Abstract
2-Amino-3-(purin-9-yl)propanoic acids substituted at position 6 of the purine base moiety by dimethylamino, cyclopropylamino, pyrrolidin-1-yl, hydroxy, and sulfanyl group as well as their 2-aminopurine analogues were prepared from corresponding 9-(2,2-diethoxyethyl)purines and 2-aminopurines, respectively, by the Strecker synthesis. 2-Aminopropanoic acid derivatives were tested for their immunostimulatory and immunomodulatory potency. Some of these compounds significantly enhanced secretion of chemokines RANTES and MIP-1alpha, the most potent was 2-amino-6-sulfanylpurine derivative. Most of these compounds also augmented NO biosynthesis triggered primarily by IFN-gamma.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Chemokine CCL3
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Chemokine CCL4
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Chemokine CCL5 / immunology
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Chemokine CCL5 / metabolism
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Female
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Immunologic Tests
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Interferon-gamma / pharmacology
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Macrophage Inflammatory Proteins / immunology
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Macrophage Inflammatory Proteins / metabolism
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Macrophages / drug effects
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Macrophages / immunology
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Mice
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Mice, Inbred C57BL
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Molecular Structure
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Nitric Oxide / biosynthesis
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Propionates / chemical synthesis*
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Propionates / immunology
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Propionates / pharmacology*
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Structure-Activity Relationship
Substances
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Chemokine CCL3
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Chemokine CCL4
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Chemokine CCL5
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Macrophage Inflammatory Proteins
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Propionates
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Nitric Oxide
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Interferon-gamma