Spark-Holland Automated online DPS Extraction and Analysis with a Q-Exactive Orbitrap. Lecture 9, Page 41
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1 Spark-Holland Automated online DPS Extraction and Analysis with a Q-Exactive Orbitrap Lecture 9, Page 41
2 Developing DPS Methods Normal regulated bioanalysis protocol: Centrifuge collected blood to get plasma Fortify control plasma (not blood) with standards and QC s to create the calibration curve Fortify test plasma samples with IS at a fixed level Extract plasma standards and QC s along with test samples and analyze by LC/MS Lecture 9, Page 42
3 Towards Higher Throughput DPS On-line SPE-LC-HRAMS DPS Extraction (Exactive Plus) Spark-Holland DPS autosampler DPS Card Exactive Plus 2 mm Lecture 9, Page 43
4 The Q Exactive: Hardware Innovations HCD Cell C-Trap Quadrupole Mass Filter Orbitrap Mass Analyzer S-lens Ion Source Enhanced FT Lecture 9, Page 44
5 Intensity (%) Intensity (%) High Resolution and Accurate Mass Example Peptide mixture: [Val 5 ]-Angiotensin II Lys-des-Arg 9 -Bradykinin Sequence: DRVYVHPF KRPPGFSPF Formula: C49H69N13O12 C50H73N13O11 Exact mass: [M+2H]2+ = [M+2H]2+ = Dm (mmu): 18.2 mmu Wrong Answer for Both Peptides Right Answer for Both Peptides RP = 15,000 RP = 56, (observed) (correct) (correct) Mass [amu] Mass [amu] Lecture 9, Page 45
6 Representative XICs (5 ppm) with Orbitrap HRAMS Lecture 9, Page 46
7 RBC Filtration Workflow 1 Standard Curve Prepared Using Filtration Device Whole blood standards, QCs, and blanks were subjected to RBC filtration device to produce DPS Offline RBC Filtration card Lecture 9, Page 47
8 Accuracy and Precision RBC Filtration Workflow 1 Guanfacine Concentration (ng/ml) LLOQ QC LQC MQC HQC Mean CV (%) RE (%) n Acceptable accuracy and precision Drawbacks Time-consuming to prepare all standards and QCs using filtration device What is the best way to approach this? Stay tuned Lecture 9, Page 48
9 Summary RBC filtration device for generating dried plasma spots Q-Exactive provides excellent selectivity in a small molecule quantitation assay providing a linear dynamic range over three orders of magnitude. A novel membrane-based device capable of filtering RBCs out of whole blood without the need for centrifugation has been presented for offline quantitative bioanalysis. Acceptable accuracy and precision for whole blood QCs subjected to our filtration device can be achieved using a fortified plasma standard curve. The DPS card is compatible with commercially available onlineextraction dried blood spot robotic autosamplers. Lecture 9, Page 49
10 Lecture 9, Page 50
11 Lecture 9, Page 51
12 Lecture 9, Page 52
13 Lecture 9, Page 53
14 The Advion TriVersa NanoMate A Robotic Workstation For Automated nano ESI Lecture 9, Page 54
15 Automated Direct Infusion nano ESI of Protein Samples TriVersa + MS Infusion can be for short or long times; the latter allowing for simultaneously screening for hundreds of compounds! MS sample orifice Lecture 9, Page 55
16 Lecture 9, Page 56
17 Lecture 9, Page 57
18 Lecture 9, Page 58
19 Another Form of Selectivity coupled with Mass Spectrometry Ion mobility Spectrometry Lecture 9, Page 59
20 Differential Mobility Spectrometry (DMS) Selexion from AB Sciex (DMS is not mass spectrometry) An orthogonal separation mechanism based upon charge-to-mass and molecular shape Lecture 9, Page 60
21 Mass Spec Vacuum draws ions and gas through planar DMS electrodes Millisecond flight times 2.8 L/min 1 mm 760 torr 2.3 torr 3 cm Lecture 9, Page 61
