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Details for Patent: 6,333,395

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Details for Patent: 6,333,395

Title: Compositions for inhibition of membrane fusion-associated events, including human parainfluenza virus transmission
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 (Cary, NC), Lambert; Dennis (Cary, NC), Petteway; Stephen Robert (Cary, NC)
Assignee:
Filing Date:Jun 07, 1995
Application Number:08/474,349
Claims:1. An isolated peptide consisting of:

(a) an amino acid sequence of a 16 to 39 amino acid residue region of a human parainfluenza virus protein, wherein said region is identified by:

(i) 4 or 5 heptad repeats of an ALLMOTI5 sequence search motif;

(ii) 4 or 5 heptad repeats of a 107.times.178.times.4 sequence search motif; or

(iii) 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, a macromolecular carrier group; and

Z comprises a carboxyl group, an amido group, a hydrophobic group, or a macromolecular carrier group.

2. The peptide of claim 1, wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the ALLMOTI5 sequence search motif.

3. The peptide of claim 1, wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the ALLMOTI5 sequence search motif.

4. The peptide of claim 1, wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the 107.times.178.times.4 sequence search motif.

5. The peptide of claim 1, wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the 107.times.178.times.4 sequence search motif.

6. The peptide of claim 1, wherein the region of the human parainfluenza virus protein is a region identified by a PLZIP sequence search motif.

7. An isolated peptide having the formula:

X-TLNNSVALDPIDISIELNKAKSDLEESKEWIRRSN-Z (SEQ ID NO:33);

X-LNNSVALDPIDISIELNKAKSDLEESKEWIRRSNQ-Z (SEQ ID NO:34);

X-NNSVALDPIDISIELNKAKSDLEESKEWIRRSNQK-Z (SEQ ID NO:35);

X-NSVALDPIDISIELNKAKSDLEESKEWIRRSNQKL-Z (SEQ ID NO:36);

X-SVALDPIDISIELNKAKSDLEESKEWIRRSNQKLD-Z (SEQ ID NO:37);

X-VALDPIDISIELNKAKSDLEESKEWIRRSNQKLDS-Z (SEQ ID NO:38);

X-ALDPIDISIELNKAKSDLEESKEWIRRSNQKLDSI-Z (SEQ ID NO:39);

X-LDPIDISIELNKAKSDLEESKEWIRRSNQKLDSIG-Z (SEQ ID NO:40);

X-DPIDISIELNKAKSDLEESKEWIRRSNQKLDSIGN-Z (SEQ ID NO:41);

X-PIDISIELNKAKSDLEESKEWIRRSNQKLDSIGNW-Z (SEQ ID NO:42);

X-IDISIELNKAKSDLEESKEWIRRSNQKLDSIGNWH-Z (SEQ ID NO:43);

X-DISIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQ-Z (SEQ ID NO:44);

X-ISIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQS-Z (SEQ ID NO:45);

X-SIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSS-Z (SEQ ID NO:46);

X-IELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSST-Z (SEQ ID NO:47);

X-ELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSSTT-Z (SEQ ID NO:48);

X-TAAVALVEAKQARSDIEKLKEAIRDTNKAVQSVQS-Z (SEQ ID NO:49);

X-AVALVEAKQARSDIEKLKEAIRDTNKAVQSVQSSI-Z (SEQ ID NO:50);

X-LVEAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNL-Z (SEQ ID NO:51);

X-VEAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLI-Z (SEQ ID NO:52);

X-EAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIV-Z (SEQ ID NO:53);

X-AKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVA-Z (SEQ ID NO:54);

X-KQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAI-Z (SEQ ID NO:55);

X-QARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIK-Z (SEQ ID NO:56);

X-ARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKS-Z (SEQ ID NO:57);

X-RSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKSV-Z (SEQ ID NO:58);

X-SDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKSVQ-Z (SEQ ID NO:59);

X-KLKEAIRDTNKAVQSVQSSIGNLIVAIKSVQDYVN-Z (SEQ ID NO:60);

X-LKEAIRDTNKAVQSVQSSIGNLIVAIKSVQDYVNK-Z (SEQ ID NO:61); or

X-AIRDTNKAVQSVQSSIGNLIVAIKSVQDYVNKEIV-Z (SEQ ID NO:62)

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;

Z comprises a carboxyl group, an amido group, a hydrophobic group, or a macromolecular carrier group.

8. The peptide of claim 7, wherein the peptide has the formula:

X-TLNNSVALDPIDISIELNKAKSDLEESKEWIRRSN-Z (SEQ ID NO:33).

