Enhanced method development workflow for modern LC and SFC
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1 Enhanced method development workflow for modern LC and SFC Davy GUILLARME 18 th of September 2014
2 What can be done with modern LC? MONOLITHS HIGH TEMPERATURE plates 12 m column 120 C µm Poroshell Minutes CORE SHELL Pressure 8 9 ΔP = 1000 bar UHPLC Minutes
3 AU AU What can be done with modern SFC? Use of modern polar column technology (sub-2 µm fully porous or sub-3 µm core-shell) associated with highly reliable SFC instrument (ΔP max = bar) Ultra-fast analysis of steroids OH Silica Column Waters Acquity UPC² BEH 100 x 3 mm, 1.7 µm Minutes Analysis of a mixture of 17 drugs 0.00 Column ChromaNik sunshell silica 150 x 3 mm, 2.6 µm Minutes A. Grand-Guillaume Perrenoud et al. J. Chrom. A, 2014, 1360,
4 H (µm) Kinetic performance of modern LC and SFC I Injection of 50 ppm of butylparaben (dissolved in water and heptane for LC and SF systems, respectively). Isocratic compositions were set at 40% of ACN in water for LC systems and 5% and 4% MeOH in CO 2 for SFC systems, respectively. T= 40 C, BPR = 150 bar. SFC: Viridis 2EP x 150mm, 5µm UHPSFC : UPC² BEH 2EP x 100mm, 1.7µm HPLC: RP18 XTERRA x 150mm, 5µm UHPLC: Acquity BEH Shield RP x 50mm, 1.7µm N L H L h d p C d f D 2 p m u opt v opt d D p m HPLC SFC UHPLC UHPSFC 0.0 u (mm/s) A. Grand-Guillaume Perrenoud et al. J. Chrom. A, 1266 (2012) 158
5 Pressure drop (bar) Kinetic performance of modern LC and SFC II Isocratic compositions were set at 40% of ACN in water for LC systems and 5% and 4% MeOH in CO 2 for SFC and UPC 2 systems, respectively. T = 40 C, BPR = 150 bar. SFC: Viridis 2EP x 150mm, 5µm UHPSFC : UPC² BEH 2EP x 100mm, 1.7µm HPLC: RP18 XTERRA x 150mm, 5µm UHPLC: Acquity BEH Shield RP x 50mm, 1.7µm UHPLC HPLC vs. SFC L u P 2 d p SFC vs. UHPSFC 500 P L u 2 d p HPLC UHPSFC SFC u (mm/s) bar
6 Phenotyping CYP450s in HLMs our cocktail acetaminophen Buproprion 5µM Phenacetin 50µM Lower activity Midazolam 2.5µM Control activity Chlorzoxazone 40µM Coumarin 5µM Flurbiprofen 5µM Omeprazole 40µM Higher activity Dextromethorphan 5µM HLMs Phase I metabolism CYP 2A6 7-hydroxylation CYP 2B6 hydroxylation CYP 2C9 4 -hydroxylation CYP 2C19 5-hydroxylation CYP 2D6 O-demethylation CYP 2E1 6-hydroxylation 7-hydroxycoumarin hydroxybupropion 4 -hydroxyflurbiprofen 5-hydroxyomeprazole Dextrorphan 6-hydroxychlorzoxazone subfamily CYP 3A 1 -hydroxylation 1 -hydroxymidazolam
7 UHPLC method development workflow 1. Estimation of physico-chemical properties Acidic / basic, polar / apolar 2. Screening procedure Test several apolar stationary phases, mobile phase ph and organic modifiers. 3. Computer-assisted optimization procedure Optimization of mobile phase temperature, gradient profile and ph.
