Table of Contents Author Guidelines Submit a Manuscript
BioMed Research International
Volume 2016, Article ID 3978010, 10 pages
http://dx.doi.org/10.1155/2016/3978010
Research Article

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

1Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autónoma de México, 15500 México City, DF, Mexico
2Laboratorio de Quimioterapia Experimental, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, 11350 México City, DF, Mexico
3Laboratorio de Farmacología Molecular, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, 11340 México City, DF, Mexico
4Departamento de Fisiología, Escuela Superior de Medicina, Instituto Politécnico Nacional, 11340 México City, DF, Mexico
5Laboratorio de Modelado Molecular y Diseño de Fármacos, Escuela Superior de Medicina, Instituto Politécnico Nacional, 11340 México City, DF, Mexico
6Department of Medicinal Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran 19419, Iran
7Laboratorio de Toxicología Preclínica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, 11350 México City, DF, Mexico

Received 19 September 2015; Revised 21 January 2016; Accepted 26 January 2016

Academic Editor: Rituraj Purohit

Copyright © 2016 Osvaldo Garrido-Acosta et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. S. Fisher, W. V. Boas, W. Blume et al., “Epileptic seizures and epilepsy: definitions proposed by the International League against Epilepsy (ILAE) and the International Bureau for Epilepsy (IBE),” Epilepsia, vol. 46, no. 4, pp. 470–472, 2005. View at Google Scholar
  2. J. O. McNamara, “Cellular and molecular basis of epilepsy,” The Journal of Neuroscience, vol. 14, no. 6, pp. 3413–3425, 1994. View at Google Scholar · View at Scopus
  3. A. K. Ngugi, C. Bottomley, I. Kleinschmidt et al., “Prevalence of active convulsive epilepsy in sub-Saharan Africa and associated risk factors: cross-sectional and case-control studies,” The Lancet Neurology, vol. 12, no. 3, pp. 253–263, 2013. View at Publisher · View at Google Scholar · View at Scopus
  4. S. Botros, N. A. Khalil, B. H. Naguib, and Y. El-Dash, “Synthesis and anticonvulsant activity of new phenytoin derivatives,” European Journal of Medicinal Chemistry, vol. 60, pp. 57–63, 2013. View at Publisher · View at Google Scholar · View at Scopus
  5. M. Angalakuditi and N. Angalakuditi, “A comprehensive review of the literature on epilepsy in selected countries in emerging markets,” Neuropsychiatric Disease and Treatment, vol. 7, no. 1, pp. 585–597, 2011. View at Google Scholar · View at Scopus
  6. J. A. French, A. M. Kanner, J. Bautista et al., “Efficacy and tolerability of the new antiepileptic drugs II: treatment of refractory epilepsy. Report of the Therapeutics and Technology Assessment Subcommittee and Quality Standards Subcommittee of the American Academy of Neurology and the American Epilepsy Society,” Neurology, vol. 62, no. 8, pp. 1261–1273, 2004. View at Google Scholar
  7. C. X. Wei, M. Bian, and G. H. Gong, “Current research on antiepileptic compounds,” Molecules, vol. 20, no. 11, pp. 20741–20776, 2015. View at Publisher · View at Google Scholar
  8. A. Ayati, S. Emami, A. Asadipour, A. Shafiee, and A. Foroumadi, “Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery,” European Journal of Medicinal Chemistry, vol. 97, pp. 699–718, 2015. View at Publisher · View at Google Scholar
  9. M. Bialer, S. I. Johannessen, R. H. Levy, E. Perucca, T. Tomson, and H. S. White, “Progress report on new antiepileptic drugs: a summary of the Twelfth Eilat Conference (EILAT XII),” Epilepsy Research, vol. 111, pp. 85–141, 2015. View at Google Scholar
  10. J. Gagoria, P. K. Verma, and A. Khatkar, “Anticonvulsant and neurological profile of benzothiazoles: a mini-review,” Central Nervous System Agents in Medicinal Chemistry, vol. 15, no. 1, pp. 11–16, 2015. View at Publisher · View at Google Scholar
  11. D. F. Weaver, “Design of innovative therapeutics for pharmacoresistant epilepsy: challenges and needs,” Epilepsia, vol. 54, supplement 2, pp. 56–59, 2013. View at Google Scholar · View at Scopus
  12. S. E. Meza-Toledo, M. T. Zenteno-Garcia, E. Juarez-Carvajal, D. Martinez-Munoz, and G. Carvajal-Sandoval, “A new homologous series of anticonvulsants: phenyl alcohol amides. Synthesis and pharmacological evaluation,” Arzneimittel-Forschung/Drug Research, vol. 40, no. 12, pp. 1289–1291, 1990. View at Google Scholar · View at Scopus
  13. A. M. Javier, G. Sánchez, and M. A. A. Martínez, “Espectro de acción antiepiléptica de la DL-4-hidroxi, 4-etil, 4-fenil butiramida y sus homólogos inferiores,” Archivos de Neurociencias, vol. 1, no. 2, pp. 76–80, 1996. View at Google Scholar
  14. S. E. Meza-Toledo and N. G. Bowery, “Reversal of GABA-mediated inhibition of the electrically and potassium chloride evoked [3H]-GABA release from rat substantia nigra slices by DL-3-hydroxy-3-phenyl pentanamide,” Arzneimittel-Forschung, vol. 58, no. 2, pp. 53–61, 2008. View at Publisher · View at Google Scholar
  15. J. L. Chávez and D. Martínez, “Mecanismo de acción del anticonvulsionante DL-3-hidroxi, 3-etil, 3-fenil propionamida (HEPP),” Archivos de Neurociencias, vol. 1, no. 3, pp. 173–177, 1996. View at Google Scholar
  16. G. Carvajal-Sandoval, E. Juárez-Carvajal, C. Cruz-Peinado, and S. E. Meza-Toledo, “Synthesis and pharmacological evaluation of a new homologous series of (+,−)-p-fluoro-phenyl alcohol amide anticonvulsant,” Drug Research I, vol. 48, no. 4, pp. 349–352, 1998. View at Google Scholar
  17. S. E. Meza-Toledo, E. Juárez-Carvajal, and G. Carvajal-Sandoval, “Synthesis of a new homologous series of p-chlorophenyl alcohol amides, their anticonvulsant activity an their testing as potential GABA-B receptor antagonists,” Drug Research, vol. 48, no. 8, pp. 797–801, 1998. View at Google Scholar · View at Scopus
  18. Secretary of Agriculture, Livestock, Rural Development, and Fisheries and Food of Mexico (SAGARPA), “Norma Official Mexicana NOM-062-ZOO-1999, Especificaciones técnicas para la producción, cuidado y uso de los animales de laboratorio,” Official Mexican Rule NOM 062-ZOO-1999, Technical Specifications for Production, Care and Use of Laboratory Animals, 1999. View at Google Scholar
  19. O. Garrido-Acosta, S. E. Meza-Toledo, L. Anguiano-Robledo, I. Valencia-Hernández, and G. Chamorro-Cevallos, “Adaptation of Lorke's method to determine and compare ED50 values: the cases of two anticonvulsants drugs,” Journal of Pharmacological and Toxicological Methods, vol. 70, no. 1, pp. 66–69, 2014. View at Publisher · View at Google Scholar · View at Scopus
  20. B. J. Jones and D. J. Roberts, “The quantitative measurement of motor inco-ordination in naive mice using an accelerating rotarod,” Journal of Pharmacy and Pharmacology, vol. 20, no. 4, pp. 302–304, 1968. View at Publisher · View at Google Scholar · View at Scopus
  21. N. W. Dunham and T. S. Miya, “A note on a simple apparatus for detecting neurological deficit in rats and mice,” Journal of the American Pharmaceutical Association, vol. 46, no. 3, pp. 208–209, 1957. View at Google Scholar · View at Scopus
  22. R. J. Hamm, B. R. Pike, D. M. O'Dell, B. G. Lyeth, and L. W. JenKins, “The rotarod test: an evaluation of its effectiveness in assessing motor deficits following traumatic brain injury,” Journal of Neurotrauma, vol. 11, no. 2, pp. 187–196, 1994. View at Publisher · View at Google Scholar · View at Scopus
  23. J. J. Stewart, “Optimization of parameters for semiempirical methods I. Method,” Journal of Computational Chemistry, vol. 10, no. 2, pp. 209–220, 1989. View at Publisher · View at Google Scholar
  24. J. J. P. Stewart, “Optimization of parameters for semiempirical methods II. Applications,” Journal of Computational Chemistry, vol. 10, no. 2, pp. 221–264, 1989. View at Publisher · View at Google Scholar
  25. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 03, Revision C.02, Gaussian, Wallingford, Conn, USA, 2004.
