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Items: 1 to 50 of 177

1.

Evaluation of Luminogenic Substrates as Probe Substrates for Bacterial Cytochrome P450 Enzymes: Application to Mycobacterium tuberculosis.

Ortega Ugalde S, Ma D, Cali JJ, Commandeur JNM.

SLAS Discov. 2019 Jun 17:2472555219853220. doi: 10.1177/2472555219853220. [Epub ahead of print]

PMID:
31208248
2.

Structural analysis of Cytochrome P450 BM3 mutant M11 in complex with dithiothreitol.

Frydenvang K, Verkade-Vreeker MCA, Dohmen F, Commandeur JNM, Rafiq M, Mirza O, Jørgensen FS, Geerke DP.

PLoS One. 2019 May 24;14(5):e0217292. doi: 10.1371/journal.pone.0217292. eCollection 2019.

3.

Function, essentiality, and expression of cytochrome P450 enzymes and their cognate redox partners in Mycobacterium tuberculosis: are they drug targets?

Ortega Ugalde S, Boot M, Commandeur JNM, Jennings P, Bitter W, Vos JC.

Appl Microbiol Biotechnol. 2019 May;103(9):3597-3614. doi: 10.1007/s00253-019-09697-z. Epub 2019 Feb 27. Review.

4.

Characterization of kinetics of human cytochrome P450s involved in bioactivation of flucloxacillin: inhibition of CYP3A-catalysed hydroxylation by sulfaphenazole.

Dekker SJ, Dohmen F, Vermeulen NPE, Commandeur JNM.

Br J Pharmacol. 2019 Feb;176(3):466-477. doi: 10.1111/bph.14548. Epub 2018 Dec 26.

5.

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

Ortega Ugalde S, de Koning CP, Wallraven K, Bruyneel B, Vermeulen NPE, Grossmann TN, Bitter W, Commandeur JNM, Vos JC.

Appl Microbiol Biotechnol. 2018 Nov;102(21):9231-9242. doi: 10.1007/s00253-018-9299-4. Epub 2018 Aug 22.

6.

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

Luirink RA, Dekker SJ, Capoferri L, Janssen LFH, Kuiper CL, Ari ME, Vermeulen NPE, Vos JC, Commandeur JNM, Geerke DP.

J Inorg Biochem. 2018 Jul;184:115-122. doi: 10.1016/j.jinorgbio.2018.04.013. Epub 2018 Apr 24.

PMID:
29723739
7.

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 SP, den Braver MW, Hiemstra S, Vermeulen NPE, van de Water B, Commandeur JNM, Vos JC.

Front Pharmacol. 2018 Apr 18;9:388. doi: 10.3389/fphar.2018.00388. eCollection 2018.

8.

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 SJ, Vermeulen NPE, Commandeur JNM.

J Pharm Biomed Anal. 2018 Jul 15;156:181-188. doi: 10.1016/j.jpba.2018.04.037. Epub 2018 Apr 23.

PMID:
29709785
9.

Inter-individual Variability in Activity of the Major Drug Metabolizing Enzymes in Liver Homogenates of 20 Individuals.

den Braver-Sewradj SP, den Braver MW, van Dijk M, Zhang Y, Dekker SJ, Wijaya L, Vermeulen NPE, Richert L, Commandeur JNM, Vos JC.

Curr Drug Metab. 2018;19(4):370-381. doi: 10.2174/1389200219666180108160046.

PMID:
29318967
10.

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 SP, den Braver MW, Toorneman RM, van Leeuwen S, Zhang Y, Dekker SJ, Vermeulen NPE, Commandeur JNM, Vos JC.

Chem Res Toxicol. 2018 Feb 19;31(2):116-126. doi: 10.1021/acs.chemrestox.7b00289. Epub 2018 Jan 11.

11.

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

Ortega Ugalde S, Luirink RA, Geerke DP, Vermeulen NPE, Bitter W, Commandeur JNM.

J Inorg Biochem. 2018 Mar;180:47-53. doi: 10.1016/j.jinorgbio.2017.12.003. Epub 2017 Dec 7.

