Carbohydrate-glycolipid conjugate vaccines
AssigneesMax-Planck-Gesellschaft zur Forderung der Wissenschaften e.V., Universitätsspital Basel
InventorsPeter H. Seeberger, Pierre Stallforth, Gennaro De Libero, Marco Cavallari
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Abstract
The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.
Claims12
Compound of the general formula (XIV):
- Wherein:
- A represents a carbohydrate antigen selected from the group consisting of a bacterial capsular saccharide, a saccharide of a viral glycoprotein, a saccharide antigen of sporozoa or parasites, a saccharide antigen of pathogenic fungi, and a saccharide antigen which is specific to cancer cells, and has a number u of 1 to 10,000 of carbohydrate monomers,
- p is the number of residues
- which are bound to the carbohydrate antigen A, and
- p is an integer defined as follows:
- p is 1 or 2 if u is 1
- p is 1, 2, 3 or 4 if u is 2
- p is 1, 2, 3, 4, 5 or 6 if u is 3
- p is 1, 2, 3, 4, 5, 6, 7 or 8 if u is 4
- 1≤p≤10 if 5≤u≤10
- 2≤p≤50 if 11≤u≤100
- 20≤p≤200 if 101≤u≤1000
- 50≤p≤400 if 1001≤u≤10000
- L represents -L1-L2-, -L2-, -L2-L3- or -L1-L2-L3-;
- L1 represents one of the following residues:
- wherein x is an integer from 1 to 60;
- Y represents a bond, —NH—, —O—, —S—;
- —S—S—;
- L2 represents —CH2—, —C2H4—, —C3H6—, —C4H8—, —C5H10—, —C6H12—, —C7H14—, —C8H16—, —C9H18—, —C10H20—, —CH(CH3)—, —C[(CH3)2]—, —CH2—CH(CH3)—, —CH(CH3)—CH2—, —CH(CH3)—C2H4—, —CH2—CH(CH3)—CH2—, —C2H4—CH(CH3)—, —CH2—C[(CH3)2]—, —C[(CH3)2]—CH2—, —CH(CH3)—CH(CH3)—, —C[(C2H5)(CH3)]—, —CH(C3H7)—, —(CH2—CH2—O)n—CH2—CH2—, —CO—CH2—, —CO—C2H4—, —CO—C3H6—, —CO—C4H8—, —CO—C5H10—, —CO—C6H12—, —CO—C7H14—, —CO—C9H16—, —CO—C9H18—, —CO—C10H20—, —CO—CH(CH3)—, —CO—C[(CH3)2]—, —CO—CH2—CH(CH3)—, —CO—CH(CH3)—CH2—, —CO—CH(CH3)—C2H4—, —CO—CH2—CH(CH3)—CH2—, —CO—C2H4—CH(CH3)—, —CO—CH2—C[(CH3)2]—, —CO—C[(CH3)2]—CH2—, —CO—CH(CH3)—CH(CH3)—, —CO—C[(C2H5)(CH3)]—, —CO—CH(C3H7)—, —Oβ—(CH2—CH2—O)n—CH2—CH2—;
- n represents an integer from 1 to 60;
- L3 represents —CO—, —O—CO—, —NH—CO—, —NH(C═NH)—, —SO2—, —O—SO2—, —NH—, —NH—CO—CH2—;
- R* and R# represent independently of each other a linear or branched or cyclic, substituted or unsubstituted, saturated or unsaturated carbon residue consisting of 1 to 30 carbon atoms.
Dependencies are inferred from the claim text.