A Sub-picogram Quantification Method for Desmopressin in Plasma using the SCIEX Triple Quad 6500 System

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1 A Sub-picogram Quantification Method for Desmopressin in Plasma using the SCIEX Triple Quad 6500 System A high-throughput method for detecting ultra-low levels (0.5 pg/ml) of a therapeutic peptide in human plasma using an SCIEX Triple Quad 6500 LC-MS/MS System and UHPLC Chromatography Rahul Baghla 1, Swati Guttikar 2, Dharmesh Patel 2, Abhishek Gandhi 2, Anoop Kumar 1, and Manoj Pillai 1 1 SCIEX, 121, Udyog Vihar, Phase IV, Gurgaon, Haryana, India 2 Veeda Clinical Research India, Ahmadabad, India Key challenges of desmopressin quantitation Impaired sensitivity in complex matrices Very low-level peptide detection (sub-pg/ml) can be suppressed by high background and competing ions in biological samples. Poor data quality Precision and accuracy can be compromised at low peptide levels, giving results below accepted bioanalytical standards. Key benefits of peptide quantitation on the SCIEX Triple Quad 6500 LC-MS/MS System Technology High sensitivity Very low level peptide detection in human plasma (at sub pg/ml concentrations) is enabled by IonDrive System Technology. Unique features of the SCIEX Triple Quad 6500 System for low-level peptide detection IonDrive Turbo V Source Increased ionization efficiency and heat transfer contribute to sensitivity enhancements, including improved signal-to-noise. IonDrive QJet Ion Guide Increased ion sampling improves method efficiency and ruggedness. IonDrive High Energy Detector Innovative detector technology boosts dynamic range and sensitivity. Excellent precision and accuracy at the LOQ level Data quality (for LOQ, LQC, MQC and HQC levels) met or exceeded USFDA bioanalytical method validation criteria. High throughput High sensitivity was achieved under high-flow conditions (0.750 ml/min), optimal for multi-sample analysis. Figure 2: Unique features of SCIEX Triple Quad 6500 System. Figure 1: SCIEX Triple Quad 6500 System. Introduction Low-level peptide detection has a number of applications in clinical studies and in the pharmaceutical discovery and development processes, highlighting the increasing relevance of sensitive and selective mass spectrometric platforms in the bioanalytical laboratory. Regulatory requirements demand intensive and rigorous quantitation of therapeutic peptides during pharmacokinetic, bioequivalence, and metabolic studies. In addition, drug discovery and development strategies seek to monitor and quantitate peptide biomarkers in complex biological samples, necessitating highly-selective separations of low concentration analytes from high background noise and prominent levels of competing ions. The SCIEX Triple Quad 6500 LC-MS/MS System, equipped with IonDrive System Technology for enhanced detector performance, has demonstrated particular strength in the detection of low-

2 level amounts of small molecules, and in this study, we extend the augmented signal-to-noise, broad dynamic range, and the efficient method development capacities of the SCIEX Triple Quad 6500 System to the detection of sub-picogram levels of a therapeutic peptide under high-throughput conditions. We have developed a reliable, fast, and sensitive method for the detection of a nine-amino-acid peptide, desmopressin (1-desamino-8-D-arginine, vasopressin), which is structurally similar to the hormone arginine vasopressin, but contains a deaminated first amino acid and dextro-arginine (rather than levo-) in the eighth position. Therapeutically, desmopressin reduces urine production, restricting water elimination from the kidneys by binding to the V2 receptors in renal-collecting ducts, thereby facilitating increased reabsorption. The longer half-life of desmopressin over vasopressin offers some therapeutic advantages, and typical doses of desmopressin to treat diabetes insipidus and bedwetting range between to 1.20 mg per day, resulting in very low plasma concentrations. In this bioanalytical study, we have established a sensitive and selective LC-MS/MS method for the quantitation of desmopressin in human plasma, detecting peptide levels as low as pg/ml with excellent accuracy and precision. This technique should facilitate additional mass spectrometric method development for accurate quantitation of a range of therapeutic peptides in biological matrices on the SCIEX Triple Quad 6500 System. Materials and Methods Sample Preparation Plasma samples (1000 µl) containing 2% desmopressin standard and 50µL internal standard were vortexed and spiked with 50µL of orthophosphoric acid (OPA). Samples were extracted on weak cation exchange cartridges conditioned with methanol followed by 100mM ammonium acetate solution. After loading, samples were washed in three steps: 1) 2% OPA:methanol (80:20 v/v); 2) 2% NaOH:Methanol (60:40 v/v); and 3) water:methanol (60:40 v/v). Analytes were eluted with 5% acetic acid in methanol, dried under nitrogen at 40 ºC, and reconstituted with 0.1% acetic acid (150 µl) prior to analysis by mass spectrometry. Chromatography LC System: GL Sciences LC 800 System Column: Agilent 300 Extend C 18 (150 x 2.1 mm, 3.5 μm) Column Temp.: 40 C Injection: 50 μl Flow Rate: ml/min Mobile phase: A) water, 0.1 % acetic acid B) acetonitrile, 0.1% acetic acid Gradient: Time/min A% B% Mass Spectrometry Analysis of desmopressin and desmopressin-d 5 required different mass spectrometry settings (Table 1). The MRM transition monitored for desmopressin was m/z 525.4/328.0 and 537.9/328.0 at a dwell time of 50 msec. Five replicate injections were performed at all concentrations. Data System: Interface: SCIEX Triple Quad 6500 System IonDrive Turbo V Source in positive ion mode Figure 3. Structure of desmopressin. Table 1. Compound-dependent parameters for desmopressin anddesmopressin-d 5 on the SCIEX Triple Quad 6500 System Instrument Parameter Desmopressin Desmopressin-d5 CUR TEM 600 C 600 C ISV GS GS CAD DP EP CE CXP Figure 4. Structure of internal standard, desmopressin-d 5.