  26. S. M. Hanson, E. V. Morlock, K. A. Satyshur, and C. Czajkowski, “Structural requirements for eszopiclone and zolpidem binding to the γ-aminobutyric acid type-A (GABAA) receptor are different,” Journal of Medicine Chemistry, vol. 51, no. 22, pp. 7243–7252, 2008. View at Publisher · View at Google Scholar
  27. G. M. Morris, D. S. Goodsell, R. S. Halliday et al., “Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function,” Journal of Computational Chemistry, vol. 19, no. 14, pp. 1639–1662, 1998. View at Publisher · View at Google Scholar · View at Scopus
  28. Y. Muroi, C. Czajkowski, and M. B. Jackson, “Local and global ligand-induced changes in the structure of the GABA A receptor,” Biochemistry, vol. 45, no. 23, pp. 7013–7022, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. G. M. Lipkind and H. A. Fozzard, “Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels,” Molecular Pharmacology, vol. 68, no. 6, pp. 1611–1622, 2005. View at Publisher · View at Google Scholar · View at Scopus
  30. E. Ramírez-San Juan, M. A. Soriano-Ursúa, J. Espinosa-Raya et al., “Anticonvulsant effects of bis-1,4-dihydropyridines and the probable role of L-type calcium channels suggested by docking simulations,” Medicinal Chemistry Research, vol. 23, pp. 5149–5159, 2014. View at Publisher · View at Google Scholar · View at Scopus
  31. W. Humphrey, A. Dalke, and K. Schulten, “VMD: visual molecular dynamics,” Journal of Molecular Graphics, vol. 14, no. 1, pp. 33–38, 1996. View at Publisher · View at Google Scholar · View at Scopus
  32. A. D. MacKerell Jr., D. Bashford, M. Bellott et al., “All-atom empirical potential for molecular modeling and dynamics studies of proteins,” The Journal of Physical Chemistry B, vol. 102, no. 18, pp. 3586–3616, 1998. View at Publisher · View at Google Scholar · View at Scopus
  33. J. C. Phillips, R. Braun, W. Wang et al., “Scalable molecular dynamics with NAMD,” Journal of Computational Chemistry, vol. 26, no. 16, pp. 1781–1802, 2005. View at Publisher · View at Google Scholar · View at Scopus
  34. P. J. Goodford, “A computational procedure for determining energetically favorable binding sites on biologically important macromolecules,” Journal of Medicinal Chemistry, vol. 28, no. 7, pp. 849–857, 1985. View at Publisher · View at Google Scholar · View at Scopus
  35. E. A. Swinyard, R. D. Sofia, and H. J. Kupferberg, “Comparative anticonvulsant activity and neurotoxicity of felbamate and four prototype antiepileptic drugs in mice and rats,” Epilepsia, vol. 27, no. 1, pp. 27–34, 1986. View at Publisher · View at Google Scholar · View at Scopus
  36. J. J. Łuszczki, T. Plech, and M. Wujec, “Influence of 5-(3-chlorophenyl)-4-(4-methylphenyl)-2,4-dihydro-3H-1,2,4- triazole-3-thioneon the anticonvulsant action of 4 classical antiepileptic drugs in the mouse maximal electroshock-induced seizure model,” Pharmacological Reports, vol. 64, no. 4, pp. 970–978, 2012. View at Publisher · View at Google Scholar · View at Scopus
  37. D. Nieoczym, K. Socała, J. J. Łuszczki, S. J. Czuczwar, and P. Wlaź, “Influence of sildenafil on the anticonvulsant action of selected antiepileptic drugs against pentylenetetrazole-induced clonic seizures in mice,” Journal of Neural Transmission, vol. 119, no. 8, pp. 923–931, 2012. View at Publisher · View at Google Scholar · View at Scopus
