WO1995008348B1 - Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructs - Google Patents
Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructsInfo
- Publication number
- WO1995008348B1 WO1995008348B1 PCT/US1994/010658 US9410658W WO9508348B1 WO 1995008348 B1 WO1995008348 B1 WO 1995008348B1 US 9410658 W US9410658 W US 9410658W WO 9508348 B1 WO9508348 B1 WO 9508348B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- moiety
- reagent
- carbohydrate
- immunogenic construct
- producing
- Prior art date
Links
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract 13
- 230000002163 immunogen Effects 0.000 title claims abstract 12
- 150000001720 carbohydrates Chemical class 0.000 title claims abstract 8
- 230000003213 activating Effects 0.000 title claims abstract 6
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 230000001588 bifunctional Effects 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 4
- 150000004676 glycans Polymers 0.000 claims 4
- 229920001282 polysaccharide Polymers 0.000 claims 4
- 239000005017 polysaccharide Substances 0.000 claims 4
- 150000004804 polysaccharides Polymers 0.000 claims 4
- 229920002307 Dextran Polymers 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 230000028993 immune response Effects 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N Adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims 1
- 229940099500 Cystamine Drugs 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 241000606768 Haemophilus influenzae Species 0.000 claims 1
- 229940047650 Haemophilus influenzae Drugs 0.000 claims 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 231100000765 Toxin Toxicity 0.000 claims 1
- 208000001877 Whooping Cough Diseases 0.000 claims 1
- 102000004965 antibodies Human genes 0.000 claims 1
- 108090001123 antibodies Proteins 0.000 claims 1
- 230000001580 bacterial Effects 0.000 claims 1
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 201000005702 pertussis Diseases 0.000 claims 1
- 229960000814 tetanus toxoid Drugs 0.000 claims 1
- 239000003053 toxin Substances 0.000 claims 1
- 230000003612 virological Effects 0.000 claims 1
- 230000021615 conjugation Effects 0.000 abstract 2
Abstract
A process for producing an immunogenic construct comprising activating at least one first carbohydrate-containing moiety with a novel cyanylating reagent and covalently joining said activated first moiety to a second moiety. Immunogenic constructs may be prepared by this process using either direct conjugation of first and second moieties or using indirect conjugation with a bifunctional reagent.
Claims
1. A process for producing an immunogenic construct comprising: a) activating at least one first carbohydrate-containing moiety with an organic cyanylating reagent; and b) covalently joining said activated carbohydrate-containing moiety to a second moiety.
2. A process for producing an immunogenic construct comprising: a) activating at least one first carbohydrate-containing moiety with an organic cyanylating reagent; b) covalently joining said first moiety to a bifunctional spacer reagent; and c) covalently joining a second moiety to the bifunctional spacer reagent of step b) .
3. The method of claim 1 or 2, wherein the organic cyanylating reagent is selected from the group consisting of CDAP, CTEA, and pNPC.
4. The method of claim 1 or 2, wherein the immunogenic construct is a dual carrier construct.
5. The method of claim 1 or 2, wherein said bifunctional reagent is selected from the group consisting of ethylene diamine, 1,6-hexane diamine, adipic dihydrazide, cystamine, glycine, and lysine.
6. A dual carrier immunogenic construct produced according to claim 1 or 2.
7. The method of claim 1 or 2, wherein the first moiety is selected from the group consisting of dextran, Pneumococcal polysaccharide, haemophilus influenzae
38 polysaccharide, a viral polysaccharide, and a bacterial polysaccharide.
8. The method of claim 1 or 2, wherein the second moiety is selected from the group consisting of BSA, pertussis toxoid, tetanus toxoid, malaria-derived peptide P28, an antibody, a toxoid, and a toxin.
9. An immunogenic construct produced according to claim 1 or 2, which is selected form the group consisting of PT-Pnl4, PT-PRP20, TT-Pnl4, Hδa/l-dextran, and P28-TT-Pnl4.
10. A method for producing an immune response, comprising: a) producing an immunogenic construct by i) activating at least one first carbohydrate-containing moiety with an organic cyanylating reagent, and ii) covalently joining said activated carbohydrate-containing moiety to a second moiety; and b) administering the immunogenic construct to a patient.
