A Standardized Procedure for the Simultaneous Determination of the Matrix Effect, Recovery, Process Efficiency and Internal Standard Association
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1 Supporting Information A Standardized Procedure for the Simultaneous Determination of the Matrix Effect, Recovery, Process Efficiency and Internal Standard Association Jean-François Bienvenu*, Gilles Provencher, Patrick Bélanger, René Bérubé, Pierre Dumas, Sébastien Gagné, Éric Gaudreau and Normand Fleury. Centre de toxicologie du Québec (CTQ), Institut national de santé publique du Québec (INSPQ), 945 Wolfe, Québec, QC, Canada G1V 5B3. * . jean-francois.bienvenu@inspq.qc.ca, Fax: (418) Table of Contents Terminology Comparison Table (table S1)... S-3 Experimental Section Complement... S-5 Details of the Mathematical Equations Used in this Paper... S-6 For STDs without Basic Amount... S-6 For STDs with Basic Amount... S-7 For ISTDs... S-8 Graphical Representation of the Links between Descriptors... S-9 STD and Associated ISTD table (table S2)... S-10 S-1
2 Complete Results for All the STDs with Associated ISTD... S-11 Table S3. 2-OH MiBP Results... S-12 Table S4. MBzP Results... S-13 Table S5. MCHP Results... S-14 Table S6. MCHpP Results... S-15 Table S7. MCiNP Results... S-16 Table S8. MCiOP Results... S-17 Table S9. MCMHP Results... S-18 Table S10. MCPP Results... S-19 Table S11. MECPP Results... S-20 Table S12. MEHHP Results... S-21 Table S13. MEHP Results... S-22 Table S14. MEOHP Results... S-23 Table S15. MEP Results... S-24 Table S16. MHBP Results... S-25 Table S17. MHiDP Results... S-26 Table S18. MHiNP Results... S-27 Table S19. MiBP Results... S-28 Table S20. MiDP Results... S-29 Table S21. MiNP Results... S-30 Table S22. MMP Results... S-31 Table S23. MnBP Results... S-32 Table S24. MnOP Results... S-33 Table S25. MOiDP Results... S-34 Table S26. MOiNP Results... S-35 Calculated Global ME for Orphan STDs (table S27)... S-36 Calculated STD Instrumental ME conc and ISTD Norm. STD RF for Orphan STDs (table S28)... S-37 QC Results Obtained for MiBP with MiBP-d 4 and MBzP- 13 C 4 (table S29)... S-38 S-2
3 Terminology Comparison Table (table S1) Table S1. Terminology Use in the Present Paper, Other Names Provided in the Analytical Scientific Literature and Units Used for the Calculation. Terminology Used Instrumental Matrix Effect (ME) ISTD normalized STD instrumental Matrix Effect Instrumental Matrix Effect on Concentration STD or ISTD Recovery (RE) ISTD normalized STD Recovery ISTD normalized STD Recovery Factor (RF) STD or ISTD Process Efficiency (PE) ISTD normalized STD Process Efficiency Global Matrix Effect Other Name(s) or description Absolute Matrix Effect 1 Absolute Instrumental Recovery 2 Matrix Effect 3 Matrix Enhancement 3 Ion Suppression 4 Ionization Efficiency 2 Ionization Suppression or Enhancement 5 IS normalized Matrix Effect 6 Provides information on the impact of the instrumental ME on the quantification of the analyte. Absolute Extraction Recovery 2 Extraction Efficiency 2 Extraction Recovery 2 Provides information on the STD recovery with the use of the ISTD to compensate for instrumental variations. Provides information on how closely the recovery of the STD and the ISTD are related. Overall Absolute Recovery 2 Overall Process Efficiency 1 Recovery 1,7-8 Provides information on how closely the process efficiency of the STD and the ISTD are related. Accuracy 3,8-9 General Matrix Effect 10 Matrix Effect on Recovery 11 Matrix Variation 10 Recovery 12 Total Matrix Effect 13 Overall Matrix Effect 13 Calculation Performed with Areas Response Ratios Concentrations Areas Response Ratios or Concentration Response Ratios or Concentration Areas Response Ratio Concentrations S-3
