Methods for the determination of mutagenic heterocyclic amines and their applications in environmental analysis

Journal of Chromatography A

Volumn 774, Issue 1-2, 1997, Pages 121-142

  Kataoka, Hiroyuki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Air analysis; Amines, heterocyclic; Cigarette smoke; Diesel exhaust; Environmental analysis; Reviews; Soil; Water analysis

Indexed keywords

CIGARETTE SMOKE; HETEROCYCLIC AMINE; MUTAGENIC AGENT; RAIN;

AIR ANALYSIS; CAPILLARY ZONE ELECTROPHORESIS; DRUG DETERMINATION; ELECTROCHEMISTRY; ENZYME LINKED IMMUNOSORBENT ASSAY; EXHAUST GAS; FLUORESCENCE; FUME; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POLLUTION; PRIORITY JOURNAL; REVIEW; SEWAGE; SOIL POLLUTION; TECHNIQUE; ULTRAVIOLET SPECTROPHOTOMETRY; WATER ANALYSIS;

AMINES; CARCINOGENS; CHROMATOGRAPHY, GAS; ELECTROPHORESIS, CAPILLARY; ENVIRONMENTAL POLLUTANTS; ENZYME-LINKED IMMUNOSORBENT ASSAY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HETEROCYCLIC COMPOUNDS; HUMANS; MASS SPECTROMETRY; MUTAGENS;

ANIMALIA;

EID: 0030820695     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9673(97)00246-X     Document Type: Review

References (159)

