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WO1998058960B1 - PEPTIDES DERIVED FROM COMPLEMENT PEPTIDE C3a SEQUENCE AND ANTIALLERGIC COMPOSITIONS COMPRISING THEM - Google Patents

PEPTIDES DERIVED FROM COMPLEMENT PEPTIDE C3a SEQUENCE AND ANTIALLERGIC COMPOSITIONS COMPRISING THEM

Info

Publication number
WO1998058960B1
WO1998058960B1 PCT/IL1998/000292 IL9800292W WO9858960B1 WO 1998058960 B1 WO1998058960 B1 WO 1998058960B1 IL 9800292 W IL9800292 W IL 9800292W WO 9858960 B1 WO9858960 B1 WO 9858960B1
Authority
WO
WIPO (PCT)
Prior art keywords
arg
leu
cys
ala
asn
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.)
Ceased
Application number
PCT/IL1998/000292
Other languages
French (fr)
Other versions
WO1998058960A1 (en
Filing date
Publication date
Priority claimed from IL12113497A external-priority patent/IL121134A0/en
Application filed filed Critical
Priority to AT98928510T priority Critical patent/ATE265467T1/en
Priority to DE69823528T priority patent/DE69823528T2/en
Priority to IL13342798A priority patent/IL133427A0/en
Priority to EP98928510A priority patent/EP1015484B1/en
Priority to AU80325/98A priority patent/AU8032598A/en
Publication of WO1998058960A1 publication Critical patent/WO1998058960A1/en
Publication of WO1998058960B1 publication Critical patent/WO1998058960B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Abstract

Peptides corresponding partially or entirely to positions 50-77 of the sequence of the complement-derived peptide C3a and analogs thereof are capable of inhibiting Ig-E mediated triggering and/or the FcεRI-induced secretory response of mucosal mast cells. These peptides are useful for prevention and/or treatment of allergic disorders caused by Ig-E mediated (Type I) hypersensitivity where mucosal-type mast cells are involved, such as hay fever, asthma, some cases of urticaria or allergic conjunctivitis.

