Abstract:
:The non-covalent interactions of benzo[a]pyrene (BP) and several of its hydroxylated metabolites with ligandin, aminoazodye-binding protein A (Z-protein, fatty acid binding protein) and lecithin bilayers have been studied by equilibrium dialysis, an adsorption technique and fluorescence spectroscopy. Binding affinities expressed as v/c (where v = moles of BP or BP metabolite bound per mole of protein or lipid and c = unbound concentration), were measured at concentrations sufficiently low that there was no self-association of the unbound compounds as judged by their fluorescence characteristics. 3-Hydroxybenzo[a]pyrene (BP-3-phenol), 4,5-dihydro-4,5-dihydroxybenzo[a]pyrene (BP-4,5-dihydrodiol) and 7,8-dihydro-7,8-dihydroxybenzo[a]pyrene (BP-7,8-dihydrodiol) bind more strongly (v/c = 10(5)-5 x 10(5) l x mol-1) to all three binders than does BP itself (v/c = 10(4)-7 x 10(4) l x mol-1). 9,10-Dihydro-9,10-dihydroxybenzo[a]pyrene (BP-9,10-dihydrodiol) binds to ligandin with an affinity similar to those of the other BP metabolites studied here, but binds much less strongly to both protein A and lecithin (v/c = 10(4) and 3 x 10(4) x mol-1, respectively). The low affinity of BP-9,10-dihydrodiol for lecithin would account for earlier findings that on incubation of BP with isolated rat hepatocytes, this metabolite egressed from the cells to the extracellular medium much more readily than either BP-4,5-dihydrodiol or BP-7,8-dihydrodiol. Calculations based on these results suggest that within hepatocytes BP and its metabolites, including BP-9,10-dihydrodiol, will be found almost exclusively associated (> 98%) with lipid membranes.
journal_name
Chem Biol Interactjournal_title
Chemico-biological interactionsauthors
Tipping E,Moore BP,Jones CA,Cohen GM,Ketterer B,Bridges JWdoi
10.1016/0009-2797(80)90096-4subject
Has Abstractpub_date
1980-11-01 00:00:00pages
291-304issue
3eissn
0009-2797issn
1872-7786pii
0009-2797(80)90096-4journal_volume
32pub_type
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