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• 2012

  Active Site Substitution A82W Improves the Regioselectivity of Steroid Hydroxylation by Cytochrome P450 BM3 Mutants As Rationalized by Spin Relaxation Nuclear Magnetic Resonance Studies

  Rea, V., Kolkman, A. J., Vottero, E. R., Stronks, E. J., Ampt, K. A., Honing, M., Vermeulen, N. P. E., Wijmenga, S. S. & Commandeur, J. N. M., 2012, In : Biochemistry. 51, 3, p. 750-760

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Regioselectivity
  • Hydroxylation
  • Nuclear magnetic resonance
  • Substitution reactions
  • Cytochrome P-450 Enzyme System

• A single active site mutation inverts stereoselectivity of 16-hydroxylation of testosterone catalyzed by engineered cytochrome P450 BM3.

  Venkataraman, H., de Beer, SB., Bergen, LA., van Essen, N., Geerke, D. P., Vermeulen, N. P. E. & Commandeur, J. N. M., 2012, In : ChemBioChem. 13, 4, p. 520-523

  Research output: Contribution to Journal › Article › Academic › peer-review

• Mass Spectrometric Characterization of Protein Adducts of Multiple P450-Dependent Reactive Intermediates of Diclofenac to Human Glutathione-S-transferase P1-1

  Boerma, J. S., Dragovic, S., Vermeulen, N. P. E. & Commandeur, J. N. M., 2012, In : Chemical Research in Toxicology. 25, 11, p. 2532-2541

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Glutathione S-Transferase pi
  • Diclofenac
  • Glutathione Transferase
  • hydroxide ion
  • Proteins

• Regio- and Stereoselective Hydroxylation of Optically Active α-Ionone Enantiomers by Engineered Cytochrome P450 BM3 Mutants

  Venkataraman, H., de Beer, S. B. A., Geerke, D. P., Vermeulen, N. P. E. & Commandeur, J. N. M., 2012, In : Advanced Synthesis and Catalysis. 354, 11-12, p. 2172-2184

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Norisoprenoids
  • Cytochrome P-450 Enzyme System
  • Hydroxylation
  • Enantiomers
  • Secondary Metabolism

• The role of protein plasticity in computational rationalization studies on regioselectivity in testosterone hydroxylation by Cytochrome P450 BM3 mutants

  de Beer, S. B. A., van Bergen, L. A. H., Keijzer, K., Rea, V., Venkataraman, H., Fonseca Guerra, C., Bickelhaupt, F. M., Vermeulen, N. P. E., Commandeur, J. N. M. & Geerke, D. P., 2012, In : Current Drug Metabolism. 13, 2, p. 155-166

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Regioselectivity
  • Hydroxylation
  • Cytochrome P-450 Enzyme System
  • Plasticity
  • Testosterone
• 2014

  Application of engineered cytochrome P450 mutants as biocatalysts for the synthesis of benzylic and aromatic metabolites of fenamic acid NSAIDs

  Venkataraman, H., Verkade-Vreeker, M. C. A., Capoferri, L., Geerke, D. P., Vermeulen, N. P. E. & Commandeur, J. N. M., 15 Oct 2014, In : Bioorganic and Medicinal Chemistry. 22, 20, p. 5613-5620

  Research output: Contribution to Journal › Article › Academic › peer-review

• Cytochrome P450-mediated bioactivation of mefenamic acid to quinoneimine intermediates and inactivation by human glutathione S-transferases

  Venkataraman, H., Den Braver, M. W., Vermeulen, N. P. E. & Commandeur, J. N. M., 15 Dec 2014, In : Chemical Research in Toxicology. 27, 12, p. 2071-2081 11 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Mefenamic Acid
  • Glutathione Transferase
  • Cytochrome P-450 Enzyme System
  • Hydroxy Acids
  • Metabolites

• Effect of human glutathione S-transferase hGSTP1-1 polymorphism on the detoxification of reactive metabolites of clozapine, diclofenac and acetaminophen

  Dragovic, S., Venkataraman, H., Begheijn, S., Vermeulen, N. P. E. & Commandeur, J. N. M., 2014, In : Toxicology Letters. 224, 2, p. 272-281

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Detoxification
  • Metabolites
  • Polymorphism
  • Diclofenac
  • Clozapine

• Human NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated inactivation of reactive quinoneimine metabolites of diclofenac and mefenamic acid

  Vredenburg, G., Elias, N. S., Venkataraman, H., Hendriks, D. F. G., Vermeulen, N. P. E., Commandeur, J. N. M. & Vos, J. C., 21 Apr 2014, In : Chemical Research in Toxicology. 27, 4, p. 576-86 11 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • human NQO1 protein
  • Mefenamic Acid
  • Metabolites
  • Diclofenac
  • Acetaminophen

• One-electron oxidation of diclofenac by human cytochrome P450s as a potential bioactivation mechanism for formation of 2'-(glutathion-S-yl)-deschloro-diclofenac.

