WO1998009985B1 - Anti-inflammatory peptides and uses thereof - Google Patents
Anti-inflammatory peptides and uses thereofInfo
- Publication number
- WO1998009985B1 WO1998009985B1 PCT/IL1997/000295 IL9700295W WO9809985B1 WO 1998009985 B1 WO1998009985 B1 WO 1998009985B1 IL 9700295 W IL9700295 W IL 9700295W WO 9809985 B1 WO9809985 B1 WO 9809985B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- arg
- glu
- peptide
- pro
- thr
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 60
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract 10
- 230000003110 anti-inflammatory effect Effects 0.000 title claims 15
- 125000000539 amino acid group Chemical group 0.000 claims abstract 14
- 210000002540 macrophage Anatomy 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract 8
- 206010061218 Inflammation Diseases 0.000 claims abstract 5
- 230000004054 inflammatory process Effects 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims abstract 3
- 210000003169 central nervous system Anatomy 0.000 claims abstract 3
- 230000028996 humoral immune response Effects 0.000 claims abstract 3
- 230000005764 inhibitory process Effects 0.000 claims abstract 3
- 238000013508 migration Methods 0.000 claims abstract 3
- 230000005012 migration Effects 0.000 claims abstract 3
- 230000000242 pagocytic effect Effects 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- JSLGXODUIAFWCF-WDSKDSINSA-N Arg-Asn Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CC(N)=O)C(O)=O JSLGXODUIAFWCF-WDSKDSINSA-N 0.000 claims 12
- 108010004914 prolylarginine Proteins 0.000 claims 12
- WVRUNFYJIHNFKD-WDSKDSINSA-N Arg-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CCCN=C(N)N WVRUNFYJIHNFKD-WDSKDSINSA-N 0.000 claims 11
- SIFXMYAHXJGAFC-WDSKDSINSA-N Arg-Asp Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CC(O)=O)C(O)=O SIFXMYAHXJGAFC-WDSKDSINSA-N 0.000 claims 11
- PMGDADKJMCOXHX-BQBZGAKWSA-N Arg-Gln Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(O)=O PMGDADKJMCOXHX-BQBZGAKWSA-N 0.000 claims 11
- XUUXCWCKKCZEAW-YFKPBYRVSA-N Arg-Gly Chemical compound OC(=O)CNC(=O)[C@@H](N)CCCN=C(N)N XUUXCWCKKCZEAW-YFKPBYRVSA-N 0.000 claims 11
- QYLJIYOGHRGUIH-CIUDSAMLSA-N Arg-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N QYLJIYOGHRGUIH-CIUDSAMLSA-N 0.000 claims 11
- WYBVBIHNJWOLCJ-IUCAKERBSA-N Arg-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N WYBVBIHNJWOLCJ-IUCAKERBSA-N 0.000 claims 11
- JQFZHHSQMKZLRU-IUCAKERBSA-N Arg-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N JQFZHHSQMKZLRU-IUCAKERBSA-N 0.000 claims 11
- PQBHGSGQZSOLIR-RYUDHWBXSA-N Arg-Phe Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PQBHGSGQZSOLIR-RYUDHWBXSA-N 0.000 claims 11
- LQJAALCCPOTJGB-YUMQZZPRSA-N Arg-Pro Chemical compound NC(N)=NCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O LQJAALCCPOTJGB-YUMQZZPRSA-N 0.000 claims 11
- IJYZHIOOBGIINM-WDSKDSINSA-N Arg-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N IJYZHIOOBGIINM-WDSKDSINSA-N 0.000 claims 11
- XNSKSTRGQIPTSE-ACZMJKKPSA-N Arg-Thr Chemical compound C[C@@H]([C@@H](C(=O)O)NC(=O)[C@H](CCCN=C(N)N)N)O XNSKSTRGQIPTSE-ACZMJKKPSA-N 0.000 claims 11
- DAQIJMOLTMGJLO-YUMQZZPRSA-N Arg-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N DAQIJMOLTMGJLO-YUMQZZPRSA-N 0.000 claims 11
- PMGDADKJMCOXHX-UHFFFAOYSA-N L-Arginyl-L-glutamin-acetat Natural products NC(=N)NCCCC(N)C(=O)NC(CCC(N)=O)C(O)=O PMGDADKJMCOXHX-UHFFFAOYSA-N 0.000 claims 11
- HFKJBCPRWWGPEY-BQBZGAKWSA-N L-arginyl-L-glutamic acid Chemical compound NC(=N)NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(O)=O HFKJBCPRWWGPEY-BQBZGAKWSA-N 0.000 claims 11
- WYBVBIHNJWOLCJ-UHFFFAOYSA-N N-L-arginyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCCN=C(N)N WYBVBIHNJWOLCJ-UHFFFAOYSA-N 0.000 claims 11
- HMNSRTLZAJHSIK-YUMQZZPRSA-N Pro-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1 HMNSRTLZAJHSIK-YUMQZZPRSA-N 0.000 claims 11
- HYLXOQURIOCKIH-VQVTYTSYSA-N Thr-Arg Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N HYLXOQURIOCKIH-VQVTYTSYSA-N 0.000 claims 11
- JXNRXNCCROJZFB-RYUDHWBXSA-N Tyr-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JXNRXNCCROJZFB-RYUDHWBXSA-N 0.000 claims 11
- 108010013835 arginine glutamate Proteins 0.000 claims 11
- 108010008355 arginyl-glutamine Proteins 0.000 claims 11
- 108010062796 arginyllysine Proteins 0.000 claims 11
- 108010060035 arginylproline Proteins 0.000 claims 11
- 108010036533 arginylvaline Proteins 0.000 claims 11
- 108010053037 kyotorphin Proteins 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 7
- MPZWMIIOPAPAKE-BQBZGAKWSA-N Glu-Arg Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=N MPZWMIIOPAPAKE-BQBZGAKWSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 108010016626 Dipeptides Proteins 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000099 in vitro assay Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000028958 macrophage cytokine production Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- SITWEMZOJNKJCH-WDSKDSINSA-N Ala-Arg Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N SITWEMZOJNKJCH-WDSKDSINSA-N 0.000 claims 1
- SVBXIUDNTRTKHE-CIUDSAMLSA-N Ala-Arg-Glu Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(O)=O SVBXIUDNTRTKHE-CIUDSAMLSA-N 0.000 claims 1
