770-9P. Sensitivity and Selectivity - A Case Study of LC/MS Enantioselective Resolution of Bupivacaine Using Vancomycin as a Chiral Stationary Phase

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1 77-9P Sensitivity and Selectivity - A Case Study of LC/MS Enantioselective Resolution of Bupivacaine Using Vancomycin as a Chiral Stationary Phase J.T. Lee 1 Maria Esther Rodriguez Rosas 2 and Thomas E. Beesley 1 1 Advanced Separation Technologies Inc, Whippany, NJ, USA. 2 Gerontology Research Center, National Institute on Aging, National Institutes of ealth, Baltimore, MD, USA. Website: info@astecusa.com

2 Abstract Racemic bupivacaine currently is the most widely used long-acting local anesthetic. owever, numerous studies have shown that in most cases the levobupivacaine is less toxic. This study is to evaluate the sensitivity and selectivity issue of enantiomeric separation of this substance in biological matrix by various mobile phase designs on LC/MS platforms. Enantioselective resolution of bupivacaine can be easily achieved by CIRBITIC V and CIRBITIC V2 columns in either polar ionic mode or reversed phase mode that is very MS-friendly. The polar ionic mode is composed of pure Me with small addition of acid and base or volatile salts while reversed phase mode contains a mixture of organic solvents and p-adjusted buffer with volatile salts. The composition of mobile phase with the use of ESI mode dictates the outcomes of sensitivity and selectivity. Furthermore, the column dimensions will have major impacts on the resolution and the overall throughput. Excellent linear relationships based on the peak heights were obtained in the range of.15ng-5ng/ml for each enantiomer standard with correlation coefficients greater than.999. This presentation will cover several key variables including mobile phase compositions, flow rate, and finally the column dimensions that will affect the overall performance. Since Macrocyclic glycopeptides chiral stationary phases have demonstrated to be highly robust and versatile in chiral assay on LC/MS platforms, the findings will be beneficial to pharmaceutical and biotech industries in the area of drug absorption, metabolism and pharmacokinetic studies.

3 Structure of Chiral Stationary Phase and Target Molecule Vancomycin Bupivacaine N 3 C N N 2 C 3 Cl N N Cl N N 3 C N C 3 3 C N 3 C N C 3 C N 2 C 3

4 Apparatus The analytical system consisted of a Series 11 Liquid Chromatography/Mass Selective Detector, LC/MSD (Agilent Technologies, Palo Alto, CA, USA) equipped with a vacuum degasser (G1379 A), a quaternary pump (1311 A), a thermostated autosampler (G1329 A), and a thermostated column compartment (G1316 A). The mass selective detector (MSD Quad SL, G1956 B) was equipped with atmospheric pressure ionization electrospray (API-ES, G298 B) or atmospheric pressure chemical ionization (APCI, G1947 A) and an on-line nitrogen generation system (Whatman, averhill, MA, USA). The chromatographic system was interfaced to a 2.8 Gz P Compaq computer (ewlett-packard, Palo Alto, CA, USA) running ChemStation software (Rev A.1.1[1635],199-23, ewlett- Packard) under Microsoft Windows XP.

5 Best PLC Condition STD Bupivacaine 1mg/mL; Inj. Vol. : 2 μl Column: CIRBITC V2, 15x2.1mm 5μ Mobile Phase: 9/1, Me/1mMN 4 Ac, p 4.1 Flow Rate:.2 ml/min UV: 23 nm mau VWD1 A, Wavelength=23 nm (SAMPLE \BUPIVA -2.D) Peak 1: 6.94 (S-) Peak 2: 8.39 (R+) min

6 Sensitivity Comparison APCI vs. ESI APCI mode M S D 3 T IC, M S F ile (E R \S IG 1 9.D ) A P C I, P o s, S IM, F ra g : 7, "B u p iv a c a in e " Corona Current: 3.5 V; Vaporizer Temperature: 35 C Fragmentor: 7; Capillary Voltage: 175 V; Drying Gas Temperature: 35 C Drying Gas Flow: 7 L/min.; Nebulizer Pressure: 2 psig LD.6ng/mL LLQ.25ng/mL M S D 3 T IC, M S F ile (E R \S IG D ) A P C I, P o s, S IM, F ra g : 7, "B u p iv a c a in e " m Column: CIRBITIC V2, 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min m

7 Sensitivity Comparison APCI vs. ESI ESI mode Fragmentor: 7; Capillary Voltage: 175 V Drying Gas Flow: 7 L/min; Nebulizer Pressure: 2 psig Drying Gas Temperature: 35 C LD.15ng/mL LLQ.62ng/mL M S D 3 TIC, M S File (E R 255\SIG 11.D) A PI-ES, Pos, SIM, Frag: 7, "Bupivacaine" M S D 3 T IC, M S F ile (E R \S IG 1 3.D ) A P I-E S, P o s, S IM, F ra g : 7, "B u p iva c a in e " Column: CIRBITIC V2, 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min m m

8 Sensitivity Comparison Dimension Issue Column: CIRBITIC V2, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Sample: 1ng/mL, 5μL inj 15x mL/min M S D 3 T I C, M S F i l e ( E R \ S I G D ) A P I - E S, P o s, S I M, F r a g : 7, " B u p i v a c a i n e " M SD 3 TIC, M S File (ER1285\SIG17.D) API-ES, Pos, SIM, Frag: 7, "Bupivacaine" m 3

