최소 단어 이상 선택하여야 합니다.
최대 10 단어까지만 선택 가능합니다.
다음과 같은 기능을 한번의 로그인으로 사용 할 수 있습니다.
NTIS 바로가기다음과 같은 기능을 한번의 로그인으로 사용 할 수 있습니다.
DataON 바로가기다음과 같은 기능을 한번의 로그인으로 사용 할 수 있습니다.
Edison 바로가기다음과 같은 기능을 한번의 로그인으로 사용 할 수 있습니다.
Kafe 바로가기국가/구분 | United States(US) Patent 등록 |
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국제특허분류(IPC7판) |
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출원번호 | US-0392341 (2014-06-26) |
등록번호 | US-10086054 (2018-10-02) |
국제출원번호 | PCT/US2014/044465 (2014-06-26) |
국제공개번호 | WO2014/210397 (2014-12-31) |
발명자 / 주소 |
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출원인 / 주소 |
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대리인 / 주소 |
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인용정보 | 피인용 횟수 : 0 인용 특허 : 192 |
Described herein are synthetic glycan conjugates, immunogenic compositions thereof, vaccines thereof, and kits thereof. The present invention further provides methods of using the synthetic glycan conjugates, immunogenic compositions, or vaccines thereof to treat and/or prevent and/or diagnose proli
Described herein are synthetic glycan conjugates, immunogenic compositions thereof, vaccines thereof, and kits thereof. The present invention further provides methods of using the synthetic glycan conjugates, immunogenic compositions, or vaccines thereof to treat and/or prevent and/or diagnose proliferative diseases such as cancer. The provided glycan conjugate comprises a carrier and a glycan moiety of Formula (I-i) or Formula (I-ii): (structurally represented).
1. A glycan conjugate having Formula (II-a) or Formula (II-b) or a pharmaceutically acceptable salt thereof,wherein each instance of R1, R2, R4, R5, R6, R10, R11, R12, and R13 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting g
1. A glycan conjugate having Formula (II-a) or Formula (II-b) or a pharmaceutically acceptable salt thereof,wherein each instance of R1, R2, R4, R5, R6, R10, R11, R12, and R13 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R1 and R2 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R4 and R5 are taken with the intervening atoms to form an optionally substituted heterocyclic ring;each instance of RN1, RN2, and RBN is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted acyl, or a nitrogen protecting group;p is an integer of 1 to 10, inclusive;each instance of L1 is independently a bond, —O—, —S—, —NRL1a—, —C(═O)—, —NRL1aC(═O)—, —NRL1aC(═O)O—, —C(═O)NRL1a—, —OC(═O)NRL1a—, —SC(═O)—, —C(═O)S—, —OC(═O)—, —C(═O)O—, —NRL1aC(═S)—, —C(═S)NRL1a—, trans-CRL1b═CRL1b—, cis-CRL1b═CRL1b—, —C≡C—, —OC(RL1b)2—, —C(RL1b)2O—, —NRL1aC(RL1b)2—, —C(RL1b)2NRL1a—, —SC(RL1b)2—, —C(RL1b)2S—, —S(═O)2O—, —OS(═O)2—, —S(═O)2NRL1a—, —NRL1aS(═O)2—, or an optionally substituted C1-20 hydrocarbon chain, optionally wherein one or more carbon units of the hydrocarbon chain is replaced with —O—, —S—, —NRL1a—, —C(═O)—, NRL1aC(═O)—, —NRL1aC(═O)O—, —C(═O)NRL1a—, —OC(═O)NRL1a—, —SC(═O)—, —C(═O)S—, —OC(═O)—, —C(═O)O—, —NRL1aC(═S)—, —C(═S)NRL1a—, trans-CRL1b═CRL1b—, cis-CRL1b═CRL1b—, —C≡C—, —S(═O)2O—, —OS(═O)2—, —S(═O)2NRL1a—, or —NRL1aS(═O)2—, wherein RL1a is hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group, or RL1a is joined with the adjacent carbon atom to form an optionally substituted heterocyclic ring, and wherein each occurrence of RL1b is independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-10 alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl, or RL1b is joined with the adjacent carbon or nitrogen or oxygen atom to form an optionally substituted carbocyclic or heterocyclic ring, or two RL1b groups are joined to form an optionally substituted carbocyclic or optionally substituted heterocyclic ring;each instance of L2 is independently a moiety derived from a crosslinking reagent capable of crosslinking the carrier and L1-H;each instance of L3C is independently a crosslinking reagent or a moiety derived from a crosslinking reagent, wherein the crosslinking reagent is capable of crosslinking the carrier and L1-H;each instance of RCN is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted acyl, or a nitrogen protecting group;w is an integer of 1 to 100, inclusive;y is 0 or an integer of 1 to 100, inclusive;R5 is independently hydrogen, optionally substituted C1-6 alkyl, or an oxygen protecting group; or optionally R4 and R5 are taken with the intervening atoms to form an optionally substituted heterocyclic ring;each instance of R3a, R3b, R3c, R3d, and R3g is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R3c and R3b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3b and R3d are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3f and R3g are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R3f and R3e is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 2. The glycan conjugate of claim 1 having Formula (III-a) or Formula (III-b) or a pharmaceutically acceptable salt thereof,wherein each instance of R3a, R3b, R3c, R3d, R3g, R5a, R5b, R5c, and R5d is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R3c and R3b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3b and R3d are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3f and R3g are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5a and R5b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b and R5c are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R3f and R3e is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 3. The glycan conjugate of claim 1 having Formula (IV-a) or (IV-b) or a pharmaceutically acceptable salt thereof, each instance of R3a, R3b, R3c, R3d, R3g, R5a, R5c, R5d, R5b1, R5b2, and R5b3 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R3c and R3b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3b and R3d are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3f and R3g are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c and R5d are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b1 and R5b2 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b2 and R5b3 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b3 and R5b4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R3f, R3e, R5b4, and R5b5 is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 4. The glycan conjugate of claim 1 having Formula (V-a) or (V-b) or a pharmaceutically acceptable salt thereof, each instance of R3a, R3b, R3c, R3d, R3g, R5a, R5b, R5d, R5c1, R5c2, R5c5, R5c6, and R5c7 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R3c and R3b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3b and R3d are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R3f and R3g are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5a and R5b are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c2 and R5c4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c5 and R5c6 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c6 and R5c7 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R3f, R3e, R5c3, and R5c4 is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 5. The glycan conjugate of claim 1 having Formula (VI-a) or Formula (VI-b) or a pharmaceutically acceptable salt thereof, each instance of R5a, R5d, R5b1, R5b2, R5b3, R5c1, R5c2, R5c5, R5c6, and R5c7 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R5b1 and R5b2 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b2 and R5b3 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b3 and R5b4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c2 and R5c4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c5 and R5c6 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c6 and R5c7 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R5b4, R5b5, R5c3, and R5c4 is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 6. The glycan conjugate of claim 1 having Formula (VII-a) or (VII-b) or a pharmaceutically acceptable salt thereof, each instance of R3a, R3b, R3c, R3d, R3g, R5a, R5d, R5b1, R5b2, R5b3, R5c1, R5c2, R5c5, R5c6, and R5c7 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted carbohydrate, or an oxygen protecting group; or optionally R5b1 and R5b2 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b2 and R5b3 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5b3 and R5b4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c2 and R5c4 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c5 and R5c6 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; or optionally R5c6 and R5c7 are taken with the intervening atoms to form an optionally substituted heterocyclic ring; andeach instance of R3f, R3e, R5b4, R5b5, R5c3, and R5c4 is independently hydrogen, optionally substituted C1-6 alkyl, or a nitrogen protecting group. 7. The glycan conjugate of any one of claims 1-6, wherein w is an integer of 1 to 20, inclusive. 8. The glycan conjugate of any one of claims 1-6, wherein y is 0 or an integer of 1 to 20, inclusive. 9. The glycan conjugate of any one of claims 1-6, wherein p is 5. 10. The glycan conjugate of any one of claims 1-6, wherein R11, R12, and R13 are hydrogen. 11. The glycan conjugate of any one of claims 1-6, wherein R10, R11, R12, and R13 are hydrogen. 12. The glycan conjugate of any one of claims 1-6, wherein R1, R2, R4, and R6 are hydrogen. 13. The glycan conjugate of any one of claims 1-6, wherein RN1 is acetyl. 