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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
Open accessAbstract
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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In the citing paper
“new imaging tools have the potential to identify biomarkers of psychoplastogen efficacy”
From Psychedelics and Other Psychoplastogens for Treating Mental Illness. (2021) · cites this paper as [104]
Experimental — accuracy not yet measuredIn the citing paper
“Of these, [ 11 C]UCB-J possessed the most suitable pharmacokinetics, i.e., rapid and high brain uptake, reversible binding kinetics, and relatively low nonspecific binding in white matter”
From Challenges and rewards of in vivo synaptic density imaging, and its application to the study of depression (2025) · cites this paper as [117]
In the citing paper
“Three of the SV2A ligands were radiolabeled as [ 11 C] UCB-A [112], [ 18 F]UCB-H [113-116], and [ 11 C]UCB-J [117], and all were evaluated in nonhuman primates (NHP).”
From Challenges and rewards of in vivo synaptic density imaging, and its application to the study of depression (2025) · cites this paper as [117]
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RetractedThe synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam
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- 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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Metadata
- 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
- 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
- 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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