1. T. Sugimura and K. Wakabayashi, in M.W. Pariza, H.-U. Aeschbacher, J.S. Felton and S. Sato (Editors), Mutagens and Carcinogens in the Diet, Wiley-Liss Inc., New York, 1990, p.1.
2. Felton J.S., Knize M.G. Mutat. Res. 259:1991;205.
3. Jagerstad M., Skog K., Grivas S., Olsson K. Mutat. Res. 259:1991;219.
4. Wakabayashi K., Nagao M., Esumi H., Sugimura T. Cancer Res. (Suppl.). 52:1992;2092s.
5. Eisenbrand G., Tang W. Toxicol. 84:1993;1.
6. Skog K. Food Chem. Toxicol. 31:1993;655.
7. Stavric B. Food Chem. Toxicol. 32:1994;977.
8. Sugimura T., Nagao M., Wakabayashi K. Environ. Health Perspect. 104(Suppl. 3):1996;429.
9. T. Sugimura, in R.H. Adamson, J-A. Gustafsson, N. Ito, M. Nagao, T. Sugimura, K. Wakabayashi and Y. Yamazoe (Editors), Heterocyclic Amines in Cooked Foods: Possible Human Carcinogens, Princeton Scientific Publishing, Princeton, NJ, USA, 1995, p. 214.
10. Wakabayashi K., Ushiyama H., Takahashi M., Nukaya H., Kim S.-B., Hirose M., Ochiai M., Sugimura T., Nagao M. Environ. Health Perspect. 99:1993;129.
11. Layton D.W., Bogen K.T., Knize M.G., Hatch F.T., Johnson V.M., Felton J.S. Carcinogenesis. 16:1995;39.
12. Robbana-Barnat S., Rabache M., Rialland E., Fradin J. Environ. Health Perspect. 104:1996;280.
13. Gooderham N.J., Murray S., Lynch A.M., Edwards R.J., Yadollahi-Farsani M., Bratt C., Rich K.J., Zhao K., Murray B.P., Bhadresa S., Crosbie S.J., Boobis A.R., Davies D.S. Br. J. Clin. Pharmacol. 42:1996;91.
14. Manabe S., Uchino E., Wada O. Mutat. Res. 226:1989;215.
15. Manabe S., Wada O., Morita M., Izumikawa S., Asakuno K., Suzuki H. Environ. Pollut. 75:1992;301.
16. Manabe S., Kurihara N., Wada O., Izumikawa S., Asakuno K., Morita M. Environ. Pollut. 80:1993;281.
17. Manabe S., Wada O. Environ. Pollut. 64:1990;121.
18. Manabe S., Izumikawa S., Asakuno K., Wada O., Kanai Y. Environ. Pollut. 70:1991;255.
19. Yoshida D., Matsumoto T. Cancer Lett. 10:1980;141.
20. Matsumoto T., Yoshida D., Tomita H. Cancer Lett. 12:1981;105.
21. Yamashita M., Wakabayashi K., Nagao M., Sato S., Yamaizumi Z., Takahashi M., Kinae N., Tomita I., Sugimura T. Jap. J. Cancer Res. 77:1986;419.
22. Manabe S., Wada O., Kanai Y. J. Chromatogr. 529:1990;125.
23. Kanai Y., Wada O., Manabe S. Carcinogenesis. 11:1990;1001.
24. Manabe S., Tohyama K., Wada O., Aramaki T. Carcinogenesis. 12:1991;1945.
25. Vainiotalo S., Matveinen K., Reunanen A. Frez. J. Anal. Chem. 345:1993;462.
26. Thiebaud H.P., Knize M.G., Kuzmicky P.A., Felton J.S., Hsieh D.P. J. Agric. Food Chem. 42:1994;1502.
27. Thiebaud H.P., Knize M.G., Kuzmicky P.A., Hsieh D.P., Felton J.S. Food Chem. Toxicol. 33:1995;821.
28. Wu J., Wong M.K., Lee H.K., Ong C.N. J. Chromatogr. Sci. 33:1995;712.
29. Murray S., Gooderham N.J., Boobis A.R., Davies D.S. Carcinogenesis. 10:1989;763.
30. Manabe S., Wada O. Environ. Mol. Mutagen. 15:1990;229.
31. Ushiyama H., Wakabayashi K., Hirose M., Itoh H., Sugimura T., Nagao M. Carcinogenesis. 12:1991;1417.