- NWVVKQZOVSTDBQ-CIUDSAMLSA-N Ala-Glu-Arg Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O NWVVKQZOVSTDBQ-CIUDSAMLSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- OMLWNBVRVJYMBQ-YUMQZZPRSA-N Arg-Arg Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O OMLWNBVRVJYMBQ-YUMQZZPRSA-N 0.000 claims 1
- UXJCMQFPDWCHKX-DCAQKATOSA-N Arg-Arg-Glu Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(O)=O)C(O)=O UXJCMQFPDWCHKX-DCAQKATOSA-N 0.000 claims 1
- OSASDIVHOSJVII-WDSKDSINSA-N Arg-Cys Chemical compound SC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N OSASDIVHOSJVII-WDSKDSINSA-N 0.000 claims 1
- HPKSHFSEXICTLI-CIUDSAMLSA-N Arg-Glu-Ala Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(O)=O HPKSHFSEXICTLI-CIUDSAMLSA-N 0.000 claims 1
- QAODJPUKWNNNRP-DCAQKATOSA-N Arg-Glu-Arg Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O QAODJPUKWNNNRP-DCAQKATOSA-N 0.000 claims 1
- RKRSYHCNPFGMTA-CIUDSAMLSA-N Arg-Glu-Asn Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O RKRSYHCNPFGMTA-CIUDSAMLSA-N 0.000 claims 1
- XLWSGICNBZGYTA-CIUDSAMLSA-N Arg-Glu-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(O)=O XLWSGICNBZGYTA-CIUDSAMLSA-N 0.000 claims 1
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- PNQWAUXQDBIJDY-GUBZILKMSA-N Arg-Glu-Glu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O PNQWAUXQDBIJDY-GUBZILKMSA-N 0.000 claims 1
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- OGUPCHKBOKJFMA-SRVKXCTJSA-N Arg-Glu-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N OGUPCHKBOKJFMA-SRVKXCTJSA-N 0.000 claims 1
- DJAIOAKQIOGULM-DCAQKATOSA-N Arg-Glu-Met Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCSC)C(O)=O DJAIOAKQIOGULM-DCAQKATOSA-N 0.000 claims 1
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Abstract
The present invention is directed to peptides of the formulas (i) Xaa - Yaa - Arg, wherein either Xaa is any amino acid residue and Yaa is Glu or Xaa is absent and Yaa is any amino acid residue with the exception of Pro; (ii) Arg - Yaa - Xaa, wherein either Xaa is any amino acid residue and Yaa is Glu or Xaa is absent and Yaa is any amino acid residue with the exception of Asn; (iii) Xaa - Arg - Yaa, wherein Xaa is any amino acid residue and Yaa is Glu; and (iv) Yaa - Arg - Xaa, wherein Xaa is any amino acid residue and Yaa is Glu, and to derivatives thereof, which exert an inhibitory effect on macrophage migration and/or macrophage phagocytic activity. In addition, the peptides and derivatives thereof exert an inhibitory effect on the ability of macrophages and T cells to adhere to extracellular matrix and/or fibronectin. The peptides and derivatives thereof exert an inhibitory effect on a humoral and/or cellular immune response. The invention is also directed to methods for use of the peptides and derivatives thereof and compositions containing them for the inhibition of inflammation, including but not limited to, inflammation at a joint, in the central nervous system generally, at specific lesions in the central nervous system, and other immune privileged sites.
Claims
1. A substantially pure anti-inflammatory peptide or a peptide derivative selected from the group consisting of: (i) a peptide of the amino acid sequence:
Xaa - Yaa - Arg wherein either Xaa is any amino acid residue and Yaa is Glu, or Xaa is absent and Yaa is any amino acid residue with the exception of Pro, Thr and Tyr;
(ii) a peptide of the amino acid sequence:
Arg -Yaa - Xaa wherein either Xaa is any amino acid residue and Yaa is Glu, or Xaa is absent and Yaa is any amino acid residue with the exception of Asn, Ala, Asp, Gin, Glu, Gly, lie, Leu, Lys, Phe, Pro, Ser, Thr and Val;
(iii) a peptide of the amino acid sequence:
Xaa - Arg - Yaa wherein Xaa is any amino acid residue and Yaa is Glu;
(iv) a peptide of the amino acid sequence:
Yaa - Arg - Xaa wherein Xaa is any amino acid residue and Yaa is Glu;
(v) a cyclic derivative of a peptide of formula (i) to (iv) , Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val;
(vi) a peptide selected from a peptide of formula (i) to (v) , Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, in which peptide one or more amino acid residues have been replaced by the corresponding
-38- D-isomer or by a non-natural amino acid residue with the exception of Tyr-D-Arg and Arg-D-Ala;
(vii) a chemical derivative of a peptide selected from a peptide of formula (i) to (vi) , Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg- Val, but excluding the derivatives Arg-Asn-NH2, Asn-Arg-NH2, Gln-Arg-NH2, Glu-Arg-NH2, Gln-Arg-OMe, Glu-Arg-OMe, Gly-Arg-4- methoxy-3-naphthylamide, Gly-Arg-p-nitroanailide and Phe-Arg- /3-naphthylamide;
(viii) a dual peptide consisting of two the same or different peptides selected from the peptides and derivatives (i) to
(vii) , Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, wherein the peptides or derivatives are covalently linked to one another either directly or through a spacer; and
(ix) a multimer comprising a number of the same or different peptides selected from the peptides and derivatives (i) to (vii) , Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val.