8 Screening procedure in UHPLC 4 stationary phases (50 x 2.1mm, 1.7µm): C18, polar embedded C18, CSH C18, Phenyl 3 ph values: 3, 7 and 9 2 organic modifiers: Acetonitrile and methanol Generic gradient 2-90% in 4 min This screening procedure is only realistic in UHPLC (rinsing steps, duplicate analysis ) Most promising combination in terms of retention, selectivity and MS sensitivity for our mixture: C18 column, ph 3, Methanol B. Debrus et al. J. Pharm. Biomed. Anal., 2014, 84,
9 Computer-assisted optimization in UHPLC Computer-assisted optimization softwares DryLab, ACDLabs, Osiris, Chromsword Factors to be optimized in gradient mode: Gradient steepness, temperature, ph, additive, ionic strength Depending on the number of investigated factors, 2 12 initial experimental runs. 2-3 runs 4-6 runs 6-12 runs Realistic approach, only if peak tracking can be efficiently performed
10 Efficient peak tracking with QDa detector When developing chromatographic methods, it is important to track peaks when changing analytical conditions. For this task, UV-DAD can be employed, but often lacks specificity. MS would be the best solution but remains expensive and difficult to use, particularly for beginners. In this study, a compact, user-friendly single quadrupole MS detector (Waters Acquity QDa) was employed to efficiently develop chromatographic methods and track peaks. D. Spaggiari et al. J. Chromatogr. A, 2014, Submitted
11 D-model T C 3D-model UHPLC method screening / optimization An HPLC modeling software (Drylab) was employed to optimize the gradient profile, temperature and ph, based on 12 initial experiments. Peak tracking was performed with QDa detector. Final optimized conditions Selected working point T 35 C ph 3.7 plate number ~ Critical resolution 2.89 Gradient Table Time (min) %MeOH t G (min) Simulated chromatogram Time (minutes) 15 16
12 peak intensity peak intensity Final UHPLC-MS separation 1. acetaminophen, 2. 6-hydroxychlorzoxazone, 3. 7-hydroxycoumarin, 4. dextrorphan, 5. coumarin, 6. hydroxybupropion, 7. phenacetin, 8. bupropion, 9. 5-hydroxyomeprazole, 10. chlorzoxazone, 11. dextromethorphan, 12. omeprazole, 13. midazolam, hydroxyflurbiprofen, hydroxymidazolam, 16. flurbiprofen. 1.3x x overlaid SIR minutes ESI+/ESI- ESI - overlaid SIR minutes The differences between predicted and experimental retention times were comprised between 0 and 5.4%. Analysis time of 7 minutes.
13 UHPSFC method development workflow 1. Estimation of physico-chemical properties Acidic / basic, H-bond donor groups, polar / apolar 2. Screening procedure Test several polar stationary phases, organic modifiers and mobile phase additives. 3. Manual optimization procedure Optimization of temperature, backpressure, gradient profile and additives concentration.
14 Screening procedure in UHPSFC 4 stationary phases (100 x 3mm, 1.7µm): Hybrid silica, C18 with no endcapping, 2-ethylpyridine, CSH PFP 2 organic modifiers: Methanol and isopropanol 2 additives: No water, 2% water Generic gradient 2-30% in 4 min 10 mm ammonium formate was systematically added to the mobile phase Most promising combination in terms of retention, selectivity and MS sensitivity: 2-EP, Methanol, 2% water
15 Why adding ammonium formate with bases? I. Benzocaine V. Alprazolam Low range bases pk a < 6 II. Noscapine III. Midazolam IV. Papaverine VI. Nortriptyline VII. Duloxetine Middle range bases 6 < pk a < 8 High-range bases pk a > 8 Without additive With 10 mm ammonium formate Silica 0.10 I 0.05 V IV II III Minutes I III V IV 0.05 II VI VII Minutes EP 0.10 I V IV 0.05 III II VI VII Minutes I V III VI IV VII 0.05 II Minutes Need to add 10 mm ammonium formate in the mobile phase 4.00
16 Interfacing SFC with MS There are various options for SFC-MS hyphenation. Some of them are more universal or userfriendly and others are more sensitive. The goal is always to avoid precipitation and improve ionization yield. Sheath pump BPR UV MS Affect sensitivity of mass-dependent ionization source (APCI). Additional extra-column volume prior to MS. Flexible operating conditions thanks to the active backpressure regulator (BPR). No analytes precipitation due to the addition of sheath liquid (Ethanol). Ionization enhancers could be added post-column. A. Grand-Guillaume Perrenoud et al. J. Chromatogr. A, 1339 (2014) 174
