Journal
MOLECULES
Volume 24, Issue 7, Pages -Publisher
MDPI
DOI: 10.3390/molecules24071279
Keywords
terpenylquinones; naphthoquinones; anthraquinones; antiviral activity; herpesvirus; dengue virus; cytotoxicity
Funding
- Colciencias (Patrimonio Autonomo del Fondo Nacional de Financiamiento para la Ciencia, la Tecnologia y la Innovacion, Francisco Jose de Caldas-Colombia) [744 2016, 648-2017, 111574455595]
- CODI (Comite para el Desarrollo de la Investigacion-Universidad de Antioquia) [2014-1041]
- Estrategia de Sostenibilidad (CODI) 2016-2017 de la Universidad de Antioquia
- Spanish MINECO - Fondo Social Europeo of the European Union (Fondos FEDER-EU) [CTQ2015-68175-R, AGL2016-79813-C2-2-R]
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Quinones are secondary metabolites of higher plants associated with many biological activities, including antiviral effects and cytotoxicity. In this study, the anti-herpetic and anti-dengue evaluation of 27 terpenyl-1,4-naphthoquinone (NQ), 1,4-anthraquinone (AQ) and heterocycle-fused quinone (HetQ) derivatives was done in vitro against Human Herpesvirus (HHV) type 1 and 2, and Dengue virus serotype 2 (DENV-2). The cytotoxicity on HeLa and Jurkat tumor cell lines was also tested. Using plaque forming unit assays, cell viability assays and molecular docking, we found that NQ 4 was the best antiviral compound, while AQ 11 was the most active and selective molecule on the tested tumor cells. NQ 4 showed a fair antiviral activity against Herpesviruses (EC50: <0.4 mu g/mL, <1.28 mu M) and DENV-2 (1.6 mu g/mL, 5.1 mu M) on pre-infective stages. Additionally, NQ 4 disrupted the viral attachment of HHV-1 to Vero cells (EC50: 0.12 mu g/mL, 0.38 mu M) with a very high selectivity index (SI = 1728). The in silico analysis predicted that this quinone could bind to the prefusion form of the E glycoprotein of DENV-2. These findings demonstrate that NQ 4 is a potent and highly selective antiviral compound, while suggesting its ability to prevent Herpes and Dengue infections. Additionally, AQ 11 can be considered of interest as a leader for the design of new anticancer agents.
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