The structure-activity relationship of skin carcinogenicity of aromatic hydrocarbons and heterocycles.
From a study of 239 aromatic and heteroaromatic compounds causing skin cancer in mice, a quantitative structure-activity relationship has been derived. Carcinogenicity depends heavily on the relative hydrophobicity of the chemicals as defined by octanol/water partition coefficients (log P). It is also correlated with the energy of the highest occupied molecular orbital and the presence of substituents on the L and K regions of the carcinogen. The results are discussed in terms of the bay region concept for carcinogenic activity.
Zhang
L
L
Department of Chemistry, Pomona College, Claremont, CA 91711-6338.
Sannes
K
K
Shusterman
A J
AJ
Hansch
C
C
D000818:Animals; D002273:Carcinogens / Q000633:toxicity*; D006571:Heterocyclic Compounds / Q000633:toxicity*; D006801:Humans; D006838:Hydrocarbons / Q000633:toxicity*; D008433:Mathematics; D015394:Molecular Structure; D012878:Skin Neoplasms / Q000139:chemically induced*; D013329:Structure-Activity Relationship
D002273:Carcinogens; D006571:Heterocyclic Compounds; D006838:Hydrocarbons