Synthesis of Dendrimer-Type AIDS Vaccine Having High Antibody Productivity

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A dendrimer-type AIDS (acquired immunodeficiency syndrome) vaccine having a possibility of high anti-HIV (human immunodeficiency virus) activity was molecularly designed and synthesized. It is expected that a medium molecular weight dendrimer-type vaccine carrying highly antigenic HIV peptide sequence can produce a large quantity of antibodies. Lysine dendrimer third (G3) and fourth (G4) generations, and ornithine dendrimer third generation were used for core dendrimers. Two methods by which a peptide sequnece included in HIV gp120 was bound to the dendrimer under mild conditions were developed. In the first method, eight amino groups in lysine dendrimer G3 were reacted with lactose, maltose, and maltotriose by reductive amination using BH3 pyridine catalyst to produce at most 16 oligosaccharides-bound dendrimers. In the next dendrimer elongation, primary 6-OH groups in the oligosaccharide were reacted with such dibasic acids as adipic acid and suberic acid to give dibasic acid-oligosaccharide-lysine dendrimer three-layered dendrimers. A four-layered dendrimer was also preprared. In the second method, cellobiose-lysine dendrimer was synthesized in which reducing end of the cellobiose moiety was directed outward the dendrimer. To the reducing end, a HIV cyclic peptide was tried to bind by reductive amination to form AIDS vaccine. Structure and molecular weight of the products were determined by NMR and TOF-MS. A model compound for AIDS vaccine was obtained. Intermolecular interactions between polypeptide and polysaccharide were detected by NMR in order to analyze an action mechanism of biologically active macromolecules such as vaccine.