4 References: (1) Matuszewski, B. K.; Constanzer, M. L.; Chavez-Eng, C. M. Anal Chem 2003, 75, (2) Chin, C.; Zhang, Z. P.; Karnes, H. T. J PharmBiomed Anal 2004, 35, (3) Matuszewski, B. K. J ChromatogrB Anal. Biomed Life Sci 2006, 830, (4) Buhrman, D. L.; Price, P. I.; Rudewiczcor, P. J. J Am Soc Mass Spectrom 1996, 7, (5) Scientific Working Group for Forensic Toxicology. J. Anal. Toxicol. 2013, 37 (7), (6) Viswanathan, C. T.; Bansal, S.; Booth, B.; DeStefano, A. J.; Rose, M. J.; Sailstad, J.; Shah, V. P.; Skelly, J. P.; Swann, P. G.; Weiner, R. Pharm.Res 2007, 24, (7) Guidance for Industry: Bioanalytical Method Validation; U.S. Department of Health and Human Services Food and Drug Administration Center for Drug Evaluation and Research (CDER) Center for Veterinary Medicine (CVM), (8) Matuszewski, B. K.; Constanzer, M. L.; Chavez-Eng, C. M. Anal Chem 1998, 70, (9) Committee for Medicinal Products for Human Use (CHMP). Guideline on bioanalytical method validation; European Medicines Agency: Canary Wharf, London E14 5EU, United Kingdom, (10) Thompson, M.; Ellison, S. L. R.; Wood, R. Pure Appl. Chem. 2002, 74, (11) Provencher, G.; Bérubé, R.; Dumas, P.; Bienvenu, J.-F.; Gaudreau, E.; Bélanger, P.; Ayotte, P. J. Chromatogr. A 2014, 1348, (12) Huang, Y.; Shi, R.; Gee, W.; Bonderud, R. Bioanalysis. 2012, 4, (13) Huang, Y.; Louie, A.; Yang, Q.; Massenkoff, N.; Xu, C.; Hunt, P. W.; Gee, W. Bioanalysis. 2013, 5, S-4
5 Experimental Section Complement Other Materials. Ammonium acetate and dimethylsulfoxide were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ethyl acetate, acetic acid, o-phosphoric acid and hexane were purchased from Fisher Scientific (Fairlawn, NJ). Acetonitrile and methanol were purchased from EMD (Omaha, NB) and β-glucuronidase (from E.coli K12) was purchased from Roche Diagnostics (Laval, Québec, Canada). Calibration curve preparation. Due to the ubiquitous presence of some phthalate metabolites in urine, the matrix used for the calibration curve was acidified to ph 3 with o-phosphoric acid, extracted twice with hexane. The washed urine was spiked with phthalate metabolite solutions in acetonitrile to obtain the calibration curve. The urine samples were not treated with β-glucuronidase. Recovery (Reconstitution) solutions preparation. For convenience and homogeneity, a recovery solution containing the STD and the ISTD was prepared by adding 50 μl of the phthalate metabolites STD solution (500 μg/ml) and 150 μl of the phthalate metabolites ISTD to the usual recovery solution (water:acetonitrile 3:1) in a 10 ml volumetric flask. The recovery solution containing only the ISTD mixture was prepared in a volumetric flask (10 ml) by adding 150 μl of the phthalates metabolites ISTD solution and completing with the usual recovery solution. Biological samples. For the tests, 6 urine samples obtained on a voluntary basis from healthy donors and having a specific gravity varying from to were used.. The recovery solution containing the STD and ISTD phthalate metabolites was transferred into 6 LC vials.. The urine samples were deconjugated and extracted as previously described, except that no ISTD solution was added, and the recovery solution was the same