  Boerma, J. S., Vermeulen, N. P. E. & Commandeur, J. N. M., 2014, In : Chemico-Biological Interactions. 207, p. 32-40

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Diclofenac
  • Cytochromes
  • Glutathione
  • Oxidation
  • Electrons
• 2015

  Activation of the anticancer drugs cyclophosphamide and ifosfamide by cytochrome P450 BM3 mutants

  Vredenburg, G., den Braver-Sewradj, S., van Vugt-Lussenburg, B. M. A., Vermeulen, N. P. E., Commandeur, J. N. M. & Vos, J. C., 5 Jan 2015, In : Toxicology Letters. 232, 1, p. 182-92 11 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Ifosfamide
  • Metabolic Activation
  • Cytochrome P-450 Enzyme System
  • Cyclophosphamide
  • Chemical activation

• Application of a Continuous-Flow Bioassay to Investigate the Organic Solvent Tolerability of Cytochrome P450 BM3 Mutants

  Reinen, J., van Hemert, D., Vermeulen, N. P. E. & Commandeur, J. N. M., Dec 2015, In : Journal of Biomolecular Screening. 20, 10, p. 1246-55 10 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Bioassay
  • Organic solvents
  • Mixed Function Oxygenases
  • Biological Assay
  • Cytochrome P-450 Enzyme System

• Biosynthesis of a steroid metabolite by an engineered Rhodococcus erythropolis strain expressing a mutant cytochrome P450 BM3 enzyme

  Venkataraman, H., te Poele, E. M., Rosłoniec, K. Z., Vermeulen, N., Commandeur, J. N. M., van der Geize, R. & Dijkhuizen, L., 18 Jun 2015, In : Applied Microbiology and Biotechnology. 99, 11, p. 4713-4721 9 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Rhodococcus
  • Cytochrome P-450 Enzyme System
  • Steroids
  • Enzymes
  • 17-Ketosteroids

• Characterization of human cytochrome P450s involved in the bioactivation of tri-Ortho-Cresyl phosphate (ToCP)

  Reinen, J., Nematollahi, L., Fidder, A., Vermeulen, N. P. E., Noort, D. & Commandeur, J. N. M., 20 Apr 2015, In : Chemical Research in Toxicology. 28, 4, p. 711-721 11 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Cytochromes
  • 2-(2-cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide
  • Phosphates
  • Butyrylcholinesterase
  • Metabolites

• Linear Interaction Energy Based Prediction of Cytochrome P450 1A2 Binding Affinities with Reliability Estimation

  Capoferri, L., Verkade-Vreeker, M. C. A., Buitenhuis, D., Commandeur, J. N. M., Pastor, M., Vermeulen, N. P. E. & Geerke, D. P., 9 Nov 2015, In : PLoS ONE. 10, 11

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

• Mini-dialysis tubes as tools to prepare drug-protein adducts of P450-dependent reactive drug metabolites

  Boerma, J. S., Elias, N. S., Vermeulen, N. P. E. & Commandeur, J. N. M., 25 Jan 2015, In : Journal of Pharmaceutical and Biomedical Analysis. 103, p. 17-25

  Research output: Contribution to Journal › Article › Academic › peer-review

• Selective whole-cell biosynthesis of the designer drug metabolites 15- or 16-betahydroxynorethisterone by engineered Cytochrome P450 BM3 mutants

  Reinen, J., Vredenburg, G., Klaering, K., Vermeulen, N. P. E., Commandeur, J. N. M., Honing, M. & Vos, J. C., 1 Nov 2015, In : Journal of Molecular Catalysis B. Enzymatic. 121, p. 64-74 11 p., 3212.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Cytochrome P-450 Enzyme System
  • Hydroxylation
  • Biosynthesis
  • Designer Drugs
  • Norethindrone
• 2016

  Application of a cocktail approach to screen cytochrome P450 BM3 libraries for metabolic activity and diversity.

  Reinen, J. R., Postma, G., Tump, C., Bloemberg, T., Engel, J., Vermeulen, N. P. E., Commandeur, J. N. M. & Honing, M., 2016, In : Analytical and Bioanalytical Chemistry. 408, 5, p. 1425-1443 19 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

• Characterization of cytochrome P450 isoforms involved in sequential two-step bioactivation of diclofenac to reactive p-benzoquinone imines.

  den Braver, M. W., Sewradj, S. P., Vermeulen, N. P. E. & Commandeur, J. N. M., 2016, In : Toxicology Letters. 253, p. 46-54

  Research output: Contribution to Journal › Article › Academic › peer-review

• Different reacive metabolites of nevirapine require distinct glutathione S-tranferase isoforms for bioinactivation.

