APPLICATIONS OF SMALL MOLECULE LCMS FOR FORENSICS AND TOXICOLOGY. Elliott Jones, Small Molecule LCMS Group Leader AB/SCIEX, Foster City CA
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1 APPLICATIS F SMALL MLECULE LCMS FR FRESICS AD TXICLGY Elliott Jones, Small Molecule LCMS Group Leader AB/SCIEX, Foster City CA
2 Why use TQ LCMS? Why use TQ LCMS? 1. TQ MRM experiments allow for the best quantitation sensitivity with minimal matrix interfreance 2. In general a large number of samples can be done in one run (30,50,100) 3. Wide range of sources cover most drug molecules ESI, APCI and APPI 4. Compounds generally do not need to be separated 5. Detection limits in matrix of 10 femotograms to 10 pictograms are generally achievable
3 Quantitation of 23 Drugs of Abuse
4 Method Conditions For 23 Drug Analysis
5 Examples of Detection limits for 4 Compounds of 23 Drug Analysis
6 Example of Control and Human Sample 23 Drug Analysis
7 23 Drug Analysis
8 ID and Quantitation in one run, TQ/LIT Quantitation by MRM is usually the preferred technique for drug analysis Since further confirmation is need for legal validation, hybrid trap/quad experiments can be done in one run This type of experiment makes use of a high sensivity trap product ion scan, for fragment/structural ID. A hybrid triple Quad/Trap can perform this experiment in one run With a dedicate TQ product ion scan sensitivity can be poor, while an ion trap has poor quantitation sensitivity and slow sampling
9 Forensic Screening Experimental Conditions: 9 common tranquilizers: Alprazolam, Bromazepam, onazepam, Diazepam, Flunitrazepam, xazepam, Prazepam, Temazepam spiked urine samples (diluted 1:10 water) LC Column: 4.6 x 50 mm Chromolith RP-18 Gradient LC conditions (5 min), 500 µl/min A: Water + 0.1% formic acid B: AC + 0.1% formic acid Target analysis using MRM as survey in IDA followed by EPI Analyte confirmed if MS/MS interpreted
10 Forensic Screening TIC of 9 MRM Transitions with confirmatory MS/MS
11 Forensic Screening XIC for Prazepam (325/271) 500 fg on column (in urine) MS/MS spectrum Prazepam Standard For Library
12 Unknown Measurements XIC of +L (176.00): Exp 1, to amu from Sample 17 (500 fg/ul L ) of Morphin % 95% 90% 85% 80% 75% 70% 65% 60% 55% 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% EPI (462.08) Charge (+1) CE (45): Exp 3, min from Sample 17 (500 fg/ul L ) of Mo... Time, min 100% 95% 90% 85% 80% 75% 70% 65% 60% 55% 50% 45% 40% 35% 30% 25% 20% 15% eut. Loss of 176: XIC of 462 m/z: Enhanced Product Ion Max. 6.0e4 cps. Max. 1.5e5 cps. 10% m/z, amu Rel. Int. (%) 100% 50% 5% Enhanced Product Ion Enh. Res m/z, amu In Experiment the neutral loss scan of 176 (specific to glucuronides) was used to trigger the Enhanced Product Ion Scan (EPI). In addition, a high resolution scan (Enhanced Resolution) was also performed to achieve better mass accuracy an important tool in qualitative analysis. As in Experiment 1, utilizing the sensitivity of the linear trap product ion scan mode, information on potential metabolites can be generated in a single run.
13 Forensic Screening library search the MS2 data for confirmation
14 Forensic Screening Experimental Conditions: Morphine and metabolites Spiked urine samples and patient samples (diluted 1:10 water) LC column: 2 x 100 mm Phenomenex Luna C18 Gradient LC conditions (20 min), 200 µl/min A: Water + 0.1% formic acid B: MeH + 0.1% formic acid eutral Loss of 176 as survey scans in IDA Metabolite confirmed if MS/MS interpreted
15 Forensic Screening TIC: eutral Loss of 176 L 176 ER EPI MS 3
16 Forensic Screening MS EPI 3 XIC of 462 m/z: Morphine-3β-Glucuronide 100% ER pg on column (Estimated LQ = 800 fg on column) 50% % m/z, amu
17 Simultaneous Quantitation and ID of piates
18 Simultaneous Quantitation and ID of piates Experimental Conditions: morphine/codeine/hydromorphone/hydrocodone/oxycodone/6- MAM and deuterated internal standards for each piates detected by MRM and Confirmed by IDA Trap MS2 6 piates + internal standard spiked into saliva then applied onto Centricon 3000mwco LC: 2 x 50 Targa C18 200uL/min, Water/Acetonitrile/0.05 formic acid
19 Simultaneous Quantitation and ID of piates Analysis of Morphine and its metabolites using targeted MRM with Product Ion Scan in Urine XIC of +MRM (3 pairs): Exp 1, 462.3/286.3 amu from Sample 20 (100 fg/ul MRM_EPI) of Morphin... Max cps. 100% 95% 90% 85% 80% 75% 70% 65% 60% 55% 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% Monitored the following transitions: Morphine 286/165 ormorphine 272/209 Morphine 3 Glucuronide 462/ Time, min Morphine-3β-Glucuronide, 500 fg on column S: = 17:1 Estimated LQ = 100 fg on column Multiple MRM s Enh.Prod.Ion The mrm XIC of morphine-3- glucuronide at 462/286 is displayed above. The peak at 9.42 minutes exceeded a predefined threshold and triggered the generation of the product ion scan spectra shown below.
