Artículo

Ríos-Luci, C.; Bonifazi, E.L.; León, L.G.; Montero, J.C.; Burton, G.; Pandiella, A.; Misico, R.I.; Padrón, J.M. "β-Lapachone analogs with enhanced antiproliferative activity" (2012) European Journal of Medicinal Chemistry. 53:264-274
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Abstract:

In this study, we describe the synthesis of a series of α- and β-lapachone containing hydroxyl or methoxyl groups on the benzene ring, by means of the selective acid promoted cyclization of the appropriate lapachol analog. The evaluation of the antiproliferative activity in human solid tumor cell lines provided 7-hydroxy-β-lapachone as lead with enhanced activity over the parent drug β-lapachone. Cell cycle studies, protein expression experiments, and reactive oxygen species analysis revealed that, similarly to β-lapachone, ROS formation and DNA damage are critical factors in the cellular toxicity of 7-hydroxy-β-lapachone. © 2012 Elsevier Masson SAS. All rights reserved.

Registro:

Documento: Artículo
Título:β-Lapachone analogs with enhanced antiproliferative activity
Autor:Ríos-Luci, C.; Bonifazi, E.L.; León, L.G.; Montero, J.C.; Burton, G.; Pandiella, A.; Misico, R.I.; Padrón, J.M.
Filiación:BioLab, Instituto Universitario de Bio-Orgánica Antonio González, Universidad de la Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain
Departamento de Química Orgánica/UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, C1428EHA Buenos Aires, Argentina
Centro de Investigación Del Cáncer, IBMCC/CSIC-Universidad de Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain
Palabras clave:β-Lapachone; Antitumor agents; Cell cycle; Naphthoquinone; Structure-activity relationships; 2 hydroxy 5 methoxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione (5 methoxylapachol); 2 hydroxy 7 methoxynaphthalene 1,4 dione (2 hydroxy 7 methoxy 1,4 naphthoquinone; 3 hydroxy 6 methoxy 2 (3 methylbut 2 en 1 yl)naphthalene 1,4 dione (7 methoxylapachol); 3,4 dihydro 10 hydroxy 2,2 dimethyl 2h benzo[g]chromene 5,6 dione (10 hydroxy beta lapachone); 3,4 dihydro 10 methoxy 2,2 dimethyl 2h benzo[g]chromene 5,6 dione (10 methoxy beta lapachone); 3,4 dihydro 6 hydroxy 2,2 dimethyl 2h benzo[g]chromene 5,10 dione (6 hydroxy alpha lapachone); 3,4 dihydro 6 hydroxy 2,2 dimethyl 2h benzo[g]chromene 5,10 dione (6 methoxy alpha lapachone); 3,4 dihydro 7 hydroxy 2,2 dimethyl 2h benzo[g]chromene 5,6 dione (7 hydroxy beta lapachone); 3,4 dihydro 7 methoxy 2,2 dimethyl 2h benzo[h]chromene 5,6 dione (7 methoxy beta lapachone); 3,4 dihydro 8 hydroxy 2,2 dimethyl 2h benzo[h]chromene 5,6 dione (8 hydroxy beta lapachone); 3,4 dihydro 8 methoxy 2,2 dimethyl 2h benzo[g]chromene 5,10 dione (8 methoxy alpha lapachone); 3,4 dihydro 8 methoxy 2,2 dimethyl 2h benzo[h]chromene 5,6 dione (8 methoxy beta lapachone); 3,4 dihydro 9 hydroxy 2,2 dimethyl 2h benzo[g]chromene 5,10 dione (9 hydroxy alpha lapachone); 3,4,5,6 tetrahydro 2,2 dimethyl 5,6 dioxo 2h benzo[h]chromen 7 yl pivalate (7 pivaloyl beta lapachone); 7 hydroxy beta lapachone; alpha lapachone; antineoplastic agent; benzene; beta lapachone; hydroxyl group; isomerase inhibitor; reactive oxygen metabolite; unclassified drug; antiproliferative activity; article; cell cycle; cyclization; cytotoxicity; DNA damage; drug synthesis; protein expression; tumor cell line; Antineoplastic Agents; Cell Cycle; Cell Line, Tumor; Cell Proliferation; DNA Topoisomerases; Humans; Naphthoquinones; Reactive Oxygen Species; Topoisomerase Inhibitors
Año:2012
Volumen:53
Página de inicio:264
Página de fin:274
DOI: http://dx.doi.org/10.1016/j.ejmech.2012.04.008
Título revista:European Journal of Medicinal Chemistry
Título revista abreviado:Eur. J. Med. Chem.
ISSN:02235234
CODEN:EJMCA
CAS:benzene, 71-43-2; beta lapachone, 4707-32-8; Antineoplastic Agents; DNA Topoisomerases, 5.99.1.-; Naphthoquinones; Reactive Oxygen Species; Topoisomerase Inhibitors; alpha-lapachone; beta-lapachone, 4707-32-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v53_n_p264_RiosLuci

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Citas:

---------- APA ----------
Ríos-Luci, C., Bonifazi, E.L., León, L.G., Montero, J.C., Burton, G., Pandiella, A., Misico, R.I.,..., Padrón, J.M. (2012) . β-Lapachone analogs with enhanced antiproliferative activity. European Journal of Medicinal Chemistry, 53, 264-274.
http://dx.doi.org/10.1016/j.ejmech.2012.04.008
---------- CHICAGO ----------
Ríos-Luci, C., Bonifazi, E.L., León, L.G., Montero, J.C., Burton, G., Pandiella, A., et al. "β-Lapachone analogs with enhanced antiproliferative activity" . European Journal of Medicinal Chemistry 53 (2012) : 264-274.
http://dx.doi.org/10.1016/j.ejmech.2012.04.008
---------- MLA ----------
Ríos-Luci, C., Bonifazi, E.L., León, L.G., Montero, J.C., Burton, G., Pandiella, A., et al. "β-Lapachone analogs with enhanced antiproliferative activity" . European Journal of Medicinal Chemistry, vol. 53, 2012, pp. 264-274.
http://dx.doi.org/10.1016/j.ejmech.2012.04.008
---------- VANCOUVER ----------
Ríos-Luci, C., Bonifazi, E.L., León, L.G., Montero, J.C., Burton, G., Pandiella, A., et al. β-Lapachone analogs with enhanced antiproliferative activity. Eur. J. Med. Chem. 2012;53:264-274.
http://dx.doi.org/10.1016/j.ejmech.2012.04.008