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@ARTICLE{Holschbach:836122,
      author       = {Holschbach, Marcus and Bier, Dirk and Sihver, Wiebke and
                      Schulze, Annette and Neumaier, Bernd},
      title        = {{S}ynthesis and {P}harmacological {E}valuation of
                      {I}dentified and {P}utative {M}etabolites of the {A} 1
                      {A}denosine {R}eceptor {A}ntagonist
                      8-{C}yclopentyl-3-(3-fluoropropyl)-1-propylxanthine
                      ({CPFPX})},
      journal      = {ChemMedChem},
      volume       = {12},
      number       = {10},
      issn         = {1860-7179},
      address      = {Weinheim [u.a.]},
      publisher    = {Wiley-VCH},
      reportid     = {FZJ-2017-05245},
      pages        = {770 - 784},
      year         = {2017},
      abstract     = {The A1 adenosine receptor (A1AR) antagonist
                      [18F]8-cyclopentyl-3-(3-fluoropropyl)-1-propylxanthine
                      ([18F]CPFPX), used in imaging human brain A1ARs by positron
                      emission tomography (PET), is stable in the brain, but
                      rapidly undergoes transformation into one major
                      (3-(3-fluoropropyl)-8-(3-oxocyclopenten-1-yl)-1-propylxanthine,
                      M1) and several minor metabolites in blood. This report
                      describes the synthesis of putative metabolites of CPFPX as
                      standards for the identification of those metabolites.
                      Analysis by (radio)HPLC revealed that extracts of human
                      liver microsomes incubated with no-carrier-added
                      (n.c.a.)[18F]CPFPX contain the major metabolite, M1, as well
                      as radioactive metabolites corresponding to derivatives
                      functionalized at the cyclopentyl moiety, but no
                      N1-despropyl species or metabolites resulting from
                      functionalization of the N3-fluoropropyl chain. The putative
                      metabolites were found to displace the binding of [3H]CPFPX
                      to the A1AR in pig brain cortex at Ki values between 1.9 and
                      380 nm and the binding of [3H]ZM241385 to the A2AAR in pig
                      striatum at Ki values >180 nm. One metabolite, a
                      derivative functionalized at the ω-position of the
                      N1-propyl chain, showed high affinity (Ki 2 nm) to and
                      very good selectivity (>9000) for the A1AR.},
      cin          = {INM-5},
      ddc          = {540},
      cid          = {I:(DE-Juel1)INM-5-20090406},
      pnm          = {573 - Neuroimaging (POF3-573)},
      pid          = {G:(DE-HGF)POF3-573},
      typ          = {PUB:(DE-HGF)16},
      UT           = {WOS:000403007000007},
      pubmed       = {pmid:28217962},
      doi          = {10.1002/cmdc.201600592},
      url          = {https://juser.fz-juelich.de/record/836122},
}