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WO1998009985B1 - Anti-inflammatory peptides and uses thereof - Google Patents

Anti-inflammatory peptides and uses thereof

Info

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
Application number
PCT/IL1997/000295
Other languages
French (fr)
Other versions
WO1998009985A3 (en
WO1998009985A2 (en
Filing date
Publication date
Priority claimed from US08/864,301 external-priority patent/US6126939A/en
Application filed filed Critical
Priority to EP97937794A priority Critical patent/EP0927191A2/en
Priority to IL12852997A priority patent/IL128529A0/en
Priority to AU40301/97A priority patent/AU4030197A/en
Priority to JP10512435A priority patent/JP2001500492A/en
Priority to CA002264285A priority patent/CA2264285A1/en
Publication of WO1998009985A2 publication Critical patent/WO1998009985A2/en
Publication of WO1998009985A3 publication Critical patent/WO1998009985A3/en
Publication of WO1998009985B1 publication Critical patent/WO1998009985B1/en

Links

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

AMENDED CLAIMS[received by the International Bureau on 7 May 1998 (07.05.98); original claims 1-24 replaced by new claims 1-28 (7 pages)]
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-
PCT/IL1997/000295 1996-09-03 1997-09-03 Anti-inflammatory peptides and uses thereof WO1998009985A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP97937794A EP0927191A2 (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
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
CA002264285A CA2264285A1 (en) 1996-09-03 1997-09-03 Anti-inflammatory peptides and uses thereof

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US2537696P 1996-09-03 1996-09-03
US60/025,376 1996-09-03
US75314196A 1996-11-20 1996-11-20
US08/753,141 1996-11-20
US08/864,301 1997-05-28
US08/864,301 US6126939A (en) 1996-09-03 1997-05-28 Anti-inflammatory dipeptide and pharmaceutical composition thereof

Publications (3)

Publication Number Publication Date
WO1998009985A2 WO1998009985A2 (en) 1998-03-12
WO1998009985A3 WO1998009985A3 (en) 1998-05-07
WO1998009985B1 true WO1998009985B1 (en) 1998-06-18

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL1997/000295 WO1998009985A2 (en) 1996-09-03 1997-09-03 Anti-inflammatory peptides and uses thereof

Country Status (7)

Country Link
US (1) US6126939A (en)
EP (1) EP0927191A2 (en)
JP (1) JP2001500492A (en)
AU (1) AU4030197A (en)
CA (1) CA2264285A1 (en)
IL (1) IL128529A0 (en)
WO (1) WO1998009985A2 (en)

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