[en] Within the family of serotonin (5-HT) receptors, the 5-HT1A subtype is particularly interesting as it may be involved in various physiological processes or psychological disorders. The p-[18F]MPPF, a highly selec- tive 5-HT1A antagonist, is used for in vivo studies in human or animal by means of positron emission tomography (PET) [1].
In order to selectively extract p-[18 F]MPPF and its main metabolites from plasma, molecularly imprinted polymer (MIP) was prepared against these compounds by using the p-MPPF as template. For the control of the selectivity, non-imprinted polymer (NIP) was also synthesized without template. The MIP sorbent, packed in disposable extraction cartridges (DECs), was then evaluated as molecularly imprinted solid- phase extraction (MISPE) prior to the LC determination. The conditions of extraction were evaluated in order to obtain the highest selective retention of the p-[18F]MPPF and its metabolites on this MIP. The MIP selectivity was exploited in the loading and washing steps by adjusting the pH of plasma samples at a suitable value and by selecting mixtures for the washing step to limit the contribution of non- specific interactions. Other important parameters involved in the conditioning and elution steps were also studied. Finally, a pre-validation was carried out with optimal extraction conditions to demonstrate the performance of this MISPE-LC method as a generic method in the context of evaluation of new MISPE for p-[18F]MPPF and its potential for metabolites extraction from human plasma.
Research center :
CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège
Disciplines :
Pharmacy, pharmacology & toxicology Chemistry
Author, co-author :
Lecomte, Frederic ✱; Université de Liège - ULiège > Département de Pharmacie > Chimie Analytique > Doct. sc. bioméd. & pharma. (Bologne)
Aerts, Joël ✱; Université de Liège - ULiège > CRC In vivo Imaging-Preclinical Imaging
Plenevaux, Alain ; Université de Liège - ULiège > CRC In vivo Imaging-Preclinical Imaging
Defraiteur, Caroline ; Université de Liège - ULiège > CRC In vivo Imaging-Preclinical Imaging
Chappuis-Hugon, Florence; ESPCI Paris, PSL University, > Dept of Analytical, Bioanalytical Sciences and Miniaturization
Rozet, Eric; Pharmalex
CHIAP, Patrice ; Centre Hospitalier Universitaire de Liège - CHU > Unilab > Unité GLP-AEPT
Luxen, André ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de chimie organique de synthèse
Pichon, Valérie; ESPCI Paris, PSL University > Dept of Analytical, Bioanalytical Sciences and Miniaturization
Hubert, Philippe ✱; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
Hubert, Cédric ✱; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
✱ These authors have contributed equally to this work.
Language :
English
Title :
Performance evaluation of a MIP for the MISPE-LC determination of p-[18F]MPPF and a potential metabolite in human plasma
Publication date :
20 February 2020
Journal title :
Journal of Pharmaceutical and Biomedical Analysis
ISSN :
0731-7085
eISSN :
1873-264X
Publisher :
Elsevier
Volume :
180
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
FP6 STRP516984 MI-lab- on-chip
Funders :
Fonds Léon Fredericq [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Plenevaux, A., Weissmann, D., Aerts, J., Lemaire, C., Brihaye, C., Degueldre, C., Lebars, D., Comar, D., Pujol, J.F., Luxen, A., Tissue distribution, autoradiography, and metabolism of 4-(2’- methoxyphenyl)-1-[2’-[N-(2’’-pyridinyl)-p- [18F]fluorobenzamido]ethyl]piperazine (p-[18F]MPPF), a new serotonin 5- HT(1A) antagonist for positron emission tomography: an in vivo study in rats. J. Neurochem. 75 (2000), 803–811, 10.1046/j.1471-4159.2000.0750803.x.
Ametamey, S.M., Honer, M., Schubiger, P.A., Molecular imaging with PET. Chem. Rev. 108 (2008), 1501–1516, 10.1021/cr0782426.
USP 39 NF 34, U.S. Pharmacopeia. 2016 USP-NF General Chapter <823>.
21 CFR361.1, US Department of Health and Human Services, Food and Drug Administration, Radioactive Drug Research Committee (RDRC), April 2015.
