2,5-Deoxyfructosazine, a D-glucosamine derivative, inhibits T-cell interleukin-2 production better than D-glucosamine.
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.
Zhu
Aiping
A
Department of Ophthalmology and Visual Sciences, The University of Michigan Medical School, Ann Arbor, MI 48105, United States.
Huang
Ji-Biao
JB
Clark
Andrea
A
Romero
Roberto
R
Petty
Howard R
HR
D000818:Animals; D005944:Glucosamine / Q000378:metabolism* / Q000494:pharmacology*; D006801:Humans; D007376:Interleukin-2 / Q000096:biosynthesis*; D019169:Jurkat Cells; D008856:Microscopy, Fluorescence; D010835:Phytohemagglutinins / Q000378:metabolism; D011719:Pyrazines / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D013601:T-Lymphocytes / Q000187:drug effects* / Q000378:metabolism*
D007376:Interleukin-2; D010835:Phytohemagglutinins; D011719:Pyrazines; C069873:deoxyfructosazine; D005944:Glucosamine