MOOC: Validation of liquid chromatography mass spectrometry (LC-MS) methods (analytical chemistry) course

References

ref 1

A. Kruve, R. Rebane, K. Kipper, M.-L. Oldekop, H. Evard, K. Herodes, P. Ravio, I. Leito. Tutorial review on validation of liquid chromatography–mass spectrometry methods: Part I. Anal. Chim. Acta 2015, 870, 29-44

ref 10

Rapid determination of meropenem in biological fluids by LC: comparison of various methods for sample preparation and investigation of meropenem stability. K. Kipper, K. Anier, I. Leito, J. Karjagin, K. Oselin, K. Herodes, Chromatographia, 2009, 70, 1423–1427.

ref 11

Bioanalytical UPLC-MS/MS method development and validation for measuring penicillins in human blood plasma – analyte stability issues. K. Kipper, C. Barker, A. Johnston. Mass spectrometry: Applications to the Clinical Lab (MSACL 2015). 8th Annual Conference & Exhibits, 2015, San Diego, CA, USA, 28.03.2015-01.04.2015.

ref 12

Harmonized Guidelines for single-laboratory validation of method of analyses (IUPAC Technical Report). M. Thompson, S.L.R. Ellison, R. Wood, Pure Appl. Chem. 2002, 74(5), 835–855.

ref 13

Council Directive 98/83/EC of 3 November 1998 on the quality of water intended for human consumption, Off. J. Eur. Commun. 2014, L221, 1-101.

ref 14

Limits for qualitative detection and quantitative determination. L. A. Currie, Anal. Chem. 1968, 40, 586–593.

ref 15

NordVal Protocol No. 2, Guide in validation of alternative proprietary chemical methods, 2010.

ref 16

40 CFR Part 136, Appendix B to Part 136 - Definition and Procedure for the Determination of the Method Detection Limit-Revision 1.11, US Environmental Protection Agency 2012

ref 17

ICH harmonized tripartite guideline: validation of analytical procedures: text and methodology Q2(R1), International Conference of harmonization of technical requirements for registration of pharmaceuticals for human use 2005. A revised/renewed draft version of this guideline: ICH guideline Q2(R2) on validation of analytical procedures 2022.

ref 18

ISO 11843-2:2000 Capability of detection - Part 2: Methodology in the linear calibration case, International Organization of Standardization 2000.

ref 19

H. Evard, A. Kruve, I. Leito, Tutorial on estimating the limit of detection using LC-MS analysis, part I: Theoretical review. Anal. Chim. Acta 2016, 942, 23-39.

ref 2

ref 20

H. Evard, A. Kruve, I. Leito, Tutorial on estimating the limit of detection using LC-MS analysis, part II: Practical aspects. Anal. Chim. Acta 2016, 942, 40-49.

ref 21

B. Magnusson, S. L. R. Ellison Treatment of uncorrected measurement bias in uncertainty estimation for chemical measurements. Anal. Bioanal. Chem. 2008, 390, 201–213

ref 22

E. Theodorsson, B. Magnusson, I. Leito, Bioanalysis 2014, 6, 2855–2875

ref 23

R. Rosen False Positives in LC-MS/MS: to what Extant Do We Have to Live with Them? Presented at IsrAnalytica, Tel Aviv, 2010.

ref 24

P. Bastos-Amador, F. Royo, E. Gonzalez, J. Conde-Vancells, L. Palomo-Diez, F.E. Borras, J.M. Falcon-Perez, Proteomic analysis of microvesicles from plasma of healthy donors reveals high individual variability, J. Proteomics 2012, 75, 3574–3584.

ref 25

P.J. Taylor “Matrix effects: The Achilles heel of quantitative high-performance liquid chromatography–electrospray–tandem mass spectrometry” Clin Biochem 38 2005, 328-334.

ref 26

S.J. Lehotay, K. Mastovska, A.R. Lightfield, R.A. Gates, Comparison of QuEChERS sample preparation methods for the analysis of pesticide residues in fruits and vegetables, J. AOAC Int. 93 (2010) 355–367.

ref 27

A. Kruve, A. Künnapas, K. Herodes , I. Leito, Matrix effects in pesticide multi-residue analysis by liquid chromatography–mass spectrometry, J. Chromatogr. A. 1187, 1-2, 2008, 58-66

ref 28

I.R. Pizzutti, A. de Kok, M. Hiemstra, C. Wickert, O.D. Prestes, Method validation and comparison of acetonitrile and acetone extraction for the analysis of 169 pesticides in soya grain by liquid chromatography–tandem mass spectrometry, J. Chromatogr. A 1216 (2009) 4539–4552

ref 29

A. Kruve, K. Herodes, I. Leito, Electrospray ionization matrix effect as an uncertainty source in HPLC/ESI-MS pesticide residue analysis, Rapid Commun. Mass Spectrom. 93 (1) (2010) 306–314.

ref 3

B. Magnusson and U. Örnemark (eds.) Eurachem Guide: The Fitness for Purpose of Analytical Methods - A Laboratory Guide to Method Validation and Related Topics, (2nd ed. 2014).

ref 30

R. Bonfiglio, R.C. King, T.V. Olah, K. Merkle, The effects of sample preparation methods on the variability of the electrospray ionization response for model drug compounds, Rapid Commun. Mass Spectrom. 13 (1999) 1175–1185.

ref 31

R. Dams, M.A. Huestis, W.E. Lambert, C.M. Murphy, Matrix effect in bio-analysis of illicit drugs with LC-MS/MS: influence of ionization type, sample preparation, and biofluid, J. Am. Soc. Mass Spectrom. 14 (2003) 1290–1294.

ref 32

P. Keski-Rahkonen, K. Huhtinen, R. Desai, D.T. Harwood, D.J. Handelsman, M. Poutanen, S. Auriola, LC–MS analysis of estradiol in human serum and endometrial tissue: comparison of electrospray ionization, atmospheric pressure chemical ionization and atmospheric pressure photoionization, J. Mass Spectrom. 48 (2013) 1050–1058.

ref 33

O.A. Ismaiel, M.S. Halquist, M.Y. Elmamly, A. Shalaby, H.T. Karnes, Monitoring phospholipids for assessment of ion enhancement and ion suppression in ESI and APCI LC/MS/MS for chlorpheniramine in human plasma and the importance of multiple source matrix effect evaluations, J. Chromatogr. B 875 (2008) 333–343.

ref 34

E. Beltrán, M. Ibánez, J.V. Sancho, F. Hernández, Determination of patulin in apple and derived products by UHPLC-MS/MS. Study of matrix effects with atmospheric pressure ionisation sources, Food Chem. 142 (2014) 400–407.

ref 35

E.M. Thurman, I. Ferrer, D. Barcelo, Choosing between atmospheric pressure chemical ionization and electrospray ionization interfaces for the HPLC/MS analysis of pesticides, Anal. Chem. 73 (2001) 5441–5449.

ref 36

Laaniste, A., Leito, I. & Kruve, A. ESI outcompetes other ion sources in LC/MS trace analysis. Anal Bioanal Chem 411, 3533–3542 (2019)

ref 37

A. Kruve, I. Leito, K. Herodes, Combating matrix effects in LC/ESI/MS: The extrapolative dilution approach, Anal. Chim. Acta, 651, 1, 2009, 75-80

ref 38

A. Kruve, I. Leito, Comparison of different methods aiming to account for/overcome matrix effects in LC/ESI/MS on the example of pesticide analyses, Anal. Methods, 2013,5, 3035-3044

ref 39

ref 4

The European Commission: Guidance document on analytical quality control and method validation procedures for pesticide residues and analysis in food and feed. Also known as SANTE (formerly SANCO). The link leads to a page where the most recent version, as well as the older versions can be found.

ref 40

Q. Sun, W. Zhang, W. Zhong, X. Sun, Z. Zhou, Pharmacological inhibition of NOX4 ameliorates alcohol-induced liver injury in mice through improving oxidative stress and mitochondrial function. Biochim Biophys Acta. 2016, 1861, 2912-2921.

ref 41

V.M. Costa, R. Silva, L.M. Ferreira, P.S. Branco, F. Carvalho, M.L. Bastos, R.A. Carvalho, M. Carvalho, F. Remião, Oxidation process of adrenaline in freshly isolated rat cardiomyocytes: formation of adrenochrome, quinoproteins, and GSH adduct. Chem Res Toxicol. 2007, 20, 1183-1191.

ref 42

R.K. Palsmeier, D.M. Radzik, C.E. Lunte. Investigation of the degradation mechanism of 5-aminosalicylic acid in aqueous solution. Pharm Res. 1992, 9, 933-938.

ref 43

P.G. Geiger, W. Korytowski, F. Lin, A.W. Girotti, Lipid Peroxidation in Photodynamically Stressed Mammalian Cells: Use of Cholesterol Hydroperoxides as Mechanistic Reporters. Free Radic Biol Med. 1997, 23, 57-68.

ref 44

A. Beuve, Thiol-Based Redox Modulation of Soluble Guanylyl Cyclase, the Nitric Oxide Receptor. Antioxid Redox Signal. 2016 Apr 1.

ref 45

J.V. Voorde, S. Sabuncuoğlu, S. Noppen, A. Hofer, F. Ranjbarian, S. Fieuws, J. Balzarini, S. Liekens, Nucleoside-catabolizing enzymes in mycoplasma-infected tumor cell cultures compromise the cytostatic activity of the anticancer drug gemcitabine. J Biol Chem. 2014, 289, 13054-13065.

ref 46

M.M. Musa, R.S. Phillips, M. Laivenieks, C. Vieille, M. Takahashi, S.M. Hamdan, Racemization of enantiopure secondary alcohols by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase. Org Biomol Chem. 2013, 11, 2911-2915.

ref 47

R.J. Guan, Y. Xiang, X.L. He, C.G. Wang, M. Wang, Y. Zhang, E.J. Sundberg, D.C. Wang, Structural mechanism governing cis and trans isomeric states and an intramolecular switch for cis/trans isomerization of a non-proline peptide bond observed in crystal structures of scorpion toxins. J Mol Biol. 2004, 341, 1189-1204.

ref 48

S. Feng, M.A. ElSohly, D.T. Duckworth, Hydrolysis of conjugated metabolites of buprenorphine. I. The quantitative enzymatic hydrolysis of buprenorphine-3-beta-D-glucuronide in human urine. J Anal Toxicol. 2001, 25, 589-593.

ref 49

M. Caswell, G.L. Schmir, Formation and hydrolysis of lactones of phenolic acids. J. Am. Chem. Soc., 1980, 102, 4815–4821.

ref 5

European Commission Decision 2002/657/EC implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results, Off. J. Eur. Commun. L221 (2002) 8-36.
Note that this directive is superseded by Commission Implementing Regulation (EU) 2021/808 of 22 March 2021 on the performance of analytical methods for residues of pharmacologically active substances used in food-producing animals and on the interpretation of results as well as on the methods to be used for sampling.

ref 50

Y. Yang, H. Aloysius, D. Inoyama, Y. Chen, L. Hu. Enzyme-mediated hydrolytic activation of prodrugs. Acta Pharm. Sin. B. 2011, 1, 143–159.

ref 51

X. Yan, J. Wang, Y. Sun, J. Zhu, S. Wu. Facilitating the evolution of Esterase Activity from a Promiscuous Enzyme Mhg with Catalytic Functions of Amide Hydrolysis and Carboxylic Acid Perhydrolysis by Engineering the Substrate Entrance Tunnel. Appl Environ Microbiol. 2016. doi: 10.1128/AEM.01817-16

ref 52

IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.

ref 53

H. Sun, F. Wang, L. Ai, C. Guo, R. Chen, Validated method for determination of eight banned nitroimidazole residues in natural casings by LC/MS/MS with solid-phase extraction, J. AOAC Int. 2009, 92, 612–621.

ref 54

R.P. Lopes, D.V. Augusti, L.F. de Souza, F.A. Santos, J.A. Lima, E.A. Vargas, R. Augusti, Development and validation (according to the 2002/657/EC regulation) of a method to quantify sulfonamides in porcine liver by fast partition at very low temperature and LC–MS/MS, Anal. Methods, 2011, 3 606–613.

ref 55

R. Thakare, Y. S. Chhonker, N. Gautam, J. A. Alamoudi, Y. Alnouti, Quantitation of a novel metalloporphyrin drug in plasma by atomic absorption spectroscopy. J. Pharm. Biomed. Anal., 2016, 128, 426–437

ref 56

A. Menditto, M. Patriarca, B. Magnusson, Understanding the meaning of accuracy, trueness and precision. Accred Qual Assur, 2007, 12, 1, 45. doi:10.1007/s00769-006-0191-z

ref 57

K.K. Murray, R.K. Boyd, M.N. Eberlin, G.J. Langley, L. Li, Y. Naito. Definitions of terms relating to mass spectrometry (IUPAC Recommendations 2013). Pure Appl. Chem 2013, 85, 7, 1515–1609.

ref 58

M. Hecht, R. Veigure, L. Couchman, C. I. S. Barker, J. F. Standing, K. Takkis, H. Evard, A. Johnston, K. Herodes, I. Leito, K. Kipper, Utilization of data below the analytical limit of quantitation in pharmacokinetic analysis and modeling: promoting interdisciplinary debate, Bioanalysis 2008, 10(15), 1229-1248

ref 59

S. Kaupmees, R. Rebane. Analysis and validation of perfluorinated compounds in water, sediment and fish with LC- ESI–MS/MS. International Journal of Environmental Analytical Chemistry 2017, 97(8), 695–709.

ref 6

JCGM 200:2008, International vocabulary of metrology — Basic and general concepts and associated terms (VIM), 3rd edition. BIPM, IEC, IFCC, ILAC, ISO, IUPAC, IUPAP and OIML, 2008.

ref 60

R. Rebane, K. Herodes. Matrix interference in LC-ESI-MS/MS analysis of metanephrines in protein precipitated plasma samples. European Journal of Mass Spectrometry 2019, 26(1), 46-54, https://doi.org/10.1177/1469066719862423.

ref 61

K. Kipper, M. Hecht, N.J. Antunes, L.D. Fairbanks, M. Levene, S. Kalkan Uçar, A. Schaefer, E.L. Blakely, B.E. Bax. Quantification of Plasma and Urine Thymidine and 2’-Deoxyuridine by LC-MS/MS for the Pharmacodynamic Evaluation of Erythrocyte Encapsulated Thymidine Phosphorylase in Patients with Mitochondrial Neurogastrointestinal Encephalomyopathy. J. Clin. Med. 2020, 9, 788.