ArticleThe Journal of biological chemistry2015
Structural and kinetic basis of steroid 17α,20-lyase activity in teleost fish cytochrome P450 17A1 and its absence in cytochrome P450 17A2.
Article in The Journal of biological chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 62 citations in OpenAlex.
- Determining the Molecular Shape of Progesterone: Insights from Laser Ablation Rotational Spectroscopy.The journal of physical chemistry letters · 2025Article
- Computational Binding Study Hints at Ecdysone 20-Mono-Oxygenase as the Hitherto Unknown Target for Ring C-Seco Limonoid-Type Insecticides.Molecules (Basel, Switzerland) · 2024Article
- Effect of Essential Oil Components on the Activity of Steroidogenic Cytochrome P450.Biomolecules · 2024Article
- Ninety-eight semesters of cytochrome P450 enzymes and related topics-What have I taught and learned?The Journal of biological chemistry · 2024Article
- Abiraterone Acetate Complexes with Biometals: Synthesis, Characterization in Solid and Solution, and the Nature of Chemical Bonding.Pharmaceutics · 2023Article
- Inhibitory mechanism of vortioxetine on CYP450 enzymes in human and rat liver microsomes.Frontiers in pharmacology · 2023Article
- Steroid 17α-hydroxylase/17, 20-lyase (cytochrome P450 17A1).Methods in enzymology · 2023Article
- Characterization of the Interrenal Gland and Sexual Traits Development inFrontiers in endocrinology · 2022Article
- Multistep Binding of the Non-Steroidal Inhibitors Orteronel and Seviteronel to Human Cytochrome P450 17A1 and Relevance to Inhibition of Enzyme Activity.Journal of medicinal chemistry · 2020Article
- Conformational selection dominates binding of steroids to human cytochrome P450 17A1.The Journal of biological chemistry · 2019Article
- Mechanisms of Cytochrome P450-Catalyzed Oxidations.ACS catalysis · 2018Article
- Human cytochrome P450 enzymes 5-51 as targets of drugs and natural and environmental compounds: mechanisms, induction, and inhibition - toxic effects and benefits.Drug metabolism reviews · 2018Review
- Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.Chemical reviews · 2018Review
- Mechanism of the Dual Activities of Human CYP17A1 and Binding to Anti-Prostate Cancer Drug Abiraterone Revealed by a Novel V366M Mutation Causing 17,20 Lyase Deficiency.Pharmaceuticals (Basel, Switzerland) · 2018Article
- Inherent steroid 17α,20-lyase activity in defunct cytochrome P450 17A enzymes.The Journal of biological chemistry · 2018Article
- Two CYP82D Enzymes Function as Flavone Hydroxylases in the Biosynthesis of Root-Specific 4'-Deoxyflavones in Scutellaria baicalensis.Molecular plant · 2018Article
- Genetic Disruption of 21-Hydroxylase in Zebrafish Causes Interrenal Hyperplasia.Endocrinology · 2017Article
- Human mitochondrial cytochrome P450 27C1 is localized in skin and preferentially desaturatesThe Journal of biological chemistry · 2017Article
- Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1.The Journal of biological chemistry · 2017Article
- Structural and Functional Evaluation of Clinically Relevant Inhibitors of Steroidogenic Cytochrome P450 17A1.Drug metabolism and disposition: the biological fate of chemicals · 2017Article
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Cytochrome P450 (P450) 17A enzymes play a critical role in the oxidation of the steroids progesterone (Prog) and pregnenolone (Preg) to glucocorticoids and androgens. In mammals, a single enzyme, P450 17A1, catalyzes both 17α-hydroxylation and a subsequent 17α,20-lyase reaction with both Prog and Preg. Teleost fish contain two 17A P450s; zebrafish P450 17A1 catalyzes both 17α-hydroxylation and lyase reactions with Prog and Preg, and P450 17A2 is more efficient in pregnenolone 17α-hydroxylation but does not catalyze the lyase reaction, even in the presence of cytochrome b5. P450 17A2 binds all substrates and products, although more loosely than P450 17A1. Pulse-chase and kinetic spectral experiments and modeling established that the two-step P450 17A1 Prog oxidation is more distributive than the Preg reaction, i.e. 17α-OH product dissociates more prior to the lyase step. The drug orteronel selectively blocked the lyase reaction of P450 17A1 but only in the case of Prog. X-ray crystal structures of zebrafish P450 17A1 and 17A2 were obtained with the ligand abiraterone and with Prog for P450 17A2. Comparison of the two fish P450 17A-abiraterone structures with human P450 17A1 (DeVore, N. M., and Scott, E. E. (2013) Nature 482, 116-119) showed only a few differences near the active site, despite only ∼50% identity among the three proteins. The P450 17A2 structure differed in four residues near the heme periphery. These residues may allow the proposed alternative ferric peroxide mechanism for the lyase reaction, or residues removed from the active site may allow conformations that lead to the lyase activity.
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