9 Sensitivity Comparison CIRBITIC V2 vs.v Column: 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Sample: 1ng/mL, 5μL inj Flow Rate:.2 ml/min CIRBITIC V CIRBITIC V2 M S D 3 T I C, M S F i l e ( E R \ S I G D ) A P I - E S, P o s, S I M, F r a g : 7, " B u p i v a c a i n e " M S D 3 T IC, M S F ile (E R \S IG 1 7.D ) A P I-E S, P o s, S IM, F rag : 7, "B u p iv a c a in e " m

10 Selectivity Comparison CIRBITIC V2 vs. V Column: 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min CIRBITIC V2 α = 1.3 CIRBITIC V α = 1.21 MSD3 TIC, M S File (ER1285\SIG17.D) API-ES, Pos, SIM, Frag: 7, "Bupivacaine" M S D 3 T I C, M S F i l e ( E R \ S I G D ) A P I - E S, P o s, S I M, F r a g : 7, " B u p i v a c a i n e " mi m

11 Polar Ionic Mode Salt Effects CIRBITIC V2 Sample: Bupivacaine Column: 25x4.6 mm Mobile Phase: 1/.1w%, Me/N 4 TFA Flow Rate: 1 ml/min α = 1.44 mau 4 3 Peak 1: 5.33 Peak 2: min Mobile Phase: 1/.1w%, Me/N 4 Formate mau Flow Rate: 1 ml/min 35 Peak 3 α = : 3.76 Peak 2: min

12 Sample: Bupivacaine Column: 25x4.6mm Reversed Phase Mode-1 CIRBITIC V2 Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate: 1 ml/min mau α = Peak 1: Peak 2: min Mobile Phase: 8/2, Me/2mM N 4 Ac, p 4.1 Flow Rate: 1 ml/min mau α = Peak 1: 8.79 Peak 2: min

13 Sample : Bupivacaine Column: 25x4.6mm Reversed Phase Mode-2 CIRBITIC V2 Mobile Phase: 5/5, Me/1mM N 4 Ac, p 4.1 mau Flow Rate: 1 ml/min 4 Peak 35 α = : 8.5 Peak 2: min Mobile Phase: 25/75, Me/1mM N 4 Ac, p 4.1 Flow Rate: 1 ml/min mau 2 α = Peak 1: Peak 2: min

14 Calibration Curves for Std Bupivacaine Solutions-ESI Column: CIRBITIC V2, 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min eight (S)-Bupivacaine, MSD3 TIC eight = *Amt eight (R)-Bupivacaine, MSD3 TIC eight = *Amt Correlation: Correlation: [ng/ml] 2 4 [ng/ml]

15 Calibration Curves for Std Bupivacaine Solutions-APCI Column: CIRBITIC V2, 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min eight (S)-Bupivacaine, MSD3 TIC eight = *Amt eight (R)-Bupivacaine, MSD3 TIC eight = *Amt Correlation: Correlation: [ng/ml] 2 4 [ng/ml]

16 SPE Extraction Method (uman Plasma Matrix) Transfer a.5 ml aliquot of sample into a 96-deep-well (2-mL) plate. Using a repeater pipette, add 5 μl of.1 M acetic acid in water to each sample. Cover the plate and vortex briefly. Load the sample plate on the Tomtec and follow the SPE procedures below. Precondition the SPEC. PLUS.96-Well SCX (Ansys, Cat. No ) with.3 ml of methanol. Precondition with.3 ml of.1 M acetic acid in water Load the sample on the SPE plate slowly Wash the SPE plate with.3 ml of.1 M acetic acid in water: methanol (5:5) twice. Elute the analyte with.2 ml of 2% ammonium hydroxide in methanol (2:98) twice (collect the eluate with a round deep well 1-mL 96-well plate). Evaporate the eluate at 4 C for 2-3 min to dryness. Reconstitute residue in.5 ml of 7:3 methanol/1 mm ammonium acetate, p 4.1. Cover plate and vortex for ~5 seconds. Inject 1 μl into LC/MS/MS system.

17 Blank in uman Plasma Column: CIRBITIC V2, 15x2.1 mm, 5μ Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min

18 Bupivacaine by LC/MS-ESI Column: CIRBITIC V2, 15x2.1 mm Mobile Phase: 9/1, Me/1mM N 4 Ac, p 4.1 Flow Rate:.2 ml/min Bupivacaine in plasma

19 Sensitivity (Ratio): Summary LC/MS Mode ESI:APCI = 4.:1. Column ID (mm) 2.1: 4.6 = 1.5:1. CIRBITIC V:V2 = 1.3:1. Selectivity (α): CIRBITIC V2:V = 1.3: 1.21 Calibration: Excellent Correlation Coefficients >.999 Linear Range =.15ng-5ng/mL

20 Conclusions CIRBITIC V2 and V showed exceptional selectivity towards basic drugs, and they are complementary in terms of sensitivity and selectivity. Unique multi-modal characteristics from 1% organic to high aqueous can be utilized to obtain best separation needs. Unique mobile phase designs can be tailored on LC/MS platforms in biological matrix for both sensitivity and selectivity issues. Unique ionic interaction between CSP and analyte is key to successful chiral recognition.

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