Structure-activity relationships for flow cytometric data of smaller polycyclic aromatic hydrocarbons.
Using flow cytometry, select polycyclic aromatic hydrocarbons (PAHs) were evaluated for induction of apoptosis in human monocytic THP-1 cells. Based on structure, the PAHs were divided into linear and bay-region-containing compounds. Except for fluorene, the linear PAHs failed to induce apoptosis; all of the bay-region-containing PAHs induce apoptosis. The relationship that a bay-region is required to induce apoptosis is supported by results for benzo[a]pyrene (positive) and 2-methylanthracene (negative). The data for bay-region containing, four-ringed PAH compounds reveal that possessing a linear-region of more than two rings diminishes the ability of a PAH to induce apoptosis. Owing to the steric interactions of the hydrogen atoms of the methyl group and those on the ring carbons, 1-methylanthracene does not have a true bay-region. However, the methyl group substituted in the 1-position does confer a bay-like conformation, which may explain its activity in contrast to its parent derivative anthracene and its 2-postion homologue.
Wan
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Department of Comparative Medicine, College of Veterinary Medicine, The University of Tennessee, Room A205, 2407 River Drive, Knoxville, Tennessee 37996-4543, USA.
Sayler
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GS
Schultz
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D000873:Anthracenes / Q000737:chemistry; D017209:Apoptosis; D002460:Cell Line; D045744:Cell Line, Tumor; D053938:DNA Fragmentation; D003627:Data Interpretation, Statistical; D005434:Flow Cytometry / Q000379:methods*; D006801:Humans; D008956:Models, Chemical; D015394:Molecular Structure; D009000:Monocytes / Q000166:cytology; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship
D000873:Anthracenes; D011084:Polycyclic Aromatic Hydrocarbons; D011083:Polycyclic Compounds