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Details for Patent: 7,794,725

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Details for Patent: 7,794,725

Title:Isolated peptides derived from human immunodeficiency virus types 1 and 2 containing fusion inhibitory domains
Abstract: The present invention relates to peptides which exhibit potent anti-retroviral activity. The peptides of the invention comprise DP178 (SEQ ID NO:1) peptide corresponding to amino acids 638 to 673 of the HIV-1.sub.LAI gp41 protein, and fragments, analogs and homologs of DP178. The invention further relates to the uses of such peptides as inhibitory of human and non-human retroviral, especially HIV, transmission to uninfected cells.
Inventor(s): Barney; Shawn O'Lin (Cary, NC), Lambert; Dennis Michael (Cary, NC), Petteway; Stephen Robert (Cary, NC)
Assignee: Trimeris, Inc. (Durham, NC)
Filing Date:Jun 07, 1995
Application Number:08/484,223
Claims:1. An isolated peptide consisting of: (a) a 28 or 35 amino acid residue region of an HIV-1 or HIV-2 protein identified by an ALLMOTI5 sequence search motif; a 28 or 35 amino acid residue region of an HIV-1 or HIV-2 protein identified by a 107.times.178.times.4 sequence search motif; or a 16 to 39 amino acid residue region of an HIV-1 or HIV-2 protein identified by a PLZIP sequence search motif, and (b) an amino terminal X and a carboxy terminal Z in which: X comprises an amino group, an acetyl group, a 9-fluorenylmethoxy-carbonyl group or a hydrophobic group; and Z comprises a carboxyl group, an amido group or a hydrophobic group.

2. An isolated peptide consisting of the formula: X-NKSLEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLELDK WASLWNWF-Z (SEQ ID NO:210); X-SLEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQ-Z (SEQ ID NO:211); X-LEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQE-Z (SEQ ID NO:212); X-EQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEK-Z (SEQ ID NO:213); X-QIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKN-Z (SEQ ID NO:214); X-IWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNE-Z (SEQ ID NO:215); X-WNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQ-Z (SEQ ID NO:216); X-NNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQE-Z (SEQ ID NO:217); X-NMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQEL-Z (SEQ ID NO:218); X-MTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLELDKWASLWNW-Z (SEQ ID NO:219); X-TWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:220); X-WMEWDREINNYTSLIHSLIEESQNQQEKNEQELLEL-Z (SEQ ID NO:221); X-WMEWDREINNYTSLIHSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:222); X-WMEWDREINNYTSLIGSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:159); X-MEWDREINNYTSLIHSLIEESQNQQEKNEQELLELD-Z (SEQ ID NO:223); X-EWDREINNYTSLIHSLIEESQNQQEKNEQELLELDK-Z (SEQ ID NO:224); X-WDREINNYTSLIHSLIEESQNQQEKNEQELLELDKW-Z (SEQ ID NO:225); X-DREINNYTSLIHSLIEESQNQQEKNEQELLELDKWA-Z (SEQ ID NO:226); X-REINNYTSLIHSLIEESQNQQEKNEQELLELDKWAS-Z (SEQ ID NO:227); X-EINNYTSLIHSLIEESQNQQEKNEQELLELDKWASL-Z (SEQ ID NO:228); X-INNYTSLIHSLIEESQNQQEKNEQELLELDKWASLW-Z (SEQ ID NO:229); X-NYTSLIHSLIEESQNQQEKNEQELLELDKWASLWNW-Z (SEQ ID NO:230); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWFNITNWLWLIKIFI-Z (SEQ ID NO:160); X-TSLIHSLIEESQNQQEKNEQELLELDKWASLWNWFN-Z (SEQ ID NO:231); X-SLIHSLIEESQNQQEKNEQELLELDKWASLWNWFNI-Z (SEQ ID NO:232); X-LIHSLIEESQNQQEKNEQELLELDKWASLWNWFNIT-Z (SEQ ID NO:233); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNAF-Z (SEQ ID NO:178); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLANWF-Z (SEQ ID NO:179); X-YTSLIHSLIEESQNQQEKNEQQLLELDKWASLWNWF-Z (SEQ ID NO:180); X-YTSLIHSLIEESQNQQEKNEQELLQLDKWASLWNWF-Z (SEQ ID NO:181); X-YTSLIHSLIEESQNQQEKNQQELLQLDKWASLWNWF-Z (SEQ ID NO:182); X-YTSLIQSLIEESQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:183); X-YTSLIHSLIEQSQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:186); X-YTSLIHSLIQESQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:187); X-YTSLIHSLIEESQNQQEKNEQQLLELDKEASLWNWF-Z (SEQ ID NO:190); X-YTSLIQSLIEESQNQQEKNEQQLLELDKWASLWNWF-Z (SEQ ID NO:191); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLFNFF-Z (SEQ ID NO:192); X-YTSLIHSLIEESQNLQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:193); X-YTSLIHSLIEESQNQQEKLEQELLELDKWASLWNWF-Z (SEQ ID NO:194); X-YTSLIHSLIEESQNQQEKNEQELLEFDKWASLWNWF-Z (SEQ ID NO:195); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASPWNWF-Z (SEQ ID NO:197); X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNSF-Z (SEQ ID NO:198); X-MTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELL-Z (SEQ ID NO:308); or X-NKSLEQIWNNMTWMEWDREINNYTSLIHSLIEESQN-Z (SEQ ID NO:309); in which: amino acid residues are presented by the single-letter code; X comprises an amino group, an acetyl group, a 9-fluorenylmethoxy-carbonyl group, a hydrophobic group, or a macromolecular carrier group; and Z comprises a carboxyl group, an amido group, a hydrophobic group, or a macromolecular carrier group.