Claims

AMENDED CLAIMS[received by the International Bureau on 20 December 1998 (20.12.98); original claims 1-20 replaced by amended claims 1-46 (9 pages)]
1. A peptide consisting partially or entirely of the 50-77 sequence of the complement-derived peptide C3a and analogs thereof capable of inhibiting IgE-mediated triggering and/or the FcεRI-induced secretory response of mucosal mast cells, said peptides and analogs being selected from the sequences:
(a) Xl-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln- His-R5-R6-R7-R8-R9-Rl 0-Gly-Leu-Ala-Rl 1
(b) Xl-Cys-Asn-Rl-X4; (c) X2-Lys-Val-Phe-Leu-Asp-X3; and
(d) X5-Asp-Ser-Ser-Asn-Tyr-Ile-Rl 1 wherein
XI is H, lower alkanoyl, Cys, Asp-Cys or Arg-Arg-Cys; X2 is H, lower alkanoyl or Lys; X3 is Arg or a sequence selected from
(i) Ala-Ala-Asn-Rl -Ile-Thr-R2-Leu-R3-R4; (ii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3; and (iii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln-His-R5-R6; X4 is Gly, (i) Ile-Thr-R2-Leu-R3; or (ii) Ile-Thr-Arg-R X5 is H, lower alkanoyl or Leu;
RI is an aromatic amino acid residue; R2 is Glu or Lys; R3 is a positively charged amino acid residue; R4 is Arg or Glu; R5 is Ala or Arg: R6 is Arg or Lys; R7 is Ala or
Asp; R8 is Ser or His; R9 is His or Val; R10 is Leu, He, Ala or Gly; and RI 1 is OH,
Arg-NH , or Agm (agmatine), and chemical derivatives and pharmaceutically acceptable salts thereof.
2. A peptide according to Claim 1, wherein RI is an aromatic amino acid residue selected from Phe, Tyr, His and Trp; and R3 is a positively charged amino acid residue selected from Arg, D-Arg, Har (homoarginine) and Lys.
3. The peptide according to Claim 1 or 2, of the sequence : Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg-NH2
4. The peptide according to Claim 1 or 2, of the sequence :
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg-NH
5. The peptide according to Claim 1 or 2, of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-NH2
6. The peptide according to Claim 1 of the sequence : Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg
7. The peptide according to Claim 1 of the sequence :
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg-NH2
8. The peptide according to Claim 1 of the sequence :
Asp-Ser-Ser-Asn-Tyr-Ile-Arg
9. The peptide according to Claim 1 of the sequence : Asp- Ser-Ser-Asn-Tyr-Ile-Arg-NH2
10. The peptide according to Claim 1 of the sequence :
Cys-Cys-Asn-Tyr-Gly
11. The peptide according to Claim 1 of the sequence : Cys-Cys-Asn-Tyr-Gly-NH2
12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a peptide consisting partially or entirely of the 50-77 sequence of the complement-derived peptide C3a, an analog thereof capable of inhibiting IgE-mediated triggering and/or the Fc εRI-induced secretory response of mucosal mast cells, said peptide and analog being selected from the sequences: (a) Xl-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln- His-R5-R6-R7-R8-R9-R10-Gly-Leu-Ala-Rl 1 ;
(b) Xl-Cys-Asn-Rl-X4;
(c) X2-Lys-Val-Phe-Leu-Asp-X3; and (d) X5-Asp-Ser-Ser-Asn-Tyr-Ile-Rl 1 wherein
XI is H, lower alkanoyl, Cys, Asp-Cys or Arg-Arg-Cys; X2 is H, lower alkanoyl or Lys; X3 is Arg or a sequence selected from (i) Ala-Ala-Asn-Rl-Ile-Thr-R2-Leu-R3-R4;
(ii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3; and (iii) Cys-Cys-Asn-Rl -Ile-Thr-R2-Leu-R3-R4-Gln-His-R5-R6; X4 is Gly, (i) Ile-Thr-R2-Leu-R3; or (ii) Ile-Thr-Arg-Rl 1 ; X5 is H, lower alkanoyl or Leu; RI is an aromatic amino acid residue; R2 is Glu or Lys; R3 is a positively charged amino acid residue; R4 is Arg or Glu; R5 is Ala or Arg: R6 is Arg or Lys; R7 is Ala or Asp; R8 is Ser or His; R9 is His or Val; RIO is Leu, He, Ala or Gly; and RI 1 is OH, Arg, Arg-NH2, or Agm (agmatine), and chemical derivatives and pharmaceutically acceptable salts thereof.
13. The pharmaceutical composition according to Claim 12, for the prevention and/or treatment of allergic disorders caused by Ig-E mediated (Type I) hypersensitivity where mucosal-type mast cells are involved.
14. The pharmaceutical composition according to Claim 13, for the prevention and/or treatment of hay fever, asthma, some cases of urticaria, and allergic conjunctivitis.
15. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide wherein RI is an aromatic amino acid residue selected from Phe, Tyr, His and Trp; and R3 is a positively charged amino acid residue selected from Arg, D-Arg, Har (homoarginine) and Lys.
16. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg
17. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg-NH2
18. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg
19. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg-NH2
20. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala
21. The The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-NH2
22. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg
23. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg-NH2
24. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Asp-Ser-Ser-Asn-Tyr-Ile-Arg
25. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Asp- Ser-Ser-Asn-Tyr-Ile-Arg-NH2
26. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence :
Cys-Cys-Asn-Tyr-Gly
27. The pharmaceutical composition according to any one of claims 12-14 comprising the peptide of the sequence : Cys-Cys-Asn-Tyr-Gly-NH2
28. Use of a peptide consisting partially or entirely of the 50-77 sequence of the complement-derived peptide C3a, an analog, a chemical derivative or a pharmaceutically acceptable salt thereof, said peptide and analog being selected from the sequences: (a) Xl-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln-
His-R5-R6-R7-R8-R9-Rl O-Gly-Leu-Ala-Rl 1 ;
(b) Xl-Cys-Asn-Rl-X4;
(c) X2-Lys-Val-Phe-Leu-Asp-X3; and
(d) X5-Asp-Ser-Ser-Asn-Tyr-Ile-Rl 1 wherein
XI is H, lower alkanoyl, Cys, Asp-Cys or Arg-Arg-Cys;
X2 is H, lower alkanoyl or Lys;