3 Data processing All SCIEX Triple Quad 6500 System data was processed using MultiQuant Software.. The concentration curves were analyzed using a linear fit with a 1/x 2 weighting. Data acquired on the SCIEX Triple Quad 6500 System was processed using the quantitation tools within Analyst 1.6 Software. Results and Discussion Method analysis and data quality The desmopressin quantitative assay was validated by generating an internal standard curve using standards alone and standards spiked into human plasma. Left side pane of Figure 5 shows representative peaks for A) blank extract, B) plasma spiked with 0.5 pg/ml desmopressin and the right side pane of Figure 5 shows the MRM response from the internal standard. Standard concentrations varied from 0.5 to 100 pg/ml generating an LLOQ in plasma of 0.5 pg/ml resulting in a signal to noise ratio of 60.7 (Figure 6). Reproducibility of the assay was assessed by multiple technical replicates of the same sample (n = 6, Figure 7) on an LLOQ quality control sample of 0.5 pg/ml. The calibration curve for desmopressin in plasma shows excellent linearity over 2.5 orders of magnitude concentration range with an r value of >0.99 (Figure 8). Figure 6: High signal-to-noise ratio for desmopressin.. The signalto-noise ratio was calculated for desmopressin extracted from plasma at LLOQ level (0.500 pg/ml in plasma, S/N = 60.7). Figure 5. Desmopressin MRM signal (shown in left side ) panes for multiple concentrations and Desmopressin D5 MRM signal (Shown in right side panes). Figure 7: Desmopressin technical replicates. Chromatograms of six LLOQ quality control samples (0.502 pg/ml) for precision and accuracy calculations are shown (Table 2).

4 The data collected for a single calibration curve are presented in Table 2. Analyte retention time and internal standard peak retention times were consistent, with both eluting at approximately 2.6 min. The calculated concentration correlates well with the actual spikedanalyte concentration in plasma matrix with a percent accuracy of the standard curve very close to 100% for all concentrations of standard, and the quality control samples had a percent accuracy of 110%. Table 3 shows the individual statistics for three separate batch runs of desmopressin. Data from Table 2 are taken from Batch 3. Table 4 shows the mean values for the percent accuracy and % CV for three separate batch runs. For the LLOQ quality control, the mean accuracy was calculated to be 108% with a %CV of 10.5%. The percent recovery and plasma matrix effect were evaluated by comparing the peak areas for standard curve samples with and without plasma (Table 5). The mean percent recovery was calculated to be 93%. The recovery of the internal standard was calculated to be 78% (Table 6). Figure 8: Calibration curve of desmopressin in plasma from pg/ml to pg/ml. The method has shown excellent linearity over the concentration range with r = Table 2. Data quality analysis of desmopressin from human plasma samples Sample ID Sample Type Analyte Retention Time (min) Analyte Peak Area IS Retention Time (min) IS Peak Area Area Ratio Analyte Conc. (pg/ml) Calculated Conc. (pg/ml) % Accuracy AQM Unknown , N/A N/A BLANK 01 Blank #DIV/0! N/A #DIV/0! N/A BLANK+IS 01 Unknown ,418 0 N/A No Peak N/A STD A 01 Standard , , STD B 01 Standard , , STD C 01 Standard , , STD D 01 Standard , , STD E 01 Standard , , STD F 01 Standard , , STD G 01 Standard , , STD H 01 Standard , , LLOQ QC 01 Qual. Control , , LQC 01 Qual. Control , , MQC 01 Qual. Control , , HQC 01 Qual. Control , , LLOQ QC 02 Qual. Control , , LQC 02 Qual. Control 2.6 5, , MQC 02 Qual. Control , , HQC 02 Qual. Control , , LLOQ QC 03 Qual. Control , , LQC 03 Qual. Control , , MQC 03 Qual. Control , , HQC 03 Qual. Control , , LLOQ QC 04 Qual. Control , , LQC 04 Qual. Control , , MQC 04 Qual. Control , , HQC 04 Qual. Control , , LLOQ QC 05 Qual. Control , , LQC 05 Qual. Control , , MQC 05 Qual. Control , , HQC 05 Qual. Control , , LLOQ QC 06 Qual. Control , , LQC 06 Qual. Control , , MQC 06 Qual. Control , , HQC 06 Qual. Control , , Table 2. Full analysis of precision and accuracy measurements for desmopressin (batch 1 samples) in human plasma.

