skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Structural and Kinetic Basis of Steroid 17[alpha],20-Lyase Activity in Teleost Fish Cytochrome P450 17A1 and Its Absence in Cytochrome P450 17A2

Journal Article · · J. Biol. Chem.

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
National Institutes of Health (NIH)
OSTI ID:
1170036
Journal Information:
J. Biol. Chem., Vol. 290, Issue (6) ; 02, 2015
Country of Publication:
United States
Language:
ENGLISH
Citation Metrics:
Cited by: 48 works
Citation information provided by
Web of Science

References (66)

Pathways Leading to Phosphorylation of P450c17 and to the Posttranslational Regulation of Androgen Biosynthesis journal January 2008
Cytochrome P-45017α,lyase-mediating pathway of androgen synthesis in bovine adrenocortical cultured cells journal March 1992
Oxidation of N-Nitrosoalkylamines by Human Cytochrome P450 2A6 journal March 2010
Effect of an investigational CYP17A1 inhibitor, orteronel (TAK-700), on estrogen- and corticoid-synthesis pathways in hypophysectomized female rats and on the serum estradiol levels in female cynomolgus monkeys journal November 2013
Global Kinetic Explorer: A new computer program for dynamic simulation and fitting of kinetic data journal April 2009
Kinetic Analysis of Successive Reactions Catalyzed by Bovine Cytochrome P450 17α,lyase journal March 1998
Reduction of cytochrome b5 by NADPH–cytochrome P450 reductase journal August 2005
Kinetic Studies of Cytochrome P-45017.alpha.,lyase Dependent Androstenedione Formation from Progesterone journal August 1995
Sequential Metabolism of Secondary Alkyl Amines to Metabolic-Intermediate Complexes: Opposing Roles for the Secondary Hydroxylamine and Primary Amine Metabolites of Desipramine, ( S )-Fluoxetine, and N- Desmethyldiltiazem journal March 2010
Kinetic Solvent Isotope Effect in Human P450 CYP17A1-Mediated Androgen Formation: Evidence for a Reactive Peroxoanion Intermediate journal October 2013
Serine phosphorylation of human P450c17 increases 17,20-lyase activity: implications for adrenarche and the polycystic ovary syndrome. journal November 1995
Cloning of zebrafish ovarian P450c17 (CYP17, 17α-hydroxylase/17, 20-lyase) and characterization of its expression in gonadal and extra-gonadal tissues journal January 2004
Trypsin Cleaves Exclusively C-terminal to Arginine and Lysine Residues journal March 2004
Kinetic studies on androstenedione production in ovarian microsomes from immature rats journal May 1992
Cytochrome b 5 Augments the 17,20-Lyase Activity of Human P450c17 without Direct Electron Transfer journal February 1998
In Situ Proteolysis to Generate Crystals for Structure Determination: An Update journal April 2009
Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer journal November 2011
A Novel Type of P450c17 Lacking the Lyase Activity Is Responsible for C21-Steroid Biosynthesis in the Fish Ovary and Head Kidney journal September 2007
The Carbon Monoxide-binding Pigment of Liver Microsomes journal July 1964
Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001 journal January 2012
Role of cytochrome b5 in the cytochrome P-450-mediated C21-steroid 17,20-lyase reaction journal September 1982
Complex reactions catalyzed by cytochrome P450 enzymes journal March 2007
Purification of cytochrome b5 book January 1978
Substrate-modulated Cytochrome P450 17A1 and Cytochrome b 5 Interactions Revealed by NMR journal April 2013
Scaling and assessment of data quality journal December 2005
The CCP4 suite programs for protein crystallography journal September 1994
Phosphorylation of Human Cytochrome P450c17 by p38α Selectively Increases 17,20 Lyase Activity and Androgen Biosynthesis journal August 2013
Role of the Alanine at Position 363 of Cytochrome P450 2B2 in Influencing the NADPH- and Hydroperoxide-Supported Activities journal February 1998
Expression of Modified Cytochrome P450 2C10 (2C9) in Escherichia coli, Purification, and Reconstitution of Catalytic Activity journal November 1993
Catalytically Relevant Electrostatic Interactions of Cytochrome P450c17 (CYP17A1) and Cytochrome b 5 journal October 2014
UCSF Chimera?A visualization system for exploratory research and analysis journal January 2004
Orteronel (TAK-700), a novel non-steroidal 17,20-lyase inhibitor: Effects on steroid synthesis in human and monkey adrenal cells and serum steroid levels in cynomolgus monkeys journal April 2012
Androgen Formation by Cytochrome P450 CYP17. Solvent Isotope Effect and pL Studies Suggest a Role for Protons in the Regulation of Oxene versus Peroxide Chemistry journal March 1994
Effect of a novel 17,20-lyase inhibitor, orteronel (TAK-700), on androgen synthesis in male rats journal March 2013
Structures of Human Steroidogenic Cytochrome P450 17A1 with Substrates journal October 2014
