A strong inhibition of HIV-induced cytopathic effects by synthetic (1----6)-alpha-D-mannopyranan sulfate.
The anti-HIV effects of mannopyranan sulfate (1) were investigated by using MT-4 cells, namely, an HTLV-I-carrying CD-4 positive cell-line, in vitro. Stereoregular (1----6)-alpha-D-mannopyranan, which had been synthesized by ring-opening polymerization of a 1,6-anhydromannose derivative, was sulfated with piperidine-N-sulfonic acid to provide 1. N.m.r. analysis of 1 indicated that the reactivity of hydroxyl groups was in the order, 3-OH greater than 2-OH much greater than 4-OH. Mannopyranan sulfate having degree of substitution (d.s.) of 1.19-1.83 effectively inhibited HIV-induced cytopathic effects at a concentration of greater than 3.3 micrograms/mL. The anticoagulant activity and the adsorption on concanavalin A of 1 indicated the possibility of selective binding of 1 having d.s. of 1.19-1.83 to HIV-protein.
Hatanaka
K
K
Institute of Industrial Science, University of Tokyo, Japan.
Kurihara
Y
Y
Uryu
T
T
Yoshida
O
O
Yamamoto
N
N
Mimura
T
T
Kaneko
Y
Y
D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002461:Cell Line, Transformed; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D006678:HIV / Q000187:drug effects* / Q000472:pathogenicity; D006801:Humans; D008351:Mannans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000925:Anticoagulants; D000998:Antiviral Agents; D008351:Mannans; C071637:(1-6)-mannopyranan sulfate