Theoretical Investigation of Cytochrome P450 Enzyme-Mediated Biotransformation Mechanism of BHPF: Unveiling the Metabolic Safety Aspects of an Alternative to BPA.

ABSTRACT: Fluorene-9-bisphenol (BHPF), emerging as an alternative to bisphenol A (BPA), is extensively utilized in industry and consumer goods. BHPF exhibits antiestrogenic effects and potential reproductive toxicity. Similar to BPA, BHPF can closely access the active site of the cytochrome P450 (CYP450) enzyme, interact with the Fe=O moiety, and potentially initiate metabolic reactions. Using density functional theory (DFT) calculations, we explored the mechanisms underlying BHPF activation using a CYP450 compound I (Cpd I) model, identifying several plausible products. Compared with the higher energy barriers associated with phenyl ring addition reactions, the formation of a phenoxyl-type radical through phenolic hydrogen atom abstraction, followed by OH rebound or radical coupling, represents an

SUBMITTER: Pan W 

PROVIDER: S-EPMC11851209 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature