Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

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-hydr...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Bonifazi, E.L., Ríos-Luci, C., León, L.G., Burton, G., Padrón, J.M., Misico, R.I.
Formato:	JOUR
Materias:	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
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_09680896_v18_n7_p2621_Bonifazi
record_format	dspace
spelling	todo:paper_09680896_v18_n7_p2621_Bonifazi2023-10-03T15:55:14Z Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol Bonifazi, E.L. Ríos-Luci, C. León, L.G. Burton, G. Padrón, J.M. Misico, R.I. 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 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. Fil:Bonifazi, E.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 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
topic_facet	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
description	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.
format	JOUR
author	Bonifazi, E.L. Ríos-Luci, C. León, L.G. Burton, G. Padrón, J.M. Misico, R.I.
author_facet	Bonifazi, E.L. Ríos-Luci, C. León, L.G. Burton, G. Padrón, J.M. Misico, R.I.
author_sort	Bonifazi, E.L.
title	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_short	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_full	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_fullStr	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_full_unstemmed	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_sort	antiproliferative activity of synthetic naphthoquinones related to lapachol. first synthesis of 5-hydroxylapachol
url	http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
work_keys_str_mv	AT bonifaziel antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT rioslucic antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT leonlg antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT burtong antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT padronjm antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT misicori antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol
_version_	1807315530416128000

Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

Ejemplares similares