22 Chemical Enhanced Separations Driven by Mobility Changes Due to Clustering / Declustering. HV=3kV F ~ 1 MHz, T= 10-6 s + High field declustering; mobility increases L V=0.3 kv Low field clusteringmobility decreases Lecture 9, Page 62 Schneider BB, Covey TR, Coy SL, Krylov EV, and Nazarov EG, Chemical Effects in the Separation Process of a Differential Mobility/Mass Spectrometer System, Anal. Chem., 2010, 82,
23 DMS Hardware on AB Sciex 5500 QTRAP Lecture 9, Page 63
24 Testosterone Female #3 Plasma Sample: LLE DMS OFF/ 289/109 Peak of interest Interference DMS OFF/ 289/97 Peak of interest Interference Ion ratio is DMS ON/ 289/109 DMS ON/ 289/97 Lecture 9, Page 64
25 Testosterone Female #3 Plasma Sample: PPT DMS OFF/ 289/109 Peak of interest DMS OFF/ 289/97 Peak of RT 3.37 min DMS ON/ 289/109 DMS ON/ 289/97 Lecture 9, Page 65
26 GC/MS or LC/MS/MS Which Technique Handles the Wider Range of Chemical Compounds? Question: If we consider the entire known organic chemical space, including proteins, peptides, RNA, DNA, as well as polar small molecule chemicals, what % of these are amenable to GC/MS? Answer: Let s take a look. Lecture 9, Page 66
27 GC/MS vs. LC/MS/MS for Range of Pesticides Detected Lutz Alder,* Kerstin Greulich, Gu nther Kempe, and Ba rbel Vieth, RESIDUE ANALYSIS OF 500 HIGH PRIORITY PESTICIDES, Mass Spectrometry Reviews, 2006, 25, Lecture 9, Page 67
28 GC/MS vs. LC/MS/MS This overview evaluates the capabilities of mass spectrometry (MS) in combination with gas chromatography (GC) and liquid chromatography (LC) for the determination of a multitude of pesticides. The selection of pesticides for this assessment is based on the status of production, the existence of regulations on maximum residue levels in food, and the frequency of residue detection. GC MS with electron impact (EI) ionization and the combination of LC with tandem mass spectrometers (LC MS/MS) using electrospray ionization (ESI) are identified as techniques most often applied in multiresidue methods for pesticides at present. Therefore, applicability and sensitivity obtained with GC EI MS and LC ESI MS/MS is individually compared for each of the selected pesticides. Only for one substance class only, the organochlorine pesticides, GC-MS achieves better performance. For all other classes of pesticides, the assessment shows a wider scope and better sensitivity if detection is based on LC MS. Ref: (Mass Spec Rev 25: , 2006) Lutz Alder,* Kerstin Greulich, Gu nther Kempe, and Ba rbel Vieth, RESIDUE ANALYSIS OF 500 HIGH PRIORITY PESTICIDES, Mass Spectrometry Reviews, 2006, 25, Lecture 9, Page 68
29 Smaller Mass Spectrometers Mini 12 Expression CMS Lecture 9, Page 69
30 Commercially Available Small Mass Spectrometers Lecture 9, Page 70
31 Mini 12 mass spectrometer Lecture 9, Page 71
32 Mini 12: Internal components Control Tablet Electronics Cassette Loading system Solvent Container Solvent Pump Bar Code Reader Vacuum System Lecture 9, Page 72
33 Paper Spray: Immediate Point-of-Care Analysis 3. Apply Solution 4. Apply HV kv 2. Load Sample 30 s 40 s 5. Acquire Data [M+H] + 1. Prick Finger 15 s 50 s 6. Report Results 0 s 60 s One drop of blood 60 second analysis of biological samples Lecture 9, Page 73
34 Paper spray/mini MS EESI (direct detection, Atenolol in blood) He Wang, Jiangjiang Liu, Guangming Huang Atenolol MW=266 Atenolol 10 ppm spiked in whole blood 0.4μl blood loaded for each sampling spot 10 μl methanol/h 2 O added for spraying m/z 267 CID 145 m/z MS paper spray of blood spiked with atenolol (4ng/spot) MS/MS spectrum to identify atenolol Lecture 9, Page 74