Zimmer, L., Le Bars, D., Current status of positron emission tomography radiotracers for serotonin receptors in humans. J. Label Compd. Radiopharm. 56 (2013), 105–113, 10.1002/jlcr.3001.
Lemaire, C., Emram, A.M., (eds.) Chemists's Views of Imaging Centers, 1995, Plenum Press, New York, 367–382.
Lemaire, C., Plenevaux, P., Aerts, J., Del Fiore, G., Brihaye, C., Le Bars, D., Comar, D., Luxen, A., Solid phase extraction - an alternative to the use of rotary evaporators for solvent removal in the rapid formulation of PET radiopharmaceuticals. J. Label Compd. Radiopharm 42 (1999), 63–75, 10.1002/(SICI)1099-1344(199901)42:1<63::AID-JLCR167>3.0.CO;2-R.
Lemaire, C., Damhaut, Ph., Lauricella, B., Mosdzianowski, C., Morelle, J.L., Monclus, M., Van Naemen, J., Mulleneers, E., Aerts, J., Plenevaux, A., Brihaye, C., Luxen, A., Fast [18F]FDG synthesis by alkaline hydrolysis on a low polarity solid phase support. J. Label Compd. Radiopharm. 45 (2002), 435–447, 10.1002/jlcr.572.
Martín-Esteban, A., Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation. Trends Anal. Chem. 45 (2013), 169–181, 10.1016/j.trac.2012.09.023.
Ansari, S., Karimi, M., Novel developments and trends of analytical methods for drug analysis in biological and environmental samples by molecularly imprinted polymers. Trends Anal. Chem. 89 (2017), 146–162, 10.1016/j.trac.2017.02.002.
Zhou, T., Ding, L., Che, G., Jiang, W., Sang, L., Recent advances and trends of molecularly imprinted polymers for specific recognition in aqueous matrix: preparation and application in sample pretreatment. Trends Anal. Chem. 114 (2019), 11–28, 10.1016/j.trac.2019.02.028.
Zheng, Z., Lee, B.H., Choi, J.Y., Ryu, Y.H., Bae, M.A., Ahn, S.-H., Determination of 5-HT receptor antagonists, MEFWAY and MPPF using liquid chromatography electrospray ionization tandem mass spectrometry in rat plasma and brain tissue. J. Chromatogr. B 913-914 (2013), 24–29, 10.1016/j.jchromb.2012.11.014.
Sanabria-Bohórquez, S.M., Biver, F., Damhaut, P., Wikler, D., Veraart, C., Goldman, S., Quantification of 5-HT1A receptors in human brain using p-MPPF kinetic modelling and PET. Eur. J. Nucl. Med. 29 (2002), 76–81, 10.1007/s00259-001-0684-2.
Plenevaux, A., Lemaire, C., Aerts, J., Lacan, G., Rubins, D., Melega, W.P., Brihaye, C., Degueldre, C., Fuchs, S., Salmon, E., Maquet, P., Laureys, S., Damhaut, P., Weissmann, D., Le Bars, D., Pujol, J.-F., Luxen, A., [18F]p-MPPF: a radiolabeled antagonist for the study of 5-HT1A receptors with PET. Nucl. Med. Biol. 27 (2000), 467–471, 10.1016/S0969-8051(00)00113-X.
Passchier, J., van Waarde, A., Visualisation of serotonin-1A (5-HT1A) receptors in the central nervous system. Eur. J. Nucl. Med. 28 (2001), 113–129, 10.1007/s002590000394.
Ludwig, F.-A., Smits, R., Fischer, S., Donat, C.K., Hoepping, A., Brust, P., Steinbach, J., LC-MS supported studies on the in vitro metabolism of both enantiomers of flubatine and the in vivo Metabolism of (+)-[18F]flubatine-a positron emission tomography radioligand for imaging α4β2 nicotinic acetylcholine receptors. Molecules, 21, 2016, 1200, 10.3390/molecules21091200.
Franck, D., Nann, H., Davi, P., Schubiger, P.A., Ametamey, S.M., Faster analysis of radiopharmaceuticals using ultra performance liquid chromatography (UPLCs) in combination with low volume radio flow cell. Appl. Radiat. Isot. 67 (2009), 1068–1070, 10.1016/j.apradiso.2009.02.077.
