Systematic LC-MS/MS bioanalytical method development that incorporates plasma phospholipids risk avoidance, usage of incurred sample and well thought-out chromatography

Biomedical Chromatography

Volumn 24, Issue 1, 2010, Pages 2-19

  Jemal, Mohammed ^a   Ouyang, Zheng ^a   Xia, Yuan Qing ^a  

^a BRISTOL MYERS SQUIBB RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Chromatographic separation of phospholipids from analyte; Incurred sample; LC column and mobile phase optimization; LC MS MS bioanalytical method development; Metabolite interference; Phospholipids matrix effect; Phospholipids removal by extraction; UPLC versus HPLC

Indexed keywords

EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOSPHOLIPIDS;

ANALYTES; BIOANALYTICAL METHODS; CHROMATOGRAPHIC SEPARATION OF PHOSPHOLIPID FROM ANALYTE; CHROMATOGRAPHIC SEPARATIONS; COLUMN PHASIS; INCURRED SAMPLES; LC COLUMN AND MOBILE PHASE OPTIMIZATION; LC-MS-MS; LC-MS/MS BIOANALYTICAL METHOD DEVELOPMENT; MATRICES EFFECT; METABOLITE INTERFERENCE; METHOD DEVELOPMENT; MOBILE-PHASE OPTIMIZATION; PHOSPHOLIPID MATRIX; PHOSPHOLIPID MATRIX EFFECT; PHOSPHOLIPID REMOVAL BY EXTRACTION; UPLC VERSUS HPLC;

METABOLITES;

DRUG METABOLITE; GLYCEROPHOSPHOLIPID; PHOSPHOLIPID; SPHINGOMYELIN;

ACCURACY; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CONFORMATIONAL TRANSITION; DRUG DETERMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; REPRODUCIBILITY; REVERSED PHASE LIQUID CHROMATOGRAPHY; REVIEW; SENSITIVITY ANALYSIS; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 75149185863     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1373     Document Type: Review

References (84)

