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Acetaminophen reduces the protein levels of high affinity amino acid permeases and causes tryptophan depletion

Huseinovic, A., Dekker, S. J., Boogaard, B., Vermeulen, N. P. E., Kooter, J. M. & Vos, J. C., Oct 2018, In : Amino Acids. 50, 10, p. 1377-1390 14 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access
Amino Acid Transport Systems
Acetaminophen
Tryptophan
Proteins
Yeast

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 JournalArticleAcademicpeer-review

Floxacillin
Hydroxylation
Cytochrome P-450 Enzyme System
Metabolites
Enzymes

A Comparative Linear Interaction Energy and MM/PBSA Study on SIRT1-Ligand Binding Free Energy Calculation

Rifai, E. A., van Dijk, M., Vermeulen, N. P. E., Yanuar, A. & Geerke, D. P., 11 Sep 2019, In : Journal of Chemical Information and Modeling. p. 4018-4033 16 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Sirtuin 1
Molecular mechanics
mechanic
Free energy
Ligands

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 JournalArticleAcademicpeer-review

Ifosfamide
Cyclophosphamide
Cytochrome P-450 Enzyme System
Chemical activation
Pharmaceutical Preparations

Active site substitution A82W improves regioselectivity of steroid hydroxylation by cytochrome P450 BM3 mutants as rationalised by spin relaxation NMR studies

Rea, V., Kolkman, ER., Vottero, E. R., Stronks, E. J., Ampt, K. A., Honing, M., Vermeulen, N. P. E., Wijmenga, S. S. & Commandeur, J. N. M., 2011, (Accepted/In press) In : The Biochemist.

Research output: Contribution to JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Regioselectivity
Hydroxylation
Cytochrome P-450 Enzyme System
Catalytic Domain
Substitution reactions

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 JournalArticleAcademicpeer-review

Open Access

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 JournalArticleAcademicpeer-review

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

Application of CYP102A1M11H as a tool for the generation of protein adducts of reactive drug metabolites

Boerma, J. S., Vermeulen, N. P. E. & Commandeur, J. N. M., 2011, In : Chemical Research in Toxicology. 24, 8, p. 1263-1274 10 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Metabolites
troglitazone
Glutathione S-Transferase pi
Cysteine
Clozapine

Application of cytochrome P450 BM3 mutants as biocatalysts for the profiling of estrogen receptor binding metabolites of the mycotoxin zearalenone

Reinen, J., Kalma, L., Begheijn, S., Heus, F. A. H., Commandeur, J. N. M. & Vermeulen, N. P. E., 2011, In : Xenobiotica. 41, 1, p. 59-70 11 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Zearalenone
Mycotoxins
Metabolites
Estrogen Receptors
Cytochrome P-450 Enzyme System

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 JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Open Access
Free energy
free energy
Ligands
Drug Design
Molecular Dynamics Simulation

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 JournalArticleAcademicpeer-review

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

Characterisation of Human Cytochrome P450s Involved in the Bioactivation of Clozapine

Dragovic, S., Gunness, P., Ingelman-Sundberg, M., Vermeulen, N. P. E. & Commandeur, J. N. M., 2013, In : Drug Metabolism and Disposition. 41, 3, p. 651-658

Research output: Contribution to JournalArticleAcademicpeer-review

Clozapine
Cytochromes
Cytochrome P-450 CYP3A
Cytochrome P-450 CYP2D6
Liver

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 JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Amodiaquine
Cytochrome P-450 Enzyme System
Liver Microsomes
Cytochromes
Cytochrome P-450 CYP3A

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 JournalArticleAcademicpeer-review

Cytochromes
Phosphates
Butyrylcholinesterase
Metabolites
Liver
Open Access
Sulfaphenazole
Floxacillin
Cytochrome P-450 CYP3A
Cytochromes
Hydroxylation
p38 Mitogen-Activated Protein Kinases
Biotransformation
Screening
Phosphotransferases
Small Molecule Libraries

Comparison of murine and human estrogen sulfotransferase inhibition in vitro and in silico-implications for differences in activity, subunit dimerization and substrate inhibition

Stjernschantz, E. M., Reinen, J., Meinl, W., George, B. J., Glatt, H., Vermeulen, N. P. E. & Oostenbrink, C., 2010, In : Molecular and Cellular Endocrinology. 137, 1-2, p. 127-140

