Literature DB >> 27566228

Structural insights into the function of steroidogenic cytochrome P450 17A1.

Rahul Yadav1, Elyse M Petrunak1, D Fernando Estrada1, Emily E Scott2.   

Abstract

Cytochrome P450 17A1 (CYP17A1) operates at the core of human steroidogenesis, directing precursors into mineralocorticoids, glucocorticoids, or sex steroids. Although the 17α-hydroxylase and 17,20-lyase activities of this dual function enzyme have been investigated extensively, until recently no CYP17A1 structures were available to inform our understanding. Structures of CYP17A1 with a range of steroidal inhibitors and substrates are now available. This review relates functional knowledge of this enzyme to structural features defining the selective differentiation between its various substrates. While both hydroxylase and lyase substrates have similar orientations with respect to the heme, subtle differences in hydrogen bonding between CYP17A1 and the C3 substituent at the opposite end of ligands appear to correlate with differential substrate utilization and product formation. Complementary structural information from solution NMR supports cytochrome b5 allosteric modulation of the lyase reaction, implicating regions involved in ligand access to the otherwise buried active site.
Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Entities:  

Keywords:  17,20-Lyase; 17α−hydroxylase; Cytochrome P450 17A1; Steroidogenesis; X-ray crystallography

Mesh:

Substances:

Year:  2016        PMID: 27566228      PMCID: PMC5235955          DOI: 10.1016/j.mce.2016.08.035

Source DB:  PubMed          Journal:  Mol Cell Endocrinol        ISSN: 0303-7207            Impact factor:   4.102


  41 in total

1.  EFFECTS OF SUBSTRATES AND COFACTORS ON STEROID SYNTHESIS IN HYPERPLASTIC ADRENALS.

Authors:  D B VILLEE
Journal:  J Clin Endocrinol Metab       Date:  1964-05       Impact factor: 5.958

2.  Human cytochrome b5 requires residues E48 and E49 to stimulate the 17,20-lyase activity of cytochrome P450c17.

Authors:  Jacqueline L Naffin-Olivos; Richard J Auchus
Journal:  Biochemistry       Date:  2006-01-24       Impact factor: 3.162

Review 3.  The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders.

Authors:  Walter L Miller; Richard J Auchus
Journal:  Endocr Rev       Date:  2010-11-04       Impact factor: 19.871

4.  Cortisol production in sheep is influenced by the functional expression of two cytochrome P450 17α-hydroxylase/17,20-lyase (CYP17) isoforms.

Authors:  D Hough; S W P Cloete; K Storbeck; A C Swart; P Swart
Journal:  J Anim Sci       Date:  2012-12-12       Impact factor: 3.159

Review 5.  Androgen synthesis in adrenarche.

Authors:  Walter L Miller
Journal:  Rev Endocr Metab Disord       Date:  2009-03       Impact factor: 6.514

Review 6.  Backdoor pathway for dihydrotestosterone biosynthesis: implications for normal and abnormal human sex development.

Authors:  Maki Fukami; Keiko Homma; Tomonobu Hasegawa; Tsutomu Ogata
Journal:  Dev Dyn       Date:  2012-11-19       Impact factor: 3.780

7.  Transcriptome profiling reveals differentially expressed transcripts between the human adrenal zona fasciculata and zona reticularis.

Authors:  Juilee Rege; Yasuhiro Nakamura; Tao Wang; Todd D Merchen; Hironobu Sasano; William E Rainey
Journal:  J Clin Endocrinol Metab       Date:  2013-01-01       Impact factor: 5.958

8.  Structures of human steroidogenic cytochrome P450 17A1 with substrates.

Authors:  Elyse M Petrunak; Natasha M DeVore; Patrick R Porubsky; Emily E Scott
Journal:  J Biol Chem       Date:  2014-10-09       Impact factor: 5.157

Review 9.  Mechanisms of cytochrome P450 substrate oxidation: MiniReview.

