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Synthesis and Opioid Activity of Tyr1 -ψ[(Z)CF=CH]-Gly2 and Tyr1 -ψ[(S)/(R)-CF3 CH-NH]-Gly2 Leu-enkephalin Fluorinated Peptidomimetics.
Karad, Somnath Narayan; Pal, Mohan; Crowley, Rachel S; Prisinzano, Thomas E; Altman, Ryan A.
Afiliación
  • Karad SN; Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
  • Pal M; Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
  • Crowley RS; Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
  • Prisinzano TE; Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
  • Altman RA; Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas, 66045, USA.
ChemMedChem ; 12(8): 571-576, 2017 04 20.
Article en En | MEDLINE | ID: mdl-28296145
We describe the design, synthesis, and opioid activity of fluoroalkene (Tyr1 -ψ[(Z)CF=CH]-Gly2 ) and trifluoroethylamine (Tyr1 -ψ[(S)/(R)-CF3 CH-NH]-Gly2 ) analogues of the endogenous opioid neuropeptide, Leu-enkephalin. The fluoroalkene peptidomimetic exhibited low nanomolar functional activity (5.0±2 nm and 60±15 nm for δ- and µ-opioid receptors, respectively) with a µ/δ-selectivity ratio that mimics that of the natural peptide. However, the trifluoroethylamine peptidomimetics, irrespective of stereochemistry, did not activate the opioid receptors, which suggest that bulky CF3 substituents are not tolerated at this position.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Encefalina Leucina / Peptidomiméticos / Hidrocarburos Fluorados / Analgésicos Opioides Límite: Animals / Humans Idioma: En Revista: ChemMedChem Asunto de la revista: FARMACOLOGIA / QUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Encefalina Leucina / Peptidomiméticos / Hidrocarburos Fluorados / Analgésicos Opioides Límite: Animals / Humans Idioma: En Revista: ChemMedChem Asunto de la revista: FARMACOLOGIA / QUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania