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Synthesis and Preclinical Evaluation of 11 C-UCB-J as a PET Tracer for Imaging the Synaptic Vesicle Glycoprotein 2A in the Brain

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Nabulsi, Nabeel B., Mercier, Joël, Holden, Daniel, Carré, Stephane, Najafzadeh, Soheila, Vandergeten, Marie-Christine, Lin, Shu-fei, Deo, Anand, Price, Nathalie, Wood, Martyn, Lara-Jaime, Teresa, Montel, Florian, Laruelle, Marc, Carson, Richard E., Hannestad, Jonas, Huang, Yiyun·2016·Journal of Nuclear Medicine

DOI 10.2967/jnumed.115.168179

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Abstract

UNLABELLED: The synaptic vesicle glycoprotein 2A (SV2A) is found in secretory vesicles in neurons and endocrine cells. PET with a selective SV2A radiotracer will allow characterization of drugs that modulate SV2A (e.g., antiepileptic drugs) and potentially could be a biomarker of synaptic density (e.g., in neurodegenerative disorders). Here we describe the synthesis and characterization of the SV2A PET radiotracer (11)C-UCB-J ((R)-1-((3-((11)C-methyl-(11)C)pyridin-4-yl)methyl)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one) in nonhuman primates, including whole-body biodistribution. METHODS: (11)C-UCB-J was prepared by C-(11)C-methylation of the 3-pyridyl trifluoroborate precursor with (11)C-methyl iodide via the Suzuki-Miyaura cross-coupling method. Rhesus macaques underwent multiple scans including coinjection with unlabeled UCB-J (17, 50, and 150 μg/kg) or preblocking with the antiepileptic drug levetiracetam at 10 and 30 mg/kg. Scans were acquired for 2 h with arterial sampling and metabolite analysis to measure the input function. Regional volume of distribution (VT) was estimated using the 1-tissue-compartment model. Target occupancy was assessed using the occupancy plot; the dissociation constant (Kd) was determined by fitting self-blocking occupancies to a 1-site model, and the maximum number of receptor binding sites (Bmax) values were derived from baseline VT and from the estimated Kd and the nondisplaceable distribution volume (VND). RESULTS: (11)C-UCB-J was synthesized with greater than 98% purity. (11)C-UCB-J exhibited high free fraction (0.46 ± 0.02) and metabolized at a moderate rate (39% ± 5% and 24% ± 3% parent remaining at 30 and 90 min) in plasma. In the monkey brain, (11)C-UCB-J displayed high uptake and fast kinetics. VT was high (∼25-55 mL/cm(3)) in all gray matter regions, consistent with the ubiquitous expression of SV2A. Preblocking with 10 and 30 mg/kg of levetiracetam resulted in approximately 60% and 90% occupancy, respectively. Analysis of the self-blocking scans yielded a Kd estimate of 3.4 nM and Bmax of 125-350 nM, in good agreement with the in vitro inhibition constant (Ki) of 6.3 nM and regional Bmax in humans. Whole-body biodistribution revealed that the liver and the brain are the dose-limiting organs for males and females, respectively. CONCLUSION: (11)C-UCB-J exhibited excellent characteristics as an SV2A PET radiotracer in nonhuman primates. The radiotracer is currently undergoing first-in-human evaluation.

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1 retracted

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The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam
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Research works printed but not linked: 2

