IP Library Granted Patent US 7,803,764
Granted Patent B2
US 7,803,764 · App. 10/594,515 · Granted Sep 28, 2010

Amphipathic glycopeptides

Assignee: The Arizona Board of Regents on Behalf of the University of Arizona
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Quick Facts
Patent No.
US 7,803,764
App. No.
10/594,515
Granted
Sep 28, 2010
Kind
B2
Abstract

Amphipathic glycopeptides, the amino acid sequence of which comprises an N-terminal opioid message sequence, a C-terminal helical address sequence, and a linker sequence between the message sequence and the helical address sequence, where the C-terminal helical address sequence has a length of nine amino acids, and at least one of the amino acid residues of the peptide is glycosylated. The peptides are useful for relieving pain, providing analgesia and treating anxiety, depression, obesity, anorexia nervosa, phobias, schizophrenia, Parkinson's disease and Alzheimer's disease.

Claims (34)

1. An amphipathic glycopeptide, the amino acid sequence of which comprises an N-terminal opioid message sequence, a C-terminal helical address sequence, and a linker sequence between the message sequence and the helical address sequence, wherein

the C-terminal helical address sequence has a length of nine amino acids, and

at least one of the amino acid residues of the peptide is glycosylated.

2. The glycopeptide of claim 1 , wherein the N-terminal opioid message sequence is Y-t-G-F- or Y-a-G-F-.

3. The glycopeptide of claim 1 , wherein the N-terminal opioid message sequence is Y-t-G-F-L-P-.

4. The glycopeptide of claim 1 , wherein the N-terminal opioid message sequence is Y-t-G-F-L-βA-.

5. The glycopeptide of claim 1 , wherein the N-terminal opioid message sequence is Y-t-G-F-L-G-G-.

6. The glycopeptide of claim 1 , which is a glycosylated enkephalin.

7. The glycopeptide of claim 1 , which is a glycosylated endorphin.

8. The glycopeptide of claim 1 , which adopts a helical conformation in the presence of a lipid bilayer.

9. The glycopeptide of claim 1 , which is substantially non-helical in water in the absence of a lipid bilayer.

10. The glycopeptide of claim 1 , which is substantially non-helical in water in the absence of a lipid bilayer and adopts a helical conformation in the presence of a lipid bilayer.

11. The glycopeptide of claim 1 , wherein one amino acid residue is glycosylated.

12. The glycopeptide of claim 1 , wherein two amino acid residues are glycosylated.

13. The glycopeptide of claim 1 , which comprises at least one serine residue that is glycosylated.

14. The glycopeptide of claim 1 , which comprises 2 serine residues that are glycosylated.

15. The glycopeptide of claim 1 , which is glycosylated with a glycosyl unit having at most 8 saccharide units.

16. The glycopeptide of claim 1 , which is glycosylated with a glycosyl unit having at most 4 saccharide units.

17. The glycopeptide of claim 1 , which is glycosylated with a glycosyl unit having at most 2 saccharide units.

18. The glycopeptide of claim 1 , which is glycosylated with a glycosyl unit having at most 1 saccharide unit.

19. The glycopeptide of claim 1 , which contains one serine glucoside residue.

20. The glycopeptide of claim 1 , which contains 2 serine glucoside residues.

21. The glycopeptide of claim 1 , which comprises at least 14 amino acid residues.

22. The glycopeptide of claim 1 , which comprises at least 15 amino acid residues.

23. The glycopeptide of claim 1 , which comprises at least 17 amino acid residues.

24. The glycopeptide of claim 1 , which comprises at least 19 amino acid residues.

25. The glycopeptide of claim 1 , which comprises at most 60 amino acid residues.

26. The glycopeptide of claim 1 , which has at most 5% helicity as measured by circular dichroism in water and at least 10% helicity in the presence of a lipid bilayer.

27. The glycopeptide of claim 1 , which crosses the blood-brain-barrier.

28. The glycopeptide of claim 1 , which is selective for at least one receptor selected from the group consisting of the delta opioid receptor, mu opioid receptor and kappa opioid receptor.

29. A pharmaceutical composition comprising the glycopeptide of claim 1 and at least one pharmaceutically acceptable carrier and/or excipient.

30. A method of relieving pain, comprising administering an effective amount of the glycopeptide of claim 1 to a subject in need thereof.

31. A method of providing analgesia, comprising administering an effective amount of the glycopeptide of claim 1 to a subject in need thereof.

32. A method of treating anxiety, depression, obesity, anorexia nervosa, phobias, schizophrenia, Parkinson's disease or Alzheimer's disease, comprising administering an effective amount of the glycopeptide of claim 1 to a subject in need thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2010
From: POLT, ROBIN; BILSKY, EDWARD
To: THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA
Reel/Frame 024780/0111 →
Continuity (4)
Provisional Application 6064149200 · Jan 5, 2005
Provisional Application 6058325700 · Jun 25, 2004
Provisional Application 6055774000 · Mar 29, 2004
Related Publication 20080207492A1 · Aug 28, 2008