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@ARTICLE{Godin:284096,
      author       = {Godin, Adriana M. and Araújo, Débora P. and Menezes,
                      Raquel R. and Brito, Ana Mercy S. and Melo, Ivo S. F. and
                      Coura, Giovanna M. E. and Soares, Darly G. and Bastos,
                      Leandro F. S. and Amaral, Flávio A. and Secchim Ribeiro,
                      Lucas and Boff, Daiane and Santos, Julliana R. A. and
                      Santos, Daniel A. and Teixeira, Mauro M. and de Fátima,
                      Ângelo and Machado, Renes R. and Coelho, Márcio M.},
      title        = {{A}ctivities of 2-phthalimidethanol and 2-phthalimidethyl
                      nitrate, phthalimide analogs devoid of the glutarimide
                      moiety, in experimental models of inflammatory pain and
                      edema},
      journal      = {Pharmacology, biochemistry and behavior},
      volume       = {122},
      issn         = {0091-3057},
      address      = {Amsterdam [u.a.]},
      publisher    = {Elsevier Science},
      reportid     = {DZNE-2026-00104},
      pages        = {291 - 298},
      year         = {2014},
      abstract     = {The reintroduction of thalidomide in the pharmacotherapy
                      greatly stimulated the interest in the synthesis and
                      pharmacological evaluation of phthalimide analogs with new
                      and improved activities and also greater safety. In the
                      present study, we evaluated the activities of two
                      phthalimide analogs devoid of the glutarimide ring, namely
                      2-phthalimidethanol (PTD-OH) and 2-phthalimidethyl nitrate
                      (PTD-NO), in experimental models of inflammatory pain and
                      edema in male C57BL/6J mice. Intraplantar (i.pl.) injection
                      of carrageenan (300 μg) induced mechanical allodynia and
                      this response was inhibited by previous per os (p.o.)
                      administration of PTD-OH and PTD-NO (750 mg/kg) and also by
                      thalidomide (500 or 750 mg/kg). The edema induced by
                      carrageenan was also inhibited by previous p.o.
                      administration of PTD-OH (500 and 750 mg/kg) and PTD-NO
                      (125, 250, 500 or 750 mg/kg), but not by thalidomide.
                      Carrageenan increased tumor necrosis factor (TNF)-α and
                      CXCL1 concentrations and also the number of neutrophils in
                      the paw tissue. Previous p.o. administration of PTD-NO (500
                      mg/kg) reduced all the parameters, while PTD-OH (500 mg/kg)
                      reduced only the accumulation of neutrophils. Thalidomide,
                      on the other hand, was devoid of effect on these biochemical
                      parameters. Plasma concentrations of nitrite were increased
                      after p.o. administration of the phthalimide analog coupled
                      to a NO donor, PTD-NO (500 mg/kg), but not after
                      administration of PTD-OH or thalidomide. In conclusion, our
                      results show that small molecules, structurally much simpler
                      than thalidomide or many of its analogs under investigation,
                      exhibit similar activities in experimental models of pain
                      and inflammation. Finally, as there is evidence that the
                      glutarimide moiety contributes to the teratogenic effect of
                      many thalidomide analogs, our results indicate that
                      phthalimide analogs devoid of this functional group could
                      represent a new class of analgesic and anti-inflammatory
                      candidates with potential greater safety.},
      keywords     = {Animals / Carrageenan: toxicity / Disease Models, Animal /
                      Edema: chemically induced / Edema: drug therapy / Edema:
                      metabolism / Inflammation: drug therapy / Inflammation:
                      metabolism / Ketoglutaric Acids: chemistry / Male / Mice /
                      Mice, Inbred C57BL / Pain: drug therapy / Pain: metabolism /
                      Pain Measurement: drug effects / Pain Measurement: methods /
                      Phthalimides: chemistry / Phthalimides: therapeutic use /
                      2-Phthalimidethanol (Other) / 2-Phthalimidethyl nitrate
                      (Other) / Inflammation (Other) / Pain (Other) / Phthalimide
                      analogs (Other) / Thalidomide (Other) / Ketoglutaric Acids
                      (NLM Chemicals) / Phthalimides (NLM Chemicals) / phthalimide
                      (NLM Chemicals) / glutaramic acid (NLM Chemicals) /
                      Carrageenan (NLM Chemicals)},
      ddc          = {540},
      pnm          = {899 - ohne Topic (POF4-899)},
      pid          = {G:(DE-HGF)POF4-899},
      typ          = {PUB:(DE-HGF)16},
      doi          = {10.1016/j.pbb.2014.04.008},
      url          = {https://pub.dzne.de/record/284096},
}