title: Synthetic galactomannans with potent anti-HIV activity.
abstract: Ring-opening polymerization of a new 1,6-anhydro disaccharide monomer, 1, 6-anhydro-2, 3-di-O-benzyl-4-O-(2', 3', 4', 6'-tetra-O-benzyl-α-d-galactopyranosyl)-α-d-mannopyranose, was carried out using PF5 as a catalyst under high vacuum at -60°C to give galactose branched mannopyranan (synthetic galactomannan), 4-O-α-d-galactopyranosyl-(1→6)-α-d-mannopyranan, after debenzylation with Na in liquid NH3. The ring-opening copolymerization with 1, 6-anhydro-tri-O-benzyl-α-d-mannopyranose in various feeds was also performed to give synthetic galactomannans with various proportions of galactose branches. After sulfation, sulfated synthetic galactomannans were found to have anti-HIV activity and cytotoxicity as high and low as those of standard curdlan and dextran sulfates, respectively, which are potent anti-HIV sulfated polysaccharides with low cytotoxicity. The anti-HIV mechanism of sulfated synthetic galactomannans used by poly-l-lysine as a model peptide of the HIV surface protein was estimated by using SPR, DSL, and zeta potential measurements, revealing the electrostatic interaction between negatively charged sulfate groups and positively charged amino groups.
authors.affiliation: Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, 090-8507, Hokkaido, Japan.
authors.forename: Davaanyam
authors.initials: D
authors.lastname: Budragchaa
authors.affiliation: Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, 090-8507, Hokkaido, Japan.
authors.forename: Shiming
authors.initials: S
authors.lastname: Bai
authors.affiliation: St Marianna University School of Medicine, Miyamae-ku, Kawasaki, 216-8511, Japan.
authors.forename: Taisei
authors.initials: T
authors.lastname: Kanamoto
authors.affiliation: St Marianna University School of Medicine, Miyamae-ku, Kawasaki, 216-8511, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Nakashima
authors.affiliation: Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, 090-8507, Hokkaido, Japan.
authors.forename: Shuqin
authors.initials: S
authors.lastname: Han
authors.affiliation: Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, 090-8507, Hokkaido, Japan. Electronic address: yoshida@chem.kitami-it.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Yoshida
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D005690:Galactose / Q000031:analogs & derivatives; D006678:HIV / Q000187:drug effects*; D015658:HIV Infections / Q000188:drug therapy* / Q000821:virology; D006801:Humans; D008351:Mannans / Q000138:chemical synthesis* / Q000494:pharmacology*; D011107:Polylysine / Q000737:chemistry
chemical_list: D019380:Anti-HIV Agents; D008351:Mannans; C012990:galactomannan; D011107:Polylysine; D005690:Galactose
keywords: Anhydro disaccharide monomer; Anti-HIV activity; Interaction mechanism; Ring-opening polymerization; Sulfation; Synthetic galactomannan