2. An anti-inflammatory dipeptide according to Claim l(i), selected from the group consisting of:
Ala-Arg, Arg-Arg, Asn-Arg, Asp-Arg, Cys-Arg, Gln-Arg, Glu-Arg, Gly-Arg, His-Arg, Ile-Arg, Leu-Arg, Lys-Arg, Met-Arg, Phe-Arg, Ser-Arg, Trp-Arg and Val-Arg.
3. An anti-inflammatory tripeptide according to Claim l(i), selected from the group consisting of: Ala-Glu-Arg, Arg-Glu-Arg, Asn-Glu-Arg, Asp-Glu-Arg, Cys-Glu-Arg. Gln-Glu-Arg, Glu-Glu-Arg, Gly-Glu-Arg, His-Glu-Arg, Ile-Glu-Arg, Leu-Glu-Arg, Lys-Glu-Arg,
-39-
ANIENDED SHEET (ARTICLE 19) Met-Glu-Arg, Phe-Glu-Arg, Pro-Glu-Arg, Ser-Glu-Arg, Thr-Glu-Arg, Trp-Glu-Arg, Tyr-Glu-Arg and Val-Glu-Arg.
4. An anti-inflammatory dipeptide according to Claim l(ii), selected from the group consisting of: Arg-Cys, Arg-His, Arg-Met, Arg-Trp and Arg-Tyr.
5. An anti-inflammatory tripeptide according to Claim l(ii), selected from the group consisting of: Arg-Glu-Ala, Arg-Glu-Asn, Arg-Glu-Asp, Arg-Glu-Cys, Arg-Glu-Gln, Arg-Glu-Glu, Arg-Glu-Gly, Arg-Glu-His, Arg-Glu-Ile, Arg-Glu-Leu, Arg-Glu-Lys, Arg-Glu-Met, Arg-Glu-Phe, Arg-Glu-Pro, Arg-Glu-Ser, Arg-Glu-Thr, Arg-Glu-Trp, Arg-Glu-Tyr and Arg-Glu-Val.
6. An anti-inflammatory tripeptide according to Claim l(iii), selected from the group consisting of: Ala-Arg-Glu, Arg-Arg-Glu, Asn-Arg-Glu, Asp-Arg-Glu, Cys-Arg-Glu, Gln-Arg-Glu, Glu-Arg-Glu, Gly-Arg-Glu, His-Arg-Glu, Ile-Arg-Glu, Leu-Arg-Glu, Lys-Arg-Glu, et-Arg-Glu, Phe-Arg-Glu, Pro-Arg-Glu, Ser-Arg-Glu, Thr-Arg-Glu, Trp-Arg-Glu, Tyr-Arg-Glu and Val-Arg-Glu.
7. An anti-inflammatory tripeptide according to Claim l(iv), selected from the group consisting of: Glu-Arg-Ala, Glu-Arg-Arg, Glu-Arg-Asn, Glu-Arg-Asp, Glu-Arg-Cys, Glu-Arg-Gln, Glu-Arg-Gly, Glu-Arg-His, Glu-Arg-Ile, Glu-Arg-Leu, Glu-Arg-Lys, Glu-Arg-Met, Glu-Arg-Phe, Glu-Arg-Pro, Glu-Arg-Ser, Glu-Arg-Thr, Glu-Arg-Trp, Glu-Arg-Tyr and Glu-Arg-Val.
8. The anti-inflammatory dipeptide of claim 2 which is Glu-Arg.
9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an anti-inflammatory peptide or peptide derivative according to Claim 1.
-40-
10. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the anti-inflammatory peptide Glu-Arg.
11. A pharmaceutical composition according to claim 10 which composition inhibits T cell activity and has T cell inhibitory activity as assessed in an in vitro assay.
12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a peptide or peptide derivative selected from the group consisting of an anti-inflammatory peptide or peptide derivative according to Claim 1, the peptide Pro-Arg or a derivative thereof, and the peptide Arg-Asn or a derivative thereof, which composition inhibits macrophage activity and has macrophage migration and/or macrophage phagocytic inhibitory activity as assessed in an in vitro assay.
13. The pharmaceutical composition according to Claim 10, which composition inhibits macrophage activity and has macrophage migration and/or macrophage phagocytic inhibitory activity as assessed in an in vitro assay.
14. A method for the inhibition or amelioration of inflammation associated with a disease, condition or disorder comprising administering to a subject in need thereof an effective amount of a peptide or a peptide derivative selected from the group consisting of an anti-inflammatory peptide or peptide derivative according to Claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg- Val, or a derivative thereof.
15. The method according to Claim 14 in which the peptide is Glu-Arg.
16. The method according to claim 15 in which the disease, condition or disorder is arthritis.
17. The method according to claim 14 in which the disease, condition or disorder is a disease, condition or disorder of the mammalian central nervous system or the eye.
