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Identification of an in vivo chrysene diol epoxide adduct in human hemoglobin
B W Day1, P L Skipper, J S Wishnok
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139.
Abstract:
Human blood samples were analyzed by fluorescence and mass spectrometry for the presence of polycyclic aromatic hydrocarbon metabolites covalently bound to hemoglobin. Globin was prepared by HCl-acetone precipitation and enzymatically digested. The polycyclic aromatic alcohols generated from ester adducts during digestion were concentrated by monoclonal antibody immunoaffinity chromatography and separated by C-18 HPLC. Analysis of collected fractions by room temperature fluorescence spectroscopy revealed the presence of the anti-tetrahydrotetrols of benzo[a]pyrene and another component possessing a phenanthrene chromophore. Gas chromatographic-mass spectral analysis of the HPLC fractions revealed that the latter compound was r-1,t-2,t-3,c-4-tetrahydroxy-1,2,3,4-tetrahydrochrysene, arising from a hemoglobin-chrysene diol epoxide adduct.