Authors:  F Peter Guengerich
Journal:  J Biochem Mol Toxicol       Date:  2007       Impact factor: 3.642

10.  Mechanism of the third oxidative step in the conversion of androgens to estrogens by cytochrome P450 19A1 steroid aromatase.

Authors:  Francis K Yoshimoto; F Peter Guengerich
Journal:  J Am Chem Soc       Date:  2014-10-10       Impact factor: 15.419

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  10 in total

1.  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.

Authors:  Charlie Fehl; Caleb D Vogt; Rahul Yadav; Kelin Li; Emily E Scott; Jeffrey Aubé
Journal:  J Med Chem       Date:  2018-05-24       Impact factor: 7.446

Review 2.  Spectroscopic studies of the cytochrome P450 reaction mechanisms.

Authors:  Piotr J Mak; Ilia G Denisov
Journal:  Biochim Biophys Acta Proteins Proteom       Date:  2017-06-28       Impact factor: 3.036

Review 3.  Human cytochrome P450 enzymes 5-51 as targets of drugs and natural and environmental compounds: mechanisms, induction, and inhibition - toxic effects and benefits.

Authors:  Slobodan P Rendic; F Peter Guengerich
Journal:  Drug Metab Rev       Date:  2018-08       Impact factor: 4.518

4.  Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1.

Authors:  Eric Gonzalez; F Peter Guengerich
Journal:  J Biol Chem       Date:  2017-07-06       Impact factor: 5.157

5.  Associations Between CYP17A1 and SERPINA6/A1 Polymorphisms, and Cardiometabolic Risk Factors in Black South Africans.

Authors:  Siphiwe N Dlamini; Ananyo Choudhury; Michèle Ramsay; Lisa K Micklesfield; Shane A Norris; Nigel J Crowther; Andrew A Crawford; Brian R Walker; Zané Lombard; Julia H Goedecke
Journal:  Front Genet       Date:  2021-08-13       Impact factor: 4.772

6.  Alternative modes of O2 activation in P450 and NOS enzymes are clarified by DFT modeling and resonance Raman spectroscopy.

Authors:  Alexandra V Soldatova; Thomas G Spiro
Journal:  J Inorg Biochem       Date:  2020-03-13       Impact factor: 4.155

7.  P450 CYP17A1 Variant with a Disordered Proton Shuttle Assembly Retains Peroxo-Mediated Lyase Efficiency.

Authors:  Yilin Liu; Ilia G Denisov; Yelena V Grinkova; Stephen G Sligar; James R Kincaid
Journal:  Chemistry       Date:  2020-11-09       Impact factor: 5.236

8.  Proteomics Recapitulates Ovarian Proteins Relevant to Puberty and Fertility in Brahman Heifers (Bos indicus L.).

Authors:  Muhammad S Tahir; Loan T Nguyen; Benjamin L Schulz; Gry A Boe-Hansen; Milton G Thomas; Stephen S Moore; Li Yieng Lau; Marina R S Fortes
Journal:  Genes (Basel)       Date:  2019-11-12       Impact factor: 4.096

9.  17α-Hydroxylase/17,20-Lyase Deficiency in 46,XY: Our Experience and Review of Literature.

Authors:  Madhur Maheshwari; Sneha Arya; Anurag Ranjan Lila; Vijaya Sarathi; Rohit Barnabas; Khushnandan Rai; Vishwambhar Vishnu Bhandare; Saba Samad Memon; Manjiri Pramod Karlekar; Virendra Patil; Nalini S Shah; Ambarish Kunwar; Tushar Bandgar
Journal:  J Endocr Soc       Date:  2022-01-29

10.  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.

Authors:  Mónica Fernández-Cancio; Núria Camats; Christa E Flück; Adam Zalewski; Bernhard Dick; Brigitte M Frey; Raquel Monné; Núria Torán; Laura Audí; Amit V Pandey
Journal:  Pharmaceuticals (Basel)       Date:  2018-04-29
  10 in total

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