Structures of Cytochrome P450 2B4 Complexed with the Antiplatelet Drugs Ticlopidine and Clopidogrel,

scientific article

Structures of Cytochrome P450 2B4 Complexed with the Antiplatelet Drugs Ticlopidine and Clopidogrel, is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/BI100914Z
P3181OpenCitations bibliographic resource ID1845279
P932PMC publication ID3005796
P698PubMed publication ID20815363
P5875ResearchGate publication ID46146726

P2093author name stringC David Stout
James R Halpert
Arthur G Roberts
Qinghai Zhang
Sean C Gay
Wen-Xu Hong
Keiko Maekawa
Jyothi C Talakad
P2860cites workCrystal structure of a cytochrome P450 2B6 genetic variant in complex with the inhibitor 4-(4-chlorophenyl)imidazole at 2.0-A resolutionQ24294558
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Structural and Thermodynamic Consequences of 1-(4-Chlorophenyl)imidazole Binding to Cytochrome P450 2B4 † , ‡Q27648413
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Refinement of macromolecular structures by the maximum-likelihood methodQ27861011
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Theory, practice, and applications of paramagnetic relaxation enhancement for the characterization of transient low-population states of biological macromolecules and their complexes.Q33671554
NMR spectral quantitation by principal component analysisQ34285111
Analysis of mammalian cytochrome P450 structure and function by site-directed mutagenesisQ34317426
Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenasesQ36255503
Structure-function analysis of cytochromes P450 2B.Q36578635
What common structural features and variations of mammalian P450s are known to date?Q36636833
NMR studies of substrate binding to cytochrome P450 BM3: comparisons to cytochrome P450 cam.Q36688144
Thermodynamics of water mediating protein-ligand interactions in cytochrome P450cam: a molecular dynamics studyQ36786061
Mechanism-based inactivation of cytochrome P450 enzymes: chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactionsQ36855287
Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humansQ37641606
A model for human cytochrome P450 2D6 based on homology modeling and NMR studies of substrate bindingQ38359211
Identification of the human cytochrome P450 enzymes involved in the two oxidative steps in the bioactivation of clopidogrel to its pharmacologically active metaboliteQ39790140
Pharmacokinetic and metabolic characteristics of ticlopidine in relation to its inhibitory properties on platelet functionQ40188721
New applications of simulated annealing in X-ray crystallography and solution NMR.Q41398215
Ticlopidine decreases the in vivo activity of CYP2C19 as measured by omeprazole metabolismQ41593466
Mechanism of interactions of alpha-naphthoflavone with cytochrome P450 3A4 explored with an engineered enzyme bearing a fluorescent probe.Q42173777
Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl)imidazole at 1.9-A resolution: insight into the range of P450 conformations and the coordination of redox partner bindingQ42625456
Investigation of bioactivation of ticlopidine using linear ion trap/orbitrap mass spectrometry and an improved mass defect filtering techniqueQ43125272
Identification of the active metabolite of ticlopidine from rat in vitro metabolitesQ43262474
Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19.Q43753143
Potent Mechanism-Based Inhibition of Human CYP2B6 by Clopidogrel and TiclopidineQ44620932
Characterization of novel dihydrothienopyridinium and thienopyridinium metabolites of ticlopidine in vitro: role of peroxidases, cytochromes p450, and monoamine oxidasesQ44717269
Effector-mediated alteration of substrate orientation in cytochrome P450 2C9.Q44902704
Selective inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitroQ44904682
Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization.Q45951521
Metabolism of ticlopidine in rats: identification of the main biliary metabolite as a glutathione conjugate of ticlopidine S-oxide.Q45960921
A statistic for local intensity differences: robustness to anisotropy and pseudo-centering and utility for detecting twinning.Q46039301
Comparison of human cytochrome P450 inhibition by the thienopyridines prasugrel, clopidogrel, and ticlopidineQ46175757
Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrelQ46220322
Cooperative binding of midazolam with testosterone and alpha-naphthoflavone within the CYP3A4 active site: a NMR T1 paramagnetic relaxation studyQ46771295
Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: insight into P450 conformational plasticity and membrane interaction.Q46864550
Conformational flexibility of mammalian cytochrome P450 2B4 in binding imidazole inhibitors with different ring chemistry and side chains. Solution thermodynamics and molecular modelingQ46913522
Cooperative binding of acetaminophen and caffeine within the P450 3A4 active siteQ46982603
Use of Voigt lineshape for quantification of in vivo 1H spectra.Q48722469
Distance-constrained molecular docking by simulated annealing.Q51655181
An analytical derivation of a popular approximation of the Voigt function for quantification of NMR spectra.Q52083351
Quantitation of resonances in biological 31P NMR spectra via principal component analysis: potential and limitations.Q52305421
High-pressure-induced transitions in microsomal cytochrome P450 2B4 in solution: evidence for conformational inhomogeneity in the oligomers.Q52335945
A simple scheme for the design of solvent-suppression pulsesQ57817878
Designing Facial Amphiphiles for the Stabilization of Integral Membrane ProteinsQ57830863
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine as a Substrate of Cytochrome P450 2D6: Allosteric Effects of NADPH−Cytochrome P450 Reductase†Q58573225
Paramagnetic probes of macromoleculesQ69377826
Metabolism of ticlopidine in rats: identification and quantitative determination of some its metabolites in plasma, urine and bileQ70906485
Choice of spectroscopic lineshape model affects metabolite peak areas and area ratiosQ73062265
Orientation of caffeine within the active site of human cytochrome P450 1A2 based on NMR longitudinal (T1) relaxation measurementsQ73370606
Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19Q73924048
Reproducibility of 1H-NMR integrals: a collaborative studyQ74761995
The antiplatelet effects of ticlopidine and clopidogrelQ77292679
The (Fo-Fc) Fourier synthesis: a probabilistic studyQ81794023
Variable path length and counter-flow continuous variation methods for the study of the formation of high-affinity complexes by absorbance spectroscopy. An application to the studies of substrate binding in cytochrome P450Q83347495
P433issue40
P407language of work or nameEnglishQ1860
P921main subjectclopidogrelQ410237
P304page(s)8709-20
P577publication date2010-10-12
P1433published inBiochemistryQ764876
P1476titleStructures of Cytochrome P450 2B4 Complexed with the Antiplatelet Drugs Ticlopidine and Clopidogrel,
P478volume49

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cites work (P2860)
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