14. The glycan conjugate of any one of claims 1-6, wherein RN2 is hydrogen. 15. The glycan conjugate of any one of claims 1-6, wherein RBN is hydrogen. 16. The glycan conjugate of any one of claims 1-6, wherein RCN is hydrogen. 17. The glycan conjugate of any one of claims 1-6, wherein the carrier is a protein, a lipid, a lipolized protein, a virus, a peptide comprising a T cell epitope, or a dendrimer of glycopeptides. 18. The glycan conjugate of claim 17, wherein the carrier is a toxin protein selected from the group consisting of diphtheria toxin cross-reacting material 197 (DT-CRM197), diphtheria toxoid, tetanus toxoid, and outer-membrane protein (OMP). 19. The glycan conjugate of claim 18, wherein the toxin protein is DT-CRM197. 20. The glycan conjugate of claim 19, wherein the glycan conjugate is of the formula 21. A glycan conjugate mixture comprising at least two of the glycan conjugates of any one of claims 1-6. 22. A glycan conjugate mixture comprising at least two of the glycan conjugates of any one of claims 1-6 wherein the average value of w is from about 1.0 to about 100.0. 23. The glycan conjugate mixture of claim 22, wherein the average value of w is about 1.0 to about 20.0. 24. The glycan conjugate mixture of claim 22, wherein the average value of w is about 1.0. 25. The glycan conjugate mixture of claim 22, wherein the average value of w is about 3.0. 26. The glycan conjugate mixture of claim 22, wherein the average value of w is about 4.7. 27. The glycan conjugate mixture of claim 22, wherein the average value of w is about 10.0. 28. The glycan conjugate mixture of claim 22, wherein the average value of w is about 12.7. 29. An immunogenic composition, comprising (i) a glycan conjugate of any one of claims 1-6; and(ii) a pharmaceutically acceptable excipient. 30. The immunogenic composition of claim 29 further comprising an adjuvant. 31. The immunogenic composition of claim 30, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 32. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to any one of claims 1-6. 33. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to any one of claims 1-6. 34. The method of claim 32, wherein the proliferative disease is cancer. 35. The method of claim 34, wherein the cancer is selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 36. The method of claim 35, wherein the cancer is prostate cancer. 37. A kit comprising a glycan conjugate according to any one of claims 1-6 and instructions for use thereof. 38. A method of preparing the glycan conjugate of claim 1, comprising coupling a compound of the following formulae: or a salt thereof,with a compound of Formula (C-2) or a salt thereof,wherein L2C is a crosslinking reagent capable of crosslinking the carrier and L1-H. 39. The method of claim 38, wherein L2C is a crosslinking reagent capable of crosslinking an amine group and —SH. 40. The method of claim 39, wherein L2C is of one of the following formulae: or a salt thereof,wherein each instance of RP1 and RP2 are each independently hydrogen, halogen, or optionally substituted C1-6 alkyl;each instance of R2Ca is a leaving group selected from —Br, —Cl, —I, —OS(═O)2R2CO, or —OS(═O)R2CO, wherein R2CO is selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl; andeach of t and i is independently an integer of 1 to 8, inclusive. 41. The method of any one of claim 38-40, wherein the molar ratio of the compound of Formula (C-1) to the compound of Formula (C-2) is from about 1 to about 100. 42. The method of claim 41, wherein the coupling is carried out in the presence of phosphate buffered saline (PBS). 43. The method of any one of claims 38-40, further comprising deprotecting a compound of the following formulae: to give a compound of the following corresponding formulae wherein each instance of RCN is optionally substituted alkyl, or a nitrogen protecting group. 44. The method of claim 43, wherein the deprotection is carried out in the presence of LiOH. 45. The method of claim 43, wherein the deprotection is carried out in the presence of LiOH, then Ac2O and NaHCO3, then LiOH. 46. The method of claim 43, further comprising (a) activating a compound of Formula (C-4a) or Formula (C-4b) to give a compound of Formula (C-1a) or Formula (C-1b); and(b) activating the carrier to give a compound of Formula (C-2). 47. An immunogenic composition, comprising (i) a glycan conjugate of claim 7; and(ii) a pharmaceutically acceptable excipient. 48. The immunogenic composition of claim 47 further comprising an adjuvant. 