Design, synthesis, and immunologic evaluation of vaccine adjuvant conjugates based on QS-21 and tucaresol

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 21, 2014, Pages 5917-5923

  Fernández Tejada, Alberto ^a   Chea, Eric K ^a   George, Constantine ^a   Gardner, Jeffrey R ^a   Livingston, Philip O ^a,b   Ragupathi, Govind ^a   Tan, Derek S ^a   Gin, David Y ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Adjuvance Technologies Inc   (United States)

Author keywords

Carbohydrates; Immunoadjuvant; Natural product; QS 21; Saponin conjugate; Tucaresol; Vaccine

Indexed keywords

ALDEHYDE; AMINE; ANTIGEN; ARYL IODIDE SAPONIN; CARRIER PROTEIN; IMMUNOGLOBULIN G; IMMUNOLOGICAL ADJUVANT; MUC1 KLH; MUCIN 1; OVALBUMIN; QS 21; SAPONIN; SAPONIN DERIVATIVE; SAPONIN TUCARESOL ADJUVANT CONJUGATE; SUBUNIT VACCINE; TUCARESOL; UNCLASSIFIED DRUG; VACCINE; VACCINE ADUVANT CONJUGATE; BENZALDEHYDE DERIVATIVE; BENZOIC ACID DERIVATIVE;

ACYLATION; ANIMAL EXPERIMENT; ANTIBODY RESPONSE; ARTICLE; CELLULAR IMMUNITY; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFICACY; DRUG FORMULATION; DRUG POTENCY; DRUG POTENTIATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOXICITY; FEMALE; HUMORAL IMMUNITY; IMMUNOREACTIVITY; MOUSE; MOUSE MODEL; NONHUMAN; TH1 CELL; TH2 CELL; VACCINATION; ANIMAL; C57BL MOUSE; CHEMISTRY; DRUG EFFECTS; IMMUNOLOGY; SYNTHESIS;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; BENZALDEHYDES; BENