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During the late 1960s, Dr Jerina and his colleagues determined the role of arene oxides in the unexpected migration of substituents during the enzymatic formation of phenols, a phenomenon that became known as the ‘NIH Shift’.
In the 1970s, Dr Jerina undertook an extensive program to identify proximate and ultimate carcinogenic metabolites derived from the environmentally prevalent polycyclic aromatic hydrocarbon, benzo[a]pyrene. The approach taken was to synthesize all of the potential oxidative metabolites of the hydrocarbon and to identify those which were metabolic intermediates in cell free systems as well as to test these synthesized molecules for mutagenicity in cell culture systems and for tumorigenicity in animal models. For this purpose, 50–100 mg amounts of all of the metabolically possible phenols, arene oxides, dihydrodiols and diol epoxides of benzo[a]pyrene were synthesized in Dr Jerina’s laboratory. Although these amounts may seem modest, novel multi-step synthetic methods had to be developed which often required kilogram amounts of starting material. For the biological studies, a highly productive collaborative program was initiated between Dr Jerina and my laboratory, then at Hoffmann-La Roche. This collaborative research program provided the first direct demonstration of proximate and ultimate carcinogenic metabolites from the polycyclic aromatic hydrocarbon class of environmental carcinogens.
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N. T. NASHED, S. K. BALANI, R. J. LONCHARICH,J. M. SAYER, D. Y. SHIPLEY,R. S. MOHAN, D. L. WHALEN,D. M. JERINA
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTSno. 1 (2008): 307-308
Chemical Research in Toxicologyno. 12 (2008): 2379-2392
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