32. Friesen M.D., Garren L., Bereziat J.-C., Kadlubar F., Lin D. Environ. Health Perspect. 99:1993;179.
33. Aeschbacher H.-U., Turesky R.J. Mutat. Res. 259:1991;235.
34. Adamson R.H., Thorgeirsson U.P., Sugimura T. Arch. Toxicol. Suppl. 18:1996;303.
35. Tohda H., Oikawa A., Kawachi T., Sugimura T. Mutat. Res. 77:1980;65.
36. Ishidate M., Sofuni T., Yoshikawa K. Gann Monograph on Cancer Res. 27:1981;95.
37. Thompson L.H., Carrano A.V., Salazar E., Felton J.S., Hatch F.T. Mutat. Res. 117:1983;243.
38. Aeschbacher H.U., Ruch E. Carcinogenesis. 10:1989;429.
39. Holme J.A., Wallin H., Brunborg G., Soderlund E.J., Hongslo J.K., Alexander J. Carcinogenesis. 10:1989;1389.
40. Ohgaki H., Takayama S., Sugimura T. Mutat. Res. 259:1991;399.
41. Adamson R.H., Thorgeirsson U.P. Adv. Exp. Med. Biol. 369:1995;211.
42. Adamson R.H., Thorgeirsson U.P., Snyderwine E.G., Thorgeirrson S.S., Reeves J., Dalgard D.W., Takayama S., Sugimura T. Jpn. J. Cancer Res. 81:1990;10.
43. Mukai T., Yamazoe Y., Kato R. Eur. J. Pharmacol. 98:1984;35.
44. Kanai Y., Wada O., Manabe S. J. Pharmacol. Exp. Ther. 252:1990;1269.
45. Manabe S., Kanai Y., Ishikawa S., Wada O. J. Clin. Chem. Biochem. 26:1988;265.
46. Ichinose H., Ozaki N., Nakahara D., Naoi M., Wakabayashi K., Sugimura T., Nagatsu T. Biochem. Pharmacol. 37:1988;3289.
47. Naoi M., Takahashi T., Ichinose H., Wakabayashi K., Sugimura T., Nagatsu T. Biochem. Biophys. Res. Commun. 157:1988;494.
48. Hasegawa R., Tanaka H., Tamano S., Shirai T., Nagao M., Sugimura T., Ito N. Carcinogenesis. 15:1994;2567.
49. Sugimura T., Kawachi T., Nagao M., Yahagi T., Seno Y., Okamoto T., Shudo K., Kosuge T., Tsuji K., Wakabayashi K., Iitaka Y., Itai A. Proc. Jpn. Acad. 53:1977;58.
50. Yoshida D., Matsumoto T., Yoshimura R., Matsuzaki T. Biochem. Biophys. Res. Commun. 83:1978;915.
51. Yamamoto T., Tsuji K., Kosuge T., Okamoto T., Shudo K., Takeda K., Iitaka Y., Yamaguchi K., Seino Y., Yahagi T., Nagao M., Sugimura T. Proc. Jpn. Acad. 54B:1978;248.
52. Yamaguchi K., Zenda H., Shudo K., Kosuge T., Okamoto T., Sugimura T. Jpn. J. Cancer Res. 71:1979;849.
53. Yokota M., Narita K., Kosuge T., Wakabayashi K., Nagao M., Sugimura T., Yamaguchi K., Shudo K., Iitaka Y., Okamoto T. Chem. Pharm. Bull. 29:1981;1473.
54. Nukaya H., Watanabe H., Ishida H., Tsuji K., Suwa Y., Wakabayashi K., Nagao M., Sugimura T., Kosuge T. Chem. Pharm. Bull. 39:1991;533.
55. Yoshida D., Sato Y., Mizusaki S. Agric. Biol. Chem. 48:1984;241.
56. Grivas S., Nyhammar T., Olsson K., Jagerstad M. J. Food Chem. 20:1986;127.
57. Knize, M.G., Shen, N.H. and Felton, J.S. (Editors), Proc. Air Pollut. Control Assoc., April 1988, p. 88.
58. J.S. Felton and M.G. Knize, in C.S. Cooper and P.L. Grover (Editors), Handbook of Experimental Pharmacology, 94/I, Springer-Verlag, Berlin, 1990, p. 471.
59. Grivas S., Nyhammar T., Olsson K., Jagerstad M. Mutat. Res. 151:1985;177.
60. Johansson M.A.E., Fay L.B., Gross G.A., Olsson K., Jagerstad M. Carcinogenesis. 16:1995;2553.
