Rodman, L. E. and Shedlofsky, S. I. and Mannschreck, Albrecht and Püttmann, Michael and Swim, A. T. and Robertson, L. W. (1991) Differential potency of atropisomers of polychlorinated biphenyls on cytochrome P450 induction and uroporphyrin accumulation in the chick embryo hepatocyte culture. Biochemical pharmacology 41 (6-7), pp. 915-922.
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The atropisomers of 2,2',3,4,6-pentachlorobiphenyl (PeCB), 2,2',3,4,4',6-hexachlorobiphenyl (HeCB), and 2,2',3,3',4,4',6,6'-octachlorobiphenyl (OCB) were studied in the chick embryo hepatocyte culture to determine if chirality plays a role in the recognition events associated with the induction of cytochromes P450 and the accumulation of uroporphyrin (URO). Concentration-related induction of cytochrome P450 content, ethoxyresorufin-O-deethylase (EROD) and benzphetamine Ndemethylase (BPDM) activities were measured. The rank order of potency for total cytochrome P450 induction was HeCB > OCB greater-or-equal, slanted PeCB. The (+)- and (-)-enantiomers of PeCB and OCB were of equal potencies as inducers of cytochromes P450, whereas the (+)-HeCB was greater than the (-)-HeCB. HeCB was a much more potent inducer of EROD activity than was either PeCB or OCB. EROD activity was induced to a much greater extent by the (+)-enantiomers of all compounds, with the (-)enantiomers of PeCB and OCB being inactive. BPDM activity was induced by all three compounds in the order of OCB greater-or-equal, slanted HeCB > PeCB. The (-)-enantiomers were more potent inducers of BPDM activities than were the (+)-enantiomers, except for HeCB, in which the (+)- was more potent than the (-)enantiomer. Analysis of porphyrin accumulation in cultures treated with δ-aminolevulinic acid revealed that (+)-HeCB caused the greatest percent URO accumulation, which also correlated with the greatest increase in EROD activity. All other enantiomers caused up to 47% URO accumulation, which did not correlate with an increase in EROD activity.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Retired Professors > Prof.Dr. Mannschreck|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||02 Dec 2010 09:31|
|Last Modified:||02 Dec 2010 09:32|