Proven Performance! ROXY EC/MS System
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1 ROXY EC/MS System 1
2 Goal Mimicking oxidative metabolism in electrochemical cell and identification of metabolites by MS Analysis of phase I metabolites of acetaminophen (APAP; paracetamol) Analysis of phase II metabolite of APAP (conjugation with glutathione (GSH)) 2
3 Metabolism of acetaminophen Glucuronidation Cytochrome P450 Sulfation GSH Conjugation Compounds related to acetaminophen metabolism GSH Name Formula Monoisotopic mass [u] m/z [Th] Acetaminophen C 8 H 9 NO NAPQI C 8 H 7 NO GSH C 10 H 17 N 3 O 6 S NAPQI-GSH C 18 H 24 N 4 O 8 S NAPQI N-acetyl-p-benzoquinoneimine 3
4 ROXY EC System upfront MS General conditions ReactorCell with Glassy Carbon WE and HyREF Flow rate 4µL/min generated with dual syringe pump equipped with 1mL syringes 10 mm ammonium formate, ph 7.4 (NH 4 OH); 25% ACN Dialogue software 4
5 Oxidative metabolism phase I Instrumental set-up APAP ReactorCell Working potential of ReactorCell was ramped from mv with steps of 100 mv. 1.0 min mass spectra were acquired. 5
6 Oxidative metabolism phase I APAP mass voltammogram H 6
7 Oxidative metabolism phase I APAP abundance vs. EC potential Intens Intensity 2000 Cell off 800mV Time [min] Time [min] APAP_FA_on_off_2uL_on_off d: EIC All MS, Smoothed (1.00,1,GA), Smoothed (1.00,1,GA), Smoothed (1.00,1,GA) APAP_FA_on_off_2uL_on_off d: EIC All MS, Smoothed (1.00,1,GA) APAP_FA_on_off_2uL_on_off d: EIC All MS, Smoothed (1.00,1,GA), Smoothed (1.00,1,GA) APAP_FA_on_off_2uL_on_off d: EIC All MS, Smoothed (1.00,1,GA) APAP_FA_on_off_2uL_on_off d: EIC All MS, Smoothed (1.00,1,GA) 7
8 Oxidative metabolism phase II? 8
9 Oxidative metabolism phase II Instrumental set-up reaction coil GSH APAP ReactorCell 9
10 Oxidative metabolism phase II Conjugation product of APAP phase I metabolite and GSH Formula: C 18 H 24 N 4 O 8 S Exact mass:
11 Oxidative metabolism phase II Intens OFF 800mV Time [min] 11
12 Oxidative metabolism phase II APAP + GSH Cell OFF Cell ON 12
13 Oxidative metabolism phase II APAP + GSH Error 0.9ppm 13
14 Oxidative metabolism phase II MS/MS Intens. 300 Reactor ON 800mV MS2( ), min #( ) -Glu 200 Abundance Gly m/z m/z 14
15 Fully automated system for Phase I and Phase II Metabolism fast, synthesis within minutes vs. days or weeks using traditional methods zero matrix effect, no isolation steps direct identification of oxidative labile sites in drug molecule high throughput screening of metabolites MS Patent pending, international application number PCT/NL2010/
16 ROXY EC/LC System Instrumental set-up Fully automated phase I and II metabolism experiment! Controlled with Clarity software. Patent pending, international application number PCT/NL2010/
17 Fully automated system for Phase I and Phase II Metabolism Extracted ion chromatograms of APAP (blue), GSH (green) and NAPQI-GSH conjugate (red). With Reactor Cell ON (800 mv) immediate formation of the NAPQI GSH conjugate (phase II reaction) is observed, eluting at 11.2 min. Reactor Cell OFF no conjugation reaction indicates no reactive metabolite (NAPQI) generation. 17
18 18
19 Complementary information 19
20 Dialogue for ROXY Controls potentiostat and syringe pump Automate and simplify mass voltammogram acquisition Controls multiple cells 20
21 Dialogue for ROXY Adjustable programs Parameter changes with 0.01min (0.6s) time resolution Automated MS data acquisition (contact closure) 21
22 Dialogue for ROXY Separate MS data files for each cell potential Includes control experiment with cell OFF Unlimited potential range (+/-4.9V) In standard procedure potential is ramped from mv with incremental steps of 100mV every 0.5 minute 22