X3 is Arg or a sequence selected from
27
D D (i) Ala-Ala-Asn-Rl-Ile-Thr-R2-Leu-R3-R4; (ii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3; and (iii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln-His-R5-R6; X4 is Gly, (i) Ile-Thr-R2-Leu-R3; or (ii) Ile-Thr-Arg-Rl 1 ; X5 is H, lower alkanoyl or Leu;
RI is an aromatic amino acid residue; R2 is Glu or Lys; R3 is a positively charged amino acid residue; R4 is Arg or Glu; R5 is Ala or Arg: R6 is Arg or Lys; R7 is Ala or Asp; R8 is Ser or His; R9 is His or Val; RIO is Leu, He, Ala or Gly; and RI 1 is OH, Arg, Arg-NH2, or Agm (agmatine), for the preparation of a pharmaceutical composition for the prevention and/or treatment of allergic disorders caused by Ig-E mediated (Type I) hypersensitivity where mucosal-type mast cells are involved.
29. The use according to Claim 28, for the prevention and/or treatment of hay fever, asthma, some cases of urticaria, and allergic conjunctivitis.
30. The use according to claim 28 or 29 of the peptide wherein RI is an aromatic amino acid residue selected from Phe, Tyr, His and Trp; and R3 is a positively charged amino acid residue selected from Arg, D-Arg, Har (homoarginine) and Lys.
31. The use according to claim 28 or 29 of the peptide of the sequence : Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg
32. The use according to claim 28 or 29 of the peptide of the sequence : Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln-
His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg-NH2
33. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg
34. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg-NH2
35. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala
36. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-NH2
37. The use according to claim 28 or 29 of the peptide of the sequence :
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg
38. The use according to claim 28 or 29 of the peptide of the sequence : Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg-NH2
39. The use according to claim 28 or 29 of the peptide of the sequence :
Asp-Ser-Ser-Asn-Tyr-Ile-Arg
40. The use according to claim 28 or 29 of the peptide of the sequence : Asp- Ser-Ser-Asn-Tyr-Ile-Arg-NH2
41. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Cys-Asn-Tyr-Gly
42. The use according to claim 28 or 29 of the peptide of the sequence :
Cys-Cys-Asn-Tyr-Gly-NH2
43. A method for the prevention and/or treatment of allergic disorders caused by Ig-E mediated (Type I) hypersensitivity where mucosal-type mast cells are involved, comprising administering to an individual in need thereof a peptide consisting partially or entirely of the 50-77 sequence of the complement-derived peptide C3a, an analog, a chemical derivative or a pharmaceutically acceptable salt thereof, said peptide and analog being selected from the sequences:
(a) Xl-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln-
His-R5-R6-R7-R8-R9-Rl O-Gly-Leu-Ala-Rl 1 ; (b) Xl-Cys-Asn-Rl-X4;
(c) X2-Lys-Val-Phe-Leu-Asp-X3; and
(d) X5-Asp-Ser-Ser-Asn-Tyr-Ile-Rl 1 wherein
XI is H, lower alkanoyl, Cys, Asp-Cys or Arg-Arg-Cys; X2 is H, lower alkanoyl or Lys;
X3 is Arg or a sequence selected from
(i) Ala-Ala- Asn-Rl-Ile-Thr-R2-Leu-R3-R4; (ii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3; and (iii) Cys-Cys-Asn-Rl-Ile-Thr-R2-Leu-R3-R4-Gln-His-R5-R6; X4 is Gly, (i) Ile-Thr-R2-Leu-R3 ; or (ii) Ile-Thr-Arg-Rl 1 ;
X5 is H, lower alkanoyl or Leu;
RI is an aromatic amino acid residue; R2 is Glu or Lys; R3 is a positively charged amino acid residue; R4 is Arg or Glu; R5 is Ala or Arg: R6 is Arg or Lys; R7 is Ala or Asp; R8 is Ser or His; R9 is His or Val; RIO is Leu, He, Ala or Gly; and RI 1 is OH, Arg, Arg-NH2, or Agm (agmatine).
44. The method according to Claim 43, for the prevention and/or treatment of hay fever, asthma, some cases of urticaria, and allergic conjunctivitis.
45. The method according to claim 43 wherein RI is an aromatic amino acid residue selected from Phe, Tyr, His and Trp; and R3 is a positively charged amino acid residue selected from Arg, D-Arg, Har (homoarginine) and Lys.
46. The method according to claim 43 wherein the peptide or analog is selected from the group consisting of:
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg
30 Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-Arg-NH2
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg
Cys-Asn-Tyr-Ile-Thr-Lys-Leu-Arg-Glu-Gln- His-Arg-Arg-Asp-His-Val-Leu-Gly-Leu-Ala-Arg-NH2
Cy s-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln-
His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala
Cys-Asn-Tyr-Ile-Thr-Glu-Leu-Arg-Arg-Gln- His-Ala-Arg-Ala-Ser-His-Leu-Gly-Leu-Ala-NH2
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg
Asp-Cys-Cys-Asn-Tyr-Ile-Thr-Arg-NH2
Asp-Ser-Ser-Asn-Tyr-Ile-Arg
Asp- Ser-Ser-Asn-Tyr-Ile-Arg-NH2
Cys-Cys-Asn-Tyr-Gly
Cys-Cys-Asn-Tyr-Gly-NH2
31
PCT/IL1998/000292 1997-06-22 1998-06-22 PEPTIDES DERIVED FROM COMPLEMENT PEPTIDE C3a SEQUENCE AND ANTIALLERGIC COMPOSITIONS COMPRISING THEM Ceased WO1998058960A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AT98928510T ATE265467T1 (en) 1997-06-22 1998-06-22 PEPTIDES DERIVED FROM COMPLEMENT PEPTIDE C3A AND ANTIALLERGIC COMPOSITIONS CONTAINING THEM
DE69823528T DE69823528T2 (en) 1997-06-22 1998-06-22 PEPTIDES DERIVED FROM COMPLEMENTEPEPTIDE C3A AND ANTIALLERGIC COMPOSITIONS CONTAINING THEM
IL13342798A IL133427A0 (en) 1997-06-22 1998-06-22 Peptides derived from complement peptide c3a sequence and antiallergic compositions comprising them
EP98928510A EP1015484B1 (en) 1997-06-22 1998-06-22 Peptides derived from complement peptide c3a sequence and antiallergic compositions comprising them
AU80325/98A AU8032598A (en) 1997-06-22 1998-06-22 Peptides derived from complement peptide c3a sequence and antiallergic compositions comprising them