3. The peptide of claim 1 or 2, wherein X is a hydrophobic group.

4. The peptide of claim 3, wherein the hydrophobic group X is carbobenzoxyl, dansyl, or t-butyloxycarbonyl.

5. The peptide of claim 1 or 2, wherein Z is a hydrophobic group.

6. The peptide of claim 5, wherein the hydrophobic group Z is t-butyloxycarbonyl.

7. The peptide of claim 1 or 2, wherein at least one bond linking adjacent amino acid residues of the peptide is a non-peptide bond.

8. The peptide of claim 7, wherein the non-peptide bond is an imino, ester, hydrazine, semicarbazide, or azo bond.

9. The peptide of claim 1 or 2, wherein at least one amino acid residue of the peptide is in a D-isomer configuration.

10. The peptide of claim 1 or 2, wherein group X is an acetyl group, and group Z is an amido group.

11. The peptide of claim 2, wherein the peptide consists of the formula: X-NKSLEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLELDK WASLWNWF-Z (SEQ ID NO:210).

12. The peptide of claim 2, wherein the peptide consists of the formula: X-SLEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQ-Z (SEQ ID NO:211).

13. The peptide of claim 2, wherein the peptide consists of the formula: X-LEQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQE-Z (SEQ ID NO:212).

14. The peptide of claim 2, wherein the peptide consists of the formula: X-EQIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEK-Z (SEQ ID NO:213).

15. The peptide of claim 2, wherein the peptide consists of the formula: X-QIWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKN-Z (SEQ ID NO:214).

16. The peptide of claim 2, wherein the peptide consists of the formula: X-IWNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNE-Z (SEQ ID NO:215).

17. The peptide of claim 2, wherein the peptide consists of the formula: X-WNNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQ-Z (SEQ ID NO:216).

18. The peptide of claim 2, wherein the peptide consists of the formula: X-NNMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQE-Z (SEQ ID NO:217).

19. The peptide of claim 2, wherein the peptide consists of the formula: X-NMTWMEWDREINNYTSLIHSLIEESQNQQEKNEQEL-Z (SEQ ID NO:218).

20. The peptide of claim 2, wherein the peptide consists of the formula: X-MTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLELDKWASLWNW-Z (SEQ ID NO:219).

21. The peptide of claim 2, wherein the peptide consists of the formula: X-TWMEWDREINNYTSLIHSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:220).

22. The peptide of claim 2, wherein the peptide consists of the formula: X-WMEWDREINNYTSLIHSLIEESQNQQEKNEQELLEL-Z (SEQ ID NO:221).

23. The peptide of claim 2, wherein the peptide consists of the formula: X-WMEWDREINNYTSLIHSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:222).

24. The peptide of claim 2, wherein the peptide consists of the formula: X-WMEWDREINNYTSLIGSLIEESQNQQEKNEQELLE-Z (SEQ ID NO:159).

25. The peptide of claim 2, wherein the peptide consists of the formula: X-MEWDREINNYTSLIHSLIEESQNQQEKNEQELLELD-Z (SEQ ID NO:223).

26. The peptide of claim 2, wherein the peptide consists of the formula: X-EWDREINNYTSLIHSLIEESQNQQEKNEQELLELDK-Z (SEQ ID NO:224).

27. The peptide of claim 2, wherein the peptide consists of the formula: X-WDREINNYTSLIHSLIEESQNQQEKNEQELLELDKW-Z (SEQ ID NO:225).

28. The peptide of claim 2, wherein the peptide consists of the formula: X-DREINNYTSLIHSLIEESQNQQEKNEQELLELDKWA-Z (SEQ ID NO:226).

29. The peptide of claim 2, wherein the peptide consists of the formula: X-REINNYTSLIHSLIEESQNQQEKNEQELLELDKWAS-Z (SEQ ID NO:227).