solution as. Set C. To the urine samples, 10 μl of the phthalate metabolites STD solution (500 μg/ml) was added, and the samples were deconjugated and extracted as described above. The recovery solution was the solution containing only the ISTD. Set D. The procedure was the same as for Set C, except that the phthalates metabolites ISTD solution was added to the urine samples, and the recovery solution contained neither the STD nor the ISTD. Set E. The general sample procedure was used, and the recovery solution contained neither the STD nor the ISTD. Set F. The procedure was the same as for Set E, except that the recovery solution was enriched with only the phthalate metabolites ISTD. S-5
6 Details of the Mathematical Equations Used in this Paper For STDs without Basic Amount When calculated with the area of the STD only, the following equations may then be used. Note that in this series of equation, set C and Set D should be similar. STD Instrumental ME (%) = STD Recovery (RE)(%) = Set C STD Recovery Factor (RF)(%) = x 100 (eq. 1) x 100 (eq. 2) Set D x 100 (eq. 3) STD Process Efficiency(PE) = STD Instrumental ME x STD RF (eq. 4) STD Process Efficiency (PE)(%) = x Set D Set D x 100 = x 100 (eq. 5) When calculated with the area of the STD divided by the area of the associated ISTD, the following equations may then be used. ISTD normalized STD Instrumental ME (%) = ISTD normalized STD Recovery (%) = STD normalized ISTD Recovery (%) = Set C Set D Set C x 100 (eq. 6) x 100 (eq. 7) x 100 (eq. 8) ISTD norm. STD RF = ISTD norm. STD RE x STD norm. ISTD RE (eq. 9) ISTD norm. STD RF (%) = Set C x Set D Set C Set D x 100 = x 100 (eq. 10) ISTD norm. STD PE = ISTD norm. STD Instrumental ME x ISTD norm. STD RF (eq. 11) ISTD normalized PE (%) = x Set D Set D x 100 = x 100 (eq. 12) When the concentrations are used for the calculations, the following equations may then be used. Curve Factor = Added conc. Instrumental ME concentration (%) = Added conc. (eq. 13) x 100 (eq. 14) Instrumental ME conc = ISTD norm. STD Instrumental ME x Curve Factor (eq. 15) Instrumental ME conc (%) = x Added conc. x 100 = Added conc x 100 (eq. 16) Global ME = Instrumental ME conc x ISTD norm. STD RF (eq. 17) Global ME (%) = Added conc Set D Set x x 100 = D Added conc x 100 (eq. 18) Global ME = ISTD norm. STD PE x Curve Factor (eq. 19) Global ME (%) = Set D x Added conc x 100 = Set D Added conc x 100 (eq. 20) S-6
7 For STDs with Basic Amount When calculated with the area of the STD only, the following equations may then be used. Note that in this series of equation, set C and set D should be similar and equally set E and set F. STD Instrumental ME (%) = ( Set F) x 100 (eq. 21) STD RE (%) = (Set C Set F) ( Set F) x 100 (eq. 22) STD RF (%) = (Set D Set E) ( Set F) x 100 (eq. 23) STD PE = STD Instrumental ME x STD RF (eq. 24) STD PE (%) = ( Set F) (Set D Set E) x ( Set F) (Set D Set E) x 100 = x 100 (eq. 25) When calculated with the area of the STD divided by the area of the associated ISTD, the following equations may then be used. ISTD normalized STD Instrumental ME (%) = ISTD normalized STD RE (%) = STD normalized ISTD RE (%) = (Set C Set F) ( Set F) (Set D Set E) (Set C Set F) ( Set F) x 100 (eq. 26) x 100 (eq. 27) x 100 (eq. 28) ISTD norm. STD RF = ISTD norm. RE x STD norm. ISTD RE (eq. 29) ISTD norm. STD RF (%) = (Set C Set F) ( Set F) x (Set D Set E) (Set C Set F) (Set D Set E) x 100 = x 100 (eq. 30) ( Set F) ISTD normalized PE = ISTD norm. STD Instrumental ME