IP Library › Granted Patent US 12,318,485
Granted Patent B2
US 12,318,485 · App. 18/629,675 · Granted Jun 3, 2025

Methods and compositions for targeted delivery by polymersomes

Inventors: Chi-Huey Wong (Rancho Santa Fe, CA); Jeng Shin Lee (Lincoln, MA); Chen-Yo Fan (Taipei, TW); Szu-Wen Wang (Taipei, TW)
Assignee: ROCK BIOMEDICAL, INC.
A61K9/1273A61K45/06C12N15/88
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Quick Facts
Patent No.
US 12,318,485
App. No.
18/629,675
Granted
Jun 3, 2025
Kind
B2
Abstract

The present disclosure relates to a copolymer and a polymersome for targeted delivery of biomolecules to a living organism. The exemplary copolymer comprises an initiator block, a propagator block, and a linkage connecting the initiator block and the propagator block. The initiator block comprises a glycan head configured to provide a targeted delivery, and the propagator block comprises a functional moiety configured to provide desired properties for the polymersome.

Claims (141)

1. A copolymer for forming a polymersome, wherein the copolymer comprises:

an initiator block, comprising a glycan head;

a propagator block, comprising a functional moiety, which comprises a guanidine group, a zwitterion group, a diethylene triamine, or a combination thereof, and

a linkage, covalently connecting the initiator block and the propagator block, wherein the linkage comprises a disulfide bond.

2. The copolymer of claim 1 , wherein the glycan head comprises a terminal mannoside.

3. The copolymer of claim 1 or claim 2 , wherein the glycan head comprises an O-aryl mannoside comprising an optionally substituted benzene ring.

4. The copolymer of claim 1 , wherein the glycan head comprises a mono-mannoside, a di-mannoside, or a tri-mannoside.

5. The copolymer of claim 4 , wherein the tri-mannoside is a linear or branched tri-mannoside.

6. The copolymer of claim 5 , wherein the branched tri-mannoside is a α-1,3-α-1,6-trimannoside.

7. The copolymer of claim 1 , wherein the initiator block further comprises an initiator spacer.

8. The copolymer of claim 7 , wherein the initiator spacer comprises a saturated carbon moiety, a polyethylene glycol (PEG) moiety, or a combination thereof.

9. The copolymer of claim 8 , wherein the saturated carbon moiety comprises at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbons (optionally, 2 to 6 carbons).

10. The copolymer of claim 8 , wherein the PEG moiety comprises 2 to 72 (OCH 2 CH 2 ) subunits.

11. The copolymer of claim 10 , wherein the PEG moiety is of a linear, branched, or star configuration.

12. The copolymer of claim 1 , wherein the glycan head is configured to bind a dendritic cell.

13. The copolymer of claim 12 , wherein the glycan head is configured to selectively bind DC-SIGN.

14. The copolymer of claim 13 , wherein the glycan head is configured to bind DC-SIGN at a K D ranging from 5 to 8000 nM at pH 7.4.

15. The copolymer of claim 14 , wherein the K D ranges from 5 to 500 nM at pH 7.4.

16. The copolymer of claim 13 , wherein the glycan head is configured to bind DC-SIGN at a K D ranging from 1 to 2000 nM at pH 5.

17. The copolymer of claim 16 , wherein the K D ranges from 1 to 600 nM at pH 5.

18. The copolymer of claim 1 , wherein the glycan head comprises a 9 BPC Neu5Ac conjugated N-glycan, Neu5Ac conjugated N-glycan, 9 TCC Neu5Ac conjugated N-glycan, or a combination thereof, wherein BPC denotes biphenylcarboxyl, TCC denotes 4H-thieno[3,2-c]chromene-2-carbamoyl), and Neu5Ac denotes N-Acetylneuraminic acid.

19. The copolymer of claim 18 , wherein the initiator block is configured to bind Siglec-2, Siglec-5/E, Siglec-1, or a combination thereof.

