April 5, 2023 Dataset Open Access

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

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  <identifier identifierType="DOI">10.14278/rodare.2252</identifier>
  <creators>
    <creator>
      <creatorName>Teodoro, Rodrigo</creatorName>
      <givenName>Rodrigo</givenName>
      <familyName>Teodoro</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0002-1425-0567</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Gündel, Daniel</creatorName>
      <givenName>Daniel</givenName>
      <familyName>Gündel</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0001-9743-2325</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Deuther-Conrad, Winnie</creatorName>
      <givenName>Winnie</givenName>
      <familyName>Deuther-Conrad</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0003-3168-3062</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Toussaint, Magali</creatorName>
      <givenName>Magali</givenName>
      <familyName>Toussaint</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0002-1136-3857</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Wenzel, Barbara</creatorName>
      <givenName>Barbara</givenName>
      <familyName>Wenzel</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0001-7390-3575</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Bormans, Guy</creatorName>
      <givenName>Guy</givenName>
      <familyName>Bormans</familyName>
    </creator>
    <creator>
      <creatorName>Kopka, Klaus</creatorName>
      <givenName>Klaus</givenName>
      <familyName>Kopka</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0003-4846-1271</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Brust, Peter</creatorName>
      <givenName>Peter</givenName>
      <familyName>Brust</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0001-5555-7058</nameIdentifier>
    </creator>
    <creator>
      <creatorName>Moldovan, Rares-Petru</creatorName>
      <givenName>Rares-Petru</givenName>
      <familyName>Moldovan</familyName>
      <nameIdentifier nameIdentifierScheme="ORCID" schemeURI="http://orcid.org/">0000-0003-3119-7945</nameIdentifier>
    </creator>
  </creators>
  <titles>
    <title>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</title>
  </titles>
  <publisher>Rodare</publisher>
  <publicationYear>2023</publicationYear>
  <subjects>
    <subject>cannabinoid receptor type 2</subject>
    <subject>indole-2-carboxamide</subject>
    <subject>binding affinity</subject>
    <subject>radiochemistry</subject>
    <subject>fluorine-18 labeling</subject>
    <subject>positron-emission tomography</subject>
  </subjects>
  <dates>
    <date dateType="Issued">2023-04-05</date>
  </dates>
  <resourceType resourceTypeGeneral="Dataset"/>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://rodare.hzdr.de/record/2252</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="URL" relationType="IsIdenticalTo">https://www.hzdr.de/publications/Publ-36778</relatedIdentifier>
    <relatedIdentifier relatedIdentifierType="URL" relationType="IsReferencedBy">https://www.hzdr.de/publications/Publ-35005</relatedIdentifier>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsVersionOf">10.14278/rodare.2251</relatedIdentifier>
    <relatedIdentifier relatedIdentifierType="URL" relationType="IsPartOf">https://rodare.hzdr.de/communities/rodare</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="https://creativecommons.org/licenses/by/4.0/legalcode">Creative Commons Attribution 4.0 International</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">&lt;p&gt;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 &amp;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 &amp;gt; 10000 nM for the rat CB2R). Metabolism studies in mice revealed high stability of [18F]RM365 with fractions of parent compound of &amp;gt; 90% in the brain and &amp;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.&lt;/p&gt;</description>
  </descriptions>
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