Lindegren, S., Jensen, H., Jacobsson, L., A radio-high-performance liquid chromatography dual-flow cell gamma-detection system for on-line radiochemical purity and labeling efficiency determination. J. Chromatogr. A 1337 (2014), 128–132, 10.1016/j.chroma.2014.02.043.
Le Bars, D., Lemaire, C., Ginovart, N., Plenevaux, A., Aerts, J., Brihaye, C., Hassoun, W., Leviel, V., Mekhsian, P., Weissmann, D., Pujol, J.F., Luxen, A., Comar, D., High-yield radiosynthesis and preliminary in vivo evaluation of p-[18F]MPPF, a fluoro analog of WAY-100635. Nucl. Med. Biol. 25 (1998), 343–350, 10.1016/S0969-8051(97)00229-1.
Defraiteur, C., Lemaire, C., Luxen, A., Plenevaux, A., Radiochemical synthesis and tissue distribution of p-[18F]DMPPF, a new 5-HT1A ligand for PET, in rats. Nucl. Med. Biol. 33 (2006), 667–675, 10.1016/j.nucmedbio.2006.03.010.
Chapuis, F., Mullot, J.-U., Pichon, V., Tuffal, G., Hennion, M.-C., Molecularly imprinted polymers for the clean-up of a basic drug from environmental and biological samples. J. Chromatogr. A 1135 (2006), 127–134, 10.1016/j.chroma.2006.09.076.
Polson, C., Sarkar, P., Incledon, B., Raguvaran, V., Grant, R., Optimization of protein precipitation based upon effectiveness of protein removal and ionization effect in liquid chromatography– tandem mass spectrometry. J. Chromatogr. B 785 (2003), 263–275, 10.1016/S1570-0232(02)00914-5.
Hendriks, G., Uges, D.R.A., Franke, J.P., pH adjustment of human blood plasma prior to bioanalytical sample preparation. J. Pharm. Biomed. Anal. 47 (2008), 126–133, 10.1016/j.jpba.2007.12.002.
Hubert, Ph., Chiap, P., Crommen, J., Boulanger, B., Chapuzet, E., Mercier, N., Bervoas-Martin, S., Chevalier, P., Grandjean, D., Lagorce, P., Lallier, M., Laparra, M.C., Laurentie, M., Nivet, J.C., The SFSTP guide on the validation of chromatographic methods for drug bioanalysis: from the Washington Conference to the laboratory. Anal. Chim. Acta 391 (1999), 135–148, 10.1016/S0003-2670(99)00106-3.
U.S. Department of Health and Human Services Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Veterinary Medicine (CVM), Guidance for Industry: Bioanalytical Method Validation. Draft Guidance, September, 2013.
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., Workshop/conference report—quantitative bioanalytical methods validation and implementation: best practices for chromatographic and ligand binding assays. AAPS J. 9 (2007), E30–E42, 10.1208/aapsj0901004.
Hubert, Ph., Nguyen-Huu, J.-J., Boulanger, B., Chapuzet, E., Chiap, P., Cohen, N., Compagnon, P.-A., Dewe, W., Feinberg, M., Lallier, M., Laurentie, M., Mercier, N., Muzard, G., Nivet, C., Valat, L., Harmonization of strategies for the validation of quantitative analytical procedures: SFSTP proposal-Part I. J. Pharm. Biomed. Anal. 36 (2004), 579–589, 10.1016/j.jpba.2004.07.027.
Hubert, Ph., Nguyen-Huu, J.J., Boulanger, B., Chapuzet, E., Cohen, N., Compagnon, P.-A., Dewé, W., Feinberg, M., Laurentie, M., Mercier, N., Muzard, G., Valat, L., Rozet, E., Harmonization of strategies for the validation of quantitative analytical procedures: SFSTP proposal-Part III. J. Pharm. Biomed. Anal. 45 (2007), 82–96, 10.1016/j.jpba.2007.06.032.
Burdick, R.K., LeBlond, D.J., Sandell, D., Yang, H., Pappa, H., Statistical methods for validation of procedure accuracy and precision. Pharm. Forum, 39, 2013.
Matuszewski, B.K., Constanzer, M.L., Chavez-Eng, C.M., Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal. Chem. 75 (2003), 3019–3030, 10.1021/ac020361s.