61. Muramatsu M., Matsushima T. Mutat. Res. 147:1985;266.
62. Skog K., Knize M.G., Jagerstad M., Felton J.S. Mutat. Res. 268:1992;191.
63. Jagerstad M., Olson K., Grivas S., Negishi C., Wakabayashi K., Tsuda M., Sato S., Sugimura T. Mutat. Res. 126:1984;239.
64. Skog K., Jagerstad M. Mutat. Res. 230:1990;263.
65. Johansson M., Skog K., Jagerstad M. Carcinogenesis. 14:1993;89.
66. Skog K., Jagerstad M. Carcinogenesis. 14:1993;2027.
67. Skog K., Jagerstad M., Laser-Reutersward A.-L. Food Chem. Toxicol. 30:1992;681.
68. Negishi C., Wakabayashi K., Tsuda M., Sato S., Sugimura T., Saito H., Maeda M., Jagerstad M. Mutat. Res. 140:1984;44.
69. Kim I.-S., Wakabayashi K., Kurosaka R., Yamaizumi Z., Jinno F., Koyota S., Tada A., Nukaya H., Takahashi M., Sugimura T., Nagao M. Carcinogenesis. 15:1994;21.
70. K. Wakabayashi, I.-S. Kim, R. Kurosaka, Z. Yamaizumi, H. Ushiyama, M. Takahashi, A Tada Koyota, H. Nukaya, S. Goto, T. Sugimura and M. Nagao, in R.H. Adamson, J-A. Gustafsson, N. Ito, M. Nagao, T. Sugimura, K. Wakabayashi and Y. Yamazoe (Editors), Heterocyclic Amines in Cooked Foods: Possible Human Carcinogens, Princeton Scientific Publishing, Princeton, NJ, USA, 1995, p. 39.
71. Shioya M., Wakabayashi K., Sato S., Nagao M., Sugimura T. Mutat. Res. 191:1987;133.
72. Skog K., Jagerstad M. Carcinogenesis. 12:1991;2297.
73. Watkins B.E., Suzuki M., Wallin H., Wakabayashi K., Alexander J., Vanderlaan M., Sugimura T., Esumi H. Carcinogenesis. 12:1991;2291.
74. Sugimura T., Nagao M. Jpn. J. Cancer Res. 83:1992;919.
75. Felton J.S., Knize M.G., Roper M., Fultz E., Shen N.H., Turteltaub K.W. Cancer Res. (Suppl.). 52:1992;2103s.
76. Knize M.G., Felton J.S., Gross G.A. J. Chromatogr. 624:1992;253.
77. G.A. Gross and L. Fay, in R.H. Adamson, J-A. Gustafsson, N. Ito, M. Nagao, T. Sugimura, K. Wakabayashi and Y. Yamazoe (Editors), Heterocyclic Amines in Cooked Foods: Possible Human Carcinogens, Princeton Scientific Publishing, Princeton, NJ, 1995, p. 20.
78. Alink G.M., Smit H.A., van Houdt J.J., Kolkman J.R., Boleij J.S.M. Mutat. Res. 116:1983;21.
79. Lewtas J., Goto S., Williams K., Chuang J.C., Petersen B.A., Wilson N.K. Atmos. Environ. 21:1987;443.
80. Nagao M., Honda M., Seino Y., Yahagi T., Sugimura T. Cancer Lett. 2:1977;221.
81. Van Houdt J.J. Atmos. Environ. 24B:1990;207.
82. Georghiou P.E., Blagden P., Snow D.A., Winsor L., Williams D.T. Environ. Sci. Technol. 25:1991;1496.
83. Lofroth G., Stensman C., Brandhorst-Satzkorn M. Mutat. Res. 261:1991;21.
84. Nardini B., Clonfero E. Mutagenesis. 7:1992;421.
85. Lofroth G. Toxicol. Lett. 72:1994;83.
86. Nardini B., Granella M., Clonfero E. Mutat. Res. 322:1994;193.
87. Kira S., Hayatsu H., Okata M. Bull. Environ. Contam. Toxicol. 43:1989;583.
88. Sakamoto H., Hayatsu H. Environ. Contam. Toxicol. 44:1990;521.
89. Sayato Y., Nakamuro K., Ueno H., Goto R. Mutat. Res. 242:1990;313.