49. The immunogenic composition of claim 48, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 50. An immunogenic composition, comprising (i) a glycan conjugate of claim 8; and(ii) a pharmaceutically acceptable excipient. 51. The immunogenic composition of claim 50 further comprising an adjuvant. 52. The immunogenic composition of claim 51, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 53. An immunogenic composition, comprising (i) a glycan conjugate of claim 9; and(ii) a pharmaceutically acceptable excipient. 54. The immunogenic composition of claim 53 further comprising an adjuvant. 55. The immunogenic composition of claim 54, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 56. An immunogenic composition, comprising (i) a glycan conjugate of claim 9; and(ii) a pharmaceutically acceptable excipient. 57. The immunogenic composition of claim 56 further comprising an adjuvant. 58. The immunogenic composition of claim 57, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 59. An immunogenic composition, comprising (i) a glycan conjugate of claim 10; and(ii) a pharmaceutically acceptable excipient. 60. The immunogenic composition of claim 59 further comprising an adjuvant. 61. The immunogenic composition of claim 60, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 62. An immunogenic composition, comprising (i) a glycan conjugate of claim 11; and(ii) a pharmaceutically acceptable excipient. 63. The immunogenic composition of claim 62 further comprising an adjuvant. 64. The immunogenic composition of claim 63, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 65. An immunogenic composition, comprising (i) a glycan conjugate of claim 12; and(ii) a pharmaceutically acceptable excipient. 66. The immunogenic composition of claim 65 further comprising an adjuvant. 67. The immunogenic composition of claim 66, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 68. An immunogenic composition, comprising (i) a glycan conjugate of claim 13; and(ii) a pharmaceutically acceptable excipient. 69. The immunogenic composition of claim 68 further comprising an adjuvant. 70. The immunogenic composition of claim 69, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 71. An immunogenic composition, comprising (i) a glycan conjugate of claim 14; and(ii) a pharmaceutically acceptable excipient. 72. The immunogenic composition of claim 71 further comprising an adjuvant. 73. The immunogenic composition of claim 72, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 74. An immunogenic composition, comprising (i) a glycan conjugate of claim 15; and(ii) a pharmaceutically acceptable excipient. 75. The immunogenic composition of claim 74 further comprising an adjuvant. 76. The immunogenic composition of claim 75, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 77. An immunogenic composition, comprising (i) a glycan conjugate of claim 16; and(ii) a pharmaceutically acceptable excipient. 78. The immunogenic composition of claim 77 further comprising an adjuvant. 79. The immunogenic composition of claim 78, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 80. An immunogenic composition, comprising (i) a glycan conjugate of claim 17; and(ii) a pharmaceutically acceptable excipient. 81. The immunogenic composition of claim 80 further comprising an adjuvant. 82. The immunogenic composition of claim 81, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 83. An immunogenic composition, comprising (i) a glycan conjugate of claim 18; and(ii) a pharmaceutically acceptable excipient. 84. The immunogenic composition of claim 83 further comprising an adjuvant. 85. The immunogenic composition of claim 84, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 86. An immunogenic composition, comprising (i) a glycan conjugate of claim 19; and(ii) a pharmaceutically acceptable excipient. 87. The immunogenic composition of claim 86 further comprising an adjuvant. 88. The immunogenic composition of claim 87, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 89. An immunogenic composition, comprising (i) a glycan conjugate of claim 20; and(ii) a pharmaceutically acceptable excipient. 90. The immunogenic composition of claim 89 further comprising an adjuvant. 91. The immunogenic composition of claim 90, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 92. An immunogenic composition, comprising (i) a glycan conjugate mixture of claim 21 and(ii) a pharmaceutically acceptable excipient. 93. The immunogenic composition of claim 92 further comprising an adjuvant. 94. The immunogenic composition of claim 93, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 95. An immunogenic composition, comprising (i) a glycan conjugate mixture of claim 22 and(ii) a pharmaceutically acceptable excipient. 96. The immunogenic composition of claim 95 further comprising an adjuvant. 97. The immunogenic composition of claim 96, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 98. An immunogenic composition, comprising (i) a glycan conjugate mixture of claim 23, and(ii) a pharmaceutically acceptable excipient. 99. The immunogenic composition of claim 98 further comprising an adjuvant. 100. The immunogenic composition of claim 99, wherein the adjuvant is C34, 7DW8-5, C17, C23, C30, α-galactoceramide, Aluminum salt, Squalene, MF59, or QS-21. 101. A kit comprising a glycan conjugate according to claim 21, and instructions for use thereof. 102. A kit comprising a glycan conjugate according to claim 22, and instructions for use thereof. 103. A kit comprising an immunogenic composition of claim 29, and instructions for use thereof. 104. A kit comprising an immunogenic composition of claim 30, and instructions for use thereof. 105. A kit comprising an immunogenic composition of claim 31, and instructions for use thereof. 106. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 17. 107. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 18. 108. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 19. 109. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 20, wherein w is an integer of 1 to 20 and y is an integer of 1 to 20. 110. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 21. 111. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 22. 112. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 23. 113. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 29. 114. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 30. 115. A method of treating a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 31. 116. The method of claim 106, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 117. The method of claim 116, wherein the cancer is prostate cancer. 118. The method of claim 107, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 119. The method of claim 118, wherein the cancer is prostate cancer. 120. The method of claim 108, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 121. The method of claim 120, wherein the cancer is prostate cancer. 122. The method of claim 109, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 123. The method of claim 122, wherein the cancer is prostate cancer. 124. The method of claim 110, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 125. The method of claim 124, wherein the cancer is prostate cancer. 126. The method of claim 111, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 127. The method of claim 126, wherein the cancer is prostate cancer. 128. The method of claim 112, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 129. The method of claim 128, wherein the cancer is prostate cancer. 130. The method of claim 113, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 131. The method of claim 130, wherein the cancer is prostate cancer. 132. The method of claim 114, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 133. The method of claim 132, wherein the cancer is prostate cancer. 134. The method of claim 115, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 135. The method of claim 134, wherein the cancer is prostate cancer. 136. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 17. 137. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 18. 138. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 19. 139. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate according to claim 20, wherein w is an integer of 1 to 20, and y is an integer of 1 to 20. 140. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 21. 141. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 22. 142. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of a glycan conjugate mixture according to claim 23. 143. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 29. 144. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 30. 145. A method of diagnosing a proliferative disease in a subject comprising administering to the subject an effective amount of an immunogenic composition according to claim 31. 146. The method of claim 33, wherein the proliferative disease is cancer selected from the group consisting of breast cancer, lung cancer, liver cancer, buccal cancer, stomach cancer, colon cancer, nasopharyngeal cancer, dermal cancer, renal cancer, brain tumor, prostate cancer, ovarian cancer, cervical cancer, intestinal cancer, and bladder cancer. 147. The method of claim 146, wherein the cancer is prostate cancer.
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