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2,4-Toluene Diamines—Their Carcinogenicity, Biodegradation, Analytical Techniques and an Approach towards Development of Biosensors

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Abstract

2,4-Toluene diamine (TDA), a class A carcinogen, is a major raw material for the production of toluene diisocyanate (TDI), which is one of the precursors for the production of polyurethane foams (PU). This review deals with 2,4-toluene diamine’s (TDA) carcinogenicity, analytical techniques, biodegradation and use as a biosensor for biogenic and synthetic amines, emphasizing various carcinogenicity studies by 2,4-TDA on animals and humans. This review reports some publications of the analysis of body fluid samples of workers from a PU producing factory for presence of TDA and TDI, since TDI gets absorbed into the worker’s body, getting metabolized into TDA. Biodegradations of 2,4-TDA by various researchers are reported and also our own research experience with biodegradation of 2,4-TDA using Aspergillus nidulans isolated from soil site at a polyurethane foam dumping site have been discussed in this review. Biosensors for various biogenic and synthetic amines are discussed.

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9 References

  1. S. Asakura and S. Okazaki, Chemosphere. 1995, 30, 2209.

    Article  CAS  PubMed  Google Scholar 

  2. Diaminotoluens, 74,1–67, “International Programme on Chemical Safety Environmental Health Criteria.”, 1987, World Health Organization, Geneva.

    Google Scholar 

  3. D. Birkett, Chem. Britain. 1997, 6, 30.

    Google Scholar 

  4. A. H. Conney, Cancer Res., 1982, 42, 4875.

    CAS  PubMed  Google Scholar 

  5. F. P. Guenerich and T. Shimada, Chem. Res. Toxicol., 1991, 4, 391.

    Article  Google Scholar 

  6. B. Glowinskil, W. W. Weber, J. B. Fysh, J. M. Vaught, and C. M. King, J. Biol. Chem., 1980, 255, 7883.

    Article  Google Scholar 

  7. S. S. Mattano, S. Land, C. M. King, and W. W. Weber, Mol. Pharmacol., 1989, 35, 599.

    CAS  PubMed  Google Scholar 

  8. Y. Oda, H. Yamazaki, M. Watanabe, T. Nohmi, and T. Shimada, Mutation Res.. 1995, 334, 145.

    Article  CAS  PubMed  Google Scholar 

  9. M. L. Cunningham and H. B. Matthews, Toxicol. Lett.,.1995, 82/83, 9.

    Article  CAS  Google Scholar 

  10. C. Batich, J. Williams, and R. King, J. Biomed. Mater. Res. Appl. Biomater., 1989, 23, 311.

    Article  CAS  Google Scholar 

  11. E. De. Lorenzi, G. Massolini, M. Macchia, and G. Caccialanza, Chromatographia. 1995, 41, 661.

    Article  Google Scholar 

  12. K. Shanmugam, Ph.D. thesis, 2000, Anna University, Tamil Nadu, India.

    Google Scholar 

  13. Y. L. Cheung, J. Snelling, N. N. D. Mohammed, T. B. Gray, and C. Ioannides, Toxicol. Appl. Pharmacol.. 1996, 139, 203.

    Article  CAS  PubMed  Google Scholar 

  14. D. Ito, Y. Hiasa, Y. Konishi, and M. Marugami, Cancer Res., 1969, 29 1137.

    CAS  PubMed  Google Scholar 

  15. R. H. Cardy, J. Natl. Cancer Inst., 1969, 62, 1107.

    Google Scholar 

  16. Technical Series No. 200, “Bioassay of 2,6-toluenediamine hydrochloride for possible carcinogenicity.”, 1980, National Cancer Institute (NCI), UK.

