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Carcinogenesis, Vol 19, 1641-1648, Copyright © 1998 by Oxford University Press

ARTICLES

Dibenzo[a,l]pyrene (dibenzo[def,p]chrysene): fjord-region distortions

AK Katz, HL Carrell and JP Glusker
The Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, PA 19111, USA.

The molecular dimensions of the potent chemical carcinogen dibenzo[def,p]chrysene, also known as dibenzo[a,l]pyrene, have been determined by X-ray diffraction methods. This analysis shows that the molecule is considerably distorted so that it is non-planar with an angle of 27.6 degrees between the outermost rings and a widening of C-C- C bond angles in the fjord region. The dimensions of the molecular distortion due to atomic overcrowding in the fjord region are presented. This polycyclic aromatic hydrocarbon is a more potent carcinogen than is benzo[a]pyrene or its 11-methyl derivative. Comparisons of the distortions in dibenzo[a,l]pyrene with the geometries of various other polycyclic aromatic hydrocarbons containing fjord- or bay-region methyl groups provide structural data on the ratio of angular to torsional distortion in such overcrowded molecules.
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