Cytochrome P450: what have we learned and what are the future issues? (Q35828009)

10 August 2017

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title

Cytochrome P450: what have we learned and what are the future issues? (English)

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10 August 2017

F Peter Guengerich

1

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10 August 2017

language of work or name

English

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publication date

1 May 2004

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10 August 2017

published in

Drug Metabolism Reviews

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10 August 2017

volume

36

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10 August 2017

issue

2

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10 August 2017

page(s)

159-197

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Interaction of adrenodoxin with P4501A1 and its truncated form P450MT2 through different domains: differential modulation of enzyme activities

10 August 2017

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Enhancement and Inhibition of Drug Metabolism

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Cytochrome b5 augments the 17,20-lyase activity of human P450c17 without direct electron transfer

21 January 2018

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Revisiting the mechanism of P450 enzymes with the radical clocks norcarane and spiro[2,5]octane

21 January 2018

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Interactions among P450 enzymes when combined in reconstituted systems: formation of a 2B4-1A2 complex with a high affinity for NADPH-cytochrome P450 reductase.

21 January 2018

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Maximizing expression of eukaryotic cytochrome P450s in Escherichia coli

21 January 2018

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Weak alignment offers new NMR opportunities to study protein structure and dynamics.

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Chip-based P450 drug metabolism coupled to electrospray ionization-mass spectrometry detection

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Unusual binding stoichiometries and cooperativity are observed during binary and ternary complex formation in the single active pore of R67 dihydrofolate reductase, a D2 symmetric protein

21 January 2018

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7,8-Benzoflavone stimulates the metabolic activation of aflatoxin B1 to mutagens by human liver

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Cytochrome P450 CYP1B1 determines susceptibility to 7, 12-dimethylbenz[a]anthracene-induced lymphomas

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Cytosine deaminase gene as a positive selection marker

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structure of the F87W/Y96F/V247L mutant of cytochrome P-450cam with 1,3,5-trichlorobenzene bound and further protein engineering for the oxidation of pentachlorobenzene and hexachlorobenzene

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Structure–function studies of aromatase and its inhibitors: a progress report

21 January 2018

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Human cholesterol side-chain cleavage enzyme, P450scc: cDNA cloning, assignment of the gene to chromosome 15, and expression in the placenta

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Transition from pharmaceutical to environmental research

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Hepatic cytochrome P450 degradation: mechanistic diversity of the cellular sanitation brigade

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Pyrene.pyrene complexes at the active site of cytochrome P450 3A4: evidence for a multiple substrate binding site

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Synergistic action of hepatocyte nuclear factors 3 and 6 on CYP2C12 gene expression and suppression by growth hormone-activated STAT5b. Proposed model for female specific expression of CYP2C12 in adult rat liver

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Genetic metabolic polymorphisms and the risk of cancer: a review of the literature

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Probing the open state of cytochrome P450cam with ruthenium-linker substrates

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Generation and Evaluation of a CYP2C9 Heteroactivation Pharmacophore

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

A passion for P450s (rememberances of the early history of research on cytochrome P450).

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Pharmacogenomics: translating functional genomics into rational therapeutics

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Ligand-induced structural changes to maltodextrin-binding protein as studied by solution NMR spectroscopy

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structures of cyanide complexes of P450cam and the oxygenase domain of inducible nitric oxide synthase-structural models of the short-lived oxygen complexes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Radicals in enzymatic reactions.

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The Pennsylvania State University College of Medicine 1991 Bernard B. Brodie Lecture. Insights into deuterium isotope effects on the metabolism of steroid hormones and foreign compounds by cytochrome P-450 enzymes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Theory for the observed isotope effects on the formation of multiple products by different kinetic mechanisms of cytochrome P450 enzymes.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Study of P450 function using gene knockout and transgenic mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Characterization of the common genetic defect in humans deficient in debrisoquine metabolism

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Identification of bile acid precursors as endogenous ligands for the nuclear xenobiotic pregnane X receptor

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Forging the links between metabolism and carcinogenesis

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Cytochrome P450 enzymes in the generation of commercial products

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Rate-limiting steps in cytochrome P450 catalysis

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Cytochromes P450, drugs, and diseases

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

Kinetics of ferric cytochrome P450 reduction by NADPH-cytochrome P450 reductase: rapid reduction in the absence of substrate and variations among cytochrome P450 systems

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

New applications of bacterial systems to problems in toxicology.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Oxidation of methoxyphenethylamines by cytochrome P450 2D6. Analysis of rate-limiting steps.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The aryl hydrocarbon receptor complex

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

SALSA: a pattern recognition algorithm to detect electrophile-adducted peptides by automated evaluation of CID spectra in LC-MS-MS analyses

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Cyclopropylamines as suicide substrates for cytochromes P-450

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Analysis of human cytochrome P450 3A4 cooperativity: construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Two-State Reactivity in the Rebound Step of Alkane Hydroxylation by Cytochrome P-450: Origins of Free Radicals with Finite Lifetimes This research was sponsored by the Israeli Science Foundation (ISF) and, in part, by the German Israeli Foundation (

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

MECHANISM OF THE PYROCATECHASE REACTION

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Atypical kinetic profiles in drug metabolism reactions

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Uncoupling of the cytochrome P-450cam monooxygenase reaction by a single mutation, threonine-252 to alanine or valine: possible role of the hydroxy amino acid in oxygen activation

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The 2002 Bernard B. Brodie Award lecture: deciphering substrate recognition by drug-metabolizing cytochromes P450.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Expression of human aromatase (CYP19) in Escherichia coli by N-terminal replacement and induction of cold stress response

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Aryl hydrocarbon hydroxylase inducibility and bronchogenic carcinoma.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Hydroperoxy-10,12-Octadecadienoic Acid Stimulates Cytochrome P450 3A Protein Aggregation by a Mechanism That Is Inhibited by Substrate

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

An orphan nuclear receptor activated by pregnanes defines a novel steroid signaling pathway

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Proteolytic degradation of heme-modified hepatic cytochromes P450: A role for phosphorylation, ubiquitination, and the 26S proteasome?

