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LC-MS/MS Targeted Screen LC-MS/MS Targeted Screen Tyren Dodgen Waters Division Microsep ©2017 Waters Corporation COMPANY CONFIDENTIAL 1 Overview Background Tandem Quadrupole targeted screen – Introduction – Methods – Results Q-ToF for Targeted Screen – Quantitative capability – Improving precision and confidence – Elucidating additional information Conclusion ©2017 Waters Corporation COMPANY CONFIDENTIAL 2 What do you want to do? 4 Fundamental Questions Are these compounds in my sample? Screening How much is in my sample? Quantitation What else is in my sample? Elucidation What is the difference between my sample and another one? Comparison ©2017 Waters Corporation COMPANY CONFIDENTIAL 3 Tools for Targeted Screening Tandem quad MS/MS remains “gold standard” – Selectivity and sensitivity in complex matrices using MRM Workflow toolkit facilitates … – Easy adoption – Rapid method development – Increased productivity ©2017 Waters Corporation COMPANY CONFIDENTIAL 4 Direct analysis of 26 urinary opioids and metabolites by mixed- mode µElution SPE combined with UPLC/MS/MS for forensic toxicology – Improved performance vs. “Dilute-and-shoot” methodology Jonathan P. Danaceau, Erin E. Chambers and Kenneth J. Fountain ©2017 Waters Corporation COMPANY CONFIDENTIAL 5 Why test for opioid drugs and metabolites Most commonly abused prescription drugs1 – In 2007, deaths from prescription opioids exceeded those from cocaine and heroin combined2 Dramatic increase in therapeutic use of opioids recently (1997-2007) 3 – Hydrocodone (283%), methadone (1293%), oxycodone (893%) Pain management Forensic toxicology Clinical research – Identification of possible PK/Metabolism issues with an individual patient Other applications – workplace testing – drug of abuse treatment monitoring – Anti-doping 1. National Institute on Drug Abuse (NIDA) DrugPubs; www.drugabuse.gov. 2. NIDA Research Reports. Prescription Drugs: Abuse and Addition; NIH Publication Number 11-4881; revised, 2011. 3. Manchikanti et al. Pain Physician, 2010 13:401-435. ©2017 Waters Corporation COMPANY CONFIDENTIAL For forensic toxicology use 6 Method Details ©2017 Waters Corporation COMPANY CONFIDENTIAL 7 Solid-Phase Extraction (SPE) SPE is gaining acceptance in clinical and forensic labs – Cleans up, concentrates, and produces a final sample that is in an appropriate solvent for further analysis Uses polymeric or silica-based chromatographic particles packed into a variety of formats – 96-well plates, cartridges, etc. SPE is considered to be a very versatile sample preparation technique for various analytes in complex matrices – Blood, serum, plasma, oral fluid, tears, nasal fluid, CSF, urine, feces, meconium, postmortem samples, and many more! It’s the best technique for minimizing matrix interferences including proteins, phospholipids, salts, and other endogenous compounds ©2017 Waters Corporation COMPANY CONFIDENTIAL 8 Oasis® Family of Sorbents: Reversed-Phase and Mixed-Mode Sorbent ALWAYS Charged (-) Sorbent ALWAYS Charged (+) Selective for Selective for Basic Acidic Compounds Compounds Selective for Selective for Strong Strong Basic Acidic Compounds For wide range of acidic, Compounds