x ISTD norm. STD RF (eq. 31) ISTD normalized PE (%) = ( Set F) (Set D Set E) x ( Set F) (Set D Set E) x 100 = x 100 (eq. 32) When the concentrations are used for the calculations, the following equations may then be used. Instrumental ME conc = ISTD norm. STD Instrumental ME x Curve Factor (eq. 33) Instrumental ME conc (%) = ( Set F) x Added conc. x 100 = ( Set F) Added conc x 100 (eq. 34) Global ME = Instrumental ME conc x ISTD norm. RF (eq. 35) Global ME (%) = ( Set F) Added conc (Set D Set E) x ( Set F) (Set D Set E) x 100 = x 100 (eq. 36) Added conc Global ME = ISTD norm. STD PE x Curve Factor (eq. 37) Global ME (%) = (Set D Set E) x Added conc (Set D Set E) x 100 = x 100 (eq. 38) Added conc S-7
8 For ISTDs When calculated with the area of the ISTD only, the following equations may then be used. Note that in this series of equation, set D and Set E should be similar, and also sets B, C and F. ISTD Instrumental ME (%) = ISTD Recovery (%) = ISTD Factor (%) = Set C Set D Set C x 100 (eq. 39) x 100 (eq. 40) x 100 (eq. 41) ISTD Recovery Factor (RF) = ISTD Recovery x ISTD Factor (eq. 42) ISTD RF (%) = ISTD RF (%) = Set D Set C Set D x Set C Set D x 100 = x 100 (eq. 43) x 100 (eq. 44) ISTD Process Efficiency = ISTD Instrumental ME x ISTD RF (eq. 45) ISTD Process Efficiency (%) = x Set D Set D x 100 = x 100 (eq. 46) S-8
9 Graphical Representation of the Links between Descriptors Figure S1. Graphical representation of the links between the different descriptors and equations for the test. Note: For clarity reasons, the equations presented in this figure are numbered according to the manuscript and not to the supporting information. S-9
10 STD and Associated ISTD table (table S2) Table S2. List of the STD Used in the Method, and Their Associated ISTD STD Associated ISTD 2-OH-MiBP 2-OH-MiBP-d 4 MBzP MBzP- 13 C 4 MCHP MCHP- 13 C 4 MCHpP MeHHP- 13 C 4 MCiNP MeHHP- 13 C 4 MCiOP MeHHP- 13 C 4 MCMHP MCMHP-d 4 MCPP MCPP- 13 C 4 MECPP MECPP- 13 C 4 MEHHP MEHHP- 13 C 4 MEHP MEHP- 13 C 4 MEOHP MEOHP- 13 C 4 MEP MEP- 13 C 4 MHBP MHBP-d 4 MHiDP MEHHP- 13 C 4 MHiNP MEHHP- 13 C 4 MiBP MiBP-d 4 MiDP MiDP-d 4 MiNP MiNP- 13 C 4 MMP MMP- 13 C 4 MnBP MnBP- 13 C 4 MnOP MnOP- 13 C 4 MOiDP MeHHP- 13 C 4 MOiNP MeHHP- 13 C 4 S-10
11 Complete Results for All the STDs with Associated ISTD The following pages contain details of the results obtained for the phthalate metabolites STD and ISTD S-11
12 Table S3. 2-OH MiBP Results S-12
13 Table S4. MBzP Results S-13
14 Table S5. MCHP Results S-14
15 Table S6. MCHpP Results S-15
16 Table S7. MCiNP Results S-16
17 Table S8. MCiOP Results S-17
18 Table S9. MCMHP Results S-18
19 Table S10. MCPP Results S-19
20 Table S11. MECPP Results S-20
21 Table S12. MEHHP Results S-21
22 Table S13. MEHP Results S-22
23 Table S14. MEOHP Results S-23
24 Table S15. MEP Results S-24
25 Table S16. MHBP Results S-25
26 Table S17. MHiDP Results S-26
27 Table S18. MHiNP Results S-27
28 Table S19. MiBP Results S-28
29 Table S20. MiDP Results S-29
30 Table S21. MiNP Results S-30
31 Table S22. MMP Results S-31
32 Table S23. MnBP Results S-32
33 Table S24. MnOP Results S-33
34 Table S25. MOiDP Results S-34
35 Table S26. MOiNP Results S-35