90. Hashizume T., Ueda K., Tokutsu S., Hanawa I., Ninae N. Environ. Contam. Toxicol. 49:1992;497.
91. Houk V.S. Mutat. Res. 277:1992;91.
92. Kusamran W.R., Wakabayashi K., Oguri A., Tepsuwan A., Nagao M., Sugimura T. Mutat. Res. 325:1994;99.
93. Filipic M. Mutat. Res. 342:1995;1.
94. Ono Y., Mohri S., Somiya I., Oda Y. Environ. Mutat. Res. Commun. 17:1995;179.
95. Sasaki Y., Kise H., Kikuchi M. Environ. Mutagen Res. 18:1996;21.
96. Grivas S., Nyhammar T. Mutat. Res. 142:1985;5.
97. Zhang X.-M., Wakabayashi K., Liu Z.-C., Sugimura T., Nagao M. Mutat. Res. 201:1988;181.
98. Manabe S., Yanagisawa H., Isjikawa S., Kitagawa Y., Kanai Y., Wada O. Cancer Res. 47:1987;6150.
99. Gross G.A., Philippossian G., Aeschbacher H.U. Carcinogenesis. 10:1989;1175.
100. Gross G.A. Carcinogenesis. 11:1990;1597.
101. Gross G.A., Gruter A., Heyland S. Food Chem. Toxicol. 30:1992;491.
102. Gross G.A., Gruter A. J. Chromatogr. 592:1992;271.
103. Gross G.A., Turesky R.J., Fay L.B., Stillwell W.G., Skipper P.L., Tannenbaum S.R. Carcinogenesis. 14:1993;2313.
104. Schwarzenbach R., Gubler D. J. Chromatogr. 624:1992;491.
105. Jackson L.S., Hargraves W.A., Stroup W.H., Diachenko G.W. Mutat. Res. 320:1994;113.
106. Johansson M.A.E., Jagerstad M. Carcinogenesis. 15:1994;1511.
107. Skog K., Steineck G., Augustsson K., Jagerstad M. Carcinogenesis. 16:1995;861.
108. Knize M.G., Dolbeare F.A., Carroll K.L., Moore D.H., Felton J.S. Food Chem. Toxicol. 32:1994;595.
109. Karamanos N.K., Tsegenidis T. J. Liq. Chromatogr. Rel. Technol. 19:1996;2247.
110. Takahashi M., Wakabayashi K., Nagao M., Yamamoto M., Masui T., Goto T., Kinae N., Tomita I., Sugimura T. Carcinogenesis. 6:1985;1195.
111. Takahashi M., Wakabayashi K., Nagao M., Yamaizumi Z., Sato S., Kinae N., Tomita I., Sugimura T. Carcinogenesis. 6:1985;1537.
112. Billedeau S.M., Bryant M.S., Holder C.L. LC·GC Int. 4:1991;38.
113. Galceran M.T., Pais P., Puignon L. J. Chromatogr. A. 655:1993;101.
114. Galceran M.T., Pais P., Puignon L. J. Chromatogr. A. 719:1996;203.
115. Van Dyck M.M.C., Rollmann B., De Meester C. J. Chromatogr. A. 697:1995;377.
116. Kanai Y., Wada O., Manabe S. Carcinogenesis. 11:1990;1001.
117. Edmonds C.G., Sethi S.K., Yamaizumi Z., Kasai H., Nishimura S., McCloskey J.A. Environ. Health Perspect. 67:1986;35.
118. Yamaizumi Z., Kasai H., Nishimura S., Edmonds C.G., McClosky J.A. Mutat. Res. 173:1986;1.
119. Millon H., Bur H., Turesky R. J. Chromatogr. 394:1987;201.
120. Turesky R.J., Bur H., Huynh-Ba T., Aeschbacher H.U., Milon H. Food Chem. Toxicol. 26:1988;501.
121. Galceran M.T., Moyano E., Puiguou L., Pais P. J. Chromatogr. A. 730:1996;185.
122. Richling E., Herderich M., Schreier P. Chromatographia. 42:1996;7.
123. Kataoka H., Kijima K. J. Chromatogr. A. 767:1997;187.
124. Murray S., Gooderham N.J., Barner V.F., Boobis A.R., Davies D.S. Carcinogenesis. 8:1987;937.
125. Murray S., Gooderham N.J., Boobis A.R., Davies D.S. Carcinogenesis. 9:1988;321.
