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Chiral LC/MS/MS Analysis with Polysaccharide-Based Stationary

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Chiral LC/MS/MS Analysis with Polysaccharide-Based Stationary Chiral LC/MS/MS Analysis with Polysaccharide-based Stationary Phases for Basic and Neutral Stereoisomeric Pharmaceutical Compounds Liming Peng, Tivadar Farkas and Swapana Jayapaian Phenomenex, Inc., 411 Madrid Ave.,Torrance, CA 90501 USA (www.phenomenex.com) PO87820611_L_2 Introduction The hyphenation of the resolving power of chiral HPLC compatible with atmospheric pressure ionization (API) with the sensitivity of MS detection is highly desired MS ion sources. Developing rapid chiral LC separations in drug metabolism and pharmacokinetic studies of compatible with MS ionization interfaces while preserving stereoisomers in the drug discovery process. Derivatives both chromatographic resolution and sensitivity in MS of polysaccharides are the most widely used chiral detection has proven to be a great challenge to analytical stationary phases due to their wide chiral recognition scientists. ability, high loading capacity, and durability. As normal phase is favorable for the principal mechanism of chiral We present the results of a systematic feasibility study recognition – hydrogen bonding interaction – the majority of using polysaccharide-based chiral stationary phases of chiral separations with polysaccharide phases are (CSPs) coupled with API-MS/MS detection for the performed in normal phase using hexane and alcohol analysis of various pharmaceutical racemates in reversed modifiers as mobile phase components. However phase (RP) elution mode. these mobile phases are highly flammable and are not Experimental Conditions HPLC System: HP 1100 series Flow Rate: 0.2 mL/min (www.agilent.com) Injection Volume: 5 µL 0.2 – 1.0 µg/mL of racemates Pump: G1312A (Binary Pump) Concentration: Columns: Lux 3 µm Cellulose-1 Autosampler: G1329A ALS 150 x 2.0 mm MS Detector: API 3000 LC/MS/MS with ESI Lux 3 µm Cellulose-2 (TurboIonSpray®) 150 x 2.0 mm (www. Appliedbiosystems.com) Lux 3 µm Amylose -2 150 x 2.0 mm Gemini®-NX 3 µm C18 50 x 2.0 mm TurbolonSpray - ESI, Positive Ion Mobile Phases: 1. Acetonitrile/Methanol : 5 mM Mode; MRM; heater gas flow 5000 NH4HCO3 2. Acetonitrile/Methanol: 5 mM cc/min; heater temperature 400 ˚C. NH4HCO3 + 0.025 % DEA* 3. Acetonitrile/Methanol: 5 mM CH3COONH4 * DEA - Diethylamine Figure 2. LC/MS/MS Responses of Representative Racemates 0.1 % Formic acid/Acetonitrile 4.E+07 5 mM Ammonium Bircarbonate/Acetonitrile 1.E+07 9.E+06 4.E+07 0.1 % Formic acid/CH3CN 8.E+06 5 mM NH4HCO3/CH3CN 7.E+06 6.E+06 esponses 3.E+07 r 5.E+06 4.E+06 3.E+06 LC/MS/MS 3.E+07 2.E+06 1.E+06 esponses r 0.E+00 Conc.: 200 ng/mL 2.E+07 Column: Gemini-NX 3 µm Ketamine Isoxsuprine Nifenolol Nisoldipine rimipramine T Norketamine 50 x 2.0 mm 2.E+07 LC/MS/MS 1.E+07 5.E+06 0.E+00 Ketamine Nifenolol Isoxsuprine Nisoldipine rimipramine T Norketamine Figure 3. Effect of Modifier and Additive on Enantiorecognition XIC of +MRM (1 pair): 225.0/165.2 amu from Sample ... Max. 6.5e5 cps. XIC of +MRM (1 pair): 295.4/100.0 amu from Sample ... Max. 1.8e5 cps. 8.83 15.18 Intensity, cps 8.42 Intensity, cps 1.8e5 16.09 6.0e5 Nifenolol 225.0/165.2 1.5e5 Trimipramine 295.4/100.0 5.0e5 Lux Cellulose-2 Lux Cellulose-2 4.0e5 60:40/MeOH: 5 mM NH4HCO3 50:50/CH3CN: 5 mM NH4HCO3 1.0e5 3.0e5 2.0e5 5.0e4 1.0e5 0.0 0.0 2 4 6 8 10 12 14 2 4 6 8 10 12 14 16 18 20 22 24 Time, min Time, min XIC of +MRM (1 pair): 225.0/165.2 amu from Sample ... Max. 1.6e4 cps. XIC of +MRM (1 pair): 295.4/100.0 amu from Sample ... Max. 1.5e5 cps. Intensity, cps 8.15 8.77 Intensity, cps 22.71 24.21 1.5e5 1.5e4 Decreased signal Decreased Nifenolol 225.0/165.2 Trimipramine 295.4/100.0 24.44 Lux Cellulose-2 Lux Cellulose-2 1.0e5 1.0e4 60:40//MeOH: 5 mM