Periodical
View in EDS

Structure–Activity Relationship Studies of Pyridine-Based Ligands and Identification of a Fluorinated Derivative for Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors

Bibliographic Details
Title: Structure–Activity Relationship Studies of Pyridine-Based Ligands and Identification of a Fluorinated Derivative for Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors
Authors: Haider, Achi, Kretz, Julian, Gobbi, Luca, Ahmed, Hazem, Atz, Kenneth, Bürkler, Markus, Bartelmus, Christian, Fingerle, Jürgen, Guba, Wolfgang, Ullmer, Christoph, Honer, Michael, Knuesel, Irene, Weber, Markus, Brink, Andreas, Herde, Adrienne Müller, Keller, Claudia, Schibli, Roger, Mu, Linjing, Grether, Uwe, Ametamey, Simon M.
Source: Journal of Medicinal Chemistry; December 2019, Vol. 62 Issue: 24 p11165-11181, 17p
Abstract: The cannabinoid type 2 (CB2) receptor has emerged as a valuable target for therapy and imaging of immune-mediated pathologies. With the aim to find a suitable radiofluorinated analogue of the previously reported CB2 positron emission tomography (PET) radioligand [11C]RSR-056, 38 fluorinated derivatives were synthesized and tested by in vitro binding assays. With a Ki(hCB2) of 6 nM and a selectivity factor of nearly 700 over cannabinoid type 1 receptors, target compound 3exhibited optimal in vitro properties and was selected for evaluation as a PET radioligand. [18F]3was obtained in an average radiochemical yield of 11 ± 4% and molar activities between 33 and 114 GBq/μmol. Specific binding of [18F]3to CB2 was demonstrated by in vitro autoradiography and in vivo PET experiments using the CB2 ligand GW-405 833. Metabolite analysis revealed only intact [18F]3in the rat brain. [18F]3detected CB2 upregulation in human amyotrophic lateral sclerosis spinal cord tissue and may thus become a candidate for diagnostic use in humans.
Database: Supplemental Index
FullText Links:
  – Type: other
Text:
  Availability: 0
CustomLinks:
  – Url: https://resolver.ebsco.com/c/xy5jbn/result?sid=EBSCO:edo&genre=article&issn=00222623&ISBN=&volume=62&issue=24&date=20191226&spage=11165&pages=11165-11181&title=Journal of Medicinal Chemistry&atitle=Structure%E2%80%93Activity%20Relationship%20Studies%20of%20Pyridine-Based%20Ligands%20and%20Identification%20of%20a%20Fluorinated%20Derivative%20for%20Positron%20Emission%20Tomography%20Imaging%20of%20Cannabinoid%20Type%202%20Receptors&aulast=Haider%2C%20Achi&id=DOI:10.1021/acs.jmedchem.9b01280
    Name: Full Text Finder (for New FTF UI) (s8985755)
    Category: fullText
    Text: Find It @ SCU Libraries
    MouseOverText: Find It @ SCU Libraries
Header DbId: edo
DbLabel: Supplemental Index
An: ejs51592698
RelevancyScore: 884
AccessLevel: 6
PubType: Periodical
PubTypeId: serialPeriodical
PreciseRelevancyScore: 884.340759277344
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Structure–Activity Relationship Studies of Pyridine-Based Ligands and Identification of a Fluorinated Derivative for Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Haider%2C+Achi%22">Haider, Achi</searchLink><br /><searchLink fieldCode="AR" term="%22Kretz%2C+Julian%22">Kretz, Julian</searchLink><br /><searchLink fieldCode="AR" term="%22Gobbi%2C+Luca%22">Gobbi, Luca</searchLink><br /><searchLink fieldCode="AR" term="%22Ahmed%2C+Hazem%22">Ahmed, Hazem</searchLink><br /><searchLink fieldCode="AR" term="%22Atz%2C+Kenneth%22">Atz, Kenneth</searchLink><br /><searchLink fieldCode="AR" term="%22Bürkler%2C+Markus%22">Bürkler, Markus</searchLink><br /><searchLink fieldCode="AR" term="%22Bartelmus%2C+Christian%22">Bartelmus, Christian</searchLink><br /><searchLink fieldCode="AR" term="%22Fingerle%2C+Jürgen%22">Fingerle, Jürgen</searchLink><br /><searchLink fieldCode="AR" term="%22Guba%2C+Wolfgang%22">Guba, Wolfgang</searchLink><br /><searchLink fieldCode="AR" term="%22Ullmer%2C+Christoph%22">Ullmer, Christoph</searchLink><br /><searchLink fieldCode="AR" term="%22Honer%2C+Michael%22">Honer, Michael</searchLink><br /><searchLink fieldCode="AR" term="%22Knuesel%2C+Irene%22">Knuesel, Irene</searchLink><br /><searchLink fieldCode="AR" term="%22Weber%2C+Markus%22">Weber, Markus</searchLink><br /><searchLink fieldCode="AR" term="%22Brink%2C+Andreas%22">Brink, Andreas</searchLink><br /><searchLink fieldCode="AR" term="%22Herde%2C+Adrienne+Müller%22">Herde, Adrienne Müller</searchLink><br /><searchLink fieldCode="AR" term="%22Keller%2C+Claudia%22">Keller, Claudia</searchLink><br /><searchLink fieldCode="AR" term="%22Schibli%2C+Roger%22">Schibli, Roger</searchLink><br /><searchLink fieldCode="AR" term="%22Mu%2C+Linjing%22">Mu, Linjing</searchLink><br /><searchLink fieldCode="AR" term="%22Grether%2C+Uwe%22">Grether, Uwe</searchLink><br /><searchLink fieldCode="AR" term="%22Ametamey%2C+Simon+M%2E%22">Ametamey, Simon M.</searchLink>