1. Ahnoff M, Wurzer A, Lindmark B and Jussila R. Characterisation of serum albumin and lysoPCs as major contributors to plasma sample matrix effects on electrospray ionisation efficiency. 51st ASMS Conference on Mass Spectrometry, Montreal, Canada, 2003.
2. Aurand C, Trinh A, Brandes HK, Bell DS and Ye M. Increased bioanalytical throughput using selective phospholipid depletion. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
3. Ayrton J, Clare, RA, Dear, GJ, Mallet, DN and Plumb R.S. Ultra-high flow rate capillary liquid chromatography with mass spectrometric detection for the direct analysis of pharmaceuticals in plasma at subnanogram per milliliter concentrations. Rapid Communications in Mass Spectrometry 1999; 13: 1657-1662.
4. Bennett PK and Van Horne KC. Identification of the major endogenous and persistent compounds in plasma, serum and tissue that cause matrix effects with electrospray LC/MS techniques. American Association of Pharmaceutical Scientists Annual Meeting and Exposition, Salt Lake City, UT, 2003.
5. Bergeron M, Lahaie M, Furtado M and Garofolo F. Selection of buffer additives for liquid-liquid extraction (LLE) procedure to remove matrix effect due to phospholipids in LC-MS/MS. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
6. Berna MJ, Ackermann BL and Murphy AT. High-throughput chromatographic approaches to liquid chromatographic/tandem mass spectrometric bioanalysis to support drug discovery and development. Analytica Chimica Acta 2004; 509: 1-9.
7. Biswas KM, Castle BC, Olsen BA, Risley DS, Skibic MJ and Wright PB. A simple and efficient approach to reversed-phase HPLC method screening. Journal of Pharmaceutical and Biomedical Analysis 2009; 49: 692-701.
8. Carr PW. Wang X and.Stoll DR. Effect of pressure, particle size, and time on optimizing performance in liquid chromatography. Analytical Chemistry 2009; 81: 5342-5353.
9. Delatour C and Leclercq L. Positive electrospray liquid chromatography/mass spectrometry using high-pH gradients: a way to combine selectivity and sensitivity for a large variety of drugs. Rapid Communications in Mass Spectrometry 2005; 19: 1359-1362.
10. De Villiers A, Lynen F and Sandra P. Effect of analyte properties on the kinetic performance of liquid chromatographic separations. Journal of Chromatography A 2009; 1216: 3431-3442.
11. Euerby MR and Petersson P. Chromatographic classification and comparison of commercially available reversed-phase liquid chromatographic columns using principal component analysis. Journal of Chromatography A 2003; 994: 13-36.
12. Fast DM, Kelley M, Viswanathan CT, O'Shaughnessy J, King SP, Chaudhary A, Weiner R, DeStefano AJ and Tang D. Workshop report and follow-up - AAPS workshop on current topics in GLP bioanalysis: assay reproducibility for incurred samples - implications of Crystal City recommendations. AAPS Journal 2009; 11: 238-241.
13. Fekete S, Ganzler K and Fekete J. Facts and myths about columns packed with sub-3 μm and sub-2 μm particles. Journal of Pharmaceutical and Biomedical Analysis 2010; 51: 56-64.
14. Ferreirós N, Dresen S, Alonso RM and Weinmann W. Hydrolysis and transesterification reactions of candesartan cilexetil observed during the solid phase extraction procedure. Journal of Chromatography B 2007; 855: 134-138.
15. Food and Drug Administration. Guidance for Industry: Bioanalytical Method Validation 2001; 1-25. US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research: Rockville, MD.
16. Garofolo F, Mess J-C and Cote CS. Guidelines for method development of HILIC-LC-MS/MS: choice of columns and chromatographic conditions to handle matrix effect due tphopholipids. American Association of Pharmaceutical Scientists Annual Meeting and Exposition, Atlanta, GA, 2008.
17. Grujic S, Vasiljevic T, Lausevic M and Ast T. Study on the formation of an amoxicillin adduct with methanol using electrospray ion trap tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2008; 22: 67-74.
18. Guillarme D, Grata E, Glauser G, Wolfender JL, Jean-Luc Veuthey JL and Rudaz S. Some solutions to obtain very efficient separations in isocratic and gradient modes using small particles size and ultrahigh pressure. Journal of Chromatography A 2009; 1216: 3232-3243.
19. Hendriks G, Uges DRA and Franke JP. Reconsideration of sample pH adjustment in bioanalytical liquid-liquid extraction of ionisable compounds. Journal of Chromatography B 2007; 853: 234-241.
20. Jemal M. High-throughput quantitative bioanalysis by LC/MS/MS. Biomedical Chromatography 2000; 14: 422-429.
21. Jemal M. Pitfalls in quantitative LC-MS/MS: metabolites contributing to measured drug concentrations. In Identification and Quantification of Drugs, Metabolites and Metabolizing Enzymes by LC-MS, Chowdhury SK (ed.). Elsevier: Oxford, 2005.
22. Jemal M and Ouyang Z. The need for chromatographic and mass Resolution in liquid chromatography-tandem mass spectrometric methods used for quantitation of lactones and corresponding hydroxy acids in biological samples. Rapid Communications in Mass Spectrometry 2000; 14: 1757-1765.
23. Jemal M and Xia Y-Q. The need for adequate chromatographic separation in the quantitative determination of drugs in biological samples by high-performance liquid chromatography with tandem mass spectrometry. Rapid Communications in Mass Spectrometry 1999; 13: 97-106.
24. Jemal M and Xia Y-Q. Bioanalytical method validation design for the simultaneous quantitation of analytes that may undergo interconversion during analysis. Journal of Pharmaceutical and Biomedical Analysis 2000; 22: 813-827.
25. Jemal M and Xia Y-Q. LC-MS development strategies for quantitative bioanalysis. Current Drug Metabolism 2006; 7: 491-502.
26. Jemal M, Ouyang Z and Powell M. Direct-injection LC-MS-MS method for high-throughput simultaneous quantitation of simvastatin and simvastatin acid in human plasma. Journal of Pharmaceutical and Biomedical Analysis 2000; 23: 323-340.
27. Jemal M, Ouyang Z and Powell M. A strategy for a post-method-validation use of incurred biological samples for establishing the acceptability of a liquid chromatography/tandem mass-spectrometric method for quantitation of drugs in biological samples. Rapid Communications in Mass Spectrometry 2002; 16: 1538-1547.
28. Kapron J, Jemal M, Duncan G, Kolakowski B and Purves R. Removal of metabolite interference during liquid chromatography/tandem mass spectrometry using high-field asymmetric waveform ion mobility spectrometry. Rapid Communications in Mass Spectrometry 2005; 19: 1979-1983.
29. Khan S, Teitz DS and Jemal M. Kinetic analysis by HPLC-electrospray mass spectrometry of the pH-dependent acyl migration and solvolysis as the decomposition pathways of ifetroban 1-O-acyl glucuronide. Analytical Chemistry 1998; 70: 1622-1628.
30. Krisko RM, McLaughlin K, Koenigbauer MJ and Lunte CE. Application of a column selection system and DryLab software for high-performance liquid chromatography method development. Journal of Chromatography A 2006; 1122: 186-193.
31. Lehninger AL. Principles of Biochemistry. Worth Publishers, New York, 1982; 707.
32. Little JL, Wempe MF and Buchanan CM. Liquid chromatography-mass spectrometry/mass spectrometry method development for drug metabolism studies: examining lipid matrix ionization effects in plasma. Journal of Chromatography B 2006; 833: 219-230.
33. Liu DQ and Pereira T. Interference of a carbamoyl glucuronide metabolite in quantitative liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2002; 16: 142-146.
34. Liu G, Snapp HM, Ji Q and Arnold ME. Method Development of a UPLC Assay for the Bioanalysis of Ketoconazole in Human Plasma. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
35. Marín A and Barbas C. Systematic comparison of different functionality columns for a classical pharmaceutical problem. Journal of Pharmaceutical and Biomedical Analysis 2006, 40: 262-270.
36. Matuszewski BK, Chavez-Eng CM. and Constanzer ML. Development of high-performance liquid chromatography-tandem mass spectrometric methods for the determination of a new oxytocin receptor antagonist (L-368,899) extracted from human plasma and urine: a case of lack of specificity due to the presence of metabolites. Journal of Chromatography B 1998; 716: 195-208.
37. McNeff CV, Yan B, Stoll DR and Henry RA. Practice and theory of high temperature liquid chromatography. Journal of Separation Science 2007; 30: 1672-1685
38. Murphy RC, Fiedler J and Hevko J. Analysis of nonvolatile lipids by mass spectrometry. Chemical Reviews 2001; 101: 479-526.
39. Naidong W. Bioanalytical liquid chromatography tandem mass spectrometry methods on underivatized silica columns with aqueous/organic mobile phases. Journal of Chromatography B 2003; 796:209-224.
40. Neue UD. HPLC columns: Theory, Technology, and Practice. Wiley-VCH: New York, 1997; 58.
41. Ouyang Z, Jemal M and Shen X. Does LC column type/brand affect LC/MS response? 53th ASMS Conference on Mass Spectrometry, San Antonio, TX, 2005.
42. Ouyang Z, Wu S and Jemal M. Biological sample phospholipids clean up: A comparison of sample preparation techniques. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
43. Pang LQ, Liang QL, Wang YM, Ping L and Luo GA. Simultaneous determination and quantification of seven major phospholipid classes in human blood using normal-phase liquid chromatography coupled with electrospray mass spectrometry and the application in diabetes nephropathy. Journal of Chromatography B 2008; 869: 118-125.
44. Patring JDM and Jastrebova JA. Application of liquid chromatography- electrospray ionisation mass spectrometry for determination of dietary folates: effects of buffer nature and mobile phase composition on sensitivity and selectivity. Journal of Chromatography A 2007; 1143: 72-82.
