Dataset Open Access

Data publication: Enantioselective Synthesis, Structure Activity Relationship, Radiofluorination and Biological Evaluation of [18F]RM365, a Novel Radioligand for Imaging the Human Cannabinoid Receptor Type 2 (CB2R) in the Brain with PET

Teodoro, Rodrigo; Gündel, Daniel; Deuther-Conrad, Winnie; Toussaint, Magali; Wenzel, Barbara; Bormans, Guy; Kopka, Klaus; Brust, Peter; Moldovan, Rares-Petru

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  "datePublished": "2023-04-05", 
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  "description": "<p>The development of cannabinoid receptor type 2 (CB2R) PET radioligands has been intensively explored due to the pronounced CB2R upregulation in various pathological conditions, such as neuroinflammation and cancer. Herein we report on the enantioselective synthesis of a series of highly affine fluorinated indole-2-carboxamide ligands targeting the CB2R in the brain. Compound RM365 was selected for PET radiotracer development due to its high CB2R affinity (Ki = 2.1 nM) and pronounced selectivity over CB1R (factor &gt; 300). A fully automated copper-mediated radiofluorination of [18F]RM365 was established starting from the corresponding aryl boronic acid pinacol ester precursor. Preliminary in vitro evaluation of [18F]RM365 indicated species differences in the binding to CB2R (KD of 2.32 nM for the human CB2R vs. KD &gt; 10000 nM for the rat CB2R). Metabolism studies in mice revealed high stability of [18F]RM365 with fractions of parent compound of &gt; 90% in the brain and &gt; 54% in the plasma at 30 min p.i. PET imaging in a rat model of local hCB2R(D80N) overexpression in the brain demonstrate the ability of [18F]RM365 to reach and selectively label the intracranial expressed hCB2R(D80N) with high signal-to-background ratio. Thus, [18F]RM365 is a very promising PET radioligand for the imaging of upregulated hCB2R expression under pathological conditions with high potential towards clinical application in humans.</p>", 
  "license": "https://creativecommons.org/licenses/by/4.0/legalcode", 
  "keywords": [
    "cannabinoid receptor type 2", 
    "indole-2-carboxamide", 
    "binding affinity", 
    "radiochemistry", 
    "fluorine-18 labeling", 
    "positron-emission tomography"
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  "creator": [
    {
      "name": "Teodoro, Rodrigo", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0002-1425-0567"
    }, 
    {
      "name": "G\u00fcndel, Daniel", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0001-9743-2325"
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    {
      "name": "Deuther-Conrad, Winnie", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0003-3168-3062"
    }, 
    {
      "name": "Toussaint, Magali", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0002-1136-3857"
    }, 
    {
      "name": "Wenzel, Barbara", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0001-7390-3575"
    }, 
    {
      "name": "Bormans, Guy", 
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    {
      "name": "Kopka, Klaus", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0003-4846-1271"
    }, 
    {
      "name": "Brust, Peter", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0001-5555-7058"
    }, 
    {
      "name": "Moldovan, Rares-Petru", 
      "@type": "Person", 
      "@id": "https://orcid.org/0000-0003-3119-7945"
    }
  ]
}
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Publication date:
April 5, 2023
DOI:
10.14278/rodare.2252

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10.14278/rodare.2252

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Keyword(s):
cannabinoid receptor type 2 indole-2-carboxamide binding affinity radiochemistry fluorine-18 labeling positron-emission tomography
Related identifiers:
Identical to:
https://www.hzdr.de/publications/Publ-36778
Referenced by:
https://www.hzdr.de/publications/Publ-35005
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License (for files):
Creative Commons Attribution 4.0 International

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