Synthesis of N-modified sTn analogs and evaluation of their immunogenicities by microarray-based immunoassay

Tetrahedron

Volumn 66, Issue 38, 2010, Pages 7510-7519

  Sahabuddin, Sk ^a   Chang, Tsung Che ^a   Lin, Chang Ching ^a   Jan, Fan Dan ^a   Hsiao, Hsuan Yi ^a   Huang, Kuo Ting ^a   Chen, Jeen Han ^b   Horng, Jia Cherng ^a   Ho, Ja An Annie ^a   Lin, Chun Cheng ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b TRI SERVICE GENERAL HOSPITAL   (Taiwan)

Author keywords

Carbohydrate antigen; Microarray; Sialic acid; Sialylation; Vaccine

Indexed keywords

CANCER VACCINE; CARBOHYDRATE ANTIGEN; KEYHOLE LIMPET HEMOCYANIN; N ACETYL SIALYL TN ANTIGEN; N BUTANOYL SIALYL TN ANTIGEN; N GLYCOLYL SIALYL TN ANTIGEN; N PROPIONYL SIALYL TN ANTIGEN; TN ANTIGEN; UNCLASSIFIED DRUG;

ANTIGEN DETECTION; ARTICLE; CONJUGATE; CROSS REACTION; DRUG SYNTHESIS; FEMALE; IMMUNIZATION; IMMUNOASSAY; IMMUNOGENICITY; MICROARRAY ANALYSIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; SIALYLATION;

EID: 77956172800     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.07.050     Document Type: Article

References (67)

