Facile biocatalytic access to 9-fluorenylmethyl polyglycosides: evaluation of antiviral activity on immunocompetent cells.
The biological activities of a series of mono- and oligosaccharides (beta-xylosides and alpha-glucosides) of 9-fluorenylmethanol were investigated together with mono-beta-galactoside and beta-glucoside of this aglycone, produced by biocatalytic routes. By using marine glycoside hydrolases and inexpensive donors such as maltose or xylan, access to mono-alpha-glucoside or mono-beta-xyloside of 9-fluorenylmethanol was obtained. Additionally, interesting polyglycoside derivatives were isolated. Biological testing indicated that in vitro treatment with these carbohydrate derivatives may influence the balance of cytokines in the environment of human peripheral blood mononuclear cells (PBMC), restricting the harmful effect of herpes simplex type 2 replication. In fact, these carbohydrate derivatives tested in WISH cells did not show any significant antiviral activity.
Tramice
Annabella
A
Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80072 Pozzuoli, Naples, Italy.
Arena
Adriana
A
De Gregorio
Ambra
A
Ottanà
Rosaria
R
Maccari
Rosanna
R
Pavone
Bernadette
B
Arena
Nicoletta
N
Iannello
Daniela
D
Vigorita
Maria Gabriella
MG
Trincone
Antonio
A
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D016207:Cytokines / Q000096:biosynthesis / Q000187:drug effects / Q000276:immunology; D004305:Dose-Response Relationship, Drug; D005449:Fluorenes / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018258:Herpesvirus 2, Human / Q000187:drug effects* / Q000276:immunology; D006801:Humans; D006867:Hydrolases / Q000737:chemistry*; D007963:Leukocytes, Mononuclear / Q000187:drug effects* / Q000276:immunology; D008320:Maltose / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D018675:Toxicity Tests; D014779:Virus Replication / Q000187:drug effects / Q000276:immunology; D014990:Xylans / Q000737:chemistry
C533733:9-fluorenylmethanol; D000998:Antiviral Agents; D016207:Cytokines; D005449:Fluorenes; D006027:Glycosides; D009844:Oligosaccharides; D014990:Xylans; D008320:Maltose; D006867:Hydrolases