Aplicación de la topología molecular a la predicción y optimización de la actividad repelente de mosquitos de derivados de la N-acypiperidina

  1. Rodríguez Martínez, María Ángeles
  2. Seguí López-Peñalver, Raimundo J.
  3. Alcácer Tomás, Gemma
  4. Gálvez Álvarez, Jorge
  5. Gálvez Llompart, María
  6. García Domenech, Ramón
Journal:
Nereis: revista iberoamericana interdisciplinar de métodos, modelización y simulación

ISSN: 1888-8550

Year of publication: 2014

Issue: 6

Pages: 19-26

Type: Article

DIALNET GOOGLE SCHOLAR lock_openDialnet editor

More publications in: Nereis: revista iberoamericana interdisciplinar de métodos, modelización y simulación

Abstract

A topological-mathematical model has been developed based on Multilinear Regression Analysis in order to search new active molecules with mosquito repellent activity. The molecular characterization was performed using topological indexes and a 5-variable model was chosen for prediction of protection times (R2 = 0.8457 and Q2 = 0.7486). The model was validated by an internal leave-one-out-type cross-validation and a randomization test. The results confirmed the predictive power for the property under study. Finally, after carrying out a virtual screening, new compounds have been proposed with expected higher potency as mosquito repellents.

Bibliographic References

  • Health Link BC January (2013). Insect Repellents and DEET, Bristish Columbia 96.
  • S. C. Basak, D. R. Mills, A. T. Balaban, B. D. Gute, Prediction of mutagenicity of aromatic and heteroaromatic amines from structure: A hierarchical QSAR approach. J Chem Inf Comput Sci 41 (2001) 671-678.
  • R. Garcia-Domenech, J. Galvez, J. V. de Julian-Ortiz, L. Pogliani, Some new trends in chemical graph theory. Chem Rev 108 (2008) 1127-1169.
  • A. R. Katritzky, Z. Wang, S. Slavov, M. Tsikolia, D. Dobchev, N. G. Akhmedov, U. Bernier, G. G. Clark and K. J. Linthicum, Synthesis and bioassay of improved mosquito repellents predicted from chemical structure. PNAS 21 (2008) 7359-7354.
  • J. Galvez, J. V. de Julian-Ortiz and R. García-Domench, Application of molecular topology to the prediction of potency and selection of novel insecticides active against malaria vectors. Theochem 727 (2005) 107-113.
  • R. García-Domenech, J. Aguilera, A. El Moncef, S. Pocovi and Jorge Gálvez, Application of molecular topology to the prediction of mosquito repellents of a group of terpenoid compounds, Molecular Diversity 14(2) (2010) 321-329.
  • R. García-Domenech, P. García-Mujica, U. Gil, C. Casanova, J. Mireilli Beltrán, J. Gálvez, Search of QSAR models for natural sesquiterpenes repellent activity against the Yellow Fever mosquito, Aedes aegypti, Afinidad 67 (547) (2010) 187- 192.
  • L. B. Kier, L. H. Hall, Molecular Connectivity in Chemistry and Drug Research. Academic Press, London (1976).
  • L. B. Kier, L. H. Hall, Molecular Connectivity in Structure-Activity Analysis, Wiley, New York (1986).
  • J. Galvez, R. García-Domenech, M. T. Salabert, R. Soler, Charge indexes. New topological Descriptors. J Chem Inf Comput Sci 34 (1994) 520-525.
  • H. J. Wiener, Structural determination of paraffin boiling points. Journal of the American Chemical Society 69(1) (1947) 17-20.
  • DESMOL11 Software. Unidad de Investigación de Diseño de Fármacos y Conectividad Molecular. Facultad de Farmacia Universitat de Valéncia, Spain. Statistica 8.0 (2008) Statsoft Inc http://www.statsoft.com
Data source: Dialnet