18. The method according to claim 15 in which the disease, condition or disorder is arthritis, systemic lupus erythematosus, vascular inflammatory disease, respiratory distress syndrome, ulcerative colitis, thyroiditis, glomerulonephritis, otitis, dermatitis, preventing rejection and complications and/or side effects of transplantation, reperfusion injury, hypersensitivity, allergy, asthma, septic shock, post-traumatic inflammation, uveitis, retinitis, retinitis pigmentosa, proliferative vitreoretinopathies, multiple sclerosis, HIV-related encephalopathy, post-polio syndrome, myelitis, encephalitis, complications and side- effects due to surgery, Huntington's disease, Parkinson's disease, Alzheimer's disease or Down's Syndrome.
19. The method according to claim 14 in which the peptide is applied locally to a site by injection, local infusion, topical application or an implant.
20. The method according to claim 14 in which the peptide is applied systemically by intravenous, intrathecal, intraarticular, retrobulbar, subconjunctival, intramuscular injection, or via eye drops.
21. The method according to claim 14 in which the peptide is administered in combination with a pharmaceutically acceptable carrier.
22. A method for the inhibition of a humoral immune response comprising administering to a subject in need thereof , in an amount effective to inhibit macrophage antigen-
-42- presenting activity, and/or macrophage cytokine production, a peptide or peptide derivative selected from the group consisting of an anti-inflammatory peptide or peptide derivative according to claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg- Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, or a derivative thereof.
23. A method for the restoration of immune privilege at an immune privileged site which has lost its immune privilege comprising administering to a subject in need thereof, in an amount effective to inhibit macrophage antigen- presenting activity, and/or macrophage cytokine production, a peptide or peptide derivative selected from the group consisting of an anti-inflammatory peptide or peptide derivative according to claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg- Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, or a derivative thereof.
24. Use of a peptide or peptide derivative according to Claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, or a derivative thereof, for the manufacture of a medicament for inhibiting or ameliorating inflammation associated with a disease, condition or disorder.
25. Use of a peptide or peptide derivative according to Claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, or a
-43- derivative thereof, for the manufacture of a medicament for inhibiting a humoral immune response.
26. Use of a peptide or peptide derivative according to Claim 1 or a peptide selected from the group consisting of Thr-Arg, Tyr-Arg, Pro-Arg, Arg-Asn, Arg-Ala, Arg-Asp, Arg-gln, Arg-Glu, Arg-Gly, Arg-Ile, Arg-Leu, Arg-Lys, Arg-Phe, Arg-Pro, Arg-Ser, Arg-Thr and Arg-Val, or a derivative thereof, for the manufacture of a medicament for restoring immune privilege at an immune privileged site which has lost its immune privilege.
27. The use according to claim 24 in which the peptide is Glu-Arg.
28. The use according to claim 24 in which the disease, condition or disorder is arthritis.
-44-
Priority Applications (5)
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EP97937794A EP0927191A2 (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
CA002264285A CA2264285A1 (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
AU40301/97A AU4030197A (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
JP10512435A JP2001500492A (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
IL12852997A IL128529A0 (en) | 1996-09-03 | 1997-09-03 | Anti-inflammatory peptides and uses thereof |
Applications Claiming Priority (6)
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US2537696P | 1996-09-03 | 1996-09-03 | |
US75314196A | 1996-11-20 | 1996-11-20 | |
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US08/864,301 US6126939A (en) | 1996-09-03 | 1997-05-28 | Anti-inflammatory dipeptide and pharmaceutical composition thereof |
US08/753,141 | 1997-05-28 |
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WO1998009985A2 WO1998009985A2 (en) | 1998-03-12 |
WO1998009985A3 WO1998009985A3 (en) | 1998-05-07 |
WO1998009985B1 true WO1998009985B1 (en) | 1998-06-18 |
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EP (1) | EP0927191A2 (en) |
JP (1) | JP2001500492A (en) |
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CA (1) | CA2264285A1 (en) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7442778B2 (en) | 2004-09-24 | 2008-10-28 | Amgen Inc. | Modified Fc molecules |