35 The Mini 12 From Purdue University A Miniature Mass Spectrometer for Clinical and Other Applications Introduction and Characterization Linfan Li, Tsung-Chi Chen, Yue Ren, Paul I. Hendricks, R. Graham Cooks,*,, and Zheng Ouyang*,, dx.doi.org/ /ac403766c Anal. Chem. 2014, 86, Lecture 9, Page 75
36 Mini 12 MS and MS/MS nano ESI Mass Spectra for Clenbuterol, Thiabendazole and Amitryptyline Lecture 9, Page 76
37 Cart-Based MS System Advion, Inc. Lecture 9, Page 77
38 ASAP Atmospheric Solids Analysis Probe Little or no sample preparation No chromatography Data in < 1 minute The closed end of a glass capillary is dipped into the sample of interest or scraped on a solid surface, and then placed into the CMS for analysis. Ideal for: Reaction monitoring Compound ID Food safety Natural products Lecture 9, Page 78
39 SPME Sample Preparation for Drugs in Urine SPME: Solid-Phase Micro Extraction. Insert a fused-silica fiber coated with an HPLC stationary phase into a biological sample Allow to equilibrate with the sample Remove and rinse with water Place fiber containing extracted sample into hot nitrogen gas Ionize by APCI Obtain mass sectra Lecture 9, Page 79
40 Amlodipine in Urine Amlodipine C 20 H 25 ClN 2 O 5 MW: Preparation of fortified urine sample The stock solution of amlodipine was 1.0 mg/ml in methanol by dissolving a 2.5 mg tablet in 2.5 ml Methanol. The 50ng/ul and 100ng/ul amlodipine in urine was made by spiking the stock solution in urine sample. Lecture 9, Page 80
41 ASAP-SPME-MS Analysis of 50 ng/ul Amlodipine in urine Extract time: 5 mins, SPME LC Tips SCX/C18 Total ion current XIC for m/z 406 Mass spectrum of Amlodipine in urine [M+H] + C 20 H 25 ClN 2 O 5 MW: Lecture 9, Pages 81
42 SPME-ASAP-SIM of Incurred urine, two hours after 2.5mg dose Extract time: 60 mins, SPME LC Tips C18 Total ion current XIC for m/z 409 after background subtraction Did not detect the m/z 409 in the full-scan mode. However, with the SIM mode, it clearly detected the m/z 409. SCX/C18 tips has similar result to C18 tips Copyright Jack Henion 2016 Lecture 9, Pages 82
43 Real-Time Monitoring of Suzuki Reaction with ASAP -MS Changtong Hao, Ph.D Advion Inc. Copyright Jack Henion 2016 Lecture 9, Pages 83
44 Experimental and Materials Reactants A and B were mixed at equi-molar amounts in a round-bottom reaction flask and stirred at room temperature. 2mL aliquots was transferred to the capillary tip of ASAP probe for ASAP -MS analysis. Suzuki Reaction H 2 N A Br + B OH B OH C D NaOH, PdCl2; 4 mol% EtOH/H2O 4:1 5ml Room temp E NH 2 Reactants and Catalyst Product A B C D E compound 4-bromaniline Phenyl Boronic acid Chemical Formula Sodium hydroxide Palladium chloride 4-aminobiphenyl C 6 H 6 BrN C 6 H 7 BO 2 NaOH PdCl 2 C 12 H 11 N MW moles mg Chemicals were purchased from Sigma-Aldrich with a purity greater than 99%. MS solvent was LC/MS grade. Copyright Jack Henion 2016 Lecture 9, Pages 84
45 m/z 79/81 doublet 0 min [M+H]+: H 2 N 4-bromaniline C 6 H 6 BrN MW: Br H 2 N Br H 2 N 10 min [M+H]+: 4-aminobiphenyl C 12 H 11 N MW: NH 2 The bromine doublet in the reactant at m/z 172/174 diminishes while the product ion increases at m/z 170! 15 min 30 min 60 min 180 min Lecture 9, Pages 85 Copyright Jack Henion 2016 Figure 1. Mass spectra of Suzuki reaction mixture at different time
46 Suzuki Reaction Monitoring by ASAP/MS Br H 2 N H 2 N Relative Ratio to Toal Peak Height of Reactant and Product (%) Product Reactant Reaction Time(mins) Reactant is consumed while product is produced: Know Copyright when Jack Henion the 2016 reaction is finished! Lecture 9, Pages 86
