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Chemical Compound Review

Benzidin     4-(4-aminophenyl)aniline

Synonyms: BENZIDINE, Bensidine, Benzidina, Benzioine, Benzydyna, ...
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Disease relevance of Benzydyna

  • Clones of Friend erythroleukemia cells, characterized by the presence of 40-70% benzidine-positive cells synthesizing hemoglobin in the absence of inducing drugs, were treated with several phorbol diesters with a known range of tumor-promoting activity on mouse skin [1].
  • Depending upon experimental conditions, benzidine treatment effected development of liver tumors, lung adenomas [2].
  • In addition, benzidine exposure was found to decrease host resistance, including resistance to the growth of transplantable tumor cells and infection with Listeria [3].
  • Prostaglandin H synthase supports the activation of benzidine to a mutagenic species in the Ames (Salmonella typhimurium) test, and our studies of the mechanism of this activation are described [4].
  • The correlation between DNA adducts and chromosomal aberrations in the target organ of benzidine exposed, partially-hepatectomized mice [5].

High impact information on Benzydyna

  • A factor from conditioned medium of a leukaemia cell line has been isolated which can induce mouse Friend cells to become benzidine-positive, and which shares a similar N-terminal sequence with porcine FRP [6].
  • Risk of bladder tumors among benzidine workers and their serum properdin levels [7].
  • IS cells did not have the character of erythroid cells: They did not contain detectable heme as measured by benzidine-peroxide reagent, did not contain globin mRNA in detectable amounts, and did not produce erythroid colonies in plasma culture in the absence or presence of erythropoietin [8].
  • Suppression of K562 growth was accompanied by increased spontaneous erythroid differentiation as measured by benzidine staining [9].
  • The impact of interindividual variation in NAT2 activity on benzidine urinary metabolites and urothelial DNA adducts in exposed workers [10].

Chemical compound and disease context of Benzydyna


Biological context of Benzydyna

  • This is shown by decrease in cell size, appearance of red and benzidine positive cells, and induced synthesis of four out of six adult globin chains [16].
  • The hybrid cells were examined for globin gene expression by benzidine staining to detect cytoplasmic hemoglobin, and by molecular hybridization of cellular RNA to globin complementary DNA (cDNA) to detect globin messenger RNA (MRNA) [17].
  • Embryos stain weakly with benzidine reagent, and yolk sac cells express globin RNAs, indicating globin gene activation in the absence of GATA-1 [18].
  • Daily after plating, hemoglobin content was scored by benzidine staining, and growth was assessed by estimating the cell number per colony [19].
  • The failure of metalloporphyrins other than hemin to stimulate the transient expression of a CAT reporter gene linked to an enhancer element containing a binding site for NF-E2 was correlated with their failure to induce benzidine-positive K562 cells and increase the steady-state level of gamma-globin mRNA [20].

Anatomical context of Benzydyna


Associations of Benzydyna with other chemical compounds


Gene context of Benzydyna

  • Furthermore, in the presence of Epo, SCF (5 to 25 ng/mL) enhanced MB-02 proliferation in a dose-dependent manner, and increased the relative and absolute number of benzidine-positive cells generated [30].
  • NAT2 slow acetylation and bladder cancer in workers exposed to benzidine [31].
  • GSTP1 A1578G (Ile105Val) polymorphism in benzidine-exposed workers: an association with cytological grading of exfoliated urothelial cells [32].
  • When K562 cells overexpressing CPOX were treated with delta-aminolevulinic acid (ALA), most became benzidine-positive without induction of the expression of CPOX or ferrochelatase, and the heme content was about twofold higher than that in ALA-treated control cells [33].
  • Analysis of the TGF beta 1 effect on 10 different HEL-T-derived clones revealed that the number of benzidine-positive cells ranged from 12 to 70% after 5 days of continuous exposure [34].