basic, and neutral compounds Sorbent charged (-) at high pH; Sorbent charged (+) at Low pH; unionized at low pH unionized at high pH ©2017 Waters Corporation COMPANY CONFIDENTIAL 9 Comprehensive opioid panel Compound 1 Morphine-3β-D-glucuronide 2 Oxymorphone-3β-D-glucuronide Natural opiates and metabolites 3 Hydromorphone-3β-D- glucuronide 4 Morphine-6β-D-glucuronide Semi-synthetic opioids 5 Morphine Synthetic narcotic analgaesics 6 Oxymorphone 7 Hydromorphone 8 Codeine-6β-D-glucuronide 9 Dihydrocodeine 10 Codeine 11 Oxycodone 12 6-Acetylmorphone (6-AM) 13 O-desmethyl Tramadol 14 Hydrocodone 15 Norbuprenorphine-glucuronide 16 Norfentanyl 17 Tramadol 18 Normeperedine 19 Meperidine 20 Buprenorphine-glucuronide 21 Norbuprenorphine 22 Fentanyl 23 Buprenorphine 24 EDDP+ 25 Propoxyphene ©201726 Waters Corporation COMPANYMethadone CONFIDENTIAL 10 Retention map for Oasis MCX All bases→ Oasis MCX Oasis® MCX SORBENT CHARGE (-) (-) max Base (H+) (Ionized) Base (N) (Not Ionized) Retention min 0 2 4 6 pH 8 10 12 14 Maximum Retention When Analyte Is Ionized ©2017 Waters Corporation COMPANY CONFIDENTIAL 11 Extraction Methodologies for Urine Oasis MCX μElution Plate Protocol Sample Dilution Protocol (Mixed-mode strong cation exchange SPE) 100 µL urine Sample Pretreatment 100 µL urine + 100 µL 4% H3PO4+ Add 100 µL IS 100 µL IS (dissolved in water) Condition Plate Vortex 200 µL MeOH then 200 µL Water Inject 10 µL Load 300 µL pretreated sample Wash • A short evaporation step (<5 min) 200 µL Water, then implemented to evaporate and 200 µL MeOH reconstitute in the mobile phase Elute • Prevents solvent effects for early 2 x 50 µL eluting compounds (60:40 ACN:MeOH + 5% NH4OH) o Evaporate under N2 @ 37 C Reconstitute in 50 µL of starting mobile phase (2% ACN/0.1% FA) Inject 10 µL ©2017 Waters Corporation COMPANY CONFIDENTIAL 12 Instrumental Conditions Column ACQUITY UPLC BEH C18 1.7 µm; 2.1 x 100 mm LC UPLC MS XEVO® TQD Flow Rate 0.4 mL/min MPA 0.1% FA in water MPB 0.1% FA in ACN Inj. Vol 10 µL Time Flow %A %B 0 0.4 98 2 6 0.4 47.2 52.8 6.5 0.4 98 2 8 0.4 98 2 ©2017 Waters Corporation COMPANY CONFIDENTIAL For forensic toxicology use 13 Prepare Analyse Interpret Decide ©2017 Waters Corporation COMPANY CONFIDENTIAL 14 RT, formulae, MS conditions Molecular Cone Coll. Compound RT Formula MRM Transitions Mass Voltage Energy 1 Morphine-3β-D-gluc 1.21 C23H27NO9 461.17 462.2>286.1, 201.1 58 30, 52 2 Oxymorphone-3β-D-gluc 1.21 C23H27NO10 477.16 478.2>284.1, 227.1 46 28, 50 3 Hydromorphone-3β-D- gluc 1.34 C23H27NO9 461.17 462.2>286.1, 185.1 58 28, 56 4 Morphine-6β-D-gluc 1.47 C23H27NO9 461.17 462.2>286.2, 201.2 64 38, 40 5 Morphine 1.50 C17H19NO3 285.14 286.2>201.1, 165.1 54 28, 34 6 Oxymorphone 1.61 C17H19NO4 301.13 302.2>227.1, 242.1 44 28, 24 7 Hydromorphone 1.76 C17H19NO3 285.13 286.2>185.1, 157.1 66 32, 42 8 Codeine-6β-D-gluc 2.00 C24H29NO9 475.18 476.2>300.2, 165.2 60 36, 40 9 Dihydrocodeine 2.07 C18H23NO3 301.17 302.2>199.1, 128.1 52 34, 58 10 Codeine 2.14 C18H21NO3 299.15 300.2>215.2, 165.1 54 26, 38 11 Oxycodone 2.37 C18H21NO4 315.15 316.2>256.2, 241.1 44 26, 26 12 6-Acetylmorphone (6-AM) 2.41 C19H21NO4 327.15 328.2>165.1, 211.1 60 26, 36 13 O-desmethyl Tramadol 2.46 C15H23NO2 249.17 250.2>58.0 26 18 14 