20 Simultaneous Quantitation and ID of piates XIC of +MRM (3 pairs): Exp 1, 462.3/286.3 amu from Sample 20 (100 fg/ul MRM_EPI) of Morphin... Max cps % 95% 90% 85% 80% 75% 70% Morphine-3-Glucuronide 65% XIC of 462/286 60% 55% 50% 45% 500 fg on column 40% 35% 30% 25% % % 10% % 0% EPI (462.30) Charge (+0) CE (45): Exp 2, to min from Sample Time, 20 min(100 fg/ul MRM_E... Max. 7.0e4 cps % 95% 90% 85% 80% 75% 70% 65% 60% Product Ion Scan 55% 50% 45% 40% 35% 30% 25% 20% % % % m/z, amu Experiments 1 and 2 above shows the utility of combining the triple quad scan modes, Multiple Reaction Monitoring (MRM) and eutral Loss Scan, with the Enhanced Product Ion Scan (EPI) in the linear trap mode. Experiment 1 was designed to provide quantitative information on morphine and two of its metabolites. More importantly, if these compounds are present, an Enhanced Product Ion Scan (EPI) scan is triggered. As shown above 500fg on column of Morphine 3β-glucuronide was more than enough to produce a strong enhanced Product Ion Scan. The product ion scan spectra can then be compared to a usergenerated library for confirmation purposes.
21 Simultaneous Quantitation and ID of piates TIC of 12 MRM s Codeine Hydrocodone D6-Codeine D6-Hydrocodone Morphine Hydropmorphone D6-Morphine D6-Hydropmorphone 6-MAM xycodone D6-6-MAM D6-xycodone
22 Simultaneous Quantitation and ID of piates Hydrocodone Hydromorphone xycodone Codeine Morphine 6-Acetylmorphine 30:1 30:1 45:1 30:1 20:1 30:1 Signal-to-noise ratio of 6 opiates based on 10ng/mL spike (1 pg on column) concentration in saliva
23 Simultaneous Quantitation and ID of piates Enhanced Product Ion Scan after MRM 10 ng/ml spike Library Search Results TIC of Enhanced Product Ion Scan Morphine Hydromorphone Codeine Hydrocodone xycodone
24 Psychotropic Quantitation and ID
25 Psychotropic Quantitation and ID
26 Psychotropic Quantitation and ID
27 Psychotropic Quantitation and ID
28 Spectral Library Analysis
29 Spectral Library Analysis
30 Spectral Library Analysis
31 Spectral Library Analysis
32 Spectral Library Analysis
33 Spectral Library Analysis
34 Example of Small Molecule Metabolite ID The following example demonstrate a comprehensive investigation of of in in vitro metabolite identification in in a Hybrid Quadrople Linear ion ion Trap MS MS Metabolite ID ID is is important for for understanding Toxcity, down stream metabolic forms and interaction of of a drug with a biological system. ften during quantitation of of a drug in in an an invitro system detection might best be be achieved by by looking for for a significant metabolite, which might be be at at a higher level after many hours then the the original drug For For these reasons assement of of major metabolites can be be critical
35 Glyburide: Phase I Metabolite Experimental Conditions: Rat liver S9 incubation LC Column: 1 x 150 mm Hypersil C18 Gradient LC conditions (40 min), 70 µl/min A: Water + 0.1% formic acid B: AC + 0.1% formic acid Compared EMS, Precursor Ion, eutral Loss and targeted MRM as survey scans in IDA. Metabolite confirmed by MS/MS Sensitivity comparison and # of metabolites: 4000 Q TRAP vs Q TRAP
36 Glyburide: Phase I Metabolite +EPI (494.00) Charge (+0) CE (37): Exp 2, min from Sample 5 (glyburide MRM 2 EPI_neve... Max. 2.3e6 cps. 100% 95% Glyburide MS/MS % 85% % 352 H 75% 70% 65% H S H 60% 55% 50% 45% 169 (A) MW of Glyburide= (B) 40% 35% 30% % 20% % % 5% m/z, amu