23 MS Voltammogram 3-D plot 900mV 400mV 800mV Metabolite 1 can be only indirectly detectable in microsomes. Metabolite 2 was detectable in EC only! Metabolite 3 was detectable in both EC and microsomes. 23
24 Voltammogram 2- D plot 24
25 Voltammogram 2-D plot 25
26 Software ROXY Potentiostat and ROXY EC system - Dialogue ROXY EC/LC system - Clarity (via contact closure from MS) Under development - XCalibur - HyStar 26
27 Xcalibur driver 27
28 Xcalibur driver ROXY EC 28
29 Xcalibur driver ROXY EC/LC 29
30 Xcalibur driver ROXY EC/LC 30
31 Conclusions ROXY EC is the ideal system for fast mimicking of oxidative metabolism of single compounds (phase I and II) ROXY EC/LC is the ideal system for automated screening of numerous samples on phase I and II metabolism and for studying the influence of chemicals (e.g. antioxidants) on the Redox behavior of target compounds 31
32 µ-prepcell - a novel tool for efficient metabolite synthesis 32
33 µ-prepcell - a novel tool for efficient metabolites synthesis Quick and clean alternative for in-vivo studies Synthesize micrograms of metabolites Collect fractions for MS or structural elucidation by NMR High efficiency conversion
34 µ-prepcell Reference electrode 34
35 ROXY EC System with µ-prepcell
36 µ-prepcell Fraction collection On the basis of time Monitoring detector output (when a peak starts to elute the fraction collector is activated) On the basis of specific potential
37 µ-prepcell Instrumental set-up: Phase I Metabolite synthesis in clean and well-defined matrix for use as reference material by MS or for structural elucidation by NMR.
38 µ-prepcell Instrumental set-up: Phase II Conjugation reactions, i.e. with GSH, drug-protein binding studies, oxidative stress of biopolymers (DNA, Proteins, etc.)
39 µ-prepcell Metabolite generation - Amiodarone m/z 646 m/z 618 m/z 590 m/z 520 m/z 492 m/z 464 m/z 394 m/z 366 m/z 338
40 µ-prepcell Amiodarone - MS Voltammogram Synonims: Amiodarone; Cordarone; Tachydaron
41 Conversion efficiency µ-prepcell vs. ReactorCell V Attenuation [%] ReactorCell µ-prepcell Flow rate [µl/min] 200µL/min
42 µ-prepcell Flow rate
43 µ-prepcell Repeatability
44 µ-prepcell Long term stability
45 µ-prepcell Amodiaquine Metabolite 1 can be only indirectly detectable in microsomes. Metabolite 2 was detectable in EC only! Metabolite 3 was detectable in both EC and microsomes. 45
46 Conversion efficiency µ-prepcell vs. ReactorCell
47 µ-prepcell Long term stability
48 µ-prepcell Flow rate 50µL/min m/z 299
49 µ-prepcell Flow rate
50 µ-prepcell ph effect - Amodiaquine
51 µ-prepcell Irinotecan 51
52 µ-prepcell Electrode-dependent Oxidation Profiles Cell OFF Magic Diamond Glassy Carbon Thermo application note 417
53 µ-prepcell Long term stability
54 µ-prepcell Conjugation with GSH m/z 661 = GSH + Metabolite 1 m/z 604 = GSH + Metabolite 2
55 µ-prepcell Conjugation with GSH
56 µ-prepcell Reduction of disulfide bridges Glutathine disulfide Glutathione
57 µ-prepcell Reduction of disulfide bridges Reduction at -1.2V
58 Conclusions µ-prepcell Excellent conversion rate, yield (µg quantities of metabolites in minutes) Zero sample adsorption due to thin layer principle Additional generation of intermediate reaction (Redox) products, impossible with coulometric cells
59 Acknowledgements WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER Prof. Dr. U. Karst Prof. Dr. H. Oberacher With special thank to Prof. Dr. Hubertus Irth and Dr. Marek Smoluch (Free University, Amsterdam, The Netherlands) for access to their MS facility.
60 Thank you for your attention!
61
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