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The Interaction of Carcinogenic Hydrocarbons with Tissues

V. Some Structural Requirements for Binding of 1,2,5,6-Dibenzanthracene^*

( McArdle Memorial Laboratory, Medical School, University of Wisconsin, Madison, Wis.)

1. Sixteen C¹⁴-labeled derivatives of 1,2,5,6-dibenzanthracene (DBA), with substituent groups either in the 9,10-positions (L region) or on the phenanthrene double bonds (K regions), and 2-phenylphenanthrene-3,2'-dicarboxylic acid-1,4-C¹⁴ (PDA) have been synthesized.

2. The amount of protein-bound radioactivity in mouse skin was measured at various times after a single topical application of the C¹⁴-labeled compounds. Relative to DBA, the following derivatives were bound to a considerably lesser extent: 3-acetoxy-, 3,4-dihydro-3,4-diacetoxy-, 3,7-dimethoxy-, 3,4,7,8-tetramethoxy-, 9-acetoxy, 9,10-diacetoxy-, 9,10-dimethoxy-, and 9,10-dimethyl-DBA, as well as DBA-3,4- and 9,10-quinones and PDA. The 3,4-dihydroxy-3, 4-dihyro-, 3-hydroxy-, 3-methoxy-, 3,4-dimethoxy-, and 9-methoxy-DBA derivatives were bound to approximately the same extent as DBA.

3. The radioactivity from the compounds investigated was present in the skin in excess of the amounts bound to protein and in amounts comparable to that from DBA. Thus, binding of a compound was a function not of the amount present in the skin, but of its chemical structure.

4. For binding, the intact aromatic dibenzanthracene ring system is necessary. The presence of substituents in one K region may cause a shift of binding to the second K region or binding may take place through the L region. "Blocking" both K regions reduces or prevents binding.

5. The rates of reaction with osmium tetroxide of some of the compounds were studied to compare the electron densities at the K region.

6. An interpretation for the binding results obtained is advanced based on theoretical considerations.

^* This work was supported in part by a grant from the Wisconsin Section of the American Cancer Society, and by a research grant, C-1132, from the National Cancer Institute, National Institutes of Health, Public Health Service. A preliminary account of this work appeared in Proc. Am. Assoc. Cancer Research, 2 (4):332–33, 1958.

Received 5/29/58.