17 peak intensity peak intensity Final UHPSFC-MS separation 1. acetaminophen, 2. 6-hydroxychlorzoxazone, 3. 7-hydroxycoumarin, 4. dextrorphan, 5. coumarin, 6. hydroxybupropion, 7. phenacetin, 8. bupropion, 9. 5-hydroxyomeprazole, 10. chlorzoxazone, 11. dextromethorphan, 12. omeprazole, 13. midazolam, hydroxyflurbiprofen, hydroxymidazolam, 16. flurbiprofen. 7.5x minutes x ESI+/ESIoverlaid SIR ESIoverlaid SIR minutes In UHPSFC, a baseline separation was achieved in about 7 minutes 2 14
18 UHPSFC-MS retention time (min) Complementarity UHPLC vs. UHPSFC In UHPLC, the retention of substrates and metabolites is driven by hydrophobic interactions with the stationary phase. In UHPSFC, the retention of these compounds is driven by H-bond interactions. The stationary phase acts mostly as a H-bond acceptor group. The presence of H-bond donor groups on analyzed compounds generally increases retention Poor LC retention 1: Acetaminophen High SFC retention 5: Coumarin : Flurbiprofen Moderate LC retention 8 5 High LC retention Poor SFC retention Moderate SFC retention UHPLC-MS retention time (min)
19 Final LOD and LOQ values CYP450 isoform Substrate / metabolite LOD (ng/ml) LOQ (ng/ml) UHPLC-MS UHPSFC-MS UHPLC-MS UHPSFC-MS S 1A2 2A6 2B6 phenacetin acetaminophen coumarin hydroxycoumarin bupropion hydroxybupropion x 5 2C9 flurbiprofen hydroxyflurbiprofen N 2C19 2D6 omeprazole hydroxyomeprazole dextromethorphan dextrorphan E1 chlorzoxazone hydroxychlorzoxazone A midazolam hydroxymidazolam Despite the fact that the QDa detector was extremely compact, the achieved sensitivities were comparable to the ones obtained with other commercially available single quadrupole detectors. In average, sensitivity was 3-fold lower in UHPSFC-MS vs. UHPLC-MS.
20 Application of the methods to in vitro incubation For in vitro metabolism study, the reaction medium is relatively complex and contains the mixture of 8 CYP probe substrates, 25 mm HEPES buffer at ph 7.4, 0.25 mg/ml of proteins (HLMs), an excess of NADPH as co-factor, acetonitrile as stopping agent for the microsomal reaction. A precipitation of proteins and centrifugation is finally performed. HEPES NADPH PROTEINS This incubation medium is perfectly compatible with UHPLC-MS conditions, but has never been tested in UHPSFC-MS. Because of a possible adsorption of HEPES, NADPH and residual proteins at the surface of the polar UHPSFC stationary phase, the retention times stability was checked. During all this study, the RSD values on retention times of the 16 compounds were in average equal to 0.14% in UHPLC-MS and 0.15% in UHPSFC-MS.
21 Inhibition study of two phytochemicals Yohimbine is a strong inhibitor of CYP2D6, while resveratrol moderately inhibits CYP2E1 activity and weakly inhibits CYP1A2 and CYP3A subfamily activities. Yohimbine Resveratrol UHPLC-MS UHPSFC-MS The conclusions drawn in UHPLC-MS and UHPSFC-MS were reliable and identical
22 SFC vs. LC? More expensive instrument than LC (20-30%) Less possibility to tune mobile phase, need several stationary phases 2.1 mm I.D. columns hardly compatible with UPC² instrument Compatibility with MS less straightforward than RPLC Alternative selectivity compared to RPLC Better retention of polar compounds in SFC (polar stationary phase) Possibility to analyze very apolar compounds (triglycerides, carotenoids ) Green technology (limited consumption of organic solvents) High throughput chiral and achiral separation on one unique system
23 Acknowledgments Dany SPAGGIARI Florence MEHL Vincent DESFONTAINE Alexandre GRAND-GUILLAUME PERRENOUD Szabolcs FEKETE Serge RUDAZ Jean-Luc VEUTHEY Hélène BOITEUX Marleen VAN WINGERDEN Joel FRICKER Frédéric FORINI
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