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Molecules 2016, 21(9), 1199; doi:10.3390/molecules21091199

Synthesis and Cytotoxic Activity on Human Cancer Cells of Novel Isoquinolinequinone–Amino Acid Derivatives

1
Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile
2
Instituto de Ciencias Exactas y Naturales Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile
3
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 26094411, Chile
4
Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile
5
Research Group of Toxicology and Cancer Biology, Louvain Drug Research Institute, Université Catholique de Louvain, 73 Avenue E. Mounier, GTOX 7309, Brussels 1200, Belgium
6
Bioanalysis and Pharmacology of Bioactive Lipids Laboratory, Louvain Drug Research Institute, Université Catholique de Louvain, 72 Avenue E. Mounier, BPBL 7201, Brussels 1200, Belgium
*
Author to whom correspondence should be addressed.
Academic Editor: Rafik Karaman
Received: 25 July 2016 / Revised: 1 September 2016 / Accepted: 2 September 2016 / Published: 8 September 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [3538 KB, uploaded 8 September 2016]   |  

Abstract

A variety of aminoisoquinoline-5,8-quinones bearing α-amino acids moieties were synthesized from 3-methyl-4-methoxycarbonylisoquinoline-5,8-quinone and diverse l- and d-α-amino acid methyl esters. The members of the series were evaluated for their cytotoxic activity against normal and cancer cell lines by using the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay. From the current investigation, structure–activity relationships demonstrate that the location and structure of the amino acid fragment plays a significant role in the cytotoxic effects. Moderate to high cytotoxic activity was observed and four members, derived from l-alanine, l-leucine, l-phenylalanine, and d-phenylalanine, were selected as promising compounds by their IC50 ranging from 0.5 to 6.25 μM and also by their good selectivity indexes (≥2.24). View Full-Text
Keywords: α-amino acid methyl ester; isoquinolinequinones; tumor cell lines; cytotoxic activity α-amino acid methyl ester; isoquinolinequinones; tumor cell lines; cytotoxic activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Valderrama, J.A.; Delgado, V.; Sepúlveda, S.; Benites, J.; Theoduloz, C.; Buc Calderon, P.; Muccioli, G.G. Synthesis and Cytotoxic Activity on Human Cancer Cells of Novel Isoquinolinequinone–Amino Acid Derivatives. Molecules 2016, 21, 1199.

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