20. The copolymer of claim 1 , wherein the initiator block is selected from a group consisting of:

wherein the solid circle represents mannoside, the open circle represents Galactose, the solid square represents GlcNAc, and the diamond represents Neu5Ac.

21. The copolymer of claim 1 , wherein the propagator block comprises more than one guanidine group.

22. The copolymer of claim 21 , wherein the propagator block comprises three guanidine groups.

23. The copolymer of claim 1 , wherein the propagator block comprises a propagator spacer, comprising a saturated carbon moiety, a polyethylene glycol (PEG) moiety, or a combination thereof.

24. The copolymer of claim 23 , wherein the saturated carbon moiety comprises at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbons (optionally, 2 to 6 carbons).

25. The copolymer of claim 23 , wherein the PEG moiety comprises 2 to 72 (OCH 2 CH 2 ) subunits.

26. The copolymer of claim 25 , wherein the PEG moiety is of a linear, branched, or star configuration.

27. The copolymer of claim 1 , comprising a plurality of the propagator blocks and a plurality of the linkages, and each propagator block of the plurality of the propagator blocks connects to at least another propagator block of the propagator blocks or the initiator block via one of the plurality of the linkages.

28. The copolymer of claim 1 ,

wherein the propagator block is a first propagator block, the linkage is a first linkage, and the copolymer further comprises a second propagator block, connecting to the first propagator block via a second linkage;

wherein the first propagator block and the second propagator block independently comprise a guanidine group, a zwitterion group, a diethylene triamine, or a combination thereof, and

wherein the second linkage comprises a disulfide bond.

29. The copolymer of claim 28 , wherein the first propagator block comprises the guanidine group, and the second propagator block comprises the zwitterion group.

30. The copolymer of claim 28 , wherein the first propagator block comprises the guanidine group, and the second propagator block comprises the diethylene triamine.

31. The copolymer of claim 28 , wherein the copolymer further comprises a third propagator block, wherein the third propagator block is linked to the first propagator block or the second propagator block via a third linkage comprising a disulfide bond.

32. The copolymer of claim 1 , wherein the propagator block is selected from a group consisting of:

33. The copolymer of claim 32 , comprising at least two propagator blocks, wherein the at least two propagator blocks are (1) PB1 and PB5, (2) PB1 and PB4, (3) PB2 and PB5, (4) PB2 and PB5, or (5) PB1, PB4, and PB5.

34. The copolymer of claim 33 , wherein the initiator block is selected from a group consisting of

wherein the solid circle represents mannoside, the open circle represents Galactose, the solid square represents GlcNAc, and the diamond represents Neu5Ac, and wherein the initiator block and the at least two propagator block are selected from a group consisting of IB5-PB1/PB5, IB5-PB1/PB4, IB5-PB2/PB5, IB5-PB2/PB4, IB5-PB1/PB4/PB5, IB6-PB1/PB5, IB6-PB1/PB4, IB6-PB2/PB5, IB6-PB2/PB4, IB6-PB1/PB4/PB5, IB7-PB1/PB5, IB7-PB1/PB4, IB7-PB2/PB5, IB7-PB2/PB4, IB7-PB1/PB4/PB5, IB8-PB1/PB5, IB8-PB1/PB4, IB8-PB2/PB5, IB8-PB2/PB4, IB8-PB1/PB4/PB5, IB9-PB1/PB5, IB9-PB1/PB4, IB9-PB2/PB5, IB9-PB2/PB4, IB9-PB1/PB4/PBS, IB10-PB1/PBS, IB10-PB1/PB4, IB10-PB2/PBS, IB10-PB2/PB4, and IB10-PB1/PB4/PB5.

35. A polymersome, comprising a membrane defining an inner space, wherein the membrane comprises the copolymer of any one of claims 1 to 34 .

36. The polymersome of claim 35 , wherein the copolymer comprises at least 50%, 70%, 80%, 90%, 95%, or 99% of the membrane.

