Potential anti-herpes and cytotoxic action of novel semisynthetic digitoxigenin-derivatives

European Journal of Medicinal Chemistry
Laurita BoffCláudia Maria Oliveira Simões

Abstract

In recent years, new therapeutic possibilities were proposed for cardiac glycosides traditionally used to treat heart diseases, such as anticancer and antiviral activities. In this sense, this work aimed to synthesize the readily accessible 3β-azido-3-deoxydigitoxigenin (5) from digitoxigenin (1). Two new series of compounds were obtained from derivative (5): (i) O-glycosyl trizols through click chemistry with propargyl glycosides; and (ii) compounds substituted in the alpha carbonyl position with different residues linked via an amino-group. All obtained derivatives have their chemical structures confirmed, and their anti-herpes (against HSV-types 1 and 2 replication) and cytotoxic (against PC3, A549, HCT-8 and LNCaP cell lines) activities evaluated. Compounds 10 and 11 exhibited the most promising results against HSV-1 (KOS and 29-R strains) and HSV-2 (333 strain) replication with SI values > 1000. Both compounds were also the most cytotoxic for the human cancer cell lines tested with IC50 values similar to those of paclitaxel. They also presented reduced toxicity toward non-cancerous cell lines (MRC-5 and HGF cells). Promising compounds were tested in regard to their ability to inhibit Na+/K+-ATPase. The inhibition rate corr...Continue Reading

Citations

Apr 21, 2020·Journal of Biomolecular Structure & Dynamics·I AanouzM Bouachrine
Feb 23, 2020·Anti-cancer Drugs·Laurita BoffCláudia Maria Oliveira Simões
Apr 30, 2020·Archives of Virology·Laurita BoffCláudia Maria Oliveira Simões
Oct 25, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Laurita BoffStephan Ludwig
Aug 3, 2019·European Journal of Medicinal Chemistry·Lucia BiasuttoMario Zoratti
Jan 1, 2020·ACS Omega·Jennifer MunkertAndré L B de Barros

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