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Comparison of Experimental Binding Data and Theoretical Models in Proteins Containing Subunits*

21 January 2018

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https://api.crossref.org/works/10.1081%2FDMR-120033996

The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2).

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Conformational dynamics in cytochrome P450-substrate interactions

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The kinetic and spectral characterization of the E. coli-expressed mammalian CYP4A7: cytochrome b5 effects vary with substrate

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

How do substrates enter and products exit the buried active site of cytochrome P450cam? 1. Random expulsion molecular dynamics investigation of ligand access channels and mechanisms.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Polymorphic hydroxylation of Debrisoquine in man.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Sulfaphenazole derivatives as tools for comparing cytochrome P450 2C5 and human cytochromes P450 2Cs: identification of a new high affinity substrate common to those enzymes.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

A new method for sequencing DNA

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Binding and oxidation of alkyl 4-nitrophenyl ethers by rabbit cytochrome P450 1A2: evidence for two binding sites

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Multiple forms of inducible drug-metabolizing enzymes: A reasonable mechanism by which any organism can cope with adversity

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The Ah locus: genetic differences in toxicity, cancer, mutation, and birth defects

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Clinical importance of the cytochromes P450

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Comparison of P450s from human and fugu: 420 million years of vertebrate P450 evolution

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Kinetic isotope effects implicate two electrophilic oxidants in cytochrome p450-catalyzed hydroxylations

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Steady-state analysis of kinetic isotope effects in enzymic reactions

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Selection and characterization of human cytochrome P450 1A2 mutants with altered catalytic properties

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structure of cytochrome P450 14 -sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Cytochrome P450: molecular architecture, mechanism, and prospects for rational inhibitor design

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

High-resolution crystal structure of cytochrome P450cam

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The structural basis for substrate-induced changes in redox potential and spin equilibrium in cytochrome P-450CAM

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structures of cytochrome P-450CAM complexed with camphane, thiocamphor, and adamantane: factors controlling P-450 substrate hydroxylation

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

A self-sufficient cytochrome p450 with a primary structural organization that includes a flavin domain and a [2Fe-2S] redox center

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Oxysterol biosynthetic enzymes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

DNA sequencing with chain-terminating inhibitors

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The catalytic pathway of cytochrome p450cam at atomic resolution

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The role of cytochrome P450 monooxygenases in plant-insect interactions

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Substrate routes to the buried active site may vary among cytochromes P450: mutagenesis of the F-G region in P450 2B1.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

An open conformation of mammalian cytochrome P450 2B4 at 1.6-Å resolution

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Two-state reactivity mechanisms of hydroxylation and epoxidation by cytochrome P-450 revealed by theory.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

A kinetic model for the metabolic interaction of two substrates at the active site of cytochrome P450 3A4.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Two mutant alleles of the human cytochrome P-450db1 gene (P450C2D1) associated with genetically deficient metabolism of debrisoquine and other drugs

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

The orphan nuclear receptor HNF4alpha determines PXR- and CAR-mediated xenobiotic induction of CYP3A4

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

NMR study on the structural changes of cytochrome P450cam upon the complex formation with putidaredoxin. Functional significance of the putidaredoxin-induced structural changes.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Cooperativity in oxidations catalyzed by cytochrome P450 3A4.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

P450 gene induction by structurally diverse xenochemicals: central role of nuclear receptors CAR, PXR, and PPAR.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Structure of a substrate complex of mammalian cytochrome P450 2C5 at 2.3 A resolution: evidence for multiple substrate binding modes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Structure of mammalian cytochrome P450 2C5 complexed with diclofenac at 2.1 A resolution: evidence for an induced fit model of substrate binding

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structure of human cytochrome P450 2C9 with bound warfarin

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Comparison of the dynamics of substrate access channels in three cytochrome P450s reveals different opening mechanisms and a novel functional role for a buried arginine

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Rapid measurement of binding constants and heats of binding using a new titration calorimeter

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Lack of electron transfer from cytochrome b5 in stimulation of catalytic activities of cytochrome P450 3A4. Characterization of a reconstituted cytochrome P450 3A4/NADPH-cytochrome P450 reductase system and studies with apo-cytochrome b5.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Reconstitution of recombinant cytochrome P450 2C10(2C9) and comparison with cytochrome P450 3A4 and other forms: effects of cytochrome P450-P450 and cytochrome P450-b5 interactions.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Roles of NADPH-P450 reductase and apo- and holo-cytochrome b5 on xenobiotic oxidations catalyzed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichia coli.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Oxidations of p-alkoxyacylanilides catalyzed by human cytochrome P450 1A2: structure-activity relationships and simulation of rate constants of individual steps in catalysis.

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Crystal structure of OxyB, a cytochrome P450 implicated in an oxidative phenol coupling reaction during vancomycin biosynthesis

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Selection of human cytochrome P450 1A2 mutants with enhanced catalytic activity for heterocyclic amine N-hydroxylation

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

Roles of Cytochrome b5in the Oxidation of Testosterone and Nifedipine by Recombinant Cytochrome P450 3A4 and by Human Liver Microsomes

21 January 2018

1 reference

https://api.crossref.org/works/10.1081%2FDMR-120033996

21 January 2018

Identifiers

DOI

10.1081/DMR-120033996

1 reference

10 August 2017

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