5 Table 3: Precision and accuracy for multi-batch desmopressin technical replicates DESMOPRESSIN Nominal Concentration (pg/ml) LLOQ QC LQC MQC HQC PA BATCH Mean S.D (+/-) C.V. (%) % Nominal N PA BATCH Mean S.D (+/-) C.V. (%) % Nominal N PA BATCH Mean S.D (+/-) C.V. (%) % Nominal N Table 3: Precision and accuracy calculations for individual batches of desmopressin samples. Table 4. Precision and accuracy of desmopressin technical replicates measured as a single group DESMOPRESSIN Nominal Concentration (pg/ml) LLOQ QC LQC MQC HQC Mean S.D (+/-) C.V. (%) % Nominal N Table 4: Mean precision and accuracy calculations for desmopressin for three batches of measurements from different days. Table 5. Recovery of desmopressin from human plasma, batch 03 LQC RESPONSE MQC RESPONSE HQC RESPONSE Sample ID Extracted Unextracted Extracted Unextracted Extracted Unextracted 01, 013 5,923 6, , , , ,315 02, 014 6,645 6, , , , ,138 03, 015 6,572 6, , , , ,730 04, 016 5,879 6, , , , ,201 05, 017 5,823 6, , , , ,383 06, 018 5,263 5, , , , ,647 Mean 6, , , , ,735.7 S.D , , , C.V N % Recovery Mean SD (+/-) CV(%) N 3 Table 5: Recovery of desmopressin from plasma at three different concentrations, LQC, MQC and HQC, was 92.72%.

6 Conclusions A highly sensitive and high-throughput bioanalytical method was developed and validated for the detection of ultra-low-levels of the therapeutic peptide, desmopressin, in human plasma on the SCIEX Triple Quad 6500 LC-MS/MS System. Method sensitivity for desmopressin detection was exceptional (0.5 pg/ml or 2.5 fg on column), and demonstrated high-reproducibility and cost effectiveness with good precision and accuracy. Analyte recovery is 92.7%, even under high-throughput conditions. Total run time for each sample was only 5 min, using a flow rate rapid enough for high-throughput analysis in the bioanalytical laboratory. References Friedman, F and Weiss JP. Desmopressin in the treatment of nocturia: clinical evidence and experience. Therapeutic Advances in Urology. 2013; 5(6): Neudert, L, Zaugg, M, Wood, S, Struwe, P. A high sensitivity dual solid phase extraction LC-MS/MS assay for the determination of the therapeutic peptide desmopressin in human plasma. Celerion white paper. Acknowledgements The authors are indebted to Dr.Venu Madhav, Chief Operating Officer (COO), Veeda Clinical Research, India, for his encouragement and support for the successful completion of the work. AB Sciex is doing business as SCIEX AB Sciex. For research use only. Not for use in diagnostic procedures. The trademarks mentioned herein are the property of the AB Sciex Pte. Ltd. or their respective owners. AB SCIEX is being used under license. RUO-MKT A Headquarters 500 Old Connecticut Path Framingham, MA USA Phone sciex.com International Sales For our office locations please call the division headquarters or refer to our website at sciex.com/offices

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