Biocatalysed synthesis of beta-O-glucosides from 9-fluorenon-2-carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties

Autor: Francesco Ortuso, Rosaria Di Bella, Stefano Alcaro, Maria Gabriella Vigorita, Rosaria Ottanà, Simonetta Neri, Bernadette Pavone, Antonio Trincone, Adriana Arena
Rok vydání: 2004
Předmět:
Models
Molecular
Glycosylation
ENZYMATIC-SYNTHESIS
SIMPLEX-VIRUS TYPE-1
POLYCYCLIC AROMATIC-COMPOUNDS
SULFOLOBUS-SOLFATARICUS
TILORONE HYDROCHLORIDE
ANTIVIRAL RESPONSES
MOLECULAR MECHANICS
INTERFERON
AGENTS
GLYCOSAMINOGLYCANS
Herpesvirus 2
Human
Clinical Biochemistry
ved/biology.organism_classification_rank.species
Pharmaceutical Science
Virus Replication
Biochemistry
Chemical synthesis
chemistry.chemical_compound
Glucosides
Interferon
Drug Discovery
Cytotoxicity
Enzymatic transglycosylation
9-Fluorenon-2-carbohydroxyesters
Molecular Structure
Sulfolobus solfataricus
Cell Differentiation
U937 Cells
9-Fluoren-b-O-glycosides
Molecular Medicine
Glucosidases
medicine.drug
IFN-inducing properties
Stereochemistry
Down-Regulation
Antineoplastic Agents
Antiviral Agents
Catalysis
Structure-Activity Relationship
medicine
Structure–activity relationship
Humans
Molecular Biology
Cell Proliferation
Fluorenes
ved/biology
Organic Chemistry
Tilorone
Interferon-alpha
Herpes Simplex
Interferon-beta
In vitro
Tilorone analogues
chemistry
Zdroj: Bioorganic & medicinal chemistry
13 (2005): 3371–3378. doi:10.1016/j.bmc.2005.03.016
info:cnr-pdr/source/autori:S Alcaro; A Arena; R Di Bella; S Neri; R Ottanà; F Ortuso; B Pavone; A Trincone; MG Vigorita/titolo:Biocatalysed synthesis of b-O-glucosides from 9-fluorenon-2-carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties/doi:10.1016%2Fj.bmc.2005.03.016/rivista:Bioorganic & medicinal chemistry (Print)/anno:2005/pagina_da:3371/pagina_a:3378/intervallo_pagine:3371–3378/volume:13
ISSN: 0968-0896
DOI: 10.1016/j.bmc.2005.03.016
Popis: In pursuing research on the antiviral, interferon (IFN)-inducing tilorone congeners, a new series of fluoren-carboxyhydroxyesters has been prepared and biologically explored. These esters have subsequently been used as sugar acceptors in the enzymatic transglycosylation reaction using the 'retaining' beta-glycosidase from the archaeon Sulfolobus solfataricus (Ssbeta-Gly). Both aglycones (1-6) and corresponding beta-glucosides (beta-glu 1-beta-glu 6) have been screened for cytotoxicity, interferon-stimulating and antiviral properties against HSV-2. It was found that the addition of compounds beta-glu 5, beta-glu 6 and beta-glu 4 to HSV-2 infected U937 cells downregulates viral replication and triggers cells to release IFN-alpha/beta. Taken together, the results showed improved pharmacological profiles as a consequence of glycosylation. A molecular modelling study carried out on this series of compounds completed the structural characterisation of the novel compounds.
Databáze: OpenAIRE
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