title: Effect of chemical modification at C1 of the glucosamine backbone of lipid A-subunit analog GLA-27 on manifestation of immunopharmacological activity.
abstract: 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.
authors.affiliation: School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kumazawa
authors.forename: H
authors.initials: H
authors.lastname: Takimoto
authors.forename: A
authors.initials: A
authors.lastname: Yamamoto
authors.forename: J Y
authors.initials: JY
authors.lastname: Homma
authors.forename: Y
authors.initials: Y
authors.lastname: Ogawa
authors.forename: M
authors.initials: M
authors.lastname: Kiso
authors.forename: A
authors.initials: A
authors.lastname: Hasegawa
mesh_terms: D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002478:Cells, Cultured; D004261:DNA Replication / Q000187:drug effects; D005944:Glucosamine; D008050:Lipid A / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008809:Mice, Inbred C3H; D008934:Mitogens / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013936:Thymidine / Q000378:metabolism; D014409:Tumor Necrosis Factor-alpha / Q000097:blood*
chemical_list: D008050:Lipid A; D008934:Mitogens; D014409:Tumor Necrosis Factor-alpha; C048988:GLA 27; D005944:Glucosamine; D013936:Thymidine