9. The peptide of claim 7, wherein the peptide has the formula:

X-LNNSVALDPIDISIELNKAKSDLEESKEWIRRSNQ-Z (SEQ ID NO:34).

10. The peptide of claim 7, wherein the peptide has the formula:

X-NNSVALDPIDISIELNKAKSDLEESKEWIRRSNQK-Z (SEQ ID NO:35).

11. The peptide of claim 7, wherein the peptide has the formula:

X-NSVALDPIDISIELNKAKSDLEESKEWIRRSNQKL-Z (SEQ ID NO:36).

12. The peptide of claim 7, wherein the peptide has the formula:

X-SVALDPIDISIELNKAKSDLEESKEWIRRSNQKLD-Z (SEQ ID NO:37).

13. The peptide of claim 7, wherein the peptide has the formula:

X-VALDPIDISIELNKAKSDLEESKEWIRRSNQKLDS-Z (SEQ ID NO:38).

14. The peptide of claim 7, wherein the peptide has the formula:

X-ALDPIDISIELNKAKSDLEESKEWIRRSNQKLDSI-Z (SEQ ID NO:39).

15. The peptide of claim 7, wherein the peptide has the formula:

X-LDPIDISIELNKAKSDLEESKEWIRRSNQKLDSIG-Z (SEQ ID NO:40).

16. The peptide of claim 7, wherein the peptide has the formula:

X-DPIDISIELNKAKSDLEESKEWIRRSNQKLDSIGN-Z (SEQ ID NO:41).

17. The peptide of claim 7, wherein the peptide has the formula:

X-PIDISIELNKAKSDLEESKEWIRRSNQKLDSIGNW-Z (SEQ ID NO:42).

18. The peptide of claim 7, wherein the peptide has the formula:

X-IDISIELNKAKSDLEESKEWIRRSNQKLDSIGNWH-Z (SEQ ID NO:43).

19. The peptide of claim 7, wherein the peptide has the formula:

X-DISIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQ-Z (SEQ ID NO:44).

20. The peptide of claim 7, wherein the peptide has the formula:

X-ISIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQS-Z (SEQ ID NO:45).

21. The peptide of claim 7, wherein the peptide has the formula:

X-SIELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSS-Z (SEQ ID NO:46).

22. The peptide of claim 7, wherein the peptide has the formula:

X-IELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSST-Z (SEQ ID NO:47).

23. The peptide of claim 7, wherein the peptide has the formula:

X-ELNKAKSDLEESKEWIRRSNQKLDSIGNWHQSSTT-Z (SEQ ID NO:48).

24. The peptide of claim 7, wherein the peptide has the formula:

X-TAAVALVEAKQARSDIEKLKEAIRDTNKAVQSVQS-Z (SEQ ID NO:49).

25. The peptide of claim 7, wherein the peptide has the formula:

X-AVALVEAKQARSDIEKLKEAIRDTNKAVQSVQSSI-Z (SEQ ID NO:50).

26. The peptide of claim 7, wherein the peptide has the formula:

X-LVEAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNL-Z (SEQ ID NO:51).

27. The peptide of claim 7, wherein the peptide has the formula:

X-VEAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLI-Z (SEQ ID NO:52).

28. The peptide of claim 7, wherein the peptide has the formula:

X-EAKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIV-Z (SEQ ID NO:53).

29. The peptide of claim 7, wherein the peptide has the formula:

X-AKQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVA-Z (SEQ ID NO:54).

30. The peptide of claim 7, wherein the peptide has the formula:

X-KQARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAI-Z (SEQ ID NO:55).

31. The peptide of claim 7, wherein the peptide has the formula:

X-QARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIK-Z (SEQ ID NO:56).

32. The peptide of claim 7, wherein the peptide has the formula:

X-ARSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKS-Z (SEQ ID NO:57).

33. The peptide of claim 7, wherein the peptide has the formula:

X-RSDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKSV-Z (SEQ ID NO:58).

34. The peptide of claim 7, wherein the peptide has the formula:

X-SDIEKLKEAIRDTNKAVQSVQSSIGNLIVAIKSVQ-Z (SEQ ID NO:59).

35. The peptide of claim 7, wherein the peptide has the formula:

X-KLKEAIRDTNKAVQSVQSSIGNLIVAIKSVQDYVN-Z (SEQ ID NO:60).

36. The peptide of claim 7, wherein the peptide has the formula:

X-LKEAIRDTNKAVQSVQSSIGNLIVAIKSVQDYVNK-Z (SEQ ID NO:61).

37. The peptide of claim 7, wherein the peptide has the formula:

X-AIRDTNKAVQSVQSSIGNLIVAIKSVQDYVNKEIV-Z (SEQ ID NO:62).

38. The peptide of claim 1 or 7 wherein X is a hydrophobic group.

39. The peptide of claim 38 wherein the hydrophobic group X is carbobenzoxyl, dansyl, or t-butyloxycarbonyl.

40. The peptide of claim 1 or 7 wherein Z is a hydrophobic group.

41. The peptide of claim 40 wherein the hydrophobic group Z is t-butyloxycarbonyl.

42. The peptide of claim 1 or 7 wherein X is a macromolecular carrier group.

43. The peptide of claim 42 wherein the macromolecular carrier group is a lipid-fatty acid conjugate, a polyethylene glycol, or a carbohydrate moiety.

44. The peptide of claim 1 or 7 wherein Z is a macromolecular carrier group.

45. The peptide of claim 44 wherein the macromolecular carrier group Z is a lipid-fatty acid conjugate, a polyethylene glycol, or a carbohydrate moiety.

46. The peptide of claim 42, wherein the macromolecular group X is a peptide group.

47. The peptide of claim 44, wherein the macromolecular group Z is a peptide group.

48. The isolated peptide of claim 1 or 7 wherein X is an acetyl group.

49. The isolated peptide of claim 1 or 7 wherein Z is an amido group.

50. The isolated peptide of claim 1 or 7 wherein

X is an acetyl group, and

Z is an amido group.

51. An isolated peptide consisting of:

(a) an amino acid sequence of a 16 to 39 amino acid residue region of a human parainfluenza virus protein, wherein said region is identified by:

(i) 4 or 5 heptad repeats of an ALLMOTI5 sequence search motif,

(ii) 4 or 5 heptad repeats of a 107.times.78.times.4 sequence search motif, or

(iii) a PLZIP sequence search motif;

(b) an amino terminal insertion of about 2 to about 50 human parainfluenza virus protein amino acid residues amino to the region of the human parainfluenza virus protein identified by the sequence search motif; and

(c) 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.

52. The isolated peptide of claim 51 wherein X is a hydrophobic group.

53. The isolated peptide of claim 52 wherein the hydrophobic group X is carbobenzoxyl, dansyl or t-butyloxycarbonyl.

54. The isolated peptide of claim 51 wherein Z is a hydrophobic group.

55. The isolated peptide of claim 54 wherein the hydrophobic group Z is t-butyloxycarbonyl.

56. The isolated peptide of claim 51 wherein X is a macromolecular carrier group.

57. The isolated peptide of claim 56 wherein the macromolecular carrier group X is a lipid-fatty acid conjugate, a polyethylene glycol or a carbohydrate moiety.

58. The isolated peptide of claim 56 wherein the macromolecular carrier group X is a peptide group.

59. The isolated peptide of claim 51 wherein Z is a macromolecular carrier group.

60. The isolated peptide of claim 59 wherein the macromolecular carrier group Z is a lipid-fatty acid conjugate, a polyethylene glycol, or a carbohydrate moiety.

61. The isolated peptide of claim 59 wherein the macromolecular carrier group Z is a peptide group.

62. The isolated peptide of claim 51 wherein X is an acetyl group.

63. The isolated peptide of claim 51 wherein Z is an amido group.

64. The isolated peptide of claim 51 wherein

X is an acetyl group, and

X is an amido group.

65. The isolated peptide of claim 51 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the ALLMOTI5 sequence search motif.

66. The isolated peptide of claim 51 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the ALLMOTI5 sequence search motif.

67. The isolated peptide of claim 51 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the 107.times.178.times.4 sequence search motif.

68. The isolated peptide of claim 51 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the 107.times.178.times.4 sequence search motif.

69. The isolated peptide of claim 51 wherein the region of the human parainfluenza virus is a region identified by a PLZIP sequence search motif.

70. An isolated peptide consisting of:

(a) an amino acid sequence of a 16 to 39 amino acid residue region of a human parainfluenza virus protein, wherein said region is identified by:

(i) 4 or 5 heptad repeats of an ALLMOTI5 sequence search motif,

(ii) 4 or 5 heptad repeats of a 107.times.178.times.4 sequence search motif, or

(iii) a PLZIP sequence search motif;

(b) an carboxy terminal insertion of about 2 to about 50 human parainfluenza virus protein amino acid residues carboxy to the region of the human parainfluenza virus protein identified by the sequence search motif; and

(c) 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.

71. The isolated peptide of claim 70 wherein X is a hydrophobic group.

72. The isolated peptide of claim 71 wherein the hydrophobic group X is carbobenzoxyl, dansyl or t-butyloxycarbonyl.

73. The isolated peptide of claim 70 wherein Z is a hydrophobic group.

74. The isolated peptide of claim 73 wherein the hydrophobic group Z is t-butyloxycarbonyl.

75. The isolated peptide of claim 70 wherein X is a macromolecular carrier group.

76. The isolated peptide of claim 75 wherein the macromolecular carrier group X is a lipid-fatty acid coniugate, a polyethylene glycol or a carbohydrate moiety.

77. The peptide of claim 75 wherein the macromolecular carrier group X is a peptide group.

78. The isolated peptide of claim 70 wherein Z is a macromolecular carrier group.

79. The isolated peptide of claim 78 wherein the macromolecular carrier group Z is a lipid-fatty acid conjugate, a polyethylene glycol, or a carbohydrate moiety.

80. The isolated peptide of claim 78 wherein the macromolecular carrier group Z is a peptide group.

81. The isolated peptide of claim 70 wherein X is an acetyl group.

82. The isolated peptide of claim 70 wherein Z is an amido group.

83. The isolated peptide of claim 70 wherein

X is an acetyl group, and

X is an amido group.

84. The isolated peptide of claim 70 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the ALLMOTI5 sequence search motif.

85. The isolated peptide of claim 70 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the ALLMOTI5 sequence search motif.

86. The isolated peptide of claim 70 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the 107.times.178.times.4 sequence search motif.

87. The isolated peptide of claim 70 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the 107.times.178.times.4 sequence search motif.

88. The isolated peptide of claim 70 wherein the region of the human parainfluenza virus is a region identified by a PLZIP sequence search motif.

89. An isolated peptide consisting of:

(a) an amino acid sequence of a 16 to 39 amino acid residue region of a human parainfluenza virus protein, wherein said region is identified by:

(i) 4 or 5 heptad repeats of an ALLMOTI5 sequence search motif,

(ii) 4 or 5 heptad repeats of a 107.times.178.times.4 sequence search motif, or

(iii) a PLZIP sequence search motif;

(b) an amino terminal insertion of about 2 to about 50 human parainfluenza virus protein amino acid residues amino to the region of the human parainfluenza virus protein identified by the sequence search motif;

(c) an carboxy terminal insertion of about 2 to about 50 human parainfluenza virus protein amino acid residues carboxy to the region of the human parainfluenza virus protein identified by the sequence search motif, and

(d) 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.

90. The isolated peptide of claim 89 wherein X is a hydrophobic group.

91. The isolated peptide of claim 90 wherein the hydrophobic group X is carbobenzoxyl, dansyl or t-butyloxycarbonyl.

92. The isolated peptide of claim 89 wherein Z is a hydrophobic group.

93. The isolated peptide of claim 92 wherein the hydrophobic group Z is t-butyloxycarbonyl.

94. The isolated peptide of claim 89 wherein X is a macromolecular carrier group.

95. The isolated peptide of claim 94 wherein the macromolecular carrier group X is a lipid-fatty acid conjugate, a polyethylene glycol or a carbohydrate moiety.

96. The isolated peptide of claim 94 wherein the macromolecular carrier group X is a peptide group.

97. The isolated peptide of claim 89 wherein Z is a macromolecular carrier group.

98. The isolated peptide of claim 97 wherein the macromolecular carrier group Z is a lipid-fatty acid conjugates a polyethylene glycol, or a carbohydrate moiety.

99. The isolated peptide of claim 97 wherein the macromolecular carrier group Z is a peptide group.

100. The isolated peptide of claim 89 wherein X is an acetyl group.

101. The isolated peptide of claim 89 wherein Z is an amido group.

102. The isolated peptide of claim 89 wherein

X is an acetyl group, and

X is an amido group.

103. The isolated peptide of claim 89 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the ALLMOTI5 sequence search motif.

104. The isolated peptide of claim 89 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the ALLMOTI5 sequence search motif.

105. The isolated peptide of claim 89 wherein the region of the human parainfluenza virus protein is a region of 28 amino acid residues identified by 4 heptad repeats of the 107.times.178.times.4 sequence search motif.

106. The isolated peptide of claim 89 wherein the region of the human parainfluenza virus protein is a region of 35 amino acid residues identified by 5 heptad repeats of the 107.times.178.times.4 sequence search motif.

107. The isolated peptide of claim 89 wherein the region of the human parainfluenza virus is a region identified by a PLZIP sequence search motif.
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