Artículo
Bonifazi, E.L.; Ríos-Luci, C.; León, L.G.; Burton, G.; Padrón, J.M.; Misico, R.I. "Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol" (2010) Bioorganic and Medicinal Chemistry. 18(7):2621-2630
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Abstract:
A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity. © 2010 Elsevier Ltd. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol |
| Autor: | Bonifazi, E.L.; Ríos-Luci, C.; León, L.G.; Burton, G.; Padrón, J.M.; Misico, R.I. |
| Filiación: | Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Universidad de La Laguna, C/Astrofisico Francisco Sanchez 2, 38206 La Laguna, Tenerife, Spain BioLab, Instituto Canario de Investigación del Cáncer (ICIC), C/Astrofisico Francisco Sanchez 2, 38206 La Laguna, Tenerife, Spain |
| Palabras clave: | Antiproliferative; Lapachol; Lapachone; Naphthoquinone; 1,4 naphthoquinone derivative; 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione; 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione; 5 hydroxylapachol; juglone; lapachol; unclassified drug; article; cancer cell culture; drug activity; drug structure; drug synthesis; human; human cell; lipophilicity; prenylation; structure activity relation; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Drug Screening Assays, Antitumor; Humans; Indicators and Reagents; Lipids; Magnetic Resonance Spectroscopy; Naphthoquinones; Prenylation; Structure-Activity Relationship |
| Año: | 2010 |
| Volumen: | 18 |
| Número: | 7 |
| Página de inicio: | 2621 |
| Página de fin: | 2630 |
| DOI: | http://dx.doi.org/10.1016/j.bmc.2010.02.032 |
| Título revista: | Bioorganic and Medicinal Chemistry |
| Título revista abreviado: | Bioorg. Med. Chem. |
| ISSN: | 09680896 |
| CODEN: | BMECE |
| CAS: | juglone, 481-39-0; lapachol, 84-79-7; 5-hydroxylapachol; Antineoplastic Agents, Phytogenic; Indicators and Reagents; Lipids; Naphthoquinones; lapachol, 84-79-7 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n7_p2621_Bonifazi |
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Citas:
---------- APA ----------
Bonifazi, E.L., Ríos-Luci, C., León, L.G., Burton, G., Padrón, J.M. & Misico, R.I. (2010) . Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol. Bioorganic and Medicinal Chemistry, 18(7), 2621-2630.http://dx.doi.org/10.1016/j.bmc.2010.02.032
---------- CHICAGO ----------
Bonifazi, E.L., Ríos-Luci, C., León, L.G., Burton, G., Padrón, J.M., Misico, R.I. "Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol" . Bioorganic and Medicinal Chemistry 18, no. 7 (2010) : 2621-2630.http://dx.doi.org/10.1016/j.bmc.2010.02.032
---------- MLA ----------
Bonifazi, E.L., Ríos-Luci, C., León, L.G., Burton, G., Padrón, J.M., Misico, R.I. "Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol" . Bioorganic and Medicinal Chemistry, vol. 18, no. 7, 2010, pp. 2621-2630.http://dx.doi.org/10.1016/j.bmc.2010.02.032
---------- VANCOUVER ----------
Bonifazi, E.L., Ríos-Luci, C., León, L.G., Burton, G., Padrón, J.M., Misico, R.I. Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol. Bioorg. Med. Chem. 2010;18(7):2621-2630.http://dx.doi.org/10.1016/j.bmc.2010.02.032