PMID:
29232638
12.

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

Lazarska KE, Dekker SJ, Vermeulen NPE, Commandeur JNM.

Toxicol Lett. 2018 Mar 1;284:70-78. doi: 10.1016/j.toxlet.2017.11.038. Epub 2017 Dec 2.

13.

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 SP, den Braver MW, Baze A, Decorde J, Fonsi M, Bachellier P, Vermeulen NPE, Commandeur JNM, Richert L, Vos JC.

Eur J Pharm Sci. 2017 Nov 15;109:96-110. doi: 10.1016/j.ejps.2017.07.032. Epub 2017 Aug 1.

PMID:
28778465
14.

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 SP, Vos JC, Vermeulen NPE, Commandeur JNM.

Toxicol Lett. 2017 Jun 5;275:83-91. doi: 10.1016/j.toxlet.2017.05.003. Epub 2017 May 3.

PMID:
28478157
15.

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

den Braver MW, Vermeulen NPE, Commandeur JNM.

J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Mar 1;1046:185-194. doi: 10.1016/j.jchromb.2017.02.004. Epub 2017 Feb 6.

PMID:
28189104
16.

Different Reactive Metabolites of Nevirapine Require Distinct Glutathione S-Transferase Isoforms for Bioinactivation.

Dekker SJ, Zhang Y, Vos JC, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2016 Dec 19;29(12):2136-2144. Epub 2016 Nov 28.

PMID:
27989146
17.

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

Zhang Y, Vermeulen NP, Commandeur JN.

Br J Clin Pharmacol. 2017 Mar;83(3):572-583. doi: 10.1111/bcp.13148. Epub 2016 Nov 16.

18.

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

den Braver MW, Zhang Y, Venkataraman H, Vermeulen NP, Commandeur JN.

Toxicol Lett. 2016 Jul 25;255:52-62. doi: 10.1016/j.toxlet.2016.05.015. Epub 2016 May 13.

PMID:
27183920
19.

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

den Braver MW, den Braver-Sewradj SP, Vermeulen NP, Commandeur JN.

Toxicol Lett. 2016 Jun 24;253:46-54. doi: 10.1016/j.toxlet.2016.04.022. Epub 2016 Apr 26.

PMID:
27130197
20.

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

den Braver-Sewradj SP, den Braver MW, Vermeulen NP, Commandeur JN, Richert L, Vos JC.

Toxicol In Vitro. 2016 Jun;33:71-9. doi: 10.1016/j.tiv.2016.02.013. Epub 2016 Feb 26.

PMID:
26921663
21.

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 AK, Grootenhuis PD, Vottero E, Commandeur JN, Vermeulen NP, Jørgensen FS, Olsen L, Geerke DP.

Proteins. 2016 Mar;84(3):383-96. doi: 10.1002/prot.24985. Epub 2016 Feb 3.

PMID:
26757175
22.

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

Reinen J, Postma G, Tump C, Bloemberg T, Engel J, Vermeulen NP, Commandeur JN, Honing M.

Anal Bioanal Chem. 2016 Feb;408(5):1425-43. doi: 10.1007/s00216-015-9241-x. Epub 2016 Jan 11.

23.

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

Capoferri L, Verkade-Vreeker MC, Buitenhuis D, Commandeur JN, Pastor M, Vermeulen NP, Geerke DP.

PLoS One. 2015 Nov 9;10(11):e0142232. doi: 10.1371/journal.pone.0142232. eCollection 2015.

24.

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

Reinen J, van Hemert D, Vermeulen NP, Commandeur JN.

J Biomol Screen. 2015 Dec;20(10):1246-55. doi: 10.1177/1087057115607183. Epub 2015 Sep 22.

PMID:
26396180
25.

Characterization of human cytochrome P450s involved in the bioactivation of tri-ortho-cresyl phosphate (ToCP).

Reinen J, Nematollahi L, Fidder A, Vermeulen NP, Noort D, Commandeur JN.