Hydrocodone 2.50 C18H21NO3 299.15 300.2>199.1, 171.0 60 30, 44 15 Norbuprenorphine-gluc 2.83 C31H43NO10 589.29 590.3>414.3, 101.0 70 34, 54 16 Norfentanyl 2.93 C14H20N2O 232.16 233.2>177.2, 150.1 30 14, 18 17 Tramadol 3.21 C16H25NO2 263.19 264.2>58.0 24 16 18 Normeperedine 3.58 C14H19NO2 233.1 234.1>160.1, 188.2 36 12, 18 19 Meperidine 3.60 C15H21NO2 247.16 248.2>174.1, 220.2 48 22, 20 20 Buprenorphine-gluc 3.64 C35H49NO10 643.34 644.3>468.3, 187.1 66 42, 62 21 Norbuprenorphine 3.77 C25H35NO4 413.26 414.3>101.0, 187.2 66 42, 34 22 Fentanyl 4.29 C22H28N2O 336.22 337.2>188.2, 105.1 48 22, 38 23 Buprenorphine 4.55 C29H41NO4 467.3 468.3>101.0, 396.3 72 40, 48 + 24 EDDP+ 4.79 C20H24N 278.19 278.3>234.2, 249.2 50 24, 32 25 Propoxyphene 5.18 C22H29NO2 339.3 340.3>266.2, 143.1 22 8, 32 26 Methadone 5.25 C21H27NO 309.2 310.2>105.0, 223.1 32 22, 28 ©2017 Waters Corporation COMPANY CONFIDENTIAL For forensic toxicology use 15 Results ©2017 Waters Corporation COMPANY CONFIDENTIAL 16 Opioid chromatography Compound Separation of isobaric compounds 1 Morphine-3β-D-glucuronide (highlighted compounds) 2 Oxymorphone-3β-D-glucuronide 3 Hydromorphone-3β-D- glucuronide 4 Morphine-6β-D-glucuronide 5 Morphine 6 Oxymorphone 13 7 Hydromorphone 8 Codeine-6β-D-glucuronide 9 Dihydrocodeine 17 10 Codeine 11 Oxycodone 18,19 12 6-Acetylmorphone (6-AM) 20 13 O-desmethyl Tramadol 1, 2 22 14 Hydrocodone % 15 Norbuprenorphine-glucuronide 10 14 26 16 Norfentanyl 3 17 Tramadol 7 9 12 18 Normeperedine 19 Meperidine 20 Buprenorphine-glucuronide 15,16 24 21 Norbuprenorphine 4, 5 11 8 21 23 25 22 Fentanyl 23 Buprenorphine 6 24 EDDP+ 25 Propoxyphene 26 Methadone 0 Time 1.00 1.50 2.00 2.50 3.00 3.50 4.00 4.50 5.00 ©2017 Waters Corporation COMPANY CONFIDENTIAL For forensic toxicology use 17 Mixed-mode SPE extraction recovery 6 Lots of matrix 120% 100% 80% 60% %Recovery 40% 20% 0% ©2017 Waters Corporation COMPANY CONFIDENTIAL For forensic toxicology use 18 Improved Matrix Factors and %CV with Oasis MCX SPE vs. dilution - 6 Lots of Urine 1.40 . Mixed-mode SPE * * . Dilution 1.20 * 1.00 0.80 0.60 * MatrixFactors 0.40 * * * * * * 0.20 * * 0.00 * Statistically significant difference in Matrix Factors (12/26 compounds) - reduced %CV in 23/26 compounds ©2017 Waters Corporation COMPANY CONFIDENTIAL 19 Linearity Comparisons 5-500 ng/mL (1.25-125 for fentanyl and norfentanyl) R2 Values Dilution SPE Improved linearity for Morphine-3-β-d-glucuronide 0.986 0.996 24/26 compounds with Oxymorphone-3-b-d-glucuronide 0.985 0.997 mixed-mode SPE Hydromorphone-3-b-d-glucuronide 0.987 0.998 Morphine-6-gluc 0.979 0.994 Morphine 0.954 0.992 Oxymorphone 0.989 0.998 Hydromorphone 0.996 0.998 Codeine-6-β-d-glucuronide 0.990 0.998 Dihydrocodeine 0.997 0.997 Codeine 0.990 0.995 Oxycodone 0.993 0.996 6-Acetylmorphone (6-AM) 0.990 0.997 O-desmethyl Tramadol 0.997 0.999 Hydrocodone 0.995 0.999 Norbuprenorphine-glucuronide 0.992 0.998 Norfentanyl 0.995 0.998 Tramadol 0.996 0.995 Normeperedine 0.996 0.997 Meperidine 0.997 1.000 Buprenorphine-gluc 0.991 0.997 Norbuprenorphine 0.995 0.997 Fentanyl 0.997 0.998 Buprenorphine 0.994 0.998 EDDP+ 0.998 0.999 Propoxyphene 0.995 0.996 Methadone 0.997 0.998 ©2017
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