37. The polymersome of claim 35 , wherein the membrane encapsulates a payload therewithin.

38. The polymersome of claim 37 , wherein the payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

39. The polymersome of claim 38 , wherein the nucleic acid is RNA or DNA.

40. The polymersome of claim 39 , wherein the payload encodes a polypeptide.

41. The polymersome of claim 37 , wherein the payload is immunogenic, or the payload is a nucleic acid configured to encode an immunogenic polypeptide or protein.

42. The polymersome of claim 35 , wherein the copolymer is a first copolymer, and the membrane further comprises a second copolymer, wherein the first copolymer and the second copolymer are independent of any one of claims 1 to 34 .

43. The polymersome of claim 35 , having a diameter of 0.001 to 5 microns or 0.01 to 5 microns.

44. The polymersome of claim 35 , wherein the payload is a first payload, and the membrane further encapsulates a second payload.

45. The polymersome of claim 44 , wherein the second payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

46. The polymersome of claim 45 , wherein the first payload and the second payload are different.

47. A formulation, comprising a polymersome of claim 35 .

48. The formulation of claim 47 , comprising 0.01 to 95% (w/w) of the polymersome.

49. The formulation of claim 47 , wherein the polymersome is a first polymersome, and the composition further comprises a second polymersome.

50. The formulation of claim 49 , wherein the first polymersome and the second polymersome are different in size, copolymers forming the membrane thereof, payload encapsulated within the polymersomes, or a combination thereof.

51. The formulation of claim 47 , further comprising a pharmaceutically acceptable excipient, adjuvant, or a combination thereof.

52. The formulation of claim 51 , wherein the excipient comprises a solvent, dispersion media, diluent, dispersion, suspension aid, surface active agent, isotonic agent, thickening or emulsifying agent, preservative, polymer, peptide, protein, cell, hyaluronidase, or mixtures thereof.

53. The formulation of claim 51 , wherein the adjuvant comprises C34, Gluco-C34, 7DW8-5, C17, C23, C30, α-galactosylceramide, Aluminum salt, Squalene, MF59, or QS-21; other examples of adjuvants in some vaccines that can be used in the composition of the present disclosure are aluminum hydroxide, aluminum phosphate, alum (potassium aluminum sulfate), mixed aluminum salts, Freund's complete adjuvant, Freund's incomplete adjuvant, AS03, MF59, and CpG 1018, or a combination thereof.

54. A kit for preparing a polymersome, comprising:

a first reagent, comprising an initiator, wherein the initiator comprises a glycan head and an initiator linking moiety, and

a second reagent, comprising a propagator, wherein the propagator comprises a functional moiety and a propagator linking moiety, wherein the functional moiety comprises a guanidine group, a zwitterion group, a diethylene triamine, or a combination thereof, and

wherein the initiator linking moiety is configured to couple with the propagator linking moiety via a linkage comprising a disulfide bond.

55. The kit of claim 54 , wherein the glycan head comprises a terminal mannoside.

56. The kit of claim 54 , wherein the glycan head comprises an O-aryl mannoside.

57. The kit of claim 54 , wherein the glycan head comprises a mono-mannoside, a di-mannoside, or a tri-mannoside.

58. The kit of claim 57 , wherein the tri-mannoside is a linear or branched tri-mannoside.

59. The kit of claim 58 , wherein the branched tri-mannoside is a α-1,3-α-1,6-trimannoside.

60. The kit of claim 54 , wherein the initiator further comprises an initiator spacer, comprising a saturated carbon moiety, a polyethylene glycol (PEG) moiety, or a combination thereof.

61. The kit of claim 60 , wherein the saturated carbon moiety comprises at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbons (optionally, 2 to 6 carbons).

62. The kit of claim 61 , wherein the PEG moiety comprises 2 to 72 (OCH 2 CH 2 ) subunits.

63. The kit of claim 62 , wherein the PEG moiety is of a linear, branched, or star configuration.

64. The kit of claim 54 , wherein the glycan head is configured to bind a dendritic cell.

65. The kit of claim 64 , wherein the glycan head is configured to selectively bind DC-SIGN.

66. The kit of claim 65 , wherein the glycan head is configured to bind DC-SIGN at a K D ranging from 5 to 8000 nM at pH 7.4.

