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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Mäkinen, Kaarina Leino, Reko Savolainen, Johannes Mukherjee, Chinmoy |
| Description | Author Affiliation: Mukherjee C ( Laboratory of Organic Chemistry, Åbo Akademi University, 20500 Åbo, Finland.) |
| Abstract | A series of oligovalent carbohydrate assemblies (ranging from mono- to pentavalent), derived from three structurally different β-linked or β-(1→2)-linked mannosides, has been chemically synthesized, and the respective compounds have been biologically evaluated in order to investigate their immunostimulatory properties. The Crich methodology for β-mannosylation was successfully utilized to introduce the β-linkages, and a click chemistry protocol was utilized to generate the oligovalent derivatives. A convenient protecting group strategy involving the simultaneous use of both p-methoxybenzyl and benzylidene groups was employed, which allowed a simple and cost-effective global deprotection step. The immunomodulatory properties of the synthesized multivalent mannosides were evaluated by assessing cytokine production in human white blood cell cultures. The Th2-type cytokines interleukin-4 and interleukin-5 (IL-4 and IL-5), the Th1 cytokine interferon-γ (IFN-γ), the Treg cytokine IL-10, and the pro-inflammatory cytokine tumor necrosis factor (TNF) were included in the screening. A single trivalent acetylated mannobiose derivative was identified as a potent inducer of Treg and Th1 immune response, resulting in strong IL-10 and moderate IFN-γ productions dose-dependently, while inducing no Th2 cytokine response. The immunomodulatory properties of this trivalent mannoside were further studied in vitro in allergen (Bet v)-stimulated human peripheral blood mononuclear cell cultures of birch pollen allergic subjects. Stimulation with birch pollen induced strong IL-4 and IL-5 responses, which could be suppressed by the trivalent acetylated mannobiose derivative. The IL-10 response was also suppressed, whereas the production of IFN-γ was strongly enhanced. The results suggest that the identified lead compound has suppressive effects on the Th2-type allergic inflammatory response and shows potential as a possible lead adjuvant for the specific immunotherapy of allergies. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 24 |
| Volume Number | 19 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2013-06-10 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Adjuvants, Immunologic Chemical Synthesis Allergens Immunology Mannosides Oligosaccharides Chemistry Blood Betula Click Chemistry Cytokines Hypersensitivity Interferon-gamma Biosynthesis Interleukin-10 Interleukin-4 Interleukin-5 Leukocytes, Mononuclear Drug Effects Molecular Structure Pollen Th1 Cells Th2 Cells Tumor Necrosis Factor-alpha Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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