47 Thin Layer Chromatography/Mass Spectrometry TLC/MS The Advion PlateExpress TM Copyright Jack Henion 2016 Lecture 9, Pages 87
48 Thin Layer Chromatography Wouldn t it be nice to know what each of those spots really is? Copyright Jack Henion 2016 Lecture 9, Pages 88
49 TLC-CMS set-up A Compact Mass Spectrometer (CMS) connected to the Plate Express sample extraction device Copyright Jack Henion 2016 Lecture 9, Pages 89
50 TLC-CMS Workflow Schematic Plate Express sample extraction device 6 port valve 200 µl/min Methanol with 0.1% Formic Acid SSI Isocratic Pump Elution Head Sealing Face TLC Plate Controlled by MS operation software (Mass Express) Programmable sealing force for different media (eg TLC) Interchangeable heads for different bed heights Copyright Jack Henion 2016 Lecture 9, Pages 90
51 TLC/MS for the detection of chemical compounds related to cannabis Daniel Eikel and Simon Prosser Advion Inc., Ithaca, NY, USA Copyright Jack Henion 2016 Lecture 9, Pages 91
52 Cannabinoids used in this study HO CH 3 H 3 C O CH 3 C H 3 C H 3 O CH 3 H 3 C CH 3 CH 3 OH C H 3 CH3 OH OH Cannabigerol Mw= (C 21 H 32 O 2 ) Cannabichromene Mw= (C 21 H 30 O 2 ) CH 3 Cannabinol (CBN) Mw= (C 21 H 26 O 2 ) H 2 C CH 3 H HO H CH 3 C H 2 CH 3 H HO H CH 3 Cannabidiolic acid (CBD-A) Mw= (C 22 H 30 O 4 ) CH 3 HO HO O CH 3 HO Cannabidiol (CBD) Mw= (C 21 H 30 O 2 ) C H 3 H 3 C H CH 3 O H OH OH O CH 3 H 3 C O H 3 C H CH 3 H OH CH 3 -Δ9-THC acid (THC-A) Mw= (C 22 H 30 O 4 ) -Δ9-THC (THC) Mw= (C 21 H 30 O 2 ) Copyright Jack Henion 2016 Lecture 9, Pages 92
53 TLC-CMS example: (M+H) + THC (M-H) - at m/z TLC-FIA-MS (TIC) H 3 C H 3 C H O H OH OH O CH 3 H 3 H 3 C C H O H OH CH 3 6 CH 3 In-source CID-MS CH 3 Copyright Jack Henion
54 References: Mini 12 Linfan Li, Tsung-Chi Chen, Yue Ren, Paul I. Hendricks, R. Graham Cooks,*,, and Zheng Ouyang*,, Mini 12, Miniature Mass Spectrometer for Clinical and Other Applications Introduction and Characterization, Anal. Chem. 2014, 86, Copyright Jack Henion 2016 Lecture 9, Pages 94
55 Relevant Publications 1. Ramagiri, S. and F. Garofolo, Large molecule bioanalysis using Q-TOF without predigestion and its data processing challenges. Bioanalysis, (5): p Zhang, J., et al., Proteoform analysis of lipocalin-type prostaglandin D-synthase from human cerebrospinal fluid by isoelectric focusing and superficially porous liquid chromatography with Fourier transform mass spectrometry. Proteomics, : p Ruan, Q., et al., Strategy and Its Implications of Protein Bioanalysis Utilizing High-Resolution Mass Spectrometric Detection of Intact Protein. Analytical Chemistry, (23): p Li, H., et al., Native Top-Down Electrospray Ionization-Mass Spectrometry of 158 kda Protein Complex by High-Resolution Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. Analytical Chemistry, (1): p Sun, L., et al., Fast Top-Down Intact Protein Characterization with Capillary Zone Electrophoresis Electrospray Ionization Tandem Mass Spectrometry. Analytical Chemistry, (12): p Zhang, J., et al., Top-Down Mass Spectrometry on Tissue Extracts and Biofluids with Isoelectric Focusing and Superficially Porous Silica Liquid Chromatography. Analytical Chemistry, (21): p Ref: Hongcheng Liu, Georgeen Gaza-Bulseco, and Chris ChumsaeJ Am Soc Mass Spectrom 2009, 20, Lecture 9, Pages 95
56 The End Thank you Jack Henion Lecture 9, Pages 96
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