37 Glyburide: Phase I Metabolite Enhanced MS (EMS): Base Peak Chrom. of +EMS: Exp 1, from Sample 5 (Sample without DFT_S) of glyburide.wiff mass range amu (Turbo S... Max. 3.0e7 cps % R l I t (%) R l I t (%) 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% % Time, min
38 Glyburide: Phase I Metabolite Precursor Ion of 169: XIC of +Prec (168.90): Exp 1, amu from Sample 1 (glyburide sample Precursor) of glyburide... Max. 3.5e6 cps. x e6 3.2e6 3.0e Q TRAP: 10 metabolites identified 2.8e6 2.6e6 2.4e6 2.2e6 2.0e6 1.8e6 1.6e6 XIC of 526 XIC of 412 XIC of 510 oxidations (5) e6 1.2e6 1.0e6 XIC of (1) 8.0e5 6.0e5 ring loss (1) e5 2.0e5 di-oxidations (3) Time, min
39 Glyburide: Phase I Metabolite eutral Loss of 125: Base Peak Chrom. of +L (125.00): Exp 1, from Sample 1 (glyburide sample eutral Loss) of glybu... Max. 5.1e6 cps. 2.6e5 2.4e Q TRAP: 5 metabolites identified 2.2e5 2.0e5 H 1.8e5 1.6e5 1.4e5 1.2e5 H S H 125 (B) 1.0e e4 6.0e4 4.0e4 2.0e Time, min
40 Base Peak Chrom. of +L (125.00): Exp 1, from Sample 1 (glyburide sample eutral Loss) of glyburide sample eutral Loss.wiff mass ra... M ax. 3.0e6 cps. 2.0% 1.8% 1.6% 1.4% 1.2% 1.0% 0.8% 0.6% 0.4% 0.2% Interesting Loss, plus xidation Found by eutral Loss Scan 0.0% Time, min +ER (476.11,401.70): Exp 2, min from Sample 1... Max. 3.5e4 cps. +ER (494.03,496.12): Exp 2, min from Sample 1... Max. 5.6e4 cps. 100 % 90% 80% 70% 60% 50% 40% 30% 20% 10% Loss of R e l. In t. (% ) 110 % 100 % 90% 80% 70% 60% 50% 40% 30% 20% 10% Signal with EP I ( ) C ha rge (+1 ) C E (3 0): Exp 3, 36 m/z,.2 12 amu m in from Sa m ple 1 (glybu ride sa m ple eutra l Loss) of glyb urid e sam p le eu tral Lo ss... m/z, amu M ax. 1.8e7 cps. 10 0% % 80 % 70 % 60 % Glyburide MS 2 50 % 40 % 30 % % % m /z, a m u + EP I ( ) C ha rge (+1 ) C E (3 0): Exp 3, m in from Sa m ple 1 (glybu ride sa m ple eutra l Loss) of glyb urid e sam p le eu tral Lo ss... M ax. 1.7e7 cps. 10 0% % 80 % 70 % 60 % Metabolite MS 2 50 % 40 % 30 % % 10 % m /z, a m u
41 Glyburide: Phase I Metabolite Targeted MRM (52 transitions monitored): XIC of +MRM (52 pairs): Exp 1, 494.0/ /169.0 amu from Sample 4 (glyburide MRM after 2 repeats_ex... repeats_e e e e5 3.8e5 3.6e5 3.6e e5 3.4e5 3.2e5 3.2e e5 2.8e e e5 2.2e e5 1.8e e5 1.4e e e5 8.0e e4 4.0e e Q TRAP: 11 metabolites identified x di-oxidations 526 (4) oxidations (5) Expand View x100 Drug (494) Max e6 cps Time, min dehydrogenation 492 (1)
42 Glyburide: Phase I Metabolite X I C o f + M R M ( 5 2 p a ir s ) : E x p 1, / a m u f r o m S a m p le 4 ( g ly b u r id e M R M a f t e r 2 r e p e a t s _ e... M a x c p s Targeted MRM di-oxidations 526 (4) dehydrogenation 492 (1) T im e, m in + E P I ( ) C E ( 3 7 ) : t o m in f r o m S a m p le 1 ( E P I ) o f g ly b u r id e s a m p le E P... M a x e 5 c p s % 9 5 % 9 0 % 8 5 % 8 0 % 7 5 % 7 0 % 6 5 % 6 0 % 5 5 % 5 0 % 4 5 % 4 0 % 3 5 % 3 0 % 2 5 % 2 0 % 1 5 % 1 0 % 5 % EPI of m/z m / z, a m u
43 Glyburide: Phase I Metabolite Enhanced Product Ion (EPI): trace level di-oxidation metabolites XIC of +EPI (526.00) CE (37): to amu from... Max. 6.1e6 cps. +EPI (526.00) CE (37): to min from Sam... Max. 5.2e5 cps. Intensity, cps Intensity, cps e6 4.0e e Time, min +EPI (526.00) CE (37): to min from Sam... Max. 2.1e5 cps e5 1.5e5 1.0e e m/z, amu +EPI (526.00) CE (37): to min from Sam... Max. 2.5e5 cps. Intensity, cps Intensity, cps e e5 3.0e5 2.0e e m/z, amu +EPI (526.00) CE (37): to min from Sam... Max. 1.3e5 cps e5 1.00e5 8.00e e4 4.00e4 2.00e m/z, amu +EPI (526.00) CE (37): to min from Sam... Max. 1.8e5 cps. 2.5e e e5 1.5e5 Intensity, cps 1.5e5 1.0e5 5.0e Intensity, cps 1.0e5 5.0e m/z, amu m/z, amu