  Dekker, S. J., Zhang, Y., Vos, J. C., Vermeulen, N. P. E. & Commandeur, J. N. M., 2016, In : Chemical Research in Toxicology. 29, 12, p. 2136-2144

  Research output: Contribution to Journal › Article › Academic › peer-review

• Different reactive metabolites of nevirapine require distinct glutathione S-transferase isoforms for bio-inactivation

  Dekker, S. J., Vos, J., Vermeulen, N. P. & Commandeur, J. N., 16 Sep 2016, In : Toxicology Letters. 29, 12, p. 2136-2144 9 p.

  Research output: Contribution to Journal › Article › Professional

• Genetic risk factors for clozapine-induced neutropenia and agranulocytosis in a Dutch psychiatric population.

  Van der Weide, K., Loovers, H., Pondman, K., Bogers, J., van der Straaten, T., Langemeijer, E. V., Cohen, D., Commandeur, J. N. M. & van der Weide, J., 2016, In : Pharmacogenomics Journal.

  Research output: Contribution to Journal › Article › Academic › peer-review

• Insights into regioselective metabolism of mefenamic acid by cytochrome P450 BM3 mutants through crystallography, docking, molecular dynamics, and free energy calculations.

  Capoferri, L., Leth, R., ter Haar, E., Mohanty, A. K., Grootenhuis, P. D. J., Vottero, E. R., Commandeur, J. N. M., Vermeulen, N. P. E., Jorgensen, F. S., Olsen, L. & Geerke, D. P., 2016, In : Proteins. 84, 3, p. 383-396

  Research output: Contribution to Journal › Article › Academic › peer-review

• Inter-donor variability of phase I/phase II metabolism of three reference drugs in cryopreserved primary human hepatocytes in suspension and monolayer.

  Sewradj, S. P., den Braver, M. W., Vermeulen, N. P. E., Commandeur, J. N. M., Richert, L. & Vos, J. C., 2016, In : Toxicology in Vitro. 33, p. 71-79 9 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

• Simulation of interindividual differences in inactivation of reactive para-benzoquinone imine metabolites of diclofenac by glutathione S-transferases in human liver cytosol.

  den Braver, M. W., Zhang, Y., Venkataraman, H., Vermeulen, N. P. E. & Commandeur, J. N. M., 2016, In : Toxicology Letters. 255, p. 52-62

  Research output: Contribution to Journal › Article › Academic › peer-review
• 2017

  Characterization of human cytochrome P450 mediated bioactivation of amodiaquine and its major metabolite N-desethylamodiaquine

  Zhang, Y., Vermeulen, N. P. E. & Commandeur, J. N. M., 1 Mar 2017, In : British Journal of Clinical Pharmacology. 83, 3, p. 572-583 12 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • desethylamodiaquine
  • Amodiaquine
  • Cytochrome P-450 Enzyme System
  • Liver Microsomes
  • Cytochromes

• Direct comparison of UDP-glucuronosyltransferase and cytochrome P450 activities in human liver microsomes, plated and suspended primary human hepatocytes from five liver donors

  den Braver-Sewradj, S. P., den Braver, M. W., Baze, A., Decorde, J., Fonsi, M., Bachellier, P., Vermeulen, N. P. E., Commandeur, J. N. M., Richert, L. & Vos, J. C., 1 Aug 2017, In : European Journal of Pharmaceutical Sciences. 109, p. 96-110 15 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Glucuronosyltransferase
  • Liver Microsomes
  • Human Activities
  • Cytochrome P-450 Enzyme System
  • Cytochromes

• Engineering a self-sufficient Mycobacterium tuberculosis CYP130 by gene fusion with the reductase-domain of CYP102A1 from Bacillus megaterium

  Ortega Ugalde, S., Luirink, R. A., Geerke, D. P., Vermeulen, N. P. E., Bitter, W. & Commandeur, J. N. M., 7 Dec 2017, In : Journal of Inorganic Biochemistry. 180, p. 48 53 p., 180.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

  • flavocytochrome P450 BM3 monoxygenases
  • Dextromethorphan
  • Demethylation
  • Gene Fusion
  • Mycobacterium tuberculosis

• Generic method for the absolute quantification of glutathione S-conjugates: Application to the conjugates of acetaminophen, clozapine and diclofenac

  den Braver, M. W., Vermeulen, N. P. E. & Commandeur, J. N. M., 1 Mar 2017, In : Journal of Chromatography B. 1046, p. 185-194 10 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • o-Phthalaldehyde
  • Diclofenac
  • Clozapine
  • Acetylcysteine
  • Acetaminophen

