2,5-Deoxyfructosazine, a d-glucosamine derivative, inhibits T-cell interleukin-2 production better than d-glucosamine

• Published in: Carbohydrate research Vol. 342; no. 18; pp. 2745 - 2749
• Main Authors: Zhu, Aiping, Huang, Ji-Biao, Clark, Andrea, Romero, Roberto, Petty, Howard R.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 28.12.2007
• Subjects: Animals; Cytokine release; d-Glucosamine; Fructosazine; Glucosamine - metabolism; Glucosamine - pharmacology; Humans; Immune cell; Interleukin-2 - biosynthesis; Jurkat Cells; Microscopy, Fluorescence; Phytohemagglutinins - metabolism; Pyrazines - chemistry; Pyrazines - metabolism; Pyrazines - pharmacology; T-Lymphocytes - drug effects; T-Lymphocytes - metabolism; Cytokine release; Fructosazine; d-Glucosamine; Immune cell
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2007.08.025

d-Glucosamine has been widely reported to have immunosuppressive actions on neutrophils, lymphocytes, and other cells of the immune system. However, under conditions used in biological experiments (e.g., neutral pH, and phosphate buffers), we have found that d-glucosamine self-reacts to form 2,5-deoxyfructosazine [2-( d- arabino-tetrahydroxybutyl)-5-( d- erythro-2,3,4-trihydroxybutyl)pyrazine] ( 1) and 2,5-fructosazine [2,5-bis( d- arabino-tetrahydroxybutyl)pyrazine] ( 2). When tested for bioactivity at nontoxic concentrations, these d-glucosamine derivatives were more effective inhibitors of IL-2 release from PHA-activated T cells than d-glucosamine. Hence, fructosazines constitute a novel class of immunomodulators.