CA2625156A1 - Adjltvant compositions comprising a mineral salt and another immunostimulating compound - Google Patents
Adjltvant compositions comprising a mineral salt and another immunostimulating compound Download PDFInfo
- Publication number
- CA2625156A1 CA2625156A1 CA002625156A CA2625156A CA2625156A1 CA 2625156 A1 CA2625156 A1 CA 2625156A1 CA 002625156 A CA002625156 A CA 002625156A CA 2625156 A CA2625156 A CA 2625156A CA 2625156 A1 CA2625156 A1 CA 2625156A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- antigen
- glycosylamide
- group
- mineral salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Adjuvant compositions for modulating an immune response to an antigen administered to a host comprise a mineral salt adjuvant and at least one other adjuvant. The compositions provide an adjuvanting effect on an antigen which is greater than the adjuvanting effect attainable by one of the adjuvants alone. An antigen is covalently bonded to a glycolipid analog to provide a discrete molecule which exhibits an enhanced adjuvanting effect on the antigen which is greater than the adjuvanting effect attainable in the absence of such covalent bonding.
Claims (12)
1. A compound comprising an antigen covalently linked to a glycosylamide.
2. The compound of claim 1 wherein the glycosylamide has the formula in which R1 denotes hydrogen or saturated or singly or multiply unsaturated alkyl radical having up to 50 carbon atoms;
X represents -CH2-, -O- or -NH-;
R2 denotes hydrogen or a saturated or singly or multiply unsaturated alkyl radical having up to 50 carbon atoms;
R3, R4, and R5, independently of one another, denotes hydrogen, or SO4 2-, or PO4 2-, or other negatively charged moiety, or -CO-R6, R6 being an alkyl radical having up to 10 carbon atoms; and R9 is a linking radical covalently linking the glysosamide moiety to the antigen.
X represents -CH2-, -O- or -NH-;
R2 denotes hydrogen or a saturated or singly or multiply unsaturated alkyl radical having up to 50 carbon atoms;
R3, R4, and R5, independently of one another, denotes hydrogen, or SO4 2-, or PO4 2-, or other negatively charged moiety, or -CO-R6, R6 being an alkyl radical having up to 10 carbon atoms; and R9 is a linking radical covalently linking the glysosamide moiety to the antigen.
3. The compound of claim 2 wherein R9 is a cross-linker.
4. The compound of claim 2 wherein the glycosylamide is N-(2-deoxy-2-L-leucylamino-.beta.-D-glycopyranosyl)-N-octadecyldodecanamide acetate.
5. The compound of any one of claims 1 to 4 wherein the antigen is selected from the group consisting of microbial pathogens, bacteria, viruses, proteins, glycoproteins, lipoproteins, peptides, glycopeptides, lipopeptides, toxoids, carbohydrates and tumor-specific antigens.
6. The compound of claim 5 wherein the antigen comprises a protein, glycoprotein or lipoprotein, or a peptide, glycopeptide or lipopeptide which includes an amino acid sequence corresponding to an antigenic determinant of an HIV, Rubella virus, Respiratory Syncytial virus, Bordetella pertussis, Haemophilus influenzae or Streptococcus pneumoniae antigen or a functional analog thereof.
7. The compound of claim 6 wherein the peptide includes an amino acid sequence shown in Table I or a functional analog thereof.
8. The compound of any one of claims 1 to 7 wherein the antigen is covalently linked to the glycosylamide at a carboxy or amino terminus of the antigen.
9. The compound of claim 8 wherein the antigen and glycosylamide are covalently linked by a cross-linker having a reactive functional group.
10. The compound of claim 9 wherein the reactive functional group is selected from the group consisting of maleimidyl, succinimidyl, 2-pyridyldithio, NH2, SH, and -O-R8 wherein R8 is -OH, N3-O-alkyl (C1-C2), -OC5F5, H, Br or Cl.
11. An immunogenic composition for eliciting an immune response in a host, comprising:
(a) a compound as claimed in any one of claims 1 to 10, and (b) a mineral salt adjuvant.
(a) a compound as claimed in any one of claims 1 to 10, and (b) a mineral salt adjuvant.
12. The composition of claim 11, wherein the mineral salt adjuvant is selected from the group consisting of aluminum hydroxide, aluminum phosphate, calcium phosphate, zinc hydroxide and calcium hydroxide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/261,194 | 1994-06-16 | ||
| US08/261,194 US6764682B1 (en) | 1994-06-16 | 1994-06-16 | Adjuvant compositions containing more than one adjuvant |
| CA002192659A CA2192659C (en) | 1994-06-16 | 1995-06-15 | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002192659A Division CA2192659C (en) | 1994-06-16 | 1995-06-15 | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2625156A1 true CA2625156A1 (en) | 1995-12-21 |
| CA2625156C CA2625156C (en) | 2012-11-13 |
Family
ID=39537715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2625156A Expired - Lifetime CA2625156C (en) | 1994-06-16 | 1995-06-15 | Adjltvant compositions comprising a mineral salt and another immunostimulating compound |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2625156C (en) |
-
1995
- 1995-06-15 CA CA2625156A patent/CA2625156C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2625156C (en) | 2012-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20150615 |