• Human glutathione S-transferases- and NAD(P)H:quinone oxidoreductase 1-catalyzed inactivation of reactive quinoneimines of amodiaquine and N-desethylamodiaquine: Possible implications for susceptibility to amodiaquine-induced liver toxicity

  Zhang, Y., den Braver-Sewradj, S. P., Vos, J. C., Vermeulen, N. P. E. & Commandeur, J. N. M., 2017, In : Toxicology Letters. 275, p. 83-91 9 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • amodiaquine quinoneimine
  • desethylamodiaquine
  • Amodiaquine
  • quinone
  • Liver
• 2018

  A combined computational and experimental study on selective flucloxacillin hydroxylation by cytochrome P450 BM3 variants

  Luirink, R. A., Dekker, S. J., Capoferri, L., Kuiper, C. L., Janssen, L. F. H., Ari, M. E., Vermeulen, N. P. E., Vos, J. C., Commandeur, J. N. M. & Geerke, D. P., Jul 2018, In : Journal of Inorganic Biochemistry. 184, p. 115-122 8 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • Hydroxylation
  • Floxacillin
  • Cytochrome P-450 Enzyme System
  • Metabolites
  • Synthetic Chemistry Techniques

• Effect of UGT2B7*2 and CYP2C8*4 polymorphisms on diclofenac metabolism

  Lazarska, K. E., Dekker, S. J., Vermeulen, N. P. E. & Commandeur, J. N. M., 1 Mar 2018, In : Toxicology Letters. 284, 1 March, p. 70-78 9 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

  • Cytochrome P-450 CYP2C8
  • Metabolism
  • Polymorphism
  • Diclofenac
  • 1-O-(2-((2',6'-dichlorophenyl)amino)phenylacetyl)glucopyranuronic acid

• Glutathione S-transferase P1 protects against Amodiaquine Quinoneimines-induced cytotoxicity but does not prevent activation of endoplasmic reticulum stress in HepG2 cells

  Zhang, Y., den Braver-Sewradj, S. P., den Braver, M. W., Hiemstra, S., Vermeulen, N. P. E., van de Water, B., Commandeur, J. N. M. & Vos, J. C., 18 Apr 2018, In : Frontiers in Pharmacology. 9, APRIL, p. 1-13 13 p., 388.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

  • amodiaquine quinoneimine
  • desethylamodiaquine
  • Amodiaquine
  • Endoplasmic Reticulum Stress
  • Hep G2 Cells

• High-performance liquid chromatography-based assay for glutathione transferase theta 2 activity: Application to characterize interindividual variability in human liver fractions

  Zhang, Y., Wijaya, L., Dekker, S. J., Vermeulen, N. P. E. & Commandeur, J. N. M., 15 Jul 2018, In : Journal of Pharmaceutical and Biomedical Analysis. 156, p. 181-188 8 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • High performance liquid chromatography
  • Liver
  • Assays
  • Sulfates
  • Glutathione Transferase

• Inter-individual variability in activity of the major drug metabolizing enzymes in liver homogenates of 20 Individuals

  den Braver-Sewradj, S. P., den Braver, M. W., van Dijk, M., Zhang, Y., Dekker, S. J., Wijaya, L., Vermeulen, N. P. E., Richert, L., Commandeur, J. N. M. & Vos, J. C., 2018, In : Current Drug Metabolism. 19, 4, p. 370-381 12 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  • quinone
  • Liver
  • Oxidoreductases
  • Glucuronosyltransferase
  • Enzyme activity

• Linking cytochrome P450 enzymes from Mycobacterium tuberculosis to their cognate ferredoxin partners

  Ortega Ugalde, S., de Koning, C. P., Wallraven, K., Bruyneel, B., Vermeulen, N. P. E., Grossmann, T. N., Bitter, W., Commandeur, J. N. M. & Vos, J. C., Nov 2018, In : Applied Microbiology and Biotechnology. 102, 21, p. 9231-9242 12 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

  • Ferredoxins
  • Mycobacterium tuberculosis
  • Cytochrome P-450 Enzyme System
  • Oxidation-Reduction
  • Electrons

• Reduction and Scavenging of Chemically Reactive Drug Metabolites by NAD(P)H: Quinone Oxidoreductase 1 and NRH:Quinone Oxidoreductase 2 and Variability in Hepatic Concentrations

  den Braver-Sewradj, S. P., den Braver, M. W., Toorneman, R. M., Van Leeuwen, S., Zhang, Y., Dekker, S. J., Vermeulen, N. P. E., Commandeur, J. N. M. & Vos, J. C., 19 Feb 2018, In : Chemical Research in Toxicology. 31, 2, p. 116-126 11 p.

  Research output: Contribution to Journal › Article › Academic › peer-review

  Open Access

  • Metabolites
  • Scavenging
  • quinone
  • NAD
  • Oxidoreductases