Anticonvulsant and Toxicological Evaluation of Parafluorinated/Chlorinated Derivatives of 3-Hydroxy-3-ethyl-3-phenylpropionamide.

Although the anticonvulsant activity of 3-hydroxy-3-ethyl-3-phenylproionamide (HEPP) is well-known, its use is limited by the pharmacotoxicological profile. We herein tested its fluorinated and chlorinated derivatives (F-HEPP andCl-HEPP)with two seizure models, maximal electroshock seizures (MES), a...

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Publicado en:BioMed Research International Vol. 2016; pp. 1 - 11
Autores principales: Garrido-Acosta, Osvaldo, Meza-Toledo, Sergio E., Anguiano-Robledo, Liliana, Soriano-Ursúa, Marvin A., Correa-Basurto, José, Davood, Asghar, Chamorro-Cevallos, Germán
Formato: research tables/charts Journal Article
Publicado: Wiley-Blackwell 1/1/2016
Acceso en línea:Ver este registro en EBSCOhost
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      dt: 1/1/2016
      vid: 2016
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      pub: Wiley-Blackwell
      place: Malden, Massachusetts
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        128194467
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        10.1155/2016/3978010
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        atl: Anticonvulsant and Toxicological Evaluation of Parafluorinated/Chlorinated Derivatives of 3-Hydroxy-3-ethyl-3-phenylpropionamide.
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        au:
          Garrido-Acosta, Osvaldo
          Meza-Toledo, Sergio E.
          Anguiano-Robledo, Liliana
          Soriano-Ursúa, Marvin A.
          Correa-Basurto, José
          Davood, Asghar
          Chamorro-Cevallos, Germán
        affil: Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autónoma de México, 15500 México City, DF, Mexico
      sug:
        subj:
          Anticonvulsants Pharmacodynamics
          Receptors, Cell Surface Drug Effects
          Toxicity Tests Evaluation
          Seizures Drug Therapy
          Electroshock
          Azepines Administration and Dosage
          Administration, Intraperitoneal
          Animal Studies
          Computer Simulation
          Phenytoin Administration and Dosage
          Mice
          Anticonvulsants Administration and Dosage
          Noxae
          Anticonvulsants Therapeutic Use
          Drug Toxicity
      ab: Although the anticonvulsant activity of 3-hydroxy-3-ethyl-3-phenylproionamide (HEPP) is well-known, its use is limited by the pharmacotoxicological profile. We herein tested its fluorinated and chlorinated derivatives (F-HEPP andCl-HEPP)with two seizure models, maximal electroshock seizures (MES), and intraperitoneal pentylenetetrazole (PTZ) administration. Neurotoxicity was examined via the rotarod test. With in silico methods, binding was probed on possible protein targets--GABAA receptors and the sodium channel Nav1.2. The median effective doses (ED50) of HEPP, F-HEPP, and Cl-HEPP in the MES seizure model were 129.6, 87.1, and 62.0mg/kg, respectively, and 66.4, 43.5, and in the PTZ seizure model 43.5mg/kg. The HEPP-induced neurotoxic effect, which occurred at twice the ED50 against MES (p < 0.05), did not occur with F-HEPP or Cl-HEPP. Docking studies revealed that all tested ligands bound to GABAA receptors on a site near to the benzodiazepine binding site. However, on the sodium channel open pore Nav1.2, R-HEPP had interactions similar to those reported for phenytoin, while its enantiomer and the ligands F-HEPP and Cl-HEPP reached a site that could disrupt the passage of sodium. Our results show that, as anticonvulsant agents, parahalogen substituted compounds have an advantageous pharmacotoxicological profile compared to their precursor.
      pubtype: Academic Journal
      doctype:
        research
        tables/charts
        Journal Article
      ougenre: Article
    language: English
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