– Name: TitleSource
  Label: Source
  Group: Src
  Data: Journal of Medicinal Chemistry; December 2019, Vol. 62 Issue: 24 p11165-11181, 17p
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: The cannabinoid type 2 (CB2) receptor has emerged as a valuable target for therapy and imaging of immune-mediated pathologies. With the aim to find a suitable radiofluorinated analogue of the previously reported CB2 positron emission tomography (PET) radioligand [11C]RSR-056, 38 fluorinated derivatives were synthesized and tested by in vitro binding assays. With a Ki(hCB2) of 6 nM and a selectivity factor of nearly 700 over cannabinoid type 1 receptors, target compound 3exhibited optimal in vitro properties and was selected for evaluation as a PET radioligand. [18F]3was obtained in an average radiochemical yield of 11 ± 4% and molar activities between 33 and 114 GBq/μmol. Specific binding of [18F]3to CB2 was demonstrated by in vitro autoradiography and in vivo PET experiments using the CB2 ligand GW-405 833. Metabolite analysis revealed only intact [18F]3in the rat brain. [18F]3detected CB2 upregulation in human amyotrophic lateral sclerosis spinal cord tissue and may thus become a candidate for diagnostic use in humans.
PLink https://login.libproxy.scu.edu/login?url=https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&scope=site&db=edo&AN=ejs51592698
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1021/acs.jmedchem.9b01280
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 17
        StartPage: 11165
    Titles:
      – TitleFull: Structure–Activity Relationship Studies of Pyridine-Based Ligands and Identification of a Fluorinated Derivative for Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Haider, Achi
      – PersonEntity:
          Name:
            NameFull: Kretz, Julian
      – PersonEntity:
          Name:
            NameFull: Gobbi, Luca
      – PersonEntity:
          Name:
            NameFull: Ahmed, Hazem
      – PersonEntity:
          Name:
            NameFull: Atz, Kenneth
      – PersonEntity:
          Name:
            NameFull: Bürkler, Markus
      – PersonEntity:
          Name:
            NameFull: Bartelmus, Christian
      – PersonEntity:
          Name:
            NameFull: Fingerle, Jürgen
      – PersonEntity:
          Name:
            NameFull: Guba, Wolfgang
      – PersonEntity:
          Name:
            NameFull: Ullmer, Christoph
      – PersonEntity:
          Name:
            NameFull: Honer, Michael
      – PersonEntity:
          Name:
            NameFull: Knuesel, Irene
      – PersonEntity:
          Name:
            NameFull: Weber, Markus
      – PersonEntity:
          Name:
            NameFull: Brink, Andreas
      – PersonEntity:
          Name:
            NameFull: Herde, Adrienne Müller
      – PersonEntity:
          Name:
            NameFull: Keller, Claudia
      – PersonEntity:
          Name:
            NameFull: Schibli, Roger
      – PersonEntity:
          Name:
            NameFull: Mu, Linjing
      – PersonEntity:
          Name:
            NameFull: Grether, Uwe
      – PersonEntity:
          Name:
            NameFull: Ametamey, Simon M.
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 26
              M: 12
              Text: December 2019
              Type: published
              Y: 2019
          Identifiers:
            – Type: issn-print
              Value: 00222623
            – Type: issn-print
              Value: 15204804
          Numbering:
            – Type: volume
              Value: 62
            – Type: issue
              Value: 24
          Titles:
            – TitleFull: Journal of Medicinal Chemistry
              Type: main
ResultId 1