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL121134 1997-06-22
IL12113497A IL121134A0 (en) 1997-06-22 1997-06-22 Peptides and antiallergic compositions comprising them

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/708,606 Continuation-In-Part US6682740B1 (en) 1997-06-22 2000-11-09 Peptides derived fram complement peptide C3a sequence and antiallergic compositions comprising them

Publications (2)

Publication Number Publication Date
WO1998058960A1 WO1998058960A1 (en) 1998-12-30
WO1998058960B1 true WO1998058960B1 (en) 1999-02-25

Family

ID=11070292

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL1998/000292 Ceased WO1998058960A1 (en) 1997-06-22 1998-06-22 PEPTIDES DERIVED FROM COMPLEMENT PEPTIDE C3a SEQUENCE AND ANTIALLERGIC COMPOSITIONS COMPRISING THEM

Country Status (7)

Country Link
US (1) US6682740B1 (en)
EP (1) EP1015484B1 (en)
AT (1) ATE265467T1 (en)
AU (1) AU8032598A (en)
DE (1) DE69823528T2 (en)
IL (1) IL121134A0 (en)
WO (1) WO1998058960A1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0301431D0 (en) 2003-05-19 2003-05-19 Dermagen Novel antimicrobial peptides
WO2006015616A1 (en) * 2004-08-13 2006-02-16 Indivumed Gmbh Use of transthyretin as a biomarker for colorectal adenoma and/or carcinoma; method for detection and test system
SE0402807D0 (en) * 2004-11-17 2004-11-17 Dermagen Ab Novel antimicrobial peptides
WO2006071843A2 (en) * 2004-12-27 2006-07-06 Vereniging Het Nederlands Kanker Instituut Biomarkers for breast cancer
WO2007013083A2 (en) * 2005-07-27 2007-02-01 Yeda Research And Development Co. Ltd. Complement c3a derived peptides and uses thereof
US20070235450A1 (en) * 2006-03-30 2007-10-11 Advanced Composite Materials Corporation Composite materials and devices comprising single crystal silicon carbide heated by electromagnetic radiation
WO2010092577A2 (en) * 2009-02-12 2010-08-19 Yeda Research And Development Co. Ltd. COMPLEMENT C3a DERIVED DIMERIC PEPTIDES AND USES THEREOF
EP2363972A1 (en) 2010-02-26 2011-09-07 Panasonic Corporation Mapping of service components to physical-layer pipes
CN111150832B (en) * 2014-02-08 2023-03-07 德赛诊断系统(上海)有限公司 Application of inhibitor SC-2 of Cyr61/CCN1 protein epitope polypeptide

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