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Reactive ring-opened aldehyde metabolites in benzene hematotoxicity

G Witz1, Z Zhang, B D Goldstein

  • 1UMDNJ-Robert Wood Johnson Medical School, Environmental and Occupational Health Sciences Institute, Piscataway 08855, USA. witz@eohsi.rutgers.edu

Environmental Health Perspectives
|December 1, 1996
PubMed
Summary

Benzene causes bone marrow damage through reactive metabolites like trans-trans-muconaldehyde (MUC). MUC and its derivatives contribute to benzene hematotoxicity, especially when combined with other metabolites.

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Area of Science:

  • Toxicology
  • Metabolism
  • Organic Chemistry

Background:

  • Benzene's hematotoxicity is linked to reactive metabolites.
  • The role of ring-opened metabolites in benzene toxicity is under investigation.

Purpose of the Study:

  • To investigate the contribution of ring-opened metabolites, specifically trans-trans-muconaldehyde (MUC), to benzene-induced hematotoxicity.
  • To characterize the metabolism and biological activity of MUC and its derivatives.

Main Methods:

  • In vitro metabolism studies of benzene.
  • Toxicological assessment of MUC and its metabolites in bone marrow and in vivo models.
  • Mechanistic studies using Fenton systems to elucidate ring-opening pathways.

Main Results:

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  • Benzene is metabolized to trans-trans-muconaldehyde (MUC), a reactive dialdehyde toxic to bone marrow.
  • MUC, particularly when co-administered with hydroquinone, exacerbates bone marrow damage.
  • MUC is further metabolized to 6-hydroxy-trans-trans-2,4-hexadienal (CHO-M-OH) and 6-hydroxy-trans-trans-2,4-hexadienoic acid (COOH-M-OH), both exhibiting reactivity and toxicity.
  • COOH-M-OH is identified as a urinary metabolite in mice, supporting in vivo MUC formation.
  • Benzene ring opening by hydroxyl radicals generates various muconaldehyde isomers, with trans-trans-muconaldehyde being a key product.

Conclusions:

  • Ring-opened metabolites, especially MUC, play a significant role in benzene hematotoxicity.
  • The toxicity of benzene likely arises from the combined effects of multiple reactive metabolites.
  • Understanding MUC metabolism and its toxicological profile is crucial for elucidating benzene's mechanism of action.