Chem Res Toxicol. 2015 Apr 20;28(4):711-21. doi: 10.1021/tx500490v. Epub 2015 Mar 2.

PMID:
25706813
26.

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

Venkataraman H, Te Poele EM, Rosłoniec KZ, Vermeulen N, Commandeur JN, van der Geize R, Dijkhuizen L.

Appl Microbiol Biotechnol. 2015 Jun;99(11):4713-21. doi: 10.1007/s00253-014-6281-7. Epub 2014 Dec 16.

PMID:
25511824
27.

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

Boerma JS, Elias NS, Vermeulen NP, Commandeur JN.

J Pharm Biomed Anal. 2015 Jan 25;103:17-25. doi: 10.1016/j.jpba.2014.10.025. Epub 2014 Oct 31.

PMID:
25462116
28.

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

Vredenburg G, den Braver-Sewradj S, van Vugt-Lussenburg BM, Vermeulen NP, Commandeur JN, Vos JC.

Toxicol Lett. 2015 Jan 5;232(1):182-92. doi: 10.1016/j.toxlet.2014.11.005. Epub 2014 Nov 6.

PMID:
25448283
29.

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

Venkataraman H, den Braver MW, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2014 Dec 15;27(12):2071-81. doi: 10.1021/tx500288b. Epub 2014 Nov 18.

PMID:
25372302
30.

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

Venkataraman H, Verkade-Vreeker MC, Capoferri L, Geerke DP, Vermeulen NP, Commandeur JN.

Bioorg Med Chem. 2014 Oct 15;22(20):5613-20. doi: 10.1016/j.bmc.2014.06.022. Epub 2014 Jun 19.

PMID:
24999003
31.

A 3D in vitro model of differentiated HepG2 cell spheroids with improved liver-like properties for repeated dose high-throughput toxicity studies.

Ramaiahgari SC, den Braver MW, Herpers B, Terpstra V, Commandeur JN, van de Water B, Price LS.

Arch Toxicol. 2014 May;88(5):1083-95. doi: 10.1007/s00204-014-1215-9. Epub 2014 Mar 6.

PMID:
24599296
32.

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

Vredenburg G, Elias NS, Venkataraman H, Hendriks DF, Vermeulen NP, Commandeur JN, Vos JC.

Chem Res Toxicol. 2014 Apr 21;27(4):576-86. doi: 10.1021/tx400431k. Epub 2014 Feb 26.

PMID:
24552538
33.

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

Boerma JS, Vermeulen NP, Commandeur JN.

Chem Biol Interact. 2014 Jan 25;207:32-40. doi: 10.1016/j.cbi.2013.11.001. Epub 2013 Nov 15.

PMID:
24246759
34.

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 NP, Commandeur JN.

Toxicol Lett. 2014 Jan 13;224(2):272-81. doi: 10.1016/j.toxlet.2013.10.023. Epub 2013 Oct 31.

PMID:
24185126
35.

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

Dragovic S, Boerma JS, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2013 Nov 18;26(11):1632-41. doi: 10.1021/tx400204d. Epub 2013 Nov 5.

PMID:
24083800
36.

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

Vredenburg G, Vassell KP, Commandeur JN, Vermeulen NP, Vos JC.

Toxicol Lett. 2013 Oct 9;222(3):247-56. doi: 10.1016/j.toxlet.2013.07.023. Epub 2013 Aug 2.

PMID:
23916688
37.

Characterization of human cytochrome P450s involved in the bioactivation of clozapine.

Dragovic S, Gunness P, Ingelman-Sundberg M, Vermeulen NP, Commandeur JN.

Drug Metab Dispos. 2013 Mar;41(3):651-8. doi: 10.1124/dmd.112.050484. Epub 2013 Jan 7. Erratum in: Drug Metab Dispos. 2013 Apr;41(4):923.

PMID:
23297297
38.

Mass spectrometric characterization of protein adducts of multiple P450-dependent reactive intermediates of diclofenac to human glutathione-S-transferase P1-1.