    Google Scholar 

  17. B. B. Furlong, R. P. Weaver, and J. A. Goldstein, Carcinogenisis. 1987, 8, 247.

    Article  CAS  Google Scholar 

  18. M. L. Cunningham, J. Foley, R. R. Maronpot, and H. B. Matthews, Toxicol. Appl. Toxicol., 1991, 107, 562.

    Article  CAS  Google Scholar 

  19. M. L. Cunningham, L. T. Burka, and H. B. Matthews, Drug. Metab. Dispos., 1989, 17, 612.

    CAS  PubMed  Google Scholar 

  20. F. J. Sandstrom, G. Skarping, and M. Dalene, J. Chromatogr., 1989, 479, 135.

    Article  Google Scholar 

  21. P. Persson, M. Dalene, G. Skarping, M. Adamsson, and L. Hagmar, British J. Ind. Med.. 1993, 50, 1111.

    CAS  Google Scholar 

  22. G. Skarping, M. Dalene, and P. Lind, J. Chromatogr., 1994, 663, 199.

    Article  CAS  Google Scholar 

  23. P. Lind, M. Dalene, G. Skarping, and L. Hagmar, Occup. Environ. Med.. 1996, 53, 94.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. H. S. Lee and W. H. Phoon, British J. Ind. Med.. 1992, 49, 423.

    CAS  Google Scholar 

  25. Hazardous Substances Data Bank (HSDB), “A report on 2,4-toluene diamine.”, 1997, Micromediex Inc., U.S.A., 1–32.

    Google Scholar 

  26. S. Matsui, T. Murakami, T. Sasaki, Y. Hirose, and Y. Iguma, Prog. Water Technol., 1975, 7, 645.

    CAS  Google Scholar 

  27. S. Matsui, Y. Okawa, and R. Ota, Water Sci. Technol., 1988, 20, 201.

    Article  CAS  Google Scholar 

  28. D. L. Freedman, R. S. Shanley, and R. J. Scholze, J. Hazardous Mater.. 1996, 49, 1.

    Article  CAS  Google Scholar 

  29. R. Guidoin, M. Therrien, C. Rolland, M. King, J. L. Grandmaison, S. Kaliaguine, P. L. Blais, H. Pakdel, and C. Roy, Ann. Plastic Surg.. 1992, 28, 1.

    Article  Google Scholar 

  30. R. M. Riggin and C. C. Howard, J. Liq. Chromatogr., 1983, 6, 1897.

    Article  CAS  Google Scholar 

  31. G. Becher, J. Chromatogr., 1981, 211, 103.

    Article  CAS  Google Scholar 

  32. E. H. Nieminen, L. H. Saarinan, and J. T. Laakso, J. Liq. Chromatogr., 1983, 6, 453.

    Article  CAS  Google Scholar 

  33. G. Skarping, L. Renman, and B. E. F. Smith, J. Chromatogr., 1983a, 267, 315.

    Article  CAS  Google Scholar 

  34. G. Skarping, L. Renman, and M. Dalene, J. Chromatogr., 1983b, 270, 207.

    Article  CAS  Google Scholar 

  35. C. M. Kottemann, J. Assoc. Off Anal. Chem., 1966, 49, 954.

    CAS  Google Scholar 

  36. K. Johansson, C. Rappe, W. Lindberg, and M. Nygren, in “Environmental carcinogens selected methods of analysis.”, ed. H. Egan, L. O. Fishbein, I. K. O’Neil, M. Castegnaro, and H. Bartsch, 1981, Vol. 4, International Agency for Research on Cancer, Lyons, 40.

    Google Scholar 

  37. D. H. Liem and J. Rooselaar, Mitt. Geb Lebensm. Hyg., 1981, 72, 164.

    CAS  Google Scholar 

  38. R. C. Snyder and C. V. Breder, J. Chromatogr., 1982a, 236, 429.

    Article  CAS  Google Scholar 

  39. R. C. Snyder, W. C. Brumely, C. V. Breder, and T. Fazio, J. Assoc. Off. Anal. Chem., 1982b, 65, 1388.

    CAS  Google Scholar 

  40. J. L. Guthrie and R. W. McKinney, Anal. Chem., 1977, 49, 1676.

    Article  CAS  Google Scholar 

  41. P. D. Unger and M. A. Friedman, J. Chromatogr., 1979, 174, 379.

    Article  CAS  PubMed  Google Scholar 

  42. A. Mathias, Anal. Chem., 1966, 38, 1931.

    Article  CAS  Google Scholar 

  43. G. F. Macke, J. Chromatogr., 1968, 36, 537.

    Article  CAS  Google Scholar 

  44. C. E. Boufford, J. Gas Chromatogr., 1968, 6, 438.

    Article  CAS  Google Scholar 

  45. F. Willeboordse, Q. Quick, and E. Bishop, Anal. Chem., 1968, 40, 1455.

    Article  CAS  Google Scholar 

  46. T. Biernack, B. Sekowska, and J. Michonska, Chem. Anal., [Warsaw], 1974, 19, 619.

    Google Scholar 

  47. G. H. Holcombe, D. A. Benoit, D. E. Hammermeister, E. N. Leonar, and R. D. Johnson, Arch. Environ. Toxicol., 1994, 28, 287.