1. S. Hakomori Adv. Exp. Med. Biol. 491 2001 369 402
2. D.H. Dube, and C.R. Bertozzi Nat. Rev. Drug Discovery 4 2005 477 488
3. (a) S.F. Slovin, S.J. Keding, and G. Ragupathi Immunol. Cell Biol. 83 2005 418 428
4. (b) M.L. Hecht, P. Stallforth, D.V. Silva, A. Adibekian, and P.H. Seeberger Curr. Opin. Chem. Biol. 13 2009 354 359
5. H.J. Jenning, and R.K. Sook Neoglycoconjugates, Preparation and Application 1994 Academic San Diego
6. (a) L. Schofield, M.C. Hewitt, K. Evans, M.A. Siomos, and P.H. Seeberger Nature 418 2002 785 789
7. (b) D.R. Bundle, J.R. Rich, S. Jacques, H.N. Yu, M. Nitz, and C.C. Lin Angew. Chem., Int. Ed. 44 2005 7725 7729
8. (c) C. Musselli, P.O. Livingston, and G. Ragupathi J. Cancer Res. Clin. Oncol. 127 2001 R20 26
9. (d) E. Kagan, G. Ragupathi, S.S. Yi, C.A. Reis, J. Gildersleeve, D. Kahne, H. Clausen, S.J. Danishefsky, and P.O. Livingstone Cancer Immunol. Immunother. 54 2005 424 430
10. (a) G. Ragupathi, R.R. Koganty, D. Qiu, K.O. Lloyd, and P.O. Livingston Glycoconjugate J. 15 1998 217 221
11. (b) G. Ragupathi, L. Howard, S. Cappello, R. Koganty, and P.O. Livingston Cancer Immunol. Immunother. 48 1999 1 8
12. (c) T. Nakagoe, T. Sawai, T. Tsuji, M.A. Jibiki, A. Nanashima, H. Yamaguchi, T. Yasutake, H. Ayabe, K. Arisawa, and H. Ishikawa Anticancer Res. 22 2002 451 458
13. (d) T.A. Gilewski, G. Ragupathi, M. Dickler, S. Powell, B. Sonal, K. Panageas, R.R. Koganty, J. Chin-Eng, C. Hudis, L. Norton, A.N. Houghton, and P.O. Livingston Clin. Cancer Res. 13 2007 2977 2985
14. L.A. Holmberg, and B.M. Sandmaier Expert Opin. Biol. Ther. 1 2001 881 891
15. L.A. Holmberg, and B.M. Sandmaier Expert Rev. Vaccines 3 2004 655 663
16. W. Zou, S. Borrelli, M. Gilbert, T. Liu, R.A. Pon, and H.J. Jennings J. Biol. Chem. 279 2004 25390 25399
17. T. Liu, Z. Guo, Q. Yang, S. Sad, and H.J. Jennings J. Biol. Chem. 275 2000 32832 32836
18. Y. Pan, P. Chefalo, N. Nagy, C. Harding, and Z. Guo J. Med. Chem. 48 2005 875 883
19. P. Chefalo, Y. Pan, N. Nagy, Z. Guo, and C.V. Harding Biochemistry 45 2006 3733 3739
20. Q. Wang, J. Zhang, and Z. Guo Bioorg. Med. Chem. 15 2007 7561 7567
21. (a) J. Wu, and Z. Guo Bioconjugate Chem. 17 2006 1537 1544
22. (b) H. Yu, H.A. Chokhawala, A. Varki, and X. Chen Org. Biomol. Chem. 5 2007 2458 2463
23. (c) Q. Wang, S.A. Ekanayaka, J. Wu, J. Zhang, and Z. Guo Bioconjugate Chem. 19 2008 2060 2067
24. G.A. Lemieux, and C.R. Bertozzi Chem. Biol. 8 2001 265 275
25. J.S. Plested, P.A. Coull, and M.A. Gidney Methods Mol. Med. 71 2003 243 261
26. (a) O. Oyelaran, and J.C. Gildersleeve Curr. Opin. Chem. Biol. 13 2009 406 413
27. (b) C.Y. Wu, P.H. Liang, and C.H. Wong Org. Biomol. Chem. 7 2009 2247 2254
28. (c) N. Laurent, J. Voglmeir, and S.L. Flitsch Chem. Commun. 2008 4400 4412
29. (d) S. Park, M.-R. Lee, and I. Shin Chem. Commun. 2008 4389 4399
30. (a) X. Zhu, and R.R. Schmidt Angew. Chem., Int. Ed. 48 2009 1900 1934
31. (b) K. Toshima Carbohydr. Res. 341 2006 1282 1297
32. (c) A.V. Demchenko Synlett 2003 1225 1240
33. (d) K.C. Nicolaou, and H.J. Mitchell Angew. Chem., Int. Ed. 40 2001 1576 1624
34. (a) D.K. Ress, and R.J. Linhardt Curr. Org. Synth. 1 2004 31 46
35. (b) C.D. Meo, and U. Priyadarshani Carbohydr. Res. 343 2008 1540 1552
36. (a) S.D. Kuduk, J.B. Schwarz, X.-T. Chen, P.W. Glunz, D. Sames, G. Ragupathi, P.O. Livingston, and S.J. Danishefsky J. Am. Chem. Soc. 120 1998 12474 12485
37. (b) J.B. Schwarz, S.D. Kuduk, X.-T. Chen, D. Sames, P.W. Glunz, and S.J. Danishefsky J. Am. Chem. Soc. 121 1999 2662 2673
38. (c) G.A. Winterfeld, and R.R. Schmidt Angew. Chem., Int. Ed. 40 2001 2654 2657
39. (d) H. Tanaka, M. Adachi, and T. Takahashi Chem. - Eur. J. 11 2005 849 862
40. (e) R. Okamoto, S. Souma, and Y. Kajihara J. Org. Chem. 73 2008 3460 3466
41. A.V. Demchenko, and G.-J. Boons Chem. - Eur. J. 5 1999 1278 1283
42. (a) C.-T. Ren, C.-S. Chen, and S.-H. Wu J. Org. Chem. 67 2002 1376 1379
43. (b) H. Ando, Y. Koike, H. Ishida, and M. Kiso Tetrahedron Lett. 44 2003 6883 6886
44. (a) C.-C. Lin, K.-T. Huang, and C.-C. Lin Org. Lett. 7 2005 4169 4172
45. (b) C.D. Meo, A.V. Demchenko, and G.-J. Boons J. Org. Chem. 66 2001 5490 5497
46. (a) C.-S. Yu, K. Niikura, C.-C. Lin, and C.-H. Wong Angew. Chem., Int. Ed. 40 2001 2900 2903
47. (b) K.-C. Lu, S.-Y. Tseng, and C.-C. Lin Carbohydr. Res. 337 2002 755 760
48. K. Tanaka, T. Goi, and K. Fukase Synlett 2005 2958 2962
49. A.A. Sherman, O.N. Yudina, A.S. Shashkov, V.M. Menshov, and N.E. Nifant'ev Carbohydr. Res. 330 2001 445 458
50. (a) H. Tanaka, Y. Nishiura, and T. Takahashi J. Am. Chem. Soc. 128 2006 7124 7125
51. (b) M.D. Farris, and C.D. Meo Tetrahedron Lett. 48 2007 1225 1227
52. (c) D. Crich, and W. Li J. Org. Chem. 72 2007 2387 2391
53. (d) D. Crich, and W. Li J. Org. Chem. 72 2007 7794 7797
54. (e) C.D. Meo, M. Farris, N. Ginder, and B. Gulley Eur. J. Org. Chem. 2008 3673 3677
55. (f) H. Tanaka, Y. Tateno, Y. Nishiura, and T. Takahashi Org. Lett. 10 2008 5597 5600
56. (g) H. Tanaka, Y. Nishiura, and T. Takahashi J. Org. Chem. 74 2009 4383 4386
57. (h) G.-W. Xing, L. Chen, and F.-F. Liang Eur. J. Org. Chem. 2009 5963 5970
58. (a) H. Kondo, Y. Ichikawa, and C.H. Wong J. Am. Chem. Soc. 114 1992 8748 8750
59. (b) T.J. Martin, and R.R. Schmidt Tetrahedron Lett. 33 1992 6123 6126
60. (a) Z. Zhang, I.R. Ollmann, X. Ye, R. Wischnat, T. Baasov, and C.-H. Wong J. Am. Chem. Soc. 121 1999 734 753
61. (b) A. Hasegawa S. Khan, Modern Methods in Carbohydrate Synthesis 1996 Harwood Academic New York, NY 277 300
62. A. Marra, and P. Sinay Carbohydr. Res. 187 1989 35 42
63. J.M. Haberman, and D.Y. Gin Org. Lett. 5 2003 2539 2541
64. C.H. Hsu, K.C. Chu, Y.S. Lin, J.L. Han, Y.S. Peng, C.T. Ren, C.Y. Wu, and C.-H. Wong Chem. - Eur. J. 16 2010 1754 1760
65. K. Kominato, S. Ogawa, and T. Suami Carbohydr. Res. 174 1988 360 368
66. R. Roy, M.-G. Baek, and K. Rittenhouse-Olson J. Am. Chem. Soc. 123 2001 1809 1816
67. L. Warren J. Biol. Chem. 234 1959 1971 1975