45. Peng L and Farkas T. Analysis of basic compounds by reversed-phase liquid chromatography-electrospray mass spectrometry in high-pH mobile phases. Journal of Chromatography A 2008; 1179: 131-144.
46. Perterson BL and Cummings BS. A review of chromatographic methods for the assessment of phospholipids in biological samples. Biomedical Chromatography 2006; 20: 227-243.
47. Piovan A, Filippini R, Borsarini A and Caniato R. Flow injection analysis mass spectrometry, a tool to investigate the problems in the quantitative analysis of hypericin using reversed-phase high-performance liquid chromatography. Rapid Communications in Mass Spectrometry 2004; 18: 131-132.
48. Plumb R, Mazzeo JR, Grumbach ES, Rainville P, Jones M; Wheat T, Neue UD, Smith B and Johnson KA. The application of small porous particles, high temperatures, and high pressures to generate very high resolution LC and LC/MS separations. Journal of Separation Science 2007; 30: 1158-1166.
49. Poppe H. Some reflections on speed and efficiency of modern chromatographic methods. Journal of Chromatography A 1997; 778: 3-21.
50. Pulfer M and Murphy RC. Electrospray mass spectrometry of phospholipids. Mass Spectrometry Reviews, 2003; 22: 332-364.
51. Ramanathan R., Su AD, Alvarez N, Blumenkranz N., Chowdhury SK, Alton, K and Patrick J. Liquid chromatography/mass spectrometry methods for distinguishing N-oxides from hydroxylated compounds. Analytical Chemistry 2000; 72: 1352-1359.
52. Schoener D and Murakami S. The use of liquid-liquid extraction along with colloidal silica and polyvalent cations to remove phospholipids that produce ESI matrix effects. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
53. Schwartz MS, Desai RB, Bi S, Miller AR and Matuszewski BK. Determination of a prostaglandin D2 antagonist and its acyl glucuronide metabolite in human plasma by high performance liquid chromatography with tandem mass spectrometric detection - a lack of MS/MS selectivity between a glucuronide conjugate and a phase I metabolite. Journal of Chromatography B 2006; 837: 116-124.
54. Schwarz HP, Dahlke MB and Drelsbach L. Phospholipid composition of blood plasma, erythrocytes, and 'ghosts' in sickle cell disease. Clinical Chemistry 1977; 23: 1548-1550.
55. Shipkova M, Armstrong VW, Oellerich M and Wieland E. Acyl glucuronide drug metabolites: toxicological and analytical implications. Therapeutic Drug Monitoring 2003; 25: 1-16.
56. Souverain S, Rudaz S and Veuthey J-L. Restricted access materials and large particle supports for on-line sample preparation: an attractive approach for biological fluids analysis. Journal of Chromatography B 2004; 801: 141-156.
57. Stella C, Rudaz S, Gauvrit JY, Lantéri P, Huteau A, Tchapla A and Veuthey JL. Characterization and comparison of the chromatographic performance of different types of reversed-phase stationary phases. Journal of Pharmaceutical and Biomedical Analysis 2007; 43: 89-98.
58. Taguchi R, Houjou T, Nakanishi H, Yamazaki T, Ishida M, Imagawa M and Shimizu T. Focused lipidomics by tandem mass spectrometry. Journal of Chromatography B 2005; 823: 26-36.
59. Takatera A, Takeuchi A, Saiki K, Morisawa T, Yokoyama N and Matsuo M. Quantification of lysophosphatidylcholines and phosphatidylcholines using liquid chromatography-tandem mass spectrometry in neonatal serum. Journal of Chromatography B 2006; 838: 31-36.
60. Testa B, Carrupt PA and Gal J. The so-called 'interconversion' of stereoisomeric drugs: an attempt at clarification. Chirality 1993; 5: 105-111
61. Tiller PR, Romanyshyn LA and Neue UD. Fast LC/MS in the analysis of small molecules. Analytical and Bioanalytical Chemistry 2003; 377:788-802.
62. Uran S, Larsen A, Jacobsen PB and Skotland T. Analysis of phospholipid species in human blood using normal-phase liquid chromatography coupled with electrospray ionization ion-trap tandem mass spectrometry. Journal of Chromatogrraphy B 2001; 758: 265-275.
63. Vanderhoeven SJ, Lindon JC, Troke J, Nicholson JK and Wilson ID. NMR spectroscopic studies of the transacylation reactivity of ibuprofen 1-β-O-acyl glucuronide. Journal of Pharmaceutical and Biomedical Analysis 2006; 41: 1002-1006.
64. Van Gyseghem E, Jimidar M, Sneyers R, De Smet M, Verhoeven E and Vander Heyden Y. Stationary phases in the screening of drug/impurity profiles and in their separation method development: Identification of columns with different and similar selectivities. Journal of Pharmaceutical and Biomedical Analysis 2006; 41: 751-760.
65. Van Horne KC and Bennett PK. Preventing matrix effects by using new sorbents to remove phospholipids from biological samples. American Association of Pharmaceutical Scientists Annual Meeting and Exposition, Salt Lake City, Utah, 2003.
66. Viswanathan CT, Bansal S, Booth B, DeStefano AJ, Rose MJ, Sailstad J, Shah VP, Skelly JP, Swann PG, Weiner R. Workshop/conference report - quantitative bioanalytical methods validation and implementation: best practices for chromatographic and ligand binding assays. AAPS Journal 2007; 9(1): E30-42.
67. Wang C, Xie S, Yang J, Yang Q and Xu G. Structural identification of human blood phospholipids using liquid chromatography/quadrupole-linear ion trap mass spectrometry. Analytica Chimica Acta 2004; 525: 1-10.
68. Wang CJ, Pao LH, Hsiong CH, Wu CY, Whang-Peng JJK and Hu OYP. Novel inhibition of cis/trans retinoic acid interconversion in biological fluids - an accurate method for determination of trans and 13-cis retinoic acid in biological fluids. Journal of Chromatography B 2003; 796: 283-291.
69. Williams L, Lindenmuth M, Jones R, Desbrow C, Caulfield J, Dowthwaite G, Calverley R, Jordan S and Lodder H. Phospholipid removal: a comparison between traditional liquid-liquid extraction (LLE) and supported liquid extraction (SLE) using LC-MS/MS analysis. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
70. Won CM. Epimerization and hydrolysis of dalvastatin, a new hydroxymethylglutaryl coenzyme A (HMG-CoA) reductase inhibitor. Pharmaceutical Research 1994; 11: 165-170.
71. Wu ST, Schoener D and Jemal M. Plasma phospholipids implicated in the matrix effect observed in liquid chromatography/tandem mass spectrometry bioanalysis: evaluation of the use of colloidal silica in combination with divalent or trivalent cations for the selective removal of phospholipids from plasma. Rapid Communications in Mass Spectrometry 2008; 22: 2873-2881.
72. Wu ST, Cao K, Bonacorsi Jr SJ, Zhang H and Jemal M. Distinguishing a phosphate ester prodrug from its isobaric sulfate metabolite by mass spectrometry without the metabolite standard. Rapid Communications in Mass Spectrometry 2009; 23: 3107-3113.
73. Xia Y-Q and Jemal M. Evaluation of UHPLC column efficiency at different flow rates and retention factors: implications of the not-so-expected results. 56th ASMS Conference on Mass Spectrometry, Denver, CO, 2008.
74. Xia Y-Q and Jemal M. High-field asymmetric waveform ion mobility spectrometry for determining the location of in-source collision-induced dissociation in electrospray ionization mass spectrometry. Analytical Chemistry 2009a; 81: 7839-7843
75. Xia Y-Q and Jemal M. Phospholipids in liquid chromatography/mass spectrometry bioanalysis: comparison of three tandem mass spectrometric techniques for monitoring plasma phospholipids, the effect of mobile phase composition on phospholipids elution and the association of phospholipids with matrix effects. Rapid Communications in Mass Spectrometry 2009b; 23: 2125-2138.
76. Xia Y-Q, Whigan DB. and Jemal M. A simple liquid-liquid extraction with hexane for low-picogram determination of drugs and their metabolites in plasma by high-performance liquid chromatography with positive ion electrospray tandem mass spectrometry. Rapid Communications in Mass Spectrometry 1999; 13: 1611-1621.
77. Xia Y-Q, Jemal M, Zheng N, Shen X. Utility of porous graphitic carbon stationary phase in quantitative LC-MS/MS bioanalysis: quantitation of diastereomers in plasma. Rapid Communications in Mass Spectrometry 2006a; 20: 1831-1837.
78. Xia Y-Q, Ouyang Z and Jemal M. Automated column/mobile phase screening system to achieve optimum chromatographic separation and sensitivity during LC-MS/MS bioanalytical method development. 54th ASMS Conference on Mass Spectrometry, Seattle, WA, 2006b.
79. Xu RN, Fan L, Rieser MJ and El-Shourbagy TA. Recent advances in high-throughput quantitative bioanalysis by LC-MS/MS. Journal of Pharmaceutical and Biomedical Analysis 2007; 44: 342-355.
80. Xue YJ, Simmons NJ, Liu J, Unger SE, Anderson DF and Jenkins RG. Separation of a BMS drug candidate and acyl glucuronide from seven glucuronide positional isomers in rat plasma via high-performance liquid chromatography with tandem mass spectrometric detection. Rapid Communications in Mass Spectrometry 2006; 20: 1776-1786.
81. Xue YJ. Akinsanya B, Raghavan N and Zhang D. Optimization to eliminate the interference of migration isomers for measuring 1-O-β-acyl glucuronide without extensive chromatographic separation. Rapid Communications in Mass Spectrometry 2008; 22: 109-120.
82. Yong B, Hudson W, Jones D and Chen Y-L. A simple way to remove phospholipids from bioanalytical samples. 57th ASMS Conference on Mass Spectrometry, Philadelphia, PA, 2009.
83. Zhang N, Yang A, Rogers JD and. Zhao JJ. Quantitative analysis of simvastatin and its β-hydroxy acid in human plasma using automated liquid-liquid extraction based on 96-well plate format and liquid chromatography-tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2004; 34: 175-187.
84. Zhang Y, Wang YX, Mukherjee P and Petersson P. Critical comparison of performances of superficially porous particles and sub-2 μm particles under optimized ultra-high pressure conditions. Journal of Chromatography A 2009; 1216: 4597-4605.