1131-6 pubmed
    ..Immobilized cells of P. fluorescens D41 efficiently degraded Direct red (82%) and Direct blue (71%) in the presence of glucose. ..
  53. Shrivastav T, Basu A, Kariya K. One step enzyme linked immunosorbent assay for direct estimation of serum testosterone. J Immunoassay Immunochem. 2003;24:205-17 pubmed
    ..8 to 11.8 and 4.8 to 10.4, respectively. The serum testosterone values, obtained by this method, were correlated well with those obtained by radioimmunoassay r = .98 (n = 100). ..