Incorporation of label from 18 O 2 into acetate during side-chain cleavage catalysed by cytochrome P-450 17α (17α-hydroxylase-17,20-lyase) journal January 1994
Cloning and expression of P450c17-I (17α-hydroxylase/17,20-lyase) in brain and ovary during gonad development in Cynoglossus semilaevis journal January 2010
Enzyme kinetic and inhibition analyses of cytochrome P450XVII, a protein with a bifunctional catalytic site. Quantification of effective substrate concentrations at the active site and their significance for intrinsic control of the hydroxylase/lyase reaction sequence. journal April 1991
Calibration of the Channel That Determines the ω-Hydroxylation Regiospecificity of Cytochrome P4504A1 journal June 2005
The 17, 20-Lyase Activity of Cytochrome P450c17 from Human Fetal Testis Favors the Δ 5 Steroidogenic Pathway journal August 2003
Kinetics of Cytochrome P450 2E1-Catalyzed Oxidation of Ethanol to Acetic Acid via Acetaldehyde journal August 1999
Differential Hydrogen Bonding in Human CYP17 Dictates Hydroxylation versus Lyase Chemistry journal April 2013
Conversion of pregnenolone to DHEA by human 17α-hydroxylase/17,20-lyase (P450c17): Evidence that DHEA is produced from the released intermediate, 17α-hydroxypregnenolone journal June 2000
xia2 : an expert system for macromolecular crystallography data reduction journal December 2009
In situ proteolysis for protein crystallization and structure determination journal November 2007
Chaperone Coexpression Plasmids: Differential and Synergistic Roles of DnaK-DnaJ-GrpE and GroEL-GroES in Assisting Folding of an Allergen of Japanese Cedar Pollen, Cryj2, inEscherichia coli journal May 1998
Coot model-building tools for molecular graphics journal November 2004
The Role of Cytochrome b5 in the Biosynthesis of Androgens by Human P450c17 journal March 1995
REFMAC 5 for the refinement of macromolecular crystal structures journal March 2011
The Molecular Biology, Biochemistry, and Physiology of Human Steroidogenesis and Its Disorders journal February 2011
Three-dimensional Structure of Steroid 21-Hydroxylase (Cytochrome P450 21A2) with Two Substrates Reveals Locations of Disease-associated Variants journal January 2012
P450c17 Mutations R347H and R358Q Selectively Disrupt 17,20-Lyase Activity by Disrupting Interactions with P450 Oxidoreductase and Cytochrome b 5 journal January 1999
Fast, scalable generation of high‐quality protein multiple sequence alignments using Clustal Omega journal January 2011
Mechanistic kinship between hydroxylation and desaturation reactions: acyl-carbon bond cleavage promoted by pig and human CYP17 (P-45017.alpha.; 17.alpha.-hydroxylase-17,20-lyase) journal October 1995
Oxidation of Methyl and Ethyl Nitrosamines by Cytochrome P450 2E1 and 2B1 journal December 2012
A Universal Approach to the Expression of Human and Rabbit Cytochrome P450s of the 2C Subfamily inEscherichia coli journal October 1995
Multi-step oxidations catalyzed by cytochrome P450 enzymes: Processive vs. distributive kinetics and the issue of carbonyl oxidation in chemical mechanisms journal March 2011
Mechanism of the Acyl-Carbon Cleavage and Related Reactions Catalyzed by Multifunctional P-450s: Studies on Cytochrome P-45017.alpha. journal April 1994
The molecular basis of isolated 17,20 lyase deficiency journal January 1998
Vitamin D 25-hydroxylase – Four decades of searching, are we there yet? journal July 2012
[20] Processing of X-ray diffraction data collected in oscillation mode book January 1997
Biochemical Differences between Rat and Human Cytochrome P450c17 Support the Different Steroidogenic Needs of These Two Species journal February 1999
Kinetic control of steroidogenesis by steroid concentration in guinea pig adrenal microsomes journal July 1991
Stereoselective Formation and Metabolism of 4-Hydroxy-Retinoic Acid Enantiomers by Cytochrome P450 Enzymes* journal December 2012
Phaser crystallographic software journal July 2007
Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction. journal January 1986

Cited By (8)

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 journal April 2018
Genetic Disruption of 21-Hydroxylase in Zebrafish Causes Interrenal Hyperplasia journal September 2017
Conformational selection dominates binding of steroids to human cytochrome P450 17A1 journal June 2019
In Situ Proteolysis for Crystallization of Membrane Bound Cytochrome P450 17A1 and 17A2 Proteins from Zebrafish journal April 2016
The Role of Protein-Protein and Protein-Membrane Interactions on P450 Function journal February 2016
Expression and activity profiling of the steroidogenic enzymes of glucocorticoid biosynthesis and the fdx1 co-factors in zebrafish journal April 2018
Protein Engineering of the Progesterone Hydroxylating P450-Monooxygenase CYP17A1 Alters Its Regioselectivity journal August 2018
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 text January 2018