Families Citing this family (148)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7074888B1 (en) * | 1995-03-17 | 2006-07-11 | The Research Foundation Of State University Of New York | Mimotopes and anti-mimotopes of human platelet glycoprotein Ib/IX |
FR2767135B1 (en) * | 1997-08-06 | 2002-07-12 | Genset Sa | LSR COMPLEX RECEPTOR, ACTIVITY, CLONING, AND APPLICATION TO DIAGNOSIS, PREVENTION AND / OR TREATMENT OF OBESITY AND THE RISKS OR COMPLICATIONS THEREOF |
SE9703531D0 (en) * | 1997-09-30 | 1997-09-30 | Rudolf Valenta | Non-anaphlactic forms of allergens and their use |
CA2225325A1 (en) * | 1997-12-19 | 1999-06-19 | The University Of British Columbia | Hemiasterlin analogs |
NZ506839A (en) * | 1998-03-09 | 2003-05-30 | Zealand Pharma As | Pharmacologically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
US6660843B1 (en) | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
US7488590B2 (en) | 1998-10-23 | 2009-02-10 | Amgen Inc. | Modified peptides as therapeutic agents |
DE69934425T2 (en) | 1998-10-23 | 2007-09-27 | Amgen Inc., Thousand Oaks | THROMBOPOIETIN SUBSTITUTE |
AR023819A1 (en) * | 1999-05-03 | 2002-09-04 | Astrazeneca Ab | PHARMACEUTICAL FORMULATION, KIT OF PARTS AND USE OF THE FORMULATION |
WO2000077166A2 (en) * | 1999-06-10 | 2000-12-21 | Digital Gene Technologies, Inc. | Gene expression modulated in gastrointestinal inflammation |
CA2378480A1 (en) * | 1999-08-09 | 2001-02-15 | Tripep Ab | Pharmaceutical compositions containing tripeptides |
US6258932B1 (en) | 1999-08-09 | 2001-07-10 | Tripep Ab | Peptides that block viral infectivity and methods of use thereof |
AU783925B2 (en) * | 1999-08-10 | 2005-12-22 | Uab Research Foundation | Method of treating traumatic brain and spinal cord injuries and other neurogenic conditions using non-steroidal anti-inflammatory drugs and naturally occurring conotoxins |
US7855181B2 (en) * | 1999-08-13 | 2010-12-21 | University Of Florida Research Foundation, Inc. | Dipeptides for prevention of muscle breakdown and microbial infection |
US6989367B2 (en) * | 2000-01-14 | 2006-01-24 | Genset S.A. | OBG3 globular head and uses thereof |
US7338787B2 (en) * | 2000-01-14 | 2008-03-04 | Serono Genetics Institute S.A. | Nucleic acids encoding OBG3 globular head and uses thereof |
US20020058617A1 (en) * | 2000-01-14 | 2002-05-16 | Joachim Fruebis | OBG3 globular head and uses thereof for decreasing body mass |
GB0009760D0 (en) | 2000-04-19 | 2000-06-07 | Oxford Biomedica Ltd | Method |
EP1294740A2 (en) * | 2000-06-16 | 2003-03-26 | Hercules Incorporated | Chemically-modified antimicrobial peptides, compositions and methods of production and use |
IL137820A (en) * | 2000-08-10 | 2009-06-15 | S I S Shulov Inst For Science | Pharmaceutical composition for topical administration comprising an analgesic peptide |
GB0020498D0 (en) | 2000-08-18 | 2000-10-11 | Sterix Ltd | Compound |
US7148197B2 (en) * | 2000-08-24 | 2006-12-12 | The Regents Of The University Of California | Orally administered small peptides synergize statin activity |
ES2294415T3 (en) * | 2000-08-25 | 2008-04-01 | Research Corporation Technologies, Inc | USE OF ANTI-CONVULSION AMINO ACIDS FOR THE TREATMENT OF BIPOLAR DISORDERS. |
WO2002068601A2 (en) * | 2001-02-28 | 2002-09-06 | Skubitz Keith M | Small peptides capable of modulating the function of cd66 (ceacam) family members |
DE60120104T2 (en) * | 2001-03-20 | 2006-09-21 | Schwarz Pharma Ag | New use of peptide compounds in the treatment of non-neuropathic inflammatory pain |
ES2185606T3 (en) * | 2001-03-21 | 2003-05-01 | Sanol Arznei Schwarz Gmbh | NEW USE OF A CLASS OF PEPTIDIC COMPOUNDS FOR TREATMENT OF ALLODINIA OR OTHER DIFFERENT TYPES OF CHRONIC OR GHOST PAIN. |
US7491702B2 (en) * | 2001-04-18 | 2009-02-17 | The Open University | Polypeptides related to amyloid precursor protein, pharmaceutical compositions thereof, and methods of treatment using the same |
US7622446B2 (en) * | 2001-04-18 | 2009-11-24 | The Open University | Polypeptides, derivatives and uses thereof |
AU2002251296A1 (en) * | 2001-04-18 | 2002-10-28 | The Open University | Polypeptides derived from amyloid precursor peptide (app) and their uses |
CA2344208A1 (en) | 2001-04-30 | 2002-10-30 | Oxford Biomedica (Uk) Limited | Method |
US6908899B2 (en) * | 2001-08-17 | 2005-06-21 | U.S. Dept. Of Veterans Affairs | Pro-inflammatory fibrinopeptide |
US6593455B2 (en) | 2001-08-24 | 2003-07-15 | Tripep Ab | Tripeptide amides that block viral infectivity and methods of use thereof |
US7605132B2 (en) | 2001-08-29 | 2009-10-20 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Protective factors against inflammation, burns and noxious stimuli |
US7528227B2 (en) | 2004-03-23 | 2009-05-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Histone H2A peptide derivatives and uses thereof |
