2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5

Adriana Arena, Nicoletta Arena, Rosella Ciurleo, Ambra de Gregorio, Rosanna Maccari, Rosaria Ottana', Bernadette Pavone, Annabella Tramice, Antonio Trincone, Maria Gabriella Vigorita

Research output: Contribution to journalArticle

Abstract

In pursuing a research on the antiviral and immunomodulatory activity of tilorone congeners, two new series of compounds were prepared and pharmacologically explored: 9-fluorenone carboxyhydroxyesters, indicated as AG, and 9-fluorenone carboxyhydroxamides, indicated as MG. Two of them, AG17 and MG3, were used as sugar acceptors in the transglycosylation reactions performed by α- and β-glucosidases extracted from the marine mollusc Aplysia fasciata providing different α- and β-, mono- and oligosaccharides. Then aglycons and saccharides were assayed for cytotoxicity, for anti-herpes virus-2 properties on peripheral blood mononuclear cells (PBMC) and for their capability to trigger human cells to produce antiviral cytokines such as IFNα and TNFα. Some promising compounds were individuated whereas the utility of the biocatalytic procedures in the preparation of pure anomeric material was further focused.

Original languageEnglish
Pages (from-to)2656-2664
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume43
Issue number12
DOIs
Publication statusPublished - Dec 2008

Keywords

  • α and β-O-Glucosides
  • 9-Fluorenone-2-carboxyhydroxamides
  • 9-Fluorenone-4-carboxyhydroxyesters
  • Antiviral activity
  • Enzymatic transglycosylation
  • Immunomodulatory

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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    Arena, A., Arena, N., Ciurleo, R., de Gregorio, A., Maccari, R., Ottana', R., Pavone, B., Tramice, A., Trincone, A., & Vigorita, M. G. (2008). 2/4-Substituted-9-fluorenones and their O-glucosides as potential immunomodulators and anti-herpes simplex virus-2 agents. Part 5. European Journal of Medicinal Chemistry, 43(12), 2656-2664. https://doi.org/10.1016/j.ejmech.2008.01.045