30. The peptide of claim 2, wherein the peptide consists of the formula: X-EINNYTSLIHSLIEESQNQQEKNEQELLELDKWASL-Z (SEQ ID NO:228).

31. The peptide of claim 2, wherein the peptide consists of the formula: X-INNYTSLIHSLIEESQNQQEKNEQELLELDKWASLW-Z (SEQ ID NO:229).

32. The peptide of claim 2, wherein the peptide consists of the formula: X-NYTSLIHSLIEESQNQQEKNEQELLELDKWASLWNW-Z (SEQ ID NO:230).

33. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWFNITNWLWLIKIFI-Z (SEQ ID NO:160).

34. The peptide of claim 2, wherein the peptide consists of the formula: X-TSLIHSLIEESQNQQEKNEQELLELDKWASLWNWFN-Z (SEQ ID NO:231).

35. The peptide of claim 2, wherein the peptide consists of the formula: X-SLIHSLIEESQNQQEKNEQELLELDKWASLWNWFNI-Z (SEQ ID NO:232).

36. The peptide of claim 2, wherein the peptide consists of the formula: X-LIHSLIEESQNQQEKNEQELLELDKWASLWNWFNIT-Z (SEQ ID NO:233).

37. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNAF-Z (SEQ ID NO:178).

38. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLANWF-Z (SEQ ID NO:179).

39. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQQLLELDKWASLWNWF-Z (SEQ ID NO:180).

40. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLQLDKWASLWNWF-Z (SEQ ID NO:181).

41. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNQQELLQLDKWASLWNWF-Z (SEQ ID NO:182).

42. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIQSLIEESQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:183).

43. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEQSQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:186).

44. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIQESQNQQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:187).

45. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQQLLELDKEASLWNWF-Z (SEQ ID NO:190).

46. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIQSLIEESQNQQEKNEQQLLELDKWASLWNWF-Z (SEQ ID NO:191).

47. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLFNFF-Z (SEQ ID NO:192).

48. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNLQEKNEQELLELDKWASLWNWF-Z (SEQ ID NO:193).

49. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKLEQELLELDKWASLWNWF-Z (SEQ ID NO:194).

50. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLEFDKWASLWNWF-Z (SEQ ID NO:195).

51. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASPWNWF-Z (SEQ ID NO:197).

52. The peptide of claim 2, wherein the peptide consists of the formula: X-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNSF-Z (SEQ ID NO:198).

53. The peptide of claim 2, wherein the peptide consists of the formula: X-LRAIEAQQHLLQLTVWGIKQLQARILAV-Z (SEQ ID NO:239).

54. The peptide of claim any one of claims 11 through 53, wherein X is an acetyl group, and Z is an amido group.

55. The peptide of claim 1, wherein the region of the HIV-1 or HIV-2 protein is a region of 28 amino acid residues identified by the ALLMOTI5 motif.

56. The peptide of claim 1, wherein the region of the HIV-1 or HIV-2 protein is a region of 35 amino acid residues identified by the ALLMOTI5 motif.

57. The peptide of claim 1, wherein the region of the HIV-1 or HIV-2 protein is a region of 28 amino acid residues identified by the 107.times.178.times.4 motif.

58. The peptide of claim 1, wherein the region of the HIV-1 or HIV-2 protein is a region of 35 amino acid residues identified by the 107.times.178.times.4 motif.

59. An isolated peptide consisting of: (a) a 16 to 39 amino acid residue region of an HIV-1 or HIV-2 protein identified by a PLZIP sequence search motif, and (b) an amino terminal X and a carboxy terminal Z in which: X comprises an amino group, an acetyl group, a 9-fluorenylmethoxy-carbonyl group, a hydrophobic group, or a macromolecular carrier group; and Z comprises a carboxyl group, an amido group, a hydrophobic group, or a macromolecular carrier group.

60. An isolated peptide consisting of: (a) a 28 or 35 amino acid residue region of an HIV-1 or HIV-2 protein identified by a 107.times.178.times.4 sequence search motif; and (b) an amino terminal X and a carboxy terminal Z in which: X comprises an amino group, an acetyl group, a 9-fluorenylmethoxy-carbonyl group or a hydrophobic group; and Z comprises a carboxyl group, an amido group or a hydrophobic group.

61. The peptide of claim 2, wherein the peptide consists of the formula: X-MTWMEWDREINNYTSLIHSLIEESQNQQEKNEQELL-Z (SEQ ID NO:308).

62. The peptide of claim 2, wherein the peptide consists of the formula: X-NKSLEQIWNNMTWMEWDREINNYTSLIHSLIEESQN-Z (SEQ ID NO:309).
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