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Rivera-Barroto, O.M.; Marrero-Ponce, Y.; Meneses-Marcel, A.; Escario, J.A.; Barrio, A.G.; Arán, V.J.; Alho, M.A.M.; Pereira, D.M.; Nogal, J.J.; Torrens, F.; Ibarra-Velarde, F.; Montenegro, Y.V.; Huesca-Guillén, A.; Rivera, N.; Vogel, C. "Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors" (2009) QSAR and Combinatorial Science. 28(1):9-26
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Abstract:

Few years ago, the World Health Organization estimated the number of adults with trichomoniasis at 170 million worldwide, more than the combined numbers for gonorrhea, syphilis, and chlamydia. To combat this sexually transmitted disease, Metronidazole (MTZ) has emerged, since 1959, as a powerful drug for the systematic treatment of infected patients. However, increasing resistance to MTZ, adverse effects associated to high-dose MTZ therapies and very expensive conventional technologies related to the development of new trichomonacidals necessitate novel computational methods that shorten the drug discovery pipeline. Therefore, bond-based bilinear indices, new 2-D bond-based TOMOCOMD-CARDD Molecular Descriptors (MDs), and Linear Discriminant Analysis (LDA) are combined to discover novel antitrichomonal agents. Generated models, using non-stochastic and stochastic indices, are able to classify correctly the 90.11% (93.75%) and the 87.92% (87.50%) of chemicals in the training (test) sets, respectively. In addition, they show large Matthews' correlation coefficients (C) of 0.80 (0.86) and 0.76 (0.71) for the training (test) sets, respectively. The result of predictions on the 10% full-out cross-validation test also evidences the quality of both models. In order to test the models' predictive power, 12 compounds, already proved against Trichomonas vaginalis (Tv), are screened in a simulated virtual screening experiment. As a result, they correctly classified 9 out of 12 (75.00%) and 10 out of 12 (83.33%) of the chemicals, respectively, which were the most important criteria to validate the models. Finally, in order to prove the reach of TOMOCOMD-CARDD approach and to discover new trichomonacidals, these classification functions were applied to a set of eight chemicals which, in turn, were synthesized and tested toward in vitro activity against Tv. As a result, experimental observations confirm theoretical predictions to a great extent, since it is gained a correct classification of 87.50% (7/8) of chemicals. Biological tests also show several candidates as antitrichomonals, since almost all the compounds [VAM2-(3-8)] exhibit pronounced cytocidal activities of 100% at the concentration of 100 mg/mL and at 24 h (48 h) but VAM2-2: 99.37% (100%), and it is remarkable that these compounds do not show toxic activity in macrophage assays at this concentration. The Quantitative Structure-Activity Relationship (QSAR) models presented here could significantly reduce the number of synthesized and tested compounds as well as could act as virtual shortcuts to new chemical entities with trichomonacidal activity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors
Autor:Rivera-Barroto, O.M.; Marrero-Ponce, Y.; Meneses-Marcel, A.; Escario, J.A.; Barrio, A.G.; Arán, V.J.; Alho, M.A.M.; Pereira, D.M.; Nogal, J.J.; Torrens, F.; Ibarra-Velarde, F.; Montenegro, Y.V.; Huesca-Guillén, A.; Rivera, N.; Vogel, C.
Filiación:Unit of Computer-Aided Molecular Biosilico Discovery and Bioinformatic Research CAMD-BIR Unit, Faculty of Chemistry-Pharmacy, Central University of Las Villas, Santa Clara 54830 Villa Clara, Cuba
Center of Studies on Bioinformatics CEI, Faculty of Mathematics Physics and Computer Science, Central University of Las Villas, Santa Clara 54830 Villa Clara, Cuba
Institut Universitari de Ciència Molecular, Universitat de València, Edifici d'Instituts de Paterna, E-46071 València, Spain
Unidad de Investigación de Diseño de Fármacos y Conectividad Molecular, Departamento de Química Física, Universitat de València, València, Spain
Departamento de Parasitología, Facultad de Farmacia, UCM, Pza. Ramón y Cajal s/n, 28040 Madrid, Spain
Instituto de Química Médica, CSIC, c/ Juan de la Cierva 3, 28006 Madrid, Spain
CIHIDECAR (CONICET), Dpto. de Química Orgánica, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Department of Parasitology, Faculty of Veterinarian Medicinal and Zootecnic, UNAM, Mexico, D. F. 04510, Mexico
Universität Rostock, Institut für Chemie, Abteilung für Organische Chemie, Albert-Einstein-Straße 3a, 18059 Rostock, Germany
Palabras clave:Bond-based bilinear indices; LDA-based QSAR model; Lead generation; TOMOCOMD-CARDD software; Trichomonacidal; abunidazole; acetarsol; aminitrozole; anisomycin; antitrichomonal agent; azanidazole; cariolin; carnidazole; clioquinol; clotrimazole; forminitrazole; furazolidone; glycarsiamidon; glycobiarzol; imoctetrazoline; lauroguadine; lauroguanidine; luthenurine; mepartricin; metronidazole; moxnidazole; nifuratel; nimorazole; propenidazole; satranidazole; secnidazole; thiacetarsamide; tivanidazole; unclassified drug; unindexed drug; virustomycin a; antiprotozoal activity; article; computer aided design; concentration (parameters); correlation coefficient; discriminant analysis; drug determination; drug research; drug screening; drug synthesis; in vitro study; incidence; macrophage; mathematical analysis; prediction; priority journal; quantitative structure activity relation; stochastic model; Trichomonas vaginalis; trichomoniasis; validation study; world health organization; Chlamydia; Trichomonas vaginalis
Año:2009
Volumen:28
Número:1
Página de inicio:9
Página de fin:26
DOI: http://dx.doi.org/10.1002/qsar.200610165
Título revista:QSAR and Combinatorial Science
Título revista abreviado:QSAR Comb. Sci.
ISSN:1611020X
CODEN:QCSSA
CAS:acetarsol, 97-44-9; aminitrozole, 140-40-9; anisomycin, 22862-76-6; azanidazole, 62973-76-6; carnidazole, 42116-76-7; clioquinol, 130-26-7, 8057-20-3; clotrimazole, 23593-75-1; furazolidone, 67-45-8; mepartricin, 11121-32-7, 62534-68-3, 62534-69-4; metronidazole, 39322-38-8, 443-48-1; moxnidazole, 30185-92-3, 52279-59-1; nifuratel, 4936-47-4; nimorazole, 6506-37-2; satranidazole, 56302-13-7; secnidazole, 3366-95-8; thiacetarsamide, 14433-82-0, 531-72-6; virustomycin a, 84777-85-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1611020X_v28_n1_p9_RiveraBarroto