WO2005090387A2 (en) * | 2004-03-23 | 2005-09-29 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Histone h2a peptide derivatives and analogs and methods of use thereof |
EP1436317A1 (en) | 2001-09-19 | 2004-07-14 | Tripep Ab | Molecules that block viral infectivity and methods of use thereof |
ES2411981T3 (en) | 2002-02-01 | 2013-07-09 | Oxford Biomedica (Uk) Limited | Lentiviral Vector |
JP2006504406A (en) | 2002-06-28 | 2006-02-09 | セントカー・インコーポレーテツド | Mammalian CH1-deficient mimetibodies, compositions, methods and uses |
CN102241741B (en) * | 2002-12-03 | 2013-11-13 | 病原体切除与诊断科技公司 | Prion protein ligands and methods of use |
WO2004094457A2 (en) * | 2003-04-16 | 2004-11-04 | Arizona Board Of Regents, Acting For And On Behalf Of, Arizona State University | Stable rgd peptidomimetic composition |
WO2005030242A1 (en) | 2003-09-26 | 2005-04-07 | University Of Florida Research Foundation, Inc | Arginyl-glutamine dipeptide for treatment of pathological vascular proliferation |
US7176185B2 (en) * | 2003-11-25 | 2007-02-13 | Tsrl, Inc. | Short peptide carrier system for cellular delivery of agent |
CA2562937A1 (en) | 2004-04-16 | 2005-10-27 | Schwarz Pharma Ag | Use of peptidic compounds for the prophylaxis and treatment of chronic headache |
GB0411562D0 (en) | 2004-05-24 | 2004-06-23 | Sterix Ltd | Compound |
GB0412492D0 (en) | 2004-06-04 | 2004-07-07 | Sterix Ltd | Compound |
EP1604656A1 (en) * | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating amyotrophic lateral sclerosis (ALS) |
WO2006010057A2 (en) | 2004-07-08 | 2006-01-26 | Amgen Inc. | Therapeutic peptides |
PL1781276T3 (en) * | 2004-08-27 | 2010-11-30 | Ucb Pharma Gmbh | Use of peptide compounds for treating bone cancer pain, chemotherapy- and nucleoside-induced pain |
WO2006056998A2 (en) * | 2004-11-29 | 2006-06-01 | Yeda Research And Development Co. Ltd. | Methods of cell therapy, neurogenesis and oligodendrogenesis |
DE602006019567D1 (en) * | 2005-03-22 | 2011-02-24 | Rohto Pharma | PEPTIDES THAT INCREASE COLLAGEN OR HYALURONIC ACID PRODUCTION |
AU2014271339B2 (en) * | 2005-04-27 | 2016-11-03 | The Procter & Gamble Company | Personal care compositions |
US20070020220A1 (en) * | 2005-04-27 | 2007-01-25 | Procter & Gamble | Personal care compositions |
US9616011B2 (en) | 2005-04-27 | 2017-04-11 | The Procter & Gamble Company | Personal care compositions |
EP3002330A1 (en) | 2005-05-27 | 2016-04-06 | Ospedale San Raffaele S.r.l. | Gene vector |
US20060293218A1 (en) * | 2005-06-22 | 2006-12-28 | Meythaler Jay M | Salicylate therapeutic compound and process for controlled delivery thereof |
GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
US8008453B2 (en) | 2005-08-12 | 2011-08-30 | Amgen Inc. | Modified Fc molecules |
EP1754476A1 (en) * | 2005-08-18 | 2007-02-21 | Schwarz Pharma Ag | Lacosamide (SPM 927) for treating myalgia, e.g. fibromyalgia |
US20070043120A1 (en) * | 2005-08-18 | 2007-02-22 | Bettina Beyreuther | Therapeutic combination for painful medical conditions |
US20070048372A1 (en) * | 2005-08-18 | 2007-03-01 | Srz Properties, Inc. | Method for treating non-inflammatory osteoarthritic pain |
FR2894142B1 (en) * | 2005-12-05 | 2009-06-12 | Oreal | USE OF THE TYROSINE-ARGININE DIPEPTIDE AND NIACIMANIDE ASSOCIATION AS A P-SUBSTANCE ANAGONIST |
US8858968B2 (en) | 2005-12-05 | 2014-10-14 | L'oreal | Use of tyrosine-arginine dipeptide and niacinamide as substance P antagonist |
GB0526033D0 (en) | 2005-12-21 | 2006-02-01 | Bioeos Ltd | Method |
GB0526210D0 (en) | 2005-12-22 | 2006-02-01 | Oxford Biomedica Ltd | Vectors |
GB0604142D0 (en) | 2006-03-01 | 2006-04-12 | Sterix Ltd | Compound |
JO3324B1 (en) | 2006-04-21 | 2019-03-13 | Amgen Inc | Lyophilized Therapeutic Peptibody Formulations |
RU2301678C1 (en) * | 2006-05-30 | 2007-06-27 | Общество С Ограниченной Ответственностью "Сиа Пептайдс" | Peptide stimulating regeneration of central nervous system neurons, pharmaceutical composition based on thereof and method for its using |
CN102846601B (en) * | 2006-06-15 | 2015-04-29 | 优时比制药有限公司 | Pharmaceutical composition with synergistic anticonvulsant effect |
WO2008084405A2 (en) | 2007-01-11 | 2008-07-17 | Erasmus University Medical Center | Circular chromosome conformation capture (4c) |
WO2008096276A2 (en) * | 2007-02-02 | 2008-08-14 | Greenpharma | Peptide inhibitors of metallo- ectopeptidases, compositions comprising said compounds and their pharmaceutical and cosmetic uses |
GB0702446D0 (en) | 2007-02-08 | 2007-03-21 | Sterix Ltd | Composition |
GB0706072D0 (en) | 2007-03-28 | 2007-05-09 | Sterix Ltd | Compound |
GB0722779D0 (en) | 2007-11-20 | 2008-01-02 | Sterix Ltd | Compound |
US8697840B2 (en) * | 2008-03-05 | 2014-04-15 | Board Of Regents, The University Of Texas System | Peptide inhibition of lung epithelial apoptosis and pulmonary fibrosis |