    Google Scholar 

  48. M. C. Pace, R. Donnelly, J. J. L. Jeter, W. C. Brumley, and G. Wayne, J. AOAC Intern.. 1996, 79, 777.

    Article  CAS  Google Scholar 

  49. J. Wang, Chem. Eur. J., 1999, 5, 681.

    Google Scholar 

  50. J. Wang, G. Rivas, D. Luo, X. Cai, F. S. Valer, and N. Dontha, Anal. Chem., 1996, 68, 4365.

    Article  CAS  Google Scholar 

  51. P. S. Divya, D. Savitri, and C. K. Mitra, J. Biosci., 1998, 23, 131.

    Article  CAS  Google Scholar 

  52. I. Frebort, L. Skoupa, and P. Pec, Food Control., 2000, 11, 13.

    Article  CAS  Google Scholar 

  53. M. Wimmerova and L. Macholan, Biosens. Bioelectron.. 1999, 14, 695.

    Article  CAS  PubMed  Google Scholar 

  54. R. Draisci, G. Volpe, L. Lucentini, A. Cecilia, R. Federicio, and G. Palleschi, Food Chem., 1998, 62, 225.

    Article  CAS  Google Scholar 

  55. P. Bouvrette, K. B. Male, J. H. T. Luong, and B. F. Gibbs, Enzyme Microb. Technol.. 1997, 20, 32.

    Article  CAS  Google Scholar 

  56. C. X. Xu, S. A. M. Marzouk, V. V. Cosofret, R. P. Buck, M. R. Neuman, and R. H. Sprinkle, Talanta. 1997, 44, 1625.

    Article  CAS  PubMed  Google Scholar 

  57. O. V. Yagodina and E. B. Nikolskaya, Sens. Actuators B. 1997, 44, 566.

    Article  CAS  Google Scholar 

  58. S. Subrahmanyam, K. Shanmugam, V. M. Madhav, M. Murugesan, T. V. Subramanian, and D. Jeyakumar, Electroanalysis. 2001, 13, 1051.

    Article  CAS  Google Scholar 

  59. S. Subrahmanyam, K. Shanmugam, V. M. Madhav, M. Murugesan, T. V. Subramanian, and D. Jeyakumar, Analyst. 2000, 125, 2166.

    Article  CAS  PubMed  Google Scholar 

  60. S. Subrahmanyam, K. Shanmugam, T. V. Subramanian, M. Murugesan, V. M. Madhav, and D. Jeyakumar, Bull. Electron., 1999, 15, 452.

    Google Scholar 

  61. S. Subrahmanyam, K. Shanmugam, V. M. Madhav, M. Murugesan, T. V. Subramanian, and D. Jeyakumar, Electroanalysis. 2001, 13, 944.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemical Engineering, Anna University, Chennai, 600 025, India

    Kumaran Shanmugam, Sreenath Subrahmanyam & Subramanian V. Tarakad

  2. Center for Ecological Sciences, Indian Institute of Science, Bangalore, 560 012, India

    Narendran Kodandapani

  3. Nuclear Agriculture and Biotechnology Division, Bhabha Atomic Research Centre, Mumbai, 400 085, India

    D’Souza F. Stanly

  4. UNESCO Laboratory of Environmental Electrochemistry, Department of Analytical Chemistry, Charles University, 128 40, Prague 2, Czech Republic

    Kumaran Shanmugam

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  1. Kumaran Shanmugam
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  2. Sreenath Subrahmanyam
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  3. Subramanian V. Tarakad
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  4. Narendran Kodandapani
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  5. D’Souza F. Stanly
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Correspondence to Kumaran Shanmugam.

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Shanmugam, K., Subrahmanyam, S., Tarakad, S.V. et al. 2,4-Toluene Diamines—Their Carcinogenicity, Biodegradation, Analytical Techniques and an Approach towards Development of Biosensors. ANAL. SCI. 17, 1369–1374 (2001). https://doi.org/10.2116/analsci.17.1369

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  • DOI: https://doi.org/10.2116/analsci.17.1369

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