Antiviral activity and metal ion-binding properties of some 2-hydroxy-3-methoxyphenyl acylhydrazones

• Published in: Biometals Vol. 31; no. 1; pp. 81 - 89
• Main Authors: Carcelli, M., Fisicaro, E., Compari, C., Contardi, L., Rogolino, D., Solinas, C., Stevaert, A., Naesens, L.
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01.02.2018; Springer Nature B.V
• Subjects: Antiviral activity; Biochemistry; Biological activity; Biomedical and Life Sciences; Cell Biology; Cervical carcinoma; Cervix; Copper; Cytotoxicity; Embryo fibroblasts; Herpes simplex; Herpes viruses; Homeostasis; Life Sciences; Ligands; Lungs; Medicine/Public Health; Metal ions; Microbiology; Parainfluenza; Pharmacology/Toxicology; Plant Physiology; Respiratory syncytial virus; Selectivity; Stomatitis; Vaccines; Viruses; Copper homeostasis; Antiviral; Copper complex; Isothermal titration calorimetry; Acylhydrazone
• ISSN: 0966-0844; 1572-8773
• DOI: 10.1007/s10534-017-0070-6

Here we report on the results obtained from an antiviral screening, including herpes simplex virus, vaccinia virus, vesicular stomatitis virus, Coxsackie B4 virus or respiratory syncytial virus, parainfluenza-3 virus, reovirus-1 and Punta Toro virus, of three 2-hydroxy-3-methoxyphenyl acylhydrazone compounds in three cell lines (i.e. human embryonic lung fibroblast cells, human cervix carcinoma cells, and African Green monkey kidney cells). Interesting antiviral EC 50 values are obtained against herpes simplex virus-1 and vaccinia virus. The biological activity of acylhydrazones is often attributed to their metal coordinating abilities, so potentiometric and microcalorimetric studies are here discussed to unravel the behavior of the three 2-hydroxy-3-methoxyphenyl compounds in solution. It is worth of note that the acylhydrazone with the higher affinity for Cu(II) ions shows the best antiviral activity against herpes simplex and vaccinia virus (EC 50  ~ 1.5 µM, minimal cytotoxic concentration = 60 µM, selectivity index = 40).