11. A method for producing an immune response, comprising: a) producing an immunogenic construct by i) activating at least one first carbohydrate-containing moiety with an organic cyanylating reagent, ii) covalently joining said first moiety to a bifunctional spacer reagent, and iii) covalently joining a second moiety to the bifunctional spacer reagent of step ii) ; and b) administering the immunogenic construct to a patient.
39
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69433341T DE69433341T2 (en) | 1993-09-22 | 1994-09-21 | METHOD FOR ACTIVATING SOLUBLE CARBOHDRATES BY USING NEW CYANYLATION REAGENTS, FOR THE PRODUCTION OF IMMUNOGENIC CONSTRUCTS |
| EP94929273A EP0720485B1 (en) | 1993-09-22 | 1994-09-21 | Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructs |
| AT94929273T ATE254475T1 (en) | 1993-09-22 | 1994-09-21 | METHOD FOR ACTIVATION OF SOLUBLE CARBOHYDRATES BY USING NEW CYANYLATION REAGENTS TO PRODUCE IMMUNOGENIC CONSTRUCTS |
| NZ274376A NZ274376A (en) | 1993-09-22 | 1994-09-21 | Activating soluble carbohydrate using cyanylating reagents for the production of immunogenic constructs |
| CA2171942A CA2171942C (en) | 1993-09-22 | 1994-09-21 | Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructs |
| DE122009000058C DE122009000058I1 (en) | 1993-09-22 | 1994-09-21 | PROCESS FOR ACTIVATING SOLUBLE CARBOHYDRATE BY USING NEW CYANYLATION REAGENTS FOR PREPARING IMMUNOGENIC CONSTRUCTS |
| JP50989795A JP3828145B2 (en) | 1993-09-22 | 1994-09-21 | A method for the activation of soluble carbohydrates using a novel cyanating reagent for the production of immunogenic components |
| AU78391/94A AU678613B2 (en) | 1993-09-22 | 1994-09-21 | Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructs |
| NL300412C NL300412I1 (en) | 1993-09-22 | 2009-09-24 | Process for using new cyanilizing reagents |
| NL300411C NL300411I1 (en) | 1993-09-22 | 2009-09-24 | Process for using new cyanilizing reagents |
| FR12C0059C FR12C0059I2 (en) | 1993-09-22 | 2012-10-18 | METHOD FOR ACTIVATING SOLUBLE CARBOHYDRATES USING NOVEL CYANYLATING REAGENTS TO PRODUCE IMMUNOGENIC STRUCTURES |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12449193A | 1993-09-22 | 1993-09-22 | |
| US08/124,491 | 1993-09-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995008348A1 WO1995008348A1 (en) | 1995-03-30 |
| WO1995008348B1 true WO1995008348B1 (en) | 1995-05-04 |
Family
ID=22415196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/010658 WO1995008348A1 (en) | 1993-09-22 | 1994-09-21 | Method of activating soluble carbohydrate using novel cyanylating reagents for the production of immunogenic constructs |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5651971A (en) |
| EP (1) | EP0720485B1 (en) |
| JP (1) | JP3828145B2 (en) |
| KR (1) | KR100376361B1 (en) |
| AT (1) | ATE254475T1 (en) |
| AU (1) | AU678613B2 (en) |
| CA (1) | CA2171942C (en) |
| DE (2) | DE122009000058I1 (en) |
| ES (1) | ES2210262T3 (en) |
| FR (1) | FR12C0059I2 (en) |
| NL (2) | NL300411I1 (en) |
| NZ (1) | NZ274376A (en) |
| WO (1) | WO1995008348A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8945588B2 (en) | 2011-05-06 | 2015-02-03 | The University Of Chicago | Methods and compositions involving protective staphylococcal antigens, such as EBH polypeptides |
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- 1994-09-21 DE DE122009000058C patent/DE122009000058I1/en active Pending
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- 1994-09-21 WO PCT/US1994/010658 patent/WO1995008348A1/en active IP Right Grant
- 1994-09-21 AU AU78391/94A patent/AU678613B2/en not_active Expired
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