WO1997015324B1 - High fluorescence specific immune enhancing factor and methods of use for same - Google Patents
High fluorescence specific immune enhancing factor and methods of use for sameInfo
- Publication number
- WO1997015324B1 WO1997015324B1 PCT/US1996/017240 US9617240W WO9715324B1 WO 1997015324 B1 WO1997015324 B1 WO 1997015324B1 US 9617240 W US9617240 W US 9617240W WO 9715324 B1 WO9715324 B1 WO 9715324B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antigen
- malondialdehyde
- factor
- group
- acetaldehyde
- Prior art date
Links
- 230000002708 enhancing Effects 0.000 title claims abstract 3
- 102000004965 antibodies Human genes 0.000 claims abstract 8
- 108090001123 antibodies Proteins 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 3
- 102000004169 proteins and genes Human genes 0.000 claims abstract 3
- 108090000623 proteins and genes Proteins 0.000 claims abstract 3
- 230000003993 interaction Effects 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 17
- 239000000427 antigen Substances 0.000 claims 17
- 102000038129 antigens Human genes 0.000 claims 17
- 108091007172 antigens Proteins 0.000 claims 17
- 229940118019 Malondialdehyde Drugs 0.000 claims 7
- WSMYVTOQOOLQHP-UHFFFAOYSA-N malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000006177 alkyl benzyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 102000008100 Human Serum Albumin Human genes 0.000 claims 2
- 210000000987 Immune System Anatomy 0.000 claims 2
- 238000002835 absorbance Methods 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 238000001514 detection method Methods 0.000 claims 2
- 230000005284 excitation Effects 0.000 claims 2
- 238000001917 fluorescence detection Methods 0.000 claims 2
- 108091003117 Bovine Serum Albumin Proteins 0.000 claims 1
- 229940098773 Bovine Serum Albumin Drugs 0.000 claims 1
- 102000001554 Hemoglobins Human genes 0.000 claims 1
- 108010054147 Hemoglobins Proteins 0.000 claims 1
- 108091006822 Human Serum Albumin Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 229920003013 deoxyribonucleic acid Polymers 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000004936 stimulating Effects 0.000 claims 1
- 238000002255 vaccination Methods 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 239000007850 fluorescent dye Substances 0.000 abstract 1
- 230000001900 immune effect Effects 0.000 abstract 1
- 108010073336 immunoenhancing factor Proteins 0.000 abstract 1
- 238000001742 protein purification Methods 0.000 abstract 1
Abstract
A high fluorescence specific immune enhancing factor and methods of its use are described. The factor comprises a malondialdehyde-acetaldehyde adduct which can be detected in the picomolar range. The specific immunoenhancing factor allowing for a shorter time course for the production of antibody and of higher titer antibodies without the need for adjuvant. The factor may further be used as a general fluorescent label for immunological techniques and can be used to visualize protein interactions and to monitor protein purification procedures.
Claims
1. A specific immune-enhancing factor comprising: a malondialdehyde- acetaldehyde adduct having the following formula:
I x wherein X is an antigen containing an amino group; and R is selected from the group consisting of a lower Cj to Cg alkyl group, benzyl, aryl and hydrogen.
2. The factor according to claim 1 wherein R is methyl.
3. The factor according to claim 1 wherein said antigen is selected from the group consisting of a carboydrate, a DNA molecule, a protein, a peptide, and a lipid.
4. The factor of claim 1 wherein said antigen is of an animal origin.
5. The factor of claim 1 wherein said antigen is of an environmental origin.
6. The factor according to claim 1 which has an excitation frequency of about 398 nanometers and an absorbance of about 460 nanometers.
7. The factor of claim 1 wherein said antigen is of human origin.
8. The factor according to claim 1 wherein the antigen is selected from the group consisting of bovine serum albumin, human interferon, hemoglobin and human serum albumin.
9. A method for stimulating the immunogenicity of an antigen comprising: contacting said antigen with malondialdehyde and acetaldehyde so that a
36 malondialdehyde acetaldehyde adduct is formed, and introducing said malondialdehyde acetaldehyde adduct to the immune system of an animal.
10. The method of claim 9 wherein said antigen is introduced for vaccination purposes.
11. The method of claim 9 wherein said antigen is introduced for the production of antibody response.
12. The method of claim 11 further comprising the step of: detecting antigen/antibody complexes found by the immune system of said animal.