Boerma JS, Dragovic S, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2012 Nov 19;25(11):2532-41. doi: 10.1021/tx300334w. Epub 2012 Oct 10.

PMID:
22998212
39.

AMAP, the alleged non-toxic isomer of acetaminophen, is toxic in rat and human liver.

Hadi M, Dragovic S, van Swelm R, Herpers B, van de Water B, Russel FG, Commandeur JN, Groothuis GM.

Arch Toxicol. 2013 Jan;87(1):155-65. doi: 10.1007/s00204-012-0924-1. Epub 2012 Aug 23.

PMID:
22914986
40.

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

Venkataraman H, Beer SB, Bergen LA, Essen Nv, Geerke DP, Vermeulen NP, Commandeur JN.

Chembiochem. 2012 Mar 5;13(4):520-3. doi: 10.1002/cbic.201100750. Epub 2012 Jan 24.

PMID:
22275147
41.

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 AJ, Vottero E, Stronks EJ, Ampt KA, Honing M, Vermeulen NP, Wijmenga SS, Commandeur JN.

Biochemistry. 2012 Jan 24;51(3):750-60. doi: 10.1021/bi201433h. Epub 2012 Jan 12.

PMID:
22208729
42.

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

de Beer SB, van Bergen LA, Keijzer K, Rea V, Venkataraman H, Guerra CF, Bickelhaupt FM, Vermeulen NP, Commandeur JN, Geerke DP.

Curr Drug Metab. 2012 Feb;13(2):155-66.

PMID:
22208530
43.

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 JS, de Kanter FJ, Vermeulen NP, Commandeur JN.

Drug Metab Dispos. 2011 Dec;39(12):2411-20. doi: 10.1124/dmd.111.041046. Epub 2011 Sep 2.

PMID:
21890734
44.

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 JS, Li Y, Sun L, Grootenhuis PD, Decker CJ, Saunders J, Vermeulen NP, Commandeur JN.

Drug Metab Dispos. 2011 Sep;39(9):1568-76. doi: 10.1124/dmd.111.039461. Epub 2011 Jun 14.

PMID:
21673132
45.

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

Boerma JS, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2011 Aug 15;24(8):1263-74. doi: 10.1021/tx2001515. Epub 2011 Jun 16.

PMID:
21639118
46.

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

Vottero E, Rea V, Lastdrager J, Honing M, Vermeulen NP, Commandeur JN.

J Biol Inorg Chem. 2011 Aug;16(6):899-912. doi: 10.1007/s00775-011-0789-4. Epub 2011 May 13.

47.

Diclofenac inhibits tumor necrosis factor-α-induced nuclear factor-κB activation causing synergistic hepatocyte apoptosis.

Fredriksson L, Herpers B, Benedetti G, Matadin Q, Puigvert JC, de Bont H, Dragovic S, Vermeulen NP, Commandeur JN, Danen E, de Graauw M, van de Water B.

Hepatology. 2011 Jun;53(6):2027-41. doi: 10.1002/hep.24314.

PMID:
21433042
48.

Application of a fluorescence-based continuous-flow bioassay to screen for diversity of cytochrome P450 BM3 mutant libraries.

Reinen J, Ferman S, Vottero E, Vermeulen NP, Commandeur JN.

J Biomol Screen. 2011 Feb;16(2):239-50. doi: 10.1177/1087057110394180.

PMID:
21297109
49.

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

Reinen J, Kalma LL, Begheijn S, Heus F, Commandeur JN, Vermeulen NP.

Xenobiotica. 2011 Jan;41(1):59-70. doi: 10.3109/00498254.2010.525762. Epub 2010 Nov 18.

PMID:
21087115
50.

Role of human glutathione S-transferases in the inactivation of reactive metabolites of clozapine.

Dragovic S, Boerma JS, van Bergen L, Vermeulen NP, Commandeur JN.

Chem Res Toxicol. 2010 Sep 20;23(9):1467-76. doi: 10.1021/tx100131f.

PMID:
20849150

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