67. The kit of claim 66 , wherein the K D ranges from 5 to 500 nM at pH 7.4.

68. The kit of claim 65 , wherein the glycan head is configured to bind DC-SIGN at a K D ranging from 1 to 800 nM at pH 5.

69. The kit of claim 68 , wherein the K D ranges from 1 to 600 nM at pH 5.

70. The kit of claim 54 , wherein the glycan head comprises a 9 BPC Neu5Ac conjugated N-glycan (I2), Neu5Ac conjugated N-glycan (I3), 9 TCC Neu5Ac conjugated N-glycan (I4), or a combination thereof; wherein BPC denotes biphenylcarboxyl, TCC denotes 4H-thieno[3,2-c]chromene-2-carbamoyl), and Neu5Ac denotes N-Acetylneuraminic acid.

71. The kit of claim 70 , wherein the glycan head is configured to bind Siglec-2, Siglec-5/E, Siglec-1, or a combination thereof.

72. The kit of claim 54 , wherein the initiator linking moiety is a thiol group or a dithiolane group.

73. The kit of claim 54 , wherein the initiator is selected from a group consisting of:

74. The kit of claim 54 , wherein the propagator comprises more than one guanidine group.

75. The kit of claim 74 , wherein the propagator comprises three guanidine groups.

76. The kit of claim 54 , wherein the propagator further comprises a propagator spacer, comprising a saturated carbon moiety, a polyethylene glycol (PEG) moiety, or a combination thereof.

77. The kit of claim 76 , wherein the saturated carbon moiety comprises at least 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbons (optionally, 2 to 6 carbons).

78. The kit of claim 76 , wherein the PEG moiety comprises 2 to 72 (OCH 2 CH 2 ) subunits.

79. The kit of claim 78 , wherein the PEG moiety is a linear PEG.

80. The kit of claim 54 ,

wherein the propagator of the second reagent is a first propagator, and wherein the second reagent further comprises a second propagator, or the kit further comprises a third reagent comprising the second propagator; and

wherein the first propagator and the second propagator independently comprise a functional moiety comprising a guanidine group, a zwitterion group, a diethylene triamine, or a combination thereof.

81. The kit of claim 80 , wherein the first propagator comprises the guanidine group, and the second propagator comprises the zwitterion group.

82. The kit of claim 80 , wherein the first propagator comprises the guanidine group, and the second propagator comprises the diethylene triamine.

83. The kit of claim 54 , wherein the propagator linking moiety is a thiol group or a dithiolane group.

84. The kit of claim 54 , wherein the propagator is selected from a group consisting of:

85. The kit of claim 54 , wherein the first reagent and the second reagent are contained in the same container.

86. The kit of claim 54 , wherein the first reagent and the second reagent are contained in separate containers.

87. The kit of claim 54 , further comprising a payload, wherein the payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

88. The kit of claim 87 , wherein the nucleic acid is RNA or DNA.

89. The kit of claim 88 , wherein the payload encodes a polypeptide.

90. The kit of claim 87 , wherein the payload is immunogenic, or the payload is a nucleic acid configured to encode an immunogenic polypeptide or protein.

91. A method of targeted delivering a payload in a subject, comprising administering to the subject an effective amount of a pharmaceutical formulation comprising a polymersome,

wherein the polymersome comprises a membrane encapsulating the payload, and wherein the membrane comprises a copolymer of any one of claims 1 to 34 .

92. The method of claim 91 , wherein the copolymer comprises at least 50%, 70%, 80%, 90%, 95%, or 99% of the membrane.

93. The method of claim 92 , wherein the copolymer is a first copolymer, and the membrane further comprises a second copolymer, wherein the first copolymer and the second copolymer are independently of any one of claims 1 to 34 .