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Citas:

---------- APA ----------
Rivera-Barroto, O.M., Marrero-Ponce, Y., Meneses-Marcel, A., Escario, J.A., Barrio, A.G., Arán, V.J., Alho, M.A.M.,..., Vogel, C. (2009) . Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors. QSAR and Combinatorial Science, 28(1), 9-26.
http://dx.doi.org/10.1002/qsar.200610165
---------- CHICAGO ----------
Rivera-Barroto, O.M., Marrero-Ponce, Y., Meneses-Marcel, A., Escario, J.A., Barrio, A.G., Arán, V.J., et al. "Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors" . QSAR and Combinatorial Science 28, no. 1 (2009) : 9-26.
http://dx.doi.org/10.1002/qsar.200610165
---------- MLA ----------
Rivera-Barroto, O.M., Marrero-Ponce, Y., Meneses-Marcel, A., Escario, J.A., Barrio, A.G., Arán, V.J., et al. "Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors" . QSAR and Combinatorial Science, vol. 28, no. 1, 2009, pp. 9-26.
http://dx.doi.org/10.1002/qsar.200610165
---------- VANCOUVER ----------
Rivera-Barroto, O.M., Marrero-Ponce, Y., Meneses-Marcel, A., Escario, J.A., Barrio, A.G., Arán, V.J., et al. Discovery of novel trichomonacidals using LDA-driven QSAR models and bond-based bilinear indices as molecular descriptors. QSAR Comb. Sci. 2009;28(1):9-26.
http://dx.doi.org/10.1002/qsar.200610165