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Related Experiment Videos

Dinitrofluoranthene: induction, identification and gene mutation.

R Nakagawa, K Horikawa, N Sera

    Mutation Research
    |June 1, 1987
    PubMed
    Summary
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    Researchers synthesized new dinitrofluoranthenes (DNFs) and trinitrofluoranthenes (TNFs) from 3-nitrofluoranthene. The synthesized DNFs demonstrated significant mutagenic activity in bacterial assays, indicating potential DNA damage.

    Area of Science:

    • Polycyclic Aromatic Hydrocarbons (PAHs)
    • Chemical Synthesis
    • Mutagenesis and Toxicology

    Background:

    • Nitration of polycyclic aromatic hydrocarbons can yield potentially hazardous derivatives.
    • Understanding the mutagenicity of fluoranthene derivatives is crucial for environmental and health risk assessment.
    • Previous studies have identified dinitropyrenes as potent mutagens.

    Purpose of the Study:

    • To synthesize and identify novel nitro-derivatives of 3-nitrofluoranthene.
    • To evaluate the DNA-damaging and mutagenic potential of the synthesized dinitrofluoranthenes (DNFs).
    • To compare the mutagenic activity of DNFs with known mutagens like dinitropyrene.

    Main Methods:

    • Renitration of 3-nitrofluoranthene using fuming nitric acid.

    Related Experiment Videos

  • Identification of nitro-derivatives using mass spectrometry and 1H-nuclear magnetic resonance.
  • Assessment of DNA-damaging activity using the rec-assay system in Bacillus subtilis.
  • Evaluation of mutagenicity using Salmonella typhimurium His- strains (TA98, TA97, TA1538).

    • Main Results:

    • Synthesis of 3,7-, 3,9-, and 3,4-dinitrofluoranthene (DNF), and two trinitrofluoranthene isomers.
    • 3,7- and 3,9-DNF were the major derivatives, yielding approximately 61.3%.
    • All synthesized DNFs showed positive results in the rec-assay, indicating DNA-damaging activity.
    • 3,7- and 3,9-DNF induced frameshift mutations in Salmonella typhimurium strains, with mutagenicity comparable to 1,6-dinitropyrene.

    Conclusions:

    • Novel dinitrofluoranthenes and trinitrofluoranthenes were successfully synthesized and identified.
    • The synthesized DNFs exhibit significant mutagenic potential, comparable to potent mutagens like dinitropyrene.
    • These findings highlight the potential genotoxicity of fluoranthene nitro-derivatives, warranting further investigation.