Lubberink M Estrada S Thibblin A . Pre-clinical evaluation and kinetic modelling of 11C-UCB-A as a PET tracer for synaptic vesicle protein 2A. Abstract presented at: The 10th International Symposium on Functional NeuroReceptor Mapping of the Living Brain; May 21–24, 2014, Amsterdam, The Netherlands.
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Additional file 19 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029033
Additional file 20 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029039
Additional file 2 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029045
Additional file 6 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029057
Additional file 9 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029066
Additional file 16 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029024
Additional file 14 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029018
Additional file 4 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029051
Additional file 15 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029021
Additional file 3 of Deep phenotyping towards precision psychiatry of first-episode depression — the Brain Drugs-Depression cohort
Jensen, K. H. R., Dam, V. H., Ganz, M., Fisher, P. M., Ip, C.-T., Sankar, A., Marstrand-Joergensen, M. R., Ozenne, B., Osler, M., Penninx, B. W. J. H., et al. (2023) · Figshare · doi:10.6084/m9.figshare.22623808
Additional file 1 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029036
Additional file 1 of Evaluation of [11C]UCB-A positron emission tomography in human brains
Xiong, M., Lubberink, M., Appel, L., Fang, X. T., Danfors, T., Kumlien, E., & Antoni, G. (2024) · Figshare · doi:10.6084/m9.figshare.26735010
Additional file 2 of A systematic review and meta-analysis of neuroimaging studies examining synaptic density in individuals with psychotic spectrum disorders
Husain, M. O., Jones, B. D. M., Arshad, U., Ameis, S. H., Mirfallah, G., Schifani, C., Rodak, T., Aiken, M., Shafique, M., Ahmed, F., et al. (2024) · Figshare · doi:10.6084/m9.figshare.26066220
Additional file 3 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029048
Additional file 2 of Deep phenotyping towards precision psychiatry of first-episode depression — the Brain Drugs-Depression cohort
Jensen, K. H. R., Dam, V. H., Ganz, M., Fisher, P. M., Ip, C.-T., Sankar, A., Marstrand-Joergensen, M. R., Ozenne, B., Osler, M., Penninx, B. W. J. H., et al. (2023) · Figshare · doi:10.6084/m9.figshare.22623805
Additional file 12 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029012
Additional file 1 of The Leuven late life depression (L3D) study: PET-MRI biomarkers of pathological brain ageing in late-life depression: study protocol
Emsell, L., Laroy, M., Cauwenberge, M. G. A. V., Vande Casteele, T., Vansteelandt, K., Van Laere, K., Sunaert, S. G., den Stock, J. V., Bouckaert, F., & Vandenbulcke, M. (2021) · Figshare · doi:10.6084/m9.figshare.13662687
Additional file 1 of Deep phenotyping towards precision psychiatry of first-episode depression — the Brain Drugs-Depression cohort
Jensen, K. H. R., Dam, V. H., Ganz, M., Fisher, P. M., Ip, C.-T., Sankar, A., Marstrand-Joergensen, M. R., Ozenne, B., Osler, M., Penninx, B. W. J. H., et al. (2023) · Figshare · doi:10.6084/m9.figshare.22623802
Additional file 3 of A systematic review and meta-analysis of neuroimaging studies examining synaptic density in individuals with psychotic spectrum disorders
Husain, M. O., Jones, B., Arshad, U., Ameis, S. H., Mirfallah, G., Schifani, C., Rodak, T., Aiken, M., Shafique, M., Ahmed, F., et al. (2024) · Figshare · doi:10.6084/m9.figshare.26736453
Additional file 1 of Drug characteristics derived from kinetic modeling: combined 11C-UCB-J human PET imaging with levetiracetam and brivaracetam occupancy of SV2A
Naganawa, M., Gallezot, J., Finnema, S. J., Maguire, R. P., Mercier, J., Nabulsi, N., Kervyn, S., Henry, S. E., Nicolas, J.-M., Huang, Y. H., et al. (2022) · Figshare · doi:10.6084/m9.figshare.21523673
Self-citation
Additional file 10 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029006
Additional file 13 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029015
Additional file 17 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029027
Additional file 1 of A systematic review and meta-analysis of neuroimaging studies examining synaptic density in individuals with psychotic spectrum disorders
Husain, M. O., Jones, B., Arshad, U., Ameis, S. H., Mirfallah, G., Schifani, C., Rodak, T., Aiken, M., Shafique, M., Ahmed, F., et al. (2024) · Figshare · doi:10.6084/m9.figshare.26066140
Additional file 21 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029042
Additional file 1 of The pharmacokinetics of [18F]UCB-H revisited in the healthy non-human primate brain
Goutal, S., Guillermier, M., Becker, G., Gaudin, M., Bramoullé, Y., Luxen, A., Lemaire, C. F., Plenevaux, A., Salmon, É., Hantraye, P., et al. (2021) · Figshare · doi:10.6084/m9.figshare.14385090
Additional file 1 of Sapap3 deletion causes dynamic synaptic density abnormalities: a longitudinal [11C]UCB-J PET study in a model of obsessive–compulsive disorder-like behaviour
Glorie, D., Verhaeghe, J., Miranda, A., Lombaerde, S. D., Stroobants, S. G., & Staelens, S. G. (2020) · Figshare · doi:10.6084/m9.figshare.13237747
Additional file 8 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029063
Additional file 11 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029009
Additional file 18 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029030
Additional file 7 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029060
Additional file 5 of Validation and test–retest repeatability performance of parametric methods for [11C]UCB-J PET
Tuncel, H., Boellaard, R., Coomans, E. M., Hollander-Meeuwsen, M. D., de Vries, E. F. J., Glaudemans, A. W. J. M., Feltes, P. K., García, D. V., Verfaillie, S. C. J., Wolters, E. E., et al. (2022) · Figshare · doi:10.6084/m9.figshare.19029054
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Authors: Nabulsi, N. B., Mercier, J., Holden, D., Carré, S., Najafzadeh, S., Vandergeten, M.-C., Lin, S.-F., Deo, A., Price, N., Wood, M., Lara-Jaime, T., Montel, F., Laruelle, M., Carson, R. E., Hannestad, J., & Huang, Y.
Affiliations: Yale University (US)
UCB Pharma (Belgium) (BE)
Intra Cellular Therapies (United States) (US)
ORCID: Nabulsi, Nabeel B.
Holden, Daniel
Najafzadeh, Soheila
Deo, Anand
Montel, Florian
Carson, Richard E.
Hannestad, Jonas
Huang, Yiyun
Venue: Journal of Nuclear Medicine
Publisher: Society of Nuclear Medicine
Published: 2016-02-04
Volume: 57
Issue: 5
Pages: 777-784
ISSN: 0161-5505 (ISSN-L)
2159-662X
DOI: 10.2967/jnumed.115.168179
OpenAlex: W2311377444
Cited by: 296
References: 31
Citations by year: 2026: 20 · 2025: 27 · 2024: 31 · 2023: 32 · 2022: 58 · 2021: 41 · 2020: 38 · 2019: 25 · 2018: 10 · 2017: 9 · 2016: 5
FWCI: 14.17
Type: journal article
Language: en
Open access: bronze
doi.org
Locations: Journal of Nuclear Medicine (publishedVersion)
PubMed (publishedVersion)
Funders: Yale University
Topics: Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Radiopharmaceutical Chemistry and Applications
Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Medical Imaging Techniques and Applications
Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuroscience and Neuropharmacology Research
Keywords: [11C]UCB-J, SV2A, PET radiotracer, radiotracer synthesis, Suzuki coupling, target occupancy, receptor binding, tissue distribution, rhesus monkeys, antiepileptic drugs
MeSH terms: Animals, Brain, Female, Humans, Macaca mulatta, Male, Membrane Glycoproteins, Permeability, Pyridines, Pyrrolidines, Pyrrolidinones, Radiochemistry, Tissue Distribution, Positron-Emission Tomography, Rats, Chemistry Techniques, Synthetic

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Synthesis and Preclinical Evaluation of 11 C-UCB-J as a PET Tracer for Imaging the Synaptic Vesicle Glycoprotein 2A in the Brain

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