Artículo

Duchowicz, P.R.; Bennardi, D.O.; Bacelo, D.E.; Bonifazi, E.L.; Rios-Luci, C.; Padrón, J.M.; Burton, G.; Misico, R.I. "QSAR on antiproliferative naphthoquinones based on a conformation- independent approach" (2014) European Journal of Medicinal Chemistry. 77:176-184
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Abstract:

The antiproliferative activities of a series of 36 naphthoquinone derivatives were subjected to a Quantitative Structure-Activity Relationships (QSAR) study. For this purpose a panel of four human cancer cell lines was used, namely HBL-100 (breast), HeLa (cervix), SW-1573 (non-small cell lung) and WiDr (colon). A conformation-independent representation of the chemical structure was established in order to avoid leading with the scarce experimental information on X-ray crystal structure of the drug interaction. The 1179 theoretical descriptors derived with E-Dragon and Recon software were simultaneously analyzed through linear regression models based on the Replacement Method variable subset selection technique. The established models were validated and tested through the use of external test sets of compounds, the Leave-One-Out Cross Validation method, Y-Randomization and Applicability Domain analysis.© 2014 Elsevier Masson SAS. All rights reserved.

Registro:

Documento: Artículo
Título:QSAR on antiproliferative naphthoquinones based on a conformation- independent approach
Autor:Duchowicz, P.R.; Bennardi, D.O.; Bacelo, D.E.; Bonifazi, E.L.; Rios-Luci, C.; Padrón, J.M.; Burton, G.; Misico, R.I.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas INIFTA, Diag. 113 y 64, C.C. 16, Sucursal 4, 1900 La Plata, Argentina
Cátedra de Química Orgánica, Facultad de Ciencias Agrarias y Forestales, Universidad Nacional de la Plata (UNLP), 60 y 119, B1904AAN La Plata, Argentina
Departamento de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Belgrano, Villanueva 1324, C1426BMJ Ciudad de Buenos Aires, Argentina
Departamento de Química Orgánica y UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Ciudad de Buenos Aires, Argentina
BioLab, Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain
Palabras clave:Cancer; Molecular descriptors; Multivariable linear regression; Naphthoquinone derivative; QSAR theory; 1,4 naphthoquinone derivative; 5 hydroxylomatiol; 6 hydroxy beta dunnione; 6 hydroxy beta isodunnione; 6 hydroxy dehydro iso beta lapachone; 8 hydroxy alpha dunnione; 8 hydroxylomatiol; 9 hdroxy beta dunnione; 9 hydroxy beta isodunnione; 9 hydroxy dehydro iso beta lapachone; antineoplastic agent; hydrochloric acid; hydroxy alpha dunnione; mesylic acid; naphthoquinone; sulfuric acid; unclassified drug; antineoplastic agent; naphthoquinone; antineoplastic activity; antiproliferative activity; article; cancer cell culture; carbon nuclear magnetic resonance; chemical structure; column chromatography; crystal structure; cyclization; deacetylation; drug conformation; drug synthesis; human; human cell; human cell culture; infrared spectroscopy; isomerization; melting point; nuclear magnetic resonance; proton nuclear magnetic resonance; quantitative structure activity relation; reaction time; thin layer chromatography; validation process; cell proliferation; cell survival; chemistry; conformation; dose response; drug effects; drug screening; HeLa cell line; structure activity relation; synthesis; tumor cell culture; Antineoplastic Agents; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HeLa Cells; Humans; Molecular Conformation; Naphthoquinones; Quantitative Structure-Activity Relationship; Structure-Activity Relationship; Tumor Cells, Cultured
Año:2014
Volumen:77
Página de inicio:176
Página de fin:184
DOI: http://dx.doi.org/10.1016/j.ejmech.2014.02.057
Título revista:European Journal of Medicinal Chemistry
Título revista abreviado:Eur. J. Med. Chem.
ISSN:02235234
CODEN:EJMCA
CAS:hydrochloric acid, 7647-01-0; mesylic acid, 2386-57-4, 75-75-2; sulfuric acid, 7664-93-9; Antineoplastic Agents; Naphthoquinones
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v77_n_p176_Duchowicz

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Citas:

---------- APA ----------
Duchowicz, P.R., Bennardi, D.O., Bacelo, D.E., Bonifazi, E.L., Rios-Luci, C., Padrón, J.M., Burton, G.,..., Misico, R.I. (2014) . QSAR on antiproliferative naphthoquinones based on a conformation- independent approach. European Journal of Medicinal Chemistry, 77, 176-184.
http://dx.doi.org/10.1016/j.ejmech.2014.02.057
---------- CHICAGO ----------
Duchowicz, P.R., Bennardi, D.O., Bacelo, D.E., Bonifazi, E.L., Rios-Luci, C., Padrón, J.M., et al. "QSAR on antiproliferative naphthoquinones based on a conformation- independent approach" . European Journal of Medicinal Chemistry 77 (2014) : 176-184.
http://dx.doi.org/10.1016/j.ejmech.2014.02.057
---------- MLA ----------
Duchowicz, P.R., Bennardi, D.O., Bacelo, D.E., Bonifazi, E.L., Rios-Luci, C., Padrón, J.M., et al. "QSAR on antiproliferative naphthoquinones based on a conformation- independent approach" . European Journal of Medicinal Chemistry, vol. 77, 2014, pp. 176-184.
http://dx.doi.org/10.1016/j.ejmech.2014.02.057
---------- VANCOUVER ----------
Duchowicz, P.R., Bennardi, D.O., Bacelo, D.E., Bonifazi, E.L., Rios-Luci, C., Padrón, J.M., et al. QSAR on antiproliferative naphthoquinones based on a conformation- independent approach. Eur. J. Med. Chem. 2014;77:176-184.
http://dx.doi.org/10.1016/j.ejmech.2014.02.057