ArticleOrganic & biomolecular chemistry2021
Effects of fluorine substitution on substrate conversion by cytochromes P450 17A1 and 21A2.
Article in Organic & biomolecular chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 8 citations in OpenAlex.
- The Evolution of Precision Anti-Doping From UGT2B17 Polymorphism Insights to Integrated Detection Frameworks.Drug testing and analysis · 2026Review
- Metabolic Stability of Fluorinated Small Molecules: A Physical Organic Chemistry Perspective.Journal of medicinal chemistry · 2026Review
- Speciation and kinetics of fluoride transfer from tetra-Chemical science · 2024Article
- Effect of Essential Oil Components on the Activity of Steroidogenic Cytochrome P450.Biomolecules · 2024Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Cytochromes P450 17A1 (CYP7A1) and 21A2 (CYP21A2) catalyze key reactions in the production of steroid hormones, including mineralocorticoids, glucocorticoids, and androgens. With the ultimate goal of designing probes that are selectively metabolized to each of these steroid types, fluorinated derivatives of the endogenous substrates, pregnenolone and progesterone, were prepared to study the effects on CYP17A1 and CYP21A2 activity. In the functional assays, the hydroxylase reactions catalysed by each of these enzymes were blocked when fluorine was introduced at the site of metabolism (positions 17 and 21 of the steroid core, respectively). CYP17A1, furthermore, performed the 17,20-lyase reaction on substrates with a fluorine installed at the 21-position. Importantly, none of the substitutions examined herein prevented compound entry into the active sites of either CYP17A1 or CYP21A2 as demonstrated by spectral binding assays. Taken together, the results suggest that fluorine might be used to redirect the metabolic pathways of pregnenolone and progesterone to specific types of steroids.
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