Analytical, diagnostic and therapeutic context of Benzydyna


  1. Tumor promoters inhibit spontaneous differentiation of Friend erythroleukemia cells in culture. Rovera, G., O'Brien, T.G., Diamond, L. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  2. Factors modulating benzidine carcinogenicity bioassay. Vesselinovitch, S.D., Rao, K.V., Mihailovich, N. Cancer Res. (1975) [Pubmed]
  3. Immunosuppressive effects of benzidine in mice: evidence of alterations in arachidonic acid metabolism. Luster, M.I., Tucker, A.N., Hayes, H.T., Pung, O.J., Burka, T., McMillan, R., Eling, T. J. Immunol. (1985) [Pubmed]
  4. Activation of aromatic amines by prostaglandin H synthase. Josephy, P.D. Free Radic. Biol. Med. (1989) [Pubmed]
  5. The correlation between DNA adducts and chromosomal aberrations in the target organ of benzidine exposed, partially-hepatectomized mice. Talaska, G., Au, W.W., Ward, J.B., Randerath, K., Legator, M.S. Carcinogenesis (1987) [Pubmed]
  6. Importance of FSH-releasing protein and inhibin in erythrodifferentiation. Yu, J., Shao, L.E., Lemas, V., Yu, A.L., Vaughan, J., Rivier, J., Vale, W. Nature (1987) [Pubmed]
  7. Risk of bladder tumors among benzidine workers and their serum properdin levels. Horton, A.W., Bingham, E.L. J. Natl. Cancer Inst. (1977) [Pubmed]
  8. Friend spleen focus-forming virus production in vitro by a nonerythroid cell line. Clarke, B.J., Axelrad, A.A., Housman, D. J. Natl. Cancer Inst. (1976) [Pubmed]
  9. Antisense SCL suppresses self-renewal and enhances spontaneous erythroid differentiation of the human leukaemic cell line K562. Green, A.R., DeLuca, E., Begley, C.G. EMBO J. (1991) [Pubmed]
  10. The impact of interindividual variation in NAT2 activity on benzidine urinary metabolites and urothelial DNA adducts in exposed workers. Rothman, N., Bhatnagar, V.K., Hayes, R.B., Zenser, T.V., Kashyap, S.K., Butler, M.A., Bell, D.A., Lakshmi, V., Jaeger, M., Kashyap, R., Hirvonen, A., Schulte, P.A., Dosemeci, M., Hsu, F., Parikh, D.J., Davis, B.B., Talaska, G. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  11. Comparative activity of 4,4'-diaminobiphenyl (benzidine) and its terphenyl analogue, 4,4'-diaminoterphenyl, in two in vitro assays for potential carcinogenicity. Ashby, J., Styles, J., Callander, R.D. Carcinogenesis (1980) [Pubmed]
  12. Dapsone decreases the cumulative incidence of diabetes in non-obese diabetic female mice. Peterson, K.P., Van Hirtum, M., Peterson, C.M. Proc. Soc. Exp. Biol. Med. (1997) [Pubmed]
  13. Mutagenicity of selected sulfonated azo dyes in the Salmonella/microsome assay: use of aerobic and anaerobic activation procedures. Brown, J.P., Dietrich, P.S. Mutat. Res. (1983) [Pubmed]
  14. Comparative activation of 3,3'-dichlorobenzidine and related benzidines to mutagens in the Salmonella typhimurium assay by hepatic S9 and microsomes from rats pretreated with different inducers of cytochrome P-450. Iba, M.M. Mutat. Res. (1987) [Pubmed]
  15. Mutagenicity of benzidine and benzidine-congener dyes and selected monoazo dyes in a modified Salmonella assay. Prival, M.J., Bell, S.J., Mitchell, V.D., Peiperl, M.D., Vaughan, V.L. Mutat. Res. (1984) [Pubmed]
  16. Dimethylsulfoxide-induced differentiation and hemoglobin synthesis in tissue cultures of rat erythroleukemia cells transformed by 7,12-dimethylbenz(a)anthracene. Kluge, N., Ostertag, W., Sugiyama, T., Arndt-Jovin, D., Steinheider, G., Furusawa, M., Dube, S.K. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  17. Hemoglobin synthesis in somatic cell hybrids: globin gene expression in hybrids between mouse erythroleukemia and human marrow cells or fibroblasts. Deisseroth, A., Burk, R., Picciano, D., Anderson, W.F., Nienhuis, A., Minna, J. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  18. Arrested development of embryonic red cell precursors in mouse embryos lacking transcription factor GATA-1. Fujiwara, Y., Browne, C.P., Cunniff, K., Goff, S.C., Orkin, S.H. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  19. K562 human erythroleukemia cells demonstrate commitment. Rowley, P.T., Ohlsson-Wilhelm, B.M., Farley, B.A. Blood (1985) [Pubmed]
  20. Iron protoporphyrin IX (hemin) but not tin or zinc protoporphyrin IX can stimulate gene expression in K562 cells from enhancer elements containing binding sites for NF-E2. Palma, J.F., Gao, X., Lin, C.H., Wu, S., Solomon, W.B. Blood (1994) [Pubmed]
  21. Use of human peripheral blood lymphocytes to measure DNA binding capacity of chemical carcinogens. Gupta, R.C., Earley, K., Sharma, S. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  22. Spleen stromal cell lines selectively support erythroid colony formation. Yanai, N., Matsuya, Y., Obinata, M. Blood (1989) [Pubmed]
  23. Initiation of hematopoiesis and vasculogenesis in murine yolk sac explants. Palis, J., McGrath, K.E., Kingsley, P.D. Blood (1995) [Pubmed]
  24. Benzidine binding to nucleic acids mediated by the peroxidative activity of prostaglandin endoperoxide synthetase. Zenser, T.V., Mattammal, M.B., Armbrecht, H.J., Davis, B.B. Cancer Res. (1980) [Pubmed]
  25. Arachidonic acid-dependent peroxidative activation of carcinogenic arylamines by extrahepatic human tissue microsomes. Flammang, T.J., Yamazoe, Y., Benson, R.W., Roberts, D.W., Potter, D.W., Chu, D.Z., Lang, N.P., Kadlubar, F.F. Cancer Res. (1989) [Pubmed]
  26. Synthesis of adult-type hemoglobin in human erythremia cell line. Kaku, M., Yagawa, K., Nakamura, K., Okano, H. Blood (1984) [Pubmed]
  27. Induction of erythropoietic colonies in a human chronic myelogenous leukemia cell line. Hoffman, R., Murnane, M.J., Benz, E.J., Prohaska, R., Floyd, V., Dainiak, N., Forget, B.G., Furthmayr, H. Blood (1979) [Pubmed]
  28. Human N-acetylation of benzidine: role of NAT1 and NAT2. Zenser, T.V., Lakshmi, V.M., Rustan, T.D., Doll, M.A., Deitz, A.C., Davis, B.B., Hein, D.W. Cancer Res. (1996) [Pubmed]
  29. Metabolic activation of N-hydroxy-N,N'-diacetylbenzidine by hepatic sulfotransferase. Morton, K.C., Beland, F.A., Evans, F.E., Fullerton, N.F., Kadlubar, F.F. Cancer Res. (1980) [Pubmed]
  30. Stem cell factor influences the proliferation and erythroid differentiation of the MB-02 human erythroleukemia cell line by binding to a high-affinity c-kit receptor. Broudy, V.C., Morgan, D.A., Lin, N., Zsebo, K.M., Jacobsen, F.W., Papayannopoulou, T. Blood (1993) [Pubmed]
  31. NAT2 slow acetylation and bladder cancer in workers exposed to benzidine. Carreón, T., Ruder, A.M., Schulte, P.A., Hayes, R.B., Rothman, N., Waters, M., Grant, D.J., Boissy, R., Bell, D.A., Kadlubar, F.F., Hemstreet, G.P., Yin, S., LeMasters, G.K. Int. J. Cancer (2006) [Pubmed]
  32. GSTP1 A1578G (Ile105Val) polymorphism in benzidine-exposed workers: an association with cytological grading of exfoliated urothelial cells. Ma, Q., Lin, G., Qin, Y., Lu, D., Golka, K., Geller, F., Chen, J., Shen, J. Pharmacogenetics (2003) [Pubmed]
  33. Expression of coproporphyrinogen oxidase and synthesis of hemoglobin in human erythroleukemia K562 cells. Taketani, S., Furukawa, T., Furuyama, K. Eur. J. Biochem. (2001) [Pubmed]
  34. Cellular kinetics of transforming growth factor-beta induced hemoglobin accumulation in the HEL erythroleukemia cell line. Hooper, W.C., Jackson, D., Pruckler, J., Evatt, B.L. Leuk. Res. (1991) [Pubmed]
  35. Induction of differentiation of murine erythroleukemia cells by aminonucleoside of puromycin and inhibition of this induction by purines and purine derivatives. Lacour, F., Harel, L., Friend, C., Huynh, T., Holland, J.G. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  36. Vascularization in the murine allantois occurs by vasculogenesis without accompanying erythropoiesis. Downs, K.M., Gifford, S., Blahnik, M., Gardner, R.L. Development (1998) [Pubmed]
  37. Metabolism and disposition of benzidine in the dog. Lakshmi, V.M., Mattammal, M.B., Spry, L.A., Kadlubar, F.F., Zenser, T.V., Davis, B.B. Carcinogenesis (1990) [Pubmed]
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