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Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile
Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile
Instituto de Etno-Farmacología (IDE), Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile
* Author to whom correspondence should be addressed.
Received: 18 April 2012; in revised form: 23 May 2012 / Accepted: 25 May 2012 / Published: 7 June 2012
Abstract: The synthesis of 4-methoxycarbonyl-3-methylisoquinolinequinone (1) and a variety of its substitution products with amino-, alkylamino and halogen groups on the quinone nucleus is reported. The series of 6-, 7- and 6,7-subtituted isoquinolinequinones were evaluated in vitro for their cytotoxic activity using the MTT colorimetric method. All the newly synthesized compounds showed moderate to high potency against MRC-5 healthy lung fibroblasts and four human tumor cell lines: AGS gastric adenocarcinoma, SK-MES-1 lung, J82 bladder carcinoma, and HL-60 leukemia cells. Among the series, compounds 4b, 12 and 13 exhibited interesting antitumor activity against human gastric adenocarcinoma, human lung and human bladder carcinoma cancer cells. 7-Amino-6-bromoisoquinoline-5,8-quinone (13) was found to be the most promising active compound against the tested cancer cell lines, with IC50 values in the 0.21−0.49 mM range, lower than the anti-cancer agent etoposide used as reference.
Keywords: aminoisoquinoline-5,8-quinones; regioselectivity; anticancer; SAR analysis
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Delgado, V.; Ibacache, A.; Theoduloz, C.; Valderrama, J.A. Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones. Molecules 2012, 17, 7042-7056.
Delgado V, Ibacache A, Theoduloz C, Valderrama JA. Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones. Molecules. 2012; 17(6):7042-7056.
Delgado, Virginia; Ibacache, Andrea; Theoduloz, Cristina; Valderrama, Jaime A. 2012. "Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones." Molecules 17, no. 6: 7042-7056.