Research output: Contribution to JournalArticleAcademicpeer-review

Dimerization
Computer Simulation
Substrates
Enzymes
In Vitro Techniques

Comprehensive and Automated Linear Interaction Energy Based Binding-Affinity Prediction for Multifarious Cytochrome P450 Aromatase Inhibitors

van Dijk, M., Ter Laak, A. M., Wichard, J. D., Capoferri, L., Vermeulen, N. P. E. & Geerke, D. P., 25 Sep 2017, In : Journal of Chemical Information and Modeling. 57, 9, p. 2294-2308 15 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access
Aromatase Inhibitors
Cytochrome P-450 Enzyme System
energy
interaction
workflow

Computational prediction of binding affinity for CYP1A2-ligand complexes using empirical free energy calculations

Vasanthanathan, P., Olsen, L., Jørgensen, F. S., Vermeulen, N. P. E. & Oostenbrink, C., Aug 2010, In : Drug Metabolism and Disposition. 38, 8, p. 1347-1354 8 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Cytochrome P-450 CYP1A2
Ligands
Cytochrome P-450 Enzyme System
Mechanics
Static Electricity

Cytochrome P450 BM3 Mutants as NOVEL Biocatalytic TOOLS for Regioselective Hydroxylation of Steroids

Rea, V., Kolkman, J. A., Vottero, E., Honing, M., Wijmenga, S., Vermeulen, N. P. E. & Commandeur, J. N. M., Aug 2010, In : Drug Metabolism Reviews. 42, p. 285-286

Research output: Contribution to JournalArticleProfessional

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 JournalArticleAcademicpeer-review

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

Determination and identification of estrogenic compounds generated with biosynthetic enzymes using hyphenated screening assays, high resolution mass spectrometry and off-line NMR

de Vlieger, J. S. B., Kolkman, A. J., Ampt, K. A. M., Commandeur, J. N. M., Vermeulen, N. P. E., Kool, J., Wijmenga, S. S., Niessen, W. M. A., Irth, H. & Honing, M., 2010, In : Journal of Chromatography B. 878, 7-8, p. 667-674 8 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Liquid chromatography
Liquid Chromatography
Mass spectrometry
Assays
Mass Spectrometry

Diclofenac inhibits tumor necrosis factor-a-induced nuclear factor-kB activation causing synergic hepatocyte apoptosis

Frederiksson, L., Herpers, B., Benedetti, G., Matadin, Q., Puigvert, J. C., de Bont, H., Dragovic, S., Vermeulen, N. P. E., Commandeur, J. N. M., Danen, E., de Graauw, M. & van de Water, B., 2011, In : Hepatology. 53, 6, p. 383-394 10 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Diclofenac
Hepatocytes
Tumor Necrosis Factor-alpha
Apoptosis
Hep G2 Cells

Differential involvement of mitochondrial dysfunction, cytochrome P450 activity, and active transport in the toxicity of structurally related NSAIDs

van Leeuwen, J. S., Unlü, B., Vermeulen, N. P. E. & Vos, J. C., 2012, In : Toxicology in Vitro. 26, 2, p. 197-205

Research output: Contribution to JournalArticleAcademicpeer-review

Active Biological Transport
Cytochrome P-450 Enzyme System
Toxicity
Anti-Inflammatory Agents
Pharmaceutical Preparations

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 JournalArticleProfessional

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 JournalArticleAcademicpeer-review

Glucuronosyltransferase
Liver Microsomes
Human Activities
Cytochrome P-450 Enzyme System
Hepatocytes

Drug toxicity profiling of a Saccharomyces cerevisiae deubiquitinase deletion panel shows that acetaminophen mimics tyrosine

Huseinovic, A., van Dijk, M., Vermeulen, N. P. E., van Leeuwen, F., Kooter, J. M. & Vos, J. C., Mar 2018, In : Toxicology in Vitro. 47, p. 259-268 10 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access
Acetaminophen
Drug-Related Side Effects and Adverse Reactions
Yeast
Toxicity
Saccharomyces cerevisiae

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 JournalArticleAcademicpeer-review

Detoxification
Diclofenac
Clozapine
Acetaminophen
Metabolites

Effect of human glutathione S-transferases on glutathione-dependent inactivation of cytochrome P450-dependent reactive intermediates of diclofenac.

