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Related Experiment Videos

Cyclopenta[c,d]pyrene: a highly mutagenic polycyclic aromatic hydrocarbon.

E Eisenstadt, A Gold

    Proceedings of the National Academy of Sciences of the United States of America
    |April 1, 1978
    PubMed
    Summary

    Cyclopenta[c,d]pyrene (CPP), a pollutant found in carbon black, is a potent mutagen. Its mutagenic metabolite is proposed to be the 3,4-oxide, similar to a known carcinogen.

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    Area of Science:

    • Environmental Chemistry
    • Toxicology
    • Organic Chemistry

    Background:

    • Polycyclic aromatic hydrocarbons (PAHs) are environmental pollutants with known mutagenic properties.
    • Cyclopenta[c,d]pyrene (CPP) is a recently identified PAH found in carbon black.
    • CPP exhibits potent mutagenicity, comparable to benzo[a]pyrene.

    Purpose of the Study:

    • To investigate the mutagenic potential of cyclopenta[c,d]pyrene (CPP).
    • To elucidate the metabolic activation pathway of CPP leading to mutagenicity.
    • To compare the mutagenic mechanism of CPP with other known carcinogenic PAHs.

    Main Methods:

    • Salmonella/mammalian-microsome mutagenicity assay.
    • Perturbational molecular orbital calculations.
    • Chemical structure analysis of potential metabolites.

    Main Results:

    • CPP demonstrates high mutagenic potency, on par with benzo[a]pyrene and dibenz[a,c]anthracene.
    • CPP is a mutagenic PAH lacking a "bay-region" structure.
    • Experimental and computational data suggest CPP 3,4-oxide as the mutagenic metabolite.

    Conclusions:

    • The 3,4-oxide metabolite of CPP is proposed as the ultimate mutagenic species.
    • The carbonium ion from CPP 3,4-oxide opening is identical to that from benzo[a]pyrene 7,8-diol-9,10-oxide.
    • CPP's widespread environmental distribution and potent mutagenicity warrant further investigation.

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