  38. K. K. Borowicz, M. Banach, B. Piskorska, and S. J. Czuczwar, “Effect of acute and chronic tianeptine on the action of classical antiepileptics in the mouse maximal electroshock model,” Pharmacological Reports, vol. 65, no. 2, pp. 379–388, 2013. View at Publisher · View at Google Scholar · View at Scopus
  39. R. L. Krall, J. K. Penry, B. G. White, H. J. Kupferberg, and E. A. Swinyard, “Antiepileptic drug development: II. Anticonvulsant drug screening,” Epilepsia, vol. 19, no. 4, pp. 409–428, 1978. View at Publisher · View at Google Scholar · View at Scopus
  40. R. K. Mishra and M. T. Baker, “Ortho Substituent effects on the anticonvulsant properties of 4-hydroxy-trifluoroethyl phenols,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 17, pp. 5608–5611, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. M. Iman, A. Saadabadi, and A. Davood, “Docking studies of phthalimide pharmacophore as a sodium channel blocker,” Iranian Journal of Basic Medical Sciences, vol. 16, no. 9, pp. 1016–1021, 2013. View at Google Scholar · View at Scopus
  42. J. M. C. Derry, S. M. J. Dunn, and M. Davies, “Identification of a residue in the γ-aminobutyric acid type A receptor α subunit that differentially affects diazepam-sensitive and -insensitive benzodiazepine site binding,” Journal of Neurochemistry, vol. 88, no. 6, pp. 1431–1438, 2004. View at Publisher · View at Google Scholar · View at Scopus
  43. E. V. Morlock and C. Czajkowski, “Different residues in the GABAA receptor benzodiazepine binding pocket mediate benzodiazepine efficacy and binding,” Molecular Pharmacology, vol. 80, pp. 14–22, 2011. View at Google Scholar
  44. L. Richter, C. De Graaf, W. Sieghart et al., “Diazepam-bound GABAA receptor models identify new benzodiazepine binding-site ligands,” Nature Chemical Biology, vol. 8, no. 5, pp. 455–464, 2012. View at Publisher · View at Google Scholar · View at Scopus
  45. J. H. Kloda and C. Czajkowski, “Agonist-, antagonist-, and benzodiazepine-induced structural changes in the α1Met113-Leu132 region of the GABA A receptor,” Molecular Pharmacology, vol. 71, no. 2, pp. 483–493, 2007. View at Publisher · View at Google Scholar · View at Scopus
  46. K. Kamiński, J. Obniska, I. Chlebek, P. Liana, and E. Pȩkala, “Synthesis and biological properties of new N-Mannich bases derived from 3-methyl-3-phenyl- and 3,3-dimethyl-succinimides. Part V,” European Journal of Medicinal Chemistry, vol. 66, pp. 12–21, 2013. View at Publisher · View at Google Scholar · View at Scopus
  47. S. E. Meza-Toledo, J. G. Cervantes-Espinoza, E. Vargas-Fernández et al., “Anticonvulsant activity and neurotoxicity of the enantiomers of DL-HEPP,” African Journal of Pharmacy and Pharmacology, vol. 7, no. 34, pp. 2397–2405, 2013. View at Publisher · View at Google Scholar
  48. A. Davood, H. Shafaroodi, M. Amini, A. Nematollahi, M. Shirazi, and M. Iman, “Design, synthesis and protection against pentylenetetrazole-induced seizure of N-aryl derivatives of the phthalimide pharmacophore,” Medicinal Chemistry, vol. 8, no. 5, pp. 953–963, 2012. View at Publisher · View at Google Scholar · View at Scopus