13. The method of claim 12 wherein said detecting is by fluorescence detection.
14. The method of claim 9 wherein said malondialdehyde acetaldehyde adduct has the following formula:
R OHC /'\.ΛH0
I I
I x the formula wherein X is an antigen containing an amino group and R is selected from the group consisting of a C to Cg alkyl group, benzyl, aryl and hydrogen.
15. A specific immune enhancing factor having the following formula:
wherein R is selected from the group consisting of a Cj to Cg alkyl group, benzyl, aryl and hydrogen.
37
16. A malondialdehyde acetaldehyde adduct formed by the process of: contacting an antigen with malondialdehyde and acetaldehyde so that an adduct is formed.
17. The method of claim 15 wherein said adduct has the following formula:
R OHC ^'\/CH0
I I
X
Wherein R is a Cj to about Cg alkyl, H, Benzyl or aryl group and X is a peptide or protein present in a biological sample.
18. A method for visualizing antigen/antibody interactions comprising: labeling said antigen or said antibody by forming a malondialdehyde acetaldehyde adduct with said antigen or antibody and thereafter detecting the presence of said antigen or antibody by fluorescence detection.
19. The method of claim 18 wherein said detection is by FACScan.
20. The method of claim 18 wherein said detection is by measuring absorbance at about 460 nanometers with an excitation frequency of 398 nanometers.
21. The method of claim 18 wherein said malondialdenyde acetaldehyde adduct has the following formula:
R
0HCN/\ H0
I I
I x
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002235599A CA2235599A1 (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immune enhancing factor and methods of use for same |
| DE69633635T DE69633635T2 (en) | 1995-10-27 | 1996-10-25 | SPECIFIC IMMUNOSTIMULATING FACTOR WITH HIGH FLUORESCENCE AND METHOD FOR USE THEREOF |
| AT96939501T ATE279207T1 (en) | 1995-10-27 | 1996-10-25 | SPECIFIC HIGH FLUORESCENCE IMMUNSTIMULATIVE FACTOR AND METHOD FOR USE THEREOF |
| DK96939501T DK0873136T3 (en) | 1995-10-27 | 1996-10-25 | Specific immune enhancing factor with high fluorescence and methods for using the same |
| US08/849,024 US6120777A (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immune enhancing factor and methods of use for same |
| EP96939501A EP0873136B1 (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immune enhancing factor and methods of use for same |
| AU76654/96A AU726344B2 (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immune enhancing factor and methods of use for same |
| JP9516852A JP2000505056A (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immunopotentiating factor and method of using the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US595995P | 1995-10-27 | 1995-10-27 | |
| US60/005,959 | 1995-10-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997015324A1 WO1997015324A1 (en) | 1997-05-01 |
| WO1997015324B1 true WO1997015324B1 (en) | 1997-12-11 |
Family
ID=21718568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/017240 WO1997015324A1 (en) | 1995-10-27 | 1996-10-25 | High fluorescence specific immune enhancing factor and methods of use for same |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6120777A (en) |
| EP (1) | EP0873136B1 (en) |
| JP (1) | JP2000505056A (en) |
| AT (1) | ATE279207T1 (en) |
| AU (1) | AU726344B2 (en) |
| CA (1) | CA2235599A1 (en) |
| DE (1) | DE69633635T2 (en) |
| DK (1) | DK0873136T3 (en) |
| WO (1) | WO1997015324A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2245805T3 (en) * | 1997-10-03 | 2006-01-16 | Galenica Pharmaceuticals, Inc. | POLISACARIDS FORMING IMINAS, PREPARATION OF THE SAME AND THE USE OF THE SAME AS ASSISTANTS OF IMMUNO STIMULANTS. |
| GB0326439D0 (en) * | 2003-11-13 | 2003-12-17 | Imp College Innovations Ltd | Methods |
-
1996
- 1996-10-25 CA CA002235599A patent/CA2235599A1/en not_active Abandoned
- 1996-10-25 US US08/849,024 patent/US6120777A/en not_active Expired - Fee Related
- 1996-10-25 JP JP9516852A patent/JP2000505056A/en active Pending
- 1996-10-25 AU AU76654/96A patent/AU726344B2/en not_active Ceased
- 1996-10-25 DE DE69633635T patent/DE69633635T2/en not_active Expired - Fee Related
- 1996-10-25 DK DK96939501T patent/DK0873136T3/en active
- 1996-10-25 WO PCT/US1996/017240 patent/WO1997015324A1/en active IP Right Grant
- 1996-10-25 EP EP96939501A patent/EP0873136B1/en not_active Expired - Lifetime
- 1996-10-25 AT AT96939501T patent/ATE279207T1/en not_active IP Right Cessation
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