Summary
A sensitive precolumn fluorescence derivatization method for low level detection of the, volatile (N-nitrosodimethylamine and N-nitrosopyrrolidine) and non-volatile N-nitrosamines (N-nitrosoproline and N-nitrosodiethanolamine) an high-performance liquid chromatography was developed. This method is based on the denitrosation of the compounds of interest by a mixture of hydrobromic acid and acetic acid to produce the corresponding secondary amines. These are, then, able to react with, a quinolizinocoumarin derivative (luminarin 9®) to form highly fluorescent labelled N-nitrosamine derivatives. The structural elucidation of the luminarin 9® derivatives of N-nitrosoproline and N-nitrosodimethylamine by way of example, were established by liquid chromatography-mass spectrometry (LC-MS) and by direct chemical ionization-mass spectrometry (CI-MS). The separation, derivatization and detection conditioins were optimized for all the studied compounds. The detection limits (signal to noise ratio=3) were between 0.4 and 1.0 pmol injected depending on the compound. The calibration graphs were linear for derivatized amounts in the range of 0.5–40 nmol for N-nitrosodimethylamine and N-nitrosopyrrolidine, 0.4–2- nmol for N-nitrosoproline and 1.0–40 nmol for N-nitrosodiethanolamine. The repeatability (RSD less than 3.5%, n=6) and reproducibility (RSD less than 4.8%, n-6) were satisfactory.
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References
P. N. Magee, J. M. Barnes, Brit. J. Cancer,10, 114 (1956).
S. S. Mirvish, J. Nat. Canc. Inst.44, 633 (1970).
R. A. Scanlan, J. F. Barbour, J. H. Hotchkiss, L. M. Libbey, Food Cosmet. Toxicol.18, 27 (1980).
N. P. Sen, S. Seaman, W. F. Miles, Food Cosmet. Toxicol.14, 167 (1976).
A. R. Tricker, M. J. Perkins, R. C. Massey, D. J. McWeeny, Food Add. Contam.,2, 247 (1985).
J. W. Pensabene, W. Fiddler, J. Assoc. Off. Anal. Chem.73, 226 (1990).
A. R. Tricker, M. J. Perkins, R. C. Massey, C. Bishop, P. E. Key, D. J. McWeeny, Food Add. Contam.1, 245 (1984).
R. Schwarzenbach, J. P. Schmid, J. Chromatogr.477, 231 (1989).
T. Y. Fan, V. Goff, L. Song, D. H. Fine, G. P. Arsenault, K. Biemann, Food Cosm. Toxicol.15, 223 (1977).
J. Y. Zhou, P. Prognon, C. Dauphin, M. Hamon, Chromatographia36, 57 (1993).
Z. El Assaf, M. Hamon, Ann. PHarm. Fr.41, 409 (1983).
G. Eisenbrand, R. Preussmann, Arzneim. Forsch.20, 1513 (1970).
D. R. Lopez, C. L. Martinez, R. G. Villanova, Anal. Chem.58, 2647 (1986).
Z. Wang, H. Xu, C. Fu, J. Chromatogr.589, 349 (1992).
H. J. Klimisch, L. Stadler, J. Chromatogr.90, 223 (1974).
J. H. Wolfram, J. I. Feinberg, R. C. Doerr, W. Fiddler J. Chromatogr.132, 37 (1977).
M. Tod, M. Prevot, J. Chalom, R. Farinotti, G. Mahuzier, J. Chromatogr.542, 295 (1991).
F. Traoré, M. Tod, J. Chalom, R. Farinotti, G. Mahuzier, Anal Chim. Acta269, 211 (1992).
F. Traoré, G. A. Pianetti, L. Dallery, M. Tod, J. Chalom, R. Farinotti, G. Mahuzier, Chromatographia362, 96 (1993).
T. A. Gough, K. S. Webb, M. A. Pringuer, B. J. Wood, J. Agric. Fd. Chem.25, 663 (1977).
B. Pignatelli, C.-S. Chen, P. Thuillier, H. Bartsch, Analyst114, 1103 (1989).
R. C. Massey, C. Crews, D. J. McWeeny, J. Chromatogr.241, 423 (1982).
J. H. Hotchkiss, D. C. Havery, T. Fazio, J. Assoc. Off. Anal. Chem.64, 929 (1981).
W. Lijinsky, L. Keefer, J. Loo, Tetrahedron26, 5137 (1970).
S. Klein, M. J. Waechter, M. Hamon, Analusis10, 120 (1982).
B. C. Challis, J. A. Challis, in “The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives”, S. Patai, Ed., The Hebrew University, Jerusalem, 1982; p. 1177.
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Zhou, Z.Y., Dauphin, C., Prognon, P. et al. Luminarin 9: A new fluorescent reagent for the precolumn derivatizatioin of main volatile and non-volatile N-nitrosamines in RP-HPLC. Chromatographia 39, 185–191 (1994). https://doi.org/10.1007/BF02274499
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DOI: https://doi.org/10.1007/BF02274499