Effect of chemical modification at C1 of the glucosamine backbone of lipid A‐subunit analog GLA‐27 on manifestation of immunopharmacological activity

FEBS Letters

Kumazawa, Yoshio¹  Hasegawa, Akira²  Ogawa, Yuji²  Takimoto, Hiroaki³  Homma, J.Yuzuru³  Kiso, Makoto²  Yamamoto, Akihiro⁴ 

[1] School of Pharmaceutical Sciences, Kitasato University, Tokyo 108, Japan;Department of Agricultural Chemistry, Gifu University, Gifu 501-11, Japan;The Kitasato Institute, Tokyo 108, Japan;Tokyo Institute for Immunopharmacology, Tokyo 171 Japan

关键词: Lipid A-subunit analog;    GLA-27;    Mitogenic activity;    Tumor necrosis factor;   

DOI  :  10.1016/0014-5793(88)80557-X

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The effect of chemical modification at the C1 position of GLA-27, 4-O-phosphono-D-glucosamine carrying N-3-tetradecanoyloxytetradecanoyl [C₁₄-O-(C₁₄)] and 3-O-tetradecanoyl (C₁₄) groups, was investigated. Replacement by SH or S-acetyl groups of the OH group resulted in the enhancement of mitogenicity but gave rise to a reduction, in macrophage-stimulating ability such as induction of tumor necrosis factor and enhancement of phagocytic and cellular acid phosphatase activities. Bisphosphorylation at C1 and C4 resulted in a slight decrease in mitogenicity or almost complete loss of the macrophage-stimulating ability.

【 授权许可】

Unknown