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@ARTICLE{Bolnder:136683,
      author       = {Boländer, Alexander and Kieser, Daniel and Voss,
                      Constantin and Bauer, Silvia and Schön, Christian and
                      Burgold, Steffen and Bittner, Tobias and Hölzer, Jana and
                      Heyny-von Haußen, Roland and Mall, Gerhard and Goetschy,
                      Valérie and Czech, Christian and Knust, Henner and Berger,
                      Robert and Herms, Jochen and Hilger, Ingrid and Schmidt,
                      Boris},
      title        = {{B}is(arylvinyl)pyrazines, -pyrimidines, and -pyridazines
                      as imaging agents for tau fibrils and β-amyloid plaques in
                      {A}lzheimer's disease models.},
      journal      = {Journal of medicinal chemistry},
      volume       = {55},
      number       = {21},
      issn         = {0022-2623},
      address      = {Washington, DC},
      publisher    = {ACS},
      reportid     = {DZNE-2020-03005},
      pages        = {9170-9180},
      year         = {2012},
      abstract     = {The in vivo diagnosis of Alzheimer's disease (AD) is of
                      high socioeconomic interest and remains a demanding field of
                      research. The biopathological hallmarks of the disease are
                      extracellular plaques consisting of aggregated β-amyloid
                      peptides (Aβ) and tau protein derived intracellular
                      tangles. Here we report the synthesis and evaluation of
                      fluorescent pyrazine, pyrimidine,and pyridazine derivatives
                      in vitro and in vivo aiming at a tau-based diagnosis of AD.
                      The probes were pre-evaluated on human brain tissue by
                      fluorescence microscopy and were found to label all known
                      disease-related alterations at high contrast and
                      specificity. To quantify the binding affinity, a new
                      thiazine red displacement assay was developed and selected
                      candidates were toxicologically profiled. The application in
                      transgenic mouse models demonstrated bioavailability and
                      brain permeability for one compound. In the course of
                      histological testing, we discovered an AD-related deposition
                      of tau aggregates in the Bowman's glands of the olfactory
                      epithelium, which holds potential for an endoscopic
                      diagnosis of AD in the olfactory system.},
      keywords     = {Aged, 80 and over / Alzheimer Disease: diagnosis /
                      Alzheimer Disease: metabolism / Animals / Biological
                      Availability / Brain: metabolism / Fluorescent Dyes:
                      chemical synthesis / Fluorescent Dyes: chemistry /
                      Fluorescent Dyes: pharmacokinetics / Humans / Mice / Mice,
                      Transgenic / Microscopy, Fluorescence / Olfactory Mucosa:
                      metabolism / Organ Specificity / Permeability / Plaque,
                      Amyloid: metabolism / Pyrazines: chemical synthesis /
                      Pyrazines: chemistry / Pyrazines: pharmacokinetics /
                      Pyridazines: chemical synthesis / Pyridazines: chemistry /
                      Pyridazines: pharmacokinetics / Pyrimidines: chemical
                      synthesis / Pyrimidines: chemistry / Pyrimidines:
                      pharmacokinetics / Stereoisomerism / Structure-Activity
                      Relationship / tau Proteins: metabolism / Fluorescent Dyes
                      (NLM Chemicals) / Pyrazines (NLM Chemicals) / Pyridazines
                      (NLM Chemicals) / Pyrimidines (NLM Chemicals) / tau Proteins
                      (NLM Chemicals)},
      cin          = {AG Herms},
      ddc          = {610},
      cid          = {I:(DE-2719)1110001},
      pnm          = {342 - Disease Mechanisms and Model Systems (POF3-342)},
      pid          = {G:(DE-HGF)POF3-342},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:22913544},
      doi          = {10.1021/jm300653b},
      url          = {https://pub.dzne.de/record/136683},
}