GB0805862D0 (en) * | 2008-04-01 | 2008-04-30 | Bioalvo Servi Os Investiga Oo | Method |
US8158366B2 (en) * | 2008-04-07 | 2012-04-17 | Auburn University | Methods of identifying peptides and compositions that bind to oocytes in a species-specific manner |
DK3192874T3 (en) | 2008-06-18 | 2019-12-16 | Oxford Biomedica Ltd | VIRUS CLEANUP |
US9938540B2 (en) | 2008-11-12 | 2018-04-10 | Ospedale San Raffaele S.R.L. | Gene vector for inducing transgene-specific immune tolerance |
WO2010088527A2 (en) * | 2009-01-30 | 2010-08-05 | Mayo Foundation For Medical Education And Research | Peptides and nanoparticles for therapeutic and diagnostic applications |
DE102009002044A1 (en) * | 2009-03-31 | 2010-10-07 | Evonik Degussa Gmbh | Dipeptides as feed additives |
KR101080271B1 (en) * | 2009-03-31 | 2011-11-08 | 주식회사 웰스킨 | Ultraviolet-induced reaction controlling cosmetic composition containing dipeptide |
BRPI1010873B1 (en) | 2009-04-30 | 2020-04-14 | Fond Centro San Raffaele Del Monte Tabor | uses of a vector of genes, a pharmaceutical composition and a cell |
GB0914767D0 (en) | 2009-08-24 | 2009-09-30 | Sterix Ltd | Compound |
KR100953900B1 (en) * | 2009-08-28 | 2010-04-22 | 전북대학교산학협력단 | Cosmetic composition for improvement of dermatitis |
WO2011126163A1 (en) * | 2010-04-08 | 2011-10-13 | 주식회사 웰스킨 | Skin-whitening composition containing dipeptide |
PL3178841T3 (en) | 2010-07-21 | 2018-12-31 | Eastern Virginia Medical School | Peptide compounds to regulate the complement system |
US10005818B2 (en) * | 2010-07-21 | 2018-06-26 | Realta Holdings, Llc | Derivative peptide compounds and methods of use |
JPWO2012029160A1 (en) * | 2010-09-02 | 2013-10-28 | 株式会社メニコン | Stabilized polyphenol solution and method for stabilizing polyphenol solution |
WO2012156839A2 (en) | 2011-05-19 | 2012-11-22 | Ospedale San Raffaele S.R.L. | New generation of splice-less lentiviral vectors for safer gene therapy applications |
CN102796165B (en) * | 2011-05-24 | 2014-02-26 | 首都医科大学 | Fatty amine/alcohol derivatives modified by reverse sequence of Kyoto phenol, preparation method and application thereof |
EP2819686A4 (en) * | 2012-03-02 | 2016-05-25 | Icahn School Med Mount Sinai | Variants of prothymosin alpha and methods of using same |
WO2014109519A1 (en) * | 2013-01-10 | 2014-07-17 | 강원대학교산학협력단 | Microphthalmia-associated transcription factor-derived peptide and composition containing same |
AU2014229506B2 (en) | 2013-03-11 | 2017-04-13 | Nobesita As | Natural lipids containing non-oxidizable fatty acids |
US9630990B2 (en) | 2013-03-15 | 2017-04-25 | Board Of Regents, The University Of Texas System | Inhibition of pulmonary fibrosis with nutlin-3A and peptides |
EP2994156A4 (en) * | 2013-05-10 | 2017-01-11 | Southern Research Institute | Compounds, compositions and methods for the treatment of diseases through inhibiting tgf- activity |
AU2014338555B2 (en) | 2013-10-24 | 2019-10-10 | Fondazione Telethon | Method |
GB201318804D0 (en) | 2013-10-24 | 2013-12-11 | Adaptimmune Ltd | Vectors for transgene expression |
GB201322798D0 (en) | 2013-12-20 | 2014-02-05 | Oxford Biomedica Ltd | Production system |
GB201407322D0 (en) | 2014-04-25 | 2014-06-11 | Ospedale San Raffaele | Gene therapy |
GB201412494D0 (en) | 2014-07-14 | 2014-08-27 | Ospedale San Raffaele And Fond Telethon | Vector production |
GB201418965D0 (en) | 2014-10-24 | 2014-12-10 | Ospedale San Raffaele And Fond Telethon | |
US10947279B2 (en) | 2015-06-26 | 2021-03-16 | Realta Holdings, Llc | Synthetic peptide compounds and methods of use |
ES2875498T3 (en) | 2015-06-26 | 2021-11-10 | Realta Holdings Llc | Synthetic Peptide Compounds and Procedures for Use |
US10464977B2 (en) * | 2016-04-11 | 2019-11-05 | University Of Maryland, Baltimore | Histatin-5 based synthetic peptides and uses thereof |
GB201608944D0 (en) | 2016-05-20 | 2016-07-06 | Ospedale San Raffaele And Fond Telethon | Gene Tharapy |
GB201613999D0 (en) * | 2016-08-16 | 2016-09-28 | Neuro-Bio Ltd | Neurodegenerative disorders |
TW201821099A (en) * | 2016-12-05 | 2018-06-16 | 日商大塚製藥股份有限公司 | Composition for inhibiting muscular dystrophy |
WO2018144718A1 (en) * | 2017-02-01 | 2018-08-09 | The Johns Hopkins University | Prodrugs of glutamine analogs |
GB201706394D0 (en) | 2017-04-21 | 2017-06-07 | Ospedale San Raffaele Srl | Gene Therapy |
CN111093687B (en) * | 2017-09-15 | 2024-07-09 | 凯恩塞恩斯株式会社 | Use of peptides as therapeutic agents for autoimmune diseases and bone diseases |
CA3080193A1 (en) * | 2017-10-26 | 2019-05-02 | Southern Research Institute | Dipeptide analogs as tgf-beta inhibitors |
CN108129561B (en) * | 2017-12-06 | 2021-05-25 | 渤海大学 | an ACE inhibitory peptide |
CN112512548A (en) | 2018-01-09 | 2021-03-16 | 瑞尔塔控股有限公司 | Inhibition of myeloperoxidase oxidative activity by PIC1 in animal models |