36 Calculated Global ME for Orphan STDs (table S27) Table S27. Results Calculated for the Global ME and the Associated SD with the Excel Tool for the Orphan STD and All the ISTDs of the Method. ISTD MCHpP MCiNP MCiOP MHiDP MHiNP MOiDP MOiNP Global ME SD Global ME SD Global ME SD Global ME SD Global ME SD Global ME SD Global ME SD 2-OH MIBP-d % 5.8% 100.6% 7.4% 101.8% 6.4% 102.6% 8.5% 102.8% 7.1% 102.6% 5.7% 103.1% 7.1% MBzP- 13 C % 11.0% 114.3% 7.3% 115.7% 7.3% 116.9% 11.8% 116.4% 5.4% 116.6% 7.6% 116.8% 7.1% MCHP- 13 C % 3.8% 103.0% 3.6% 104.4% 3.6% 105.1% 4.9% 105.3% 4.1% 105.2% 3.1% 105.5% 3.6% MCMHP-d % 4.1% 98.4% 3.6% 99.1% 2.9% 100.1% 3.3% 100.5% 5.0% 100.2% 2.8% 100.6% 4.5% MCPP- 13 C % 5.0% 90.2% 8.3% 91.1% 8.4% 91.8% 5.0% 92.1% 9.3% 92.0% 8.0% 92.2% 8.3% MECPP- 13 C % 3.9% 95.8% 4.8% 96.7% 4.3% 97.5% 2.9% 97.7% 6.4% 97.6% 4.0% 97.9% 5.7% MEHHP- 13 C % 3.1% 95.8% 2.9% 97.1% 2.8% 97.7% 4.3% 97.9% 3.1% 97.8% 2.2% 98.1% 2.8% MEHP- 13 C % 9.8% 113.0% 5.1% 114.9% 6.6% 115.6% 9.6% 115.5% 7.4% 115.6% 6.3% 115.7% 6.2% MeOHP- 13 C % 9.4% 112.0% 7.0% 113.4% 6.7% 114.3% 9.1% 114.3% 6.4% 114.3% 7.1% 114.7% 7.6% MEP- 13 C % 9.5% 106.0% 6.1% 107.9% 5.4% 108.5% 9.7% 108.1% 4.0% 108.4% 6.0% 108.5% 6.0% MHBP-d % 2.7% 102.5% 6.7% 103.6% 6.0% 104.3% 5.7% 104.5% 5.8% 104.5% 5.6% 104.6% 5.4% MiBP-d % 13.9% 120.7% 11.3% 122.0% 10.5% 123.2% 15.1% 122.9% 8.5% 122.9% 11.1% 123.3% 10.6% MiDP-d % 16.1% 132.9% 11.6% 135.1% 13.1% 136.1% 15.6% 135.7% 14.4% 135.9% 12.9% 135.9% 12.8% MiNP- 13 C % 10.4% 116.6% 6.2% 118.4% 7.7% 119.3% 11.1% 118.9% 8.4% 119.1% 7.1% 119.1% 6.7% MMP- 13 C % 8.7% 116.6% 7.7% 118.0% 6.7% 119.0% 10.3% 118.4% 4.1% 118.9% 7.2% 118.9% 6.3% MnBP- 13 C % 6.3% 107.0% 1.7% 108.3% 3.5% 109.2% 6.7% 109.2% 3.8% 109.2% 3.3% 109.4% 2.5% MnOP- 13 C % 8.7% 113.1% 4.3% 115.1% 5.8% 115.6% 8.2% 115.5% 7.6% 115.7% 5.4% 115.7% 5.8% S-36
37 Calculated STD Instrumental MEconc and ISTD Norm. STD RF for Orphan STDs (table S28) Table S28. Results Calculated for the STD Instrumental MEconc and the ISTD Normalize STD RF and Their Associated SD, with the Excel Tool for the Orphan STD and the Selected ISTD. ISTD MCHpP MCiNP MCiOP MHiDP STD instr SD STD instr SD STD instr SD STD instr SD Me conc Me conc Me conc Me conc MHiNP MOiDP MOiNP STD instr SD STD instr SD STD instr SD MCMHP-d % 4.3% 104.5% 4.0% 108.2% 2.1% 110.9% 3.8% 109.1% 5.2% 109.0% 3.5% 110.6% 4.8% MECPP- 13 C % 4.3% 101.2% 3.4% 104.8% 2.1% 107.4% 3.3% 105.7% 5.3% 105.5% 3.4% 107.1% 3.9% MEHHP- 13 C % 2.7% 97.3% 1.1% 101.5% 1.5% 103.5% 3.9% 101.4% 4.3% 101.7% 1.1% 103.0% 3.2% Me conc Me conc Me conc ISTD ISTD Norm STD RF MCHpP MCiNP MCiOP MHiDP MHiNP SD ISTD Norm STD RF SD ISTD Norm STD RF SD ISTD Norm STD RF SD ISTD Norm STD RF SD MOiDP ISTD Norm STD RF SD MOiNP ISTD Norm STD RF MCMHP-d % 4.7% 94.2% 2.5% 91.7% 3.2% 90.3% 1.1% 92.2% 4.3% 92.1% 3.0% 91.2% 5.6% MECPP- 13 C % 4.5% 94.7% 3.5% 92.3% 4.1% 90.8% 2.3% 92.5% 4.7% 92.6% 3.4% 91.6% 6.2% MEHHP- 13 C % 3.0% 98.4% 2.5% 95.7% 2.6% 94.3% 1.7% 96.7% 2.5% 96.1% 1.8% 95.3% 4.7% SD S-37
38 QC Results Obtained for MiBP with MiBP-d4 and MBzP- 13 C4 (table S29) Table S29. Concentrations expected and obtained for MiBP with MiBP-d4 and MBzP- 13 C4 as ISTD with the different QC and reference materials. Concentration Concentration Sample Expected ISTD MiBP-d 4 ISTD MBzP- 13 C 4 Sample Expected ISTD MiBP-d 4 ISTD MBzP- 13 C 4 µg/l µg/l µg/l µg/l µg/l µg/l Low QC A Low QC A Low QC A Low QC A Average Average SD SD RSD 5.0% 7.7% RSD 5.5% 5.5% Medium QC B Medium QC B Medium QC B Medium QC B Average Average SD SD 7 5 RSD 4.8% 6.2% RSD 2.9% 2.0% High QC A High QC A High QC A High QC A High QC Average High QC SD Average RSD 5.7% 3.4% SD 9 5 RSD 5.9% 3.1% 54-9B B B B Average SD 6 2 RSD 5.7% 2.0% S-38
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