NH4HCO3 +0.025 % DEA 45:55/CH3CN: 5 mM NH4HCO3 5000.0 5.0e4 Broader peaks & delayed RT 0.0 0.0 2 4 6 8 10 12 14 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 Time, min Time, min XIC of +MRM (1 pair): 225.0/165.2 amu from Sample... Max. 3881.0 cps. XIC of +MRM (1 pair): 295.4/100.0 amu from Sample ... Max. 4.8e4 cps. Intensity, cps 25.77 Intensity, cps 18.69 19.92 3881 4.8e4 29.12 Trimipramine 295.4/100.0 signal Decreased Nifenolol 225.0/165.2 4.0e4 3000 Lux Cellulose-2 Lux Cellulose-2 50:50/CH3CN: 5 mM NH4HCO3 +0.025 % DEA 45:55/MeOH: 5 mM NH4HCO3 + 0.025 % DEA 3.0e4 2000 35 min 2.0e4 1000 1.0e4 0 0.0 5 10 15 20 25 30 2 4 6 8 10 12 14 16 18 20 22 24 Time, min Time, min Figure 4. Effects of Temperature and Additive on Enantiorecognition XIC of +MRM (4 pairs): 180.0/124.1 amu from Sample... Max. 4.4e5 cps. XIC of +MRM (2 pairs): 321.4/275.1 amu from Sample... Max. 8.8e4 cps. Intensity, cps 4.66 Intensity, cps 5.83 4.4e5 8.8e4 6.52 4.0e5 5.52 8.0e4 Lorazepam 321.4/275.1 3.0e5 Adrenaline 180.0/124.1 6.0e4 Lux Cellulose-2 Lux Cellulose-2 80:20/MeOH: 5 mM NH4HCO3 2.0e5 50:50/MeOH: 5 mM NH4HCO3 4.0e4 @ ambient @ ambient 1.0e5 2.0e4 0.0 0.0 2 4 6 8 10 2 4 6 8 Time, min Time, min XIC of +MRM (4 pairs): 180.0/124.1 amu from Samplee... Max. 1.9e5 cps. XIC of +MRM (2 pairs): 321.4/275.1 amu from Sample... Max. 1.9e4 cps. Intensity, cps 6.61 Intensity, cps 7.81 1.9e5 1.9e4 Broad peaks & delayed retention 9.03 8.50 1.5e5 1.5e4 1.0e5 Adrenaline 180.0/124.1 1.0e4 Lorazepam 321.4/275.1 Lux Cellulose-2 Lux Cellulose-2 5.0e4 50:50/MeOH: 5 mM NH4HCO3 5000.0 80:20/MeOH: 5 mM NH4HCO3 @ 5ºC @ 5ºC 2.95 0.0 0.0 2 4 6 8 10 2 4 6 8 10 Time, min Time, min XIC of +MRM (4 pairs): 180.0/124.1 amu from Sample... Max. 2.0e5 cps. XIC of +MRM (2 pairs): 321.4/275.1 amu from Sample... Max. 2313.2 cps. Intensity, cps 4.55 Intensity, cps 5.66 2.0e5 2313 6.32 Decreased signal Decreased 5.40 2000 1.5e5 Lorazepam 321.4/275.1 Adrenaline 180.0/124.1 1500 Lux Cellulose-2 Lux Cellulose-2 80:20/MeOH: 5 mM 1.0e5 50:50/MeOH: 5 mM 1000 NH HCO +0.025 % DEA NH HCO + 0.025 % DEA 4 3 4 3 @ ambient 5.0e4 @ ambient 500 0.0 0 2 4 6 8 10 2 4 6 8 10 Time, min Time, min Figure 5a. Effect of Buffer on Chiral Resolution in RP LC/MS/MS on Lux Cellulose-1 XIC of +MRM (9 pairs): 233.2/188.3 amu from Sample... Max. 1.6e4 cps. XIC of +MRM (9 pairs): 233.2/188.3 amu from Sample... Max. 4120.0 cps. Intensity, cps 4.30 Intensity, cps 3.45 1.6e4 3.75 4000 3.96 1.0e4 Aminoglutethimide 233.2/188.3 Aminoglutethimide 233.2/188.3 60:40/CH3CN: 5 mM NH4HCO3 2000 60:40/CH3CN: 5 mM NH4AC 2.74 0.0 0 2 4 6 8 10 12 14 2 4 6 8 10 12 14 Time, min Time, min XIC of +MRM (9 pairs): 181.2/141.2 amu from Sampl... Max. 3.3e4 cps. XIC of +MRM (9 pairs): 181.2/141.2 amu from Sample... Max. 4.1e4 cps. Intensity, cps 4.41 Intensity, cps 2.63 3.3e4 5.94 4.0e4 2.43 Orphenadrin 181.2/141.2 Orphenadrin 181.2/141.2 60:40/CH3CN: 5 mM NH4HCO3 2.0e4 60:40/CH3CN: 5 mM NH4AC 0.0 0.0 2 4 6 8 10 12 14 2 4 6 8 10 12 14 Time, min Time, min XIC of +MRM (13 pairs): 366.1/132.2 amu from Sample... Max. 2.9e5 cps. XIC of +MRM (14 pairs): 366.1/132.2 amu from Sample... Max. 2.3e4 cps. Intensity, cps 4.76 Intensity, cps 4.33 2.9e5 6.17 2.0e4 2.0e5 Indapamide 366.1/132.2 5.65 Indapamide 366.1/132.2 60:40/CH3CN: 5 mM NH4HCO3 60:40/CH3CN: 5 mM NH4AC 1.0e5 1.0e4 0.0 0.0 2 4 6 8 10 12 14 2 4 6 8 10 12 14 Time, min Time, min XIC of +MRM (9 pairs): 346.3/125.1 amu from Sample... Max. 2.6e5 cps. XIC of +MRM (9 pairs): 346.3/125.1 amu from Sample... Max. 1.4e5 cps. Intensity, cps 8.73 9.41 Intensity, cps 4.63 4.89 2.6e5 1.4e5 2.0e5 Motofoline 346.3/125.1 1.0e5 Motofoline 346.3/125.1 60:40/CH CN: 5 mM NH HCO 60:40/CH CN: 5 mM NH AC 1.0e5 3 4 3 5.0e4 3 4 0.0 0.0 2 4 6 8 10 12 14 2 4 6 8 10 12 14 Time, min Time, min XIC of +MRM (9 pairs): 370.4/252.1 amu from Sample..
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