Dragovic, S., Boerma, J. S., Vermeulen, N. P. E. & Commandeur, J. N. M., 2013, In : Chemical Research in Toxicology. 26, 11, p. 1632-1641

Research output: Contribution to JournalArticleAcademicpeer-review

Diclofenac
Glutathione Transferase
Cytochrome P-450 Enzyme System
Glutathione
Liver

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 JournalArticleAcademicpeer-review

Open Access
Diclofenac
Polymorphism
Metabolism
Liver
Chemical and Drug Induced Liver Injury

Efficient screening of cytochrome P450 BM3 mutants for their metabolic activity and diversity toward a wide set of drug-like molecules in chemical space

Reinen, J., van Leeuwen, J. S., Li, Y., Sun, L., Grootenhuis, P. D. J., Decker, C. J., Saunders, J., Vermeulen, N. P. E. & Commandeur, J. N. M., 2011, (Accepted/In press) In : Drug Metabolism and Disposition.

Research output: Contribution to JournalArticleAcademicpeer-review

Cytochrome P-450 Enzyme System
Pharmaceutical Preparations
Liquid Chromatography
Libraries
Mass Spectrometry

Endocrine disrupting chemicals-linking internal exposure to vitellogenin levels and ovotestis in Abramis brama from Dutch surface waters

Reinen, J., Suter, M. J. F., Vogeli, A. C., Fernandez, M. F., Kiviranta, H., Eggen, R. I. L. & Vermeulen, N. P. E., 2010, In : Environmental Toxicology and Pharmacology. 30, p. 209-223

Research output: Contribution to JournalArticleAcademicpeer-review

Vitellogenins
Endocrine Disruptors
Surface waters
Fish
Fishes

eTOX ALLIES: an automated pipeLine for linear interaction energy-based simulations

Capoferri, C. L., van Dijk, M., Rustenburg, A. S., Wassenaar, T., Kooi, D. P., Rifai, E. A., Vermeulen, N. P. E. & Geerke, D. P., 2017, In : Journal of Cheminformatics. 9, 58, p. 1-13 13 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access
Pipelines
Ligands
Free energy
energy
ligands

Evidence-based selection of training compounds for use in the mechanism-based integrated prediction of drug-induced liver injury in man.

Dragovic, S., Vermeulen, N. P. E., Gerets, H. H., Hewitt, P. G., Ingelman-Sundberg, M., Park, B. K., Juhila, S., Snoeys, J. & Weaver, R. J., 2016, In : Archives of Toxicology. 90, 12, p. 2979-3003

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access

Free energy calculations give insight into the stereoselective hydroxylation of α-ionones by engineered cytochrome P450 BM3 mutants

De Beer, S. B., Venkataraman, H., Geerke, D. P., Oostenbrink, C. & Vermeulen, N. P. E., 2012, In : Journal of Chemical Information and Modeling. 52, 8, p. 2139-2148

Research output: Contribution to JournalArticleAcademicpeer-review

Norisoprenoids
Hydroxylation
Cytochrome P-450 Enzyme System
Free energy
energy

Functional characterization of eight human cytochrome P450 1A2 gene variants by recombinant protein expression

Brito Palma, B., Silva e Sousa, M., Vosmeer, C. R., Lastdrager, J., Rueff, J., Vermeulen, N. P. E. & Kranendonk, M., 2010, In : Pharmacogenomics Journal. p. 1-11 10 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Cytochrome P-450 CYP1A2
Recombinant Proteins
Apoproteins
Genes
Carcinogens

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 JournalArticleAcademicpeer-review

o-Phthalaldehyde
Diclofenac
Clozapine
Acetylcysteine
Acetaminophen

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 JournalArticleAcademicpeer-review

Open Access
Endoplasmic Reticulum Stress
Hep G2 Cells
Amodiaquine
Glutathione Transferase
Glutathione
High performance liquid chromatography
Glutathione Transferase
Liver
Sulfates
Assays
Amodiaquine
Glutathione Transferase
Liver
NAD
Toxicity

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 JournalArticleAcademicpeer-review

Mefenamic Acid
Diclofenac
Acetaminophen
Metabolites
Drug-Related Side Effects and Adverse Reactions

Identification of CYP1A2 ligands by structure-based and ligand-based virtual screening

Vasanthanathan, P., Lastdrager, J., Oostenbrink, C., Commandeur, J. N. M., Vermeulen, N. P. E., Jorgensen, F. S. & Olsen, L., Sep 2011, In : MedChemComm. 2, 9, p. 853-859

Research output: Contribution to JournalArticleAcademicpeer-review

Improving the iterative linear interaction energy approach using automated recognition of configurational transitions.

Vosmeer, C. R., Kooi, D. P., Capoferri, L., Terpstra, M. M., Vermeulen, N. P. E. & Geerke, D. P., 2016, In : Journal of Molecular Modeling. 1, 31.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access