CN112020366A (en) * | 2018-04-26 | 2020-12-01 | 志瑞亚新药工业株式会社 | Pharmaceutical composition containing dipeptide |
GB201807945D0 (en) | 2018-05-16 | 2018-06-27 | Ospedale San Raffaele Srl | Vector production |
GB201807944D0 (en) | 2018-05-16 | 2018-06-27 | Ospedale San Raffaele Srl | Compositions and methods for haematopoietic stem cell transplantation |
WO2020002380A1 (en) | 2018-06-25 | 2020-01-02 | Ospedale San Raffaele S.R.L | Gene therapy |
WO2020055812A1 (en) | 2018-09-10 | 2020-03-19 | Lung Therapeutics, Inc. | Modified peptide fragments of cav-1 protein and the use thereof in the treatment of fibrosis |
EP3864146A1 (en) | 2018-10-11 | 2021-08-18 | Ospedale San Raffaele S.r.l. | Selection by means of artificial transactivators |
CN109232718B (en) | 2018-11-09 | 2020-04-14 | 泰安市启航生物科技有限公司 | Synthetic peptide sp2 and application thereof |
CN113260360A (en) | 2019-01-18 | 2021-08-13 | 雀巢产品有限公司 | Reagents and methods for increasing stem cell function |
CN114667161A (en) | 2019-11-12 | 2022-06-24 | 牛津生物医学(英国)有限公司 | production system |
EP4103723A1 (en) | 2020-02-13 | 2022-12-21 | Oxford BioMedica (UK) Limited | Production of lentiviral vectors |
KR20220154734A (en) | 2020-03-13 | 2022-11-22 | 옥스포드 바이오메디카(유케이) 리미티드 | lentiviral vectors |
GB202007106D0 (en) | 2020-05-14 | 2020-07-01 | Ucl Business Plc | Cyclosporine analogues |
GB202007199D0 (en) | 2020-05-15 | 2020-07-01 | Oxford Biomedica Ltd | Viral vector production |
AU2021348257A1 (en) | 2020-09-28 | 2023-03-02 | Ludwig Institute For Cancer Research | Compositions and methods for increasing stem cell function |
BR112023005375A2 (en) | 2020-09-28 | 2023-04-25 | Nestle Sa | COMPOSITIONS AND METHODS TO ENHANCE STEM CELL FUNCTION |
GB202017725D0 (en) | 2020-11-10 | 2020-12-23 | Oxford Biomedica Ltd | Method |
CN112724238B (en) * | 2021-01-21 | 2022-05-31 | 浙江辉肽生命健康科技有限公司 | Bioactive peptide with amino acid structure FREGTTPKPK, and preparation method and application thereof |
JP2024506751A (en) | 2021-02-01 | 2024-02-14 | イプシレン バイオ エス.アール.エル. | gene silencing |
AU2021202658A1 (en) | 2021-04-28 | 2022-11-17 | Fondazione Telethon | Gene therapy |
AU2022270331A1 (en) | 2021-05-05 | 2023-10-12 | Ludwig Institute For Cancer Research | Urolithin for increasing stem cell function |
GB202114528D0 (en) | 2021-10-12 | 2021-11-24 | Oxford Biomedica Ltd | Lentiviral vectors |
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EP4602153A1 (en) | 2022-10-11 | 2025-08-20 | Fondazione Telethon ETS | 3d cell culture methods |
IT202300011790A1 (en) | 2023-06-08 | 2024-12-08 | Fond Telethon Ets | GENE MANIPULATION PROTOCOLS IN IMMUNE CELLS |
CN118126120B (en) * | 2023-09-14 | 2024-12-06 | 海南大学 | Tripeptide compounds that inhibit Aβ42 aggregation and reduce its cytotoxicity |
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Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4244946A (en) * | 1979-06-11 | 1981-01-13 | The Salk Institute For Biological Studies | Water-soluble peptides affecting gonadal function |
US4305872A (en) * | 1979-10-19 | 1981-12-15 | Kenneth Wingrove | Polypeptide derivatives |
US4316891A (en) * | 1980-06-14 | 1982-02-23 | The Salk Institute For Biological Studies | Extended N-terminal somatostatin |
FR2529461B1 (en) * | 1982-07-02 | 1988-06-03 | Pasteur Institut | TRIPEPTIDE FROM AN IMMUNOGLOBULIN FRAGMENT, PREPARATION METHOD THEREOF AND APPLICATIONS THEREOF |
EP0215805A1 (en) * | 1985-01-18 | 1987-04-01 | MERCK PATENT GmbH | Immunoregulatory peptides |
US5510329A (en) * | 1988-04-26 | 1996-04-23 | Ramot University For Applied Research And Industrial Development Ltd. | Preparations for the treatment of eyes |
US5506231A (en) * | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
US5455279A (en) * | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
IT1264129B1 (en) * | 1993-04-09 | 1996-09-16 | Codev S A | PEPTIDES WITH IMMUNOMODULATORY ACTIVITY DERIVED FROM LEUCOQUININ FRAGMENTS |
AU7392294A (en) * | 1993-07-21 | 1995-02-20 | Vladimir Khatskelevich Khavinson | Pharmaceutical with immunomodulating activity |
-
1997
- 1997-05-28 US US08/864,301 patent/US6126939A/en not_active Expired - Fee Related
- 1997-09-03 WO PCT/IL1997/000295 patent/WO1998009985A2/en not_active Application Discontinuation
- 1997-09-03 EP EP97937794A patent/EP0927191A2/en not_active Withdrawn
- 1997-09-03 AU AU40301/97A patent/AU4030197A/en not_active Abandoned
- 1997-09-03 CA CA002264285A patent/CA2264285A1/en not_active Abandoned
- 1997-09-03 IL IL12852997A patent/IL128529A0/en unknown
- 1997-09-03 JP JP10512435A patent/JP2001500492A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7442778B2 (en) | 2004-09-24 | 2008-10-28 | Amgen Inc. | Modified Fc molecules |
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