126. Murray S., Lynch A.M., Knize M.G., Gooderham N.J. J. Chromatogr. 616:1993;211.
127. Tikkanen L.M., Sauri T.M., Latva-Kala K.J. Food Chem. Toxicol. 31:1993;717.
128. Wu J., Wong M.K., Li S.F.Y., Lee H.K., Wong C.N. J. Chromatogr. A. 709:1995;351.
129. Wu J., Wong M.K., Lee H.K., Wong C.N. J. Chromatogr. Sci. 34:1996;139.
130. Vanderlaan M., Watkins B.E., Hwang M., Knize M.G., Felton J.S. Carcinogenesis. 9:1988;153.
131. Vanderlaan M., Hwang M., Knize M.G., Watkins B.E., Felton J.S. Prog. Clin. Biol. Res. 340E:1990;189.
132. Vanderlaan M., Alexander J., Thomas C., Djanegara T., Hwang M., Watkins, William H. Carcinogenesis. 12:1991;349.
133. Dragsted L.D., Nielsen S.E., Heitmann B.L., Grivas S., Frandsen H. Arch. Toxicol. Suppl. 18:1996;259.
134. Kataoka H. J. Chromatogr. A. 733:1996;19.
135. H. Kataoak, K. Kijima and G. Maruo, in preparation.
136. Hayatsu H. J. Chromatogr. 597:1992;37.
137. Hayatsu H., Hayatsu T., Arimoto S., Sakamoto H. Anal. Biochem. 235:1996;185.
138. Heinrich U., Muhle H., Takenaka S., Ernst H., Fuhst R., Mohr U., Pott F., Stoeber W. J. Appl. Toxicol. 6:1986;383.
139. Iwai K., Udagawa T., Yamagishi M., Yamada H. Dev. Toxicol. Environ. Sci. 13:1986;349.
140. Brightwell J., Fouillet X., Cassano-Zoppi A.L., Bernstein D., Crawley F., Duchosal F., Gatz R., Perczel S., Pfeifer H. J. Appl. Toxicol. 9:1989;23.
141. Dubrow R., Wegman D.H. J. Natl. Cancer Inst. 71:1983;1123.
142. McClellan R.O. Ann. Rev. Pharmacol. Toxicol. 27:1987;279.
143. Hayes R.B., Thmas T., Silverman D.T., Vineis P., Blot W.J., Mason T.J., Pickle L.W., Crrea P., Fontham E.T.H., Schoenberg J. Am. J. Ind. Med. 16:1989;685.
144. Doll R. Nature. 265:1977;589.
145. Wynder E.L., Gori G.B. J. Natl. Cancer Inst. 58:1977;825.
146. Brinton L.A., Blot W.J., Becher J.A., Winn D.M., Browder J.P., Farmer J.C., Fraumeni J.F. Am. J. Epidemiol. 119:1984;896.
147. Kier L.D., Yamasaki E., Ames B.N. Proc. Natl. Acad. Sci. USA. 71:1974;4159.
148. Sato S., Seino Y., Ohka T., Yahagi T., Nagao M., Matsushima T., Sugimura T. Cancer Lett. 3:1977;1.
149. Wynder E.L., Hoffman D. Science. 162:1968;862.
150. Hayatsu H., Oka T., Wakata A., Ohara Y., Hayatsu T., Kobayashi H., Arimoto S. Mutat. Res. 119:1983;233.
151. Kobayashi H., Hayatsu H. Gann. 75:1984;489.
152. Mohtashamipur E., Norpoth K., Lieder F. Carcinogenesis. 6:1985;783.
153. Peluso M., Castegnaro M., Malaveille C., Friesen M., Garren L., Hautefeuille A., Vineis P., Kadlubar F., Bartsch H. Carcinogenesis. 12:1991;713.
154. Coggon D., Pannet B., Osmond C., Acheson E. Br. J. Ind. Med. 43:1986;332.
155. Lund E., Borgan J.K. Scand. J. Work. Environ. Health. 13:1987;156.
156. Rappaport S., McCartney M., Wei T. Cancer Lett. 8:1979;145.
157. Felton J.S., Healy S., Stuermer D., Berry C., Timourian H., Hatch F. Mutat. Res. 88:1981;33.
158. Berg I., Overvik E., Nord C.E., Gustafsson J.A. Mutat. Res. 207:1988;199.
159. Berg I., Overvik E., Gustafsson J.A. Food Chem. Toxicol. 28:1990;421.