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  • Nico P.E. Vermeulen
2011

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

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

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

Conventional and novel approaches in generating and characterization of reactive intermediates from drugs/drug candidates

Orhan, H. & Vermeulen, N. P. E., May 2011, In : Current Drug Metabolism. 12, 4, p. 383-394 12 p.

Research output: Contribution to JournalReview articleAcademicpeer-review

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

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

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

Managing the challenge of chemically reactive metabolites in drug development

Park, B. K., Boobis, A., Clarke, S., Goldring, C. E. P., Jones, D. T., Kenna, J. G., Lambert, C., Laverty, H. G., Naisbitt, D. J., Nelson, S., Nicoll-Griffith, D. A., Obach, R. S., Routledge, P., Smith, D. A., Tweedie, D. J., Vermeulen, N., Williams, D. P., Wilson, I. D. & Baillie, T. A., Apr 2011, In : Nature Reviews Drug Discovery. 10, 4, p. 292-306 15 p.

Research output: Contribution to JournalReview articleAcademicpeer-review

Molecular dynamics simulations and free energy calculations on the enzyme 4-hydroxyphenylpyruvate dioxygenase

de Beer, S. B. A., Glättli, A., Hutzler, J., Vermeulen, N. P. E. & Oostenbrink, B. C., 2011, In : Journal of Computational Chemistry.

Research output: Contribution to JournalArticleAcademicpeer-review

Role of residue 87 in substrate selectivity and regioselectivity of drug-metabolizing cytochrome P450 CYP102A1 M11

Vottero, E. R., Rea, V., Lastdrager, J., Honing, M., Vermeulen, N. P. E. & Commandeur, J. N. M., 2011, In : Journal of Biological Inorganic Chemistry - JBIC. 16, 6, p. 899-912 13 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access

Role of residue 87 in the activity and regioselectivity of clozapine metabolism by drug-metabolizing CYP102A1 M11H: application for structural characterization of clozapine GSH conjugates

Rea, V., Dragovic, S., Boerma, J. S., de Kanter, F. J. J., Vermeulen, N. P. E. & Commandeur, J. N. M., 2011, (Accepted/In press) In : Drug Metabolism and Disposition. p. 39(12): 2411-20. doi: 10.1124/dmd.111.041046.

Research output: Contribution to JournalArticleAcademicpeer-review

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 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

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

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

Interactions of organophosphates with keratins in the cornified epithelium of human skin

Verstappen, D. R. W., Hulst, A. G., Fidder, A., Vermeulen, N. P. E. & Noort, D., 2012, In : Chemico-Biological Interactions. 197, 2-3, p. 93-102

Research output: Contribution to JournalArticleAcademicpeer-review

Malleability and versatility of Cytochrome P450 active sites studied by molecular simulations

Oostenbrink, B. C., de Ruiter, A., Hritz, J. & Vermeulen, N. P. E., 2012, In : Current Drug Metabolism. 13, 2, p. 190-196

Research output: Contribution to JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Yeast as a humanized model organism for biotransformation-related toxicity

van Leeuwen, J. S., Vermeulen, N. P. E. & Vos, J. C., 2012, In : Current Drug Metabolism. 13, 10, p. 1464-1475

Research output: Contribution to JournalArticleAcademicpeer-review

2013

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

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

Reconstitution of the interplay between cytochrome P450 and human glutathione S-transferases in clozapine metabolism in yeast.

Vredenburg, G., Vassell, K. P., Commandeur, J. N. M., Vermeulen, N. P. E. & Vos, J. C., 2013, In : Toxicology Letters. 222, 3, p. 247-256

Research output: Contribution to JournalArticleAcademicpeer-review

Translational strategies for identifying chemically reactive metabolites as cause for Adverse Drug Reactions

Vermeulen, N. P. E., 28 Aug 2013, In : Toxicology Letters. 221, p. S28-S28

Research output: Contribution to JournalArticleProfessional

Urinary lipid and protein oxidation products upon halothane, isoflurane, or sevoflurane anesthesia in humans: potential biomarkers for a subclinical nephrotoxicity

Orhan, H., Sahin, A., Sahin, G., Aypar, U. & Vermeulen, N. P. E., 2013, In : Biomarkers. 18, 1, p. 73-81

Research output: Contribution to JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-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 JournalArticleAcademicpeer-review

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

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

Towards automated binding affinity prediction using an iterative linear interaction energy approach

Vosmeer, C. R., Pool, R., van Stee, M. F., Peric-Hassler, L., Vermeulen, N. P. E. & Geerke, D. P., 2014, In : International Journal of Molecular Sciences. 15, 1, p. 798-816 19 p.

Research output: Contribution to JournalArticleAcademicpeer-review

Open Access
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 JournalArticleAcademicpeer-review

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

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

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

Integrative Modeling Strategies for Predicting Drug Toxicities at the eTOX Project

Sanz, F., Carrio, P., Lopez, O., Capoferri, L., Kooi, D. P., Vermeulen, N. P. E., Geerke, D. P., Montanari, F., Ecker, G. F., Schwab, C. H., Kleinoeder, T., Magdziarz, T. & Pastor, M., Jun 2015, In : Molecular Informatics. 34, 6-7, p. 477-484

Research output: Contribution to JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Open Access

Mass spectrometric identification of isocyanate-induced modifications of keratins in human skin

Hulst, A. G., Verstappen, D. R. W., Van Der Riet - Van Oeveren, D., Vermeulen, N. P. E. & Noort, D., 22 Jun 2015, In : Chemico-Biological Interactions. 237, p. 141-150 10 p.

Research output: Contribution to JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-review

Principles of pharmacology and toxicology also govern effects of chemicals on the endocrine system

Autrup, H., Barile, F. A., Blaauboer, B. J., Degen, G. H., Dekant, W., Dietrich, D., Domingo, J. L., Gori, G. B., Greim, H., Hengstler, J. G., Kacew, S., Marquardt, H., Pelkonen, O., Savolainen, K. & Vermeulen, N. P., 1 Jul 2015, In : Toxicological Sciences. 146, 1, p. 11-15 5 p., kfv082.

Research output: Contribution to JournalArticleAcademicpeer-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 JournalArticleAcademicpeer-review

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 JournalArticleAcademicpeer-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 JournalArticleAcademicpeer-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 JournalArticleProfessional

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