44 Glyburide: Phase I Metabolite Metabolite EMS Precursor Ion eutral Loss MRM Drug (494) xidation (510) Di-oxidation (526) Dehydrogenation (492) Loss of + oxidation (476) A -Ring Loss + 2 oxidation (427) A -dealkylation (412) A 4000 QTRAP Total (14) QTRAP Total (9)
45 Ketoconazole Analysis Goal: conclusively identify metabolites of ketoconazole Method: use accurate mass and MS/MS Ketoconazole m/z A broad spectrum anti-fungal agent P450 inhibitor (3A4) Metabolism in human in vitro systems at least 14 metabolites were tentatively identified -deacetylation xidations piperazine and imidazole ring -dealkylation Conjugation
46 Proposed Ketoconazole Metabolites Proposed K etoconazole M etabolites produced by Cryopreserved H um an Hepatocyte and H um an S9 system s H 2 H 561 H 329 H H H KC H H ? GX H 547 H H 505 H 503 H 2 H 463 H H 563 H G X : A glucuronolactone like com pound H 565
47 Experimental Conditions Biological Experiments Ketoconazole (KC) incubated with cryo-preserved human hepatocytes or human hepatic S-9 Final concentration of 1ml incubation mixture had 10 µm of KC HLB-solid phase was used to clean up samples HPLC conditions Column: 1x50 mm, C18 Betasil Solvent A: Water with 0.5% formic acid (v/v) Solvent B: Methanol with 0.5% formic acid (v/v) Flow Rate: 50 µl/min 2 minute hold with 20% B, linearly programmed to 100% B in 20 minutes and held 10 minutes Mass Spectrometry, QStar Positive IonSpray Mode Lock Mass for [MH] + Ions : Reserpine Lock Mass for Product Ions : Metabolite [MH] + Resolution: 10, 000 (full width at half height) at m/z 800 Injection Amount Injected approximately 40 to 50 ng of parent and 0.5 to 5 ng of a metabolite Calculations are based on 1 ml of 10 µm KC incubation Final metabolite extract samples were reconstituted in 400 µl with 5 to 10 µl injected
48 TIC of KC incubated with Cryopreserved Human Hepatocyte TIC of +Q1: from KC0826FS e8 cps 1.35e e8 1.25e8 1.20e8 1.15e8 Ketoconazole (KC) 1.10e8 1.05e8 1.00e8 9.50e7 9.00e7 8.50e7 8.00e7 Intensity, cps 7.50e7 7.00e7 6.50e7 Metabolite e7 5.50e7 5.00e7 4.50e e7 3.50e7 3.00e Metabolite 329 Metabolite e7 2.00e7 1.50e7 1.00e7 5.00e Time, min
49 Product Ions of Metabolite 489 +TF PRDUCT: 8.89 min (19 scans) from ew S-9 DS=489.2, run 5, 40 ev, baseline subtracted 5.89e0 +TF PRDUCT: 8.88 min (20 scans) from ew S-9 DS=489.2, run 5, 40 ev, smoothed 5.15e m/z m/z and m/z, amu m/z, amu
50 ID Metabolites and Compounds by Accurate Mass Product Ion Spectrum H MH Accurate bserved (2.2 ppm) + H H H +. Less then 5 ppm mass accuracy narrows the list of to just a few possibilities molecular formulas m/z Accurate bserved (0 ppm) m/z Accurate bserved (6.7 ppm) IF 178 is H Accurate bserved ( 142 ppm) It is unlikely to have this structure due to large difference
51 Summary of Toxicology API LCMS Techniques TQ API LCMS techniques allows for polar to non-polar multi-component analysis TQ/LIT instruments allow for quantitation and verification in a simultaneous run Single MS, Precursor, eutral Loss and MRM IDA runs provide a very effective method for drug metabolite ID in vitro and vivo Accurate mass measurements for single and production analysis allow for strong molecular formula ID
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