94. The method of claim 91 , wherein the payload is a nucleic acid, a compound, a peptide, a protein, a glycan, or a combination thereof.

95. The method of claim 94 , wherein the nucleic acid is RNA or DNA.

96. The method of claim 95 , wherein the payload encodes a polypeptide.

97. The method of claim 91 , wherein the payload is immunogenic, or the payload is a nucleic acid configured to encode an immunogenic polypeptide or protein.

98. The method of claim 91 , wherein the payload is a first payload, and the membrane further encapsulates a second payload.

99. The method of claim 98 , wherein the second payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

100. The method of claim 99 , wherein the first payload and the second payload are different.

101. A method of preventing or treating a disease in a subject, comprising administering to the subject an effective amount of a pharmaceutical formulation comprising a polymersome,

wherein the polymersome comprises a membrane, wherein the membrane comprises the polymeric component of any one of claims 1 to 34 ; and a payload, encapsulated within the membrane; and

wherein the payload is a therapeutic agent or derives a therapeutic agent.

102. The method of claim 101 , wherein the polymeric component comprises at least 50%, 70%, 80%, 90%, 95%, or 99% of the membrane.

103. The method of claim 101 , wherein the payload is a nucleic acid, a compound, a peptide, a protein, a glycan, or a combination thereof.

104. The method of claim 103 , wherein nucleic acid is RNA or DNA.

105. The method of claim 104 , wherein the payload encodes a polypeptide.

106. The method of claim 101 , wherein the payload is a first payload, and the membrane further encapsulates a second payload.

107. The method of claim 106 , wherein the second payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

108. The method of claim 107 , wherein the first payload and the second payload are different.

109. The method of claim 101 , wherein the polymersome is administered in an initial dose and followed by one, two, three, four, five, or more booster doses.

110. The method of claim 109 , wherein the booster doses are administered about one month, about two months, about three months, about four months, about five months, or about six months or more following the initial dose.

111. The method of claim 101 , wherein the effective amount ranges from about 5 μg to 1000 μg.

112. A method of boosting an adaptive immune response, comprising administering to a subject an effective amount of an effective amount of a pharmaceutical formulation comprising a polymersome;

wherein the polymersome comprises a membrane encapsulating the payload, and

wherein the membrane comprises a copolymer of any one of claims 1 to 34 ;

wherein the payload is immunogenic or derives an immunogenic biomolecule.

113. The method of claim 112 , wherein the polymeric component comprises at least 50%, 70%, 80%, 90%, 95%, or 99% of the membrane.

114. The method of claim 112 , wherein the payload is a nucleic acid, a compound, a peptide, a protein, a glycan, or a combination thereof.

115. The method of claim 114 , wherein nucleic acid is RNA or DNA.

116. The method of claim 112 , wherein the biomolecule is a polypeptide or a protein.

117. The method of claim 112 , wherein the payload is a first payload, and the membrane further encapsulates a second payload.

118. The method of claim 117 , wherein the second payload is a nucleic acid, a compound, a polypeptide, a protein, a glycan, or a combination thereof.

119. The method of claim 118 , wherein the first payload and the second payload are different.

120. The method of claim 112 , wherein the polymersome is administered in an initial dose followed by one, two, three, four, five, or more booster doses.

121. The method of claim 120 , wherein the booster doses are administered about one month, about two months, about three months, about four months, about five months, or about six months or more following the initial dose.

122. The method of claim 112 , wherein the effective amount ranges from about 5 μg to 1000 μg.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2025
From: WONG, CHI-HUEY; LEE, JENG SHIN; FAN, CHEN-YO; WANG, SZU-WEN
To: ROCK BIOMEDICAL INC.
Reel/Frame 070915/0478 →
Continuity (4)
Provisional Application 63575056 · Apr 5, 2024
Provisional Application 63587231 · Oct 2, 2023
Provisional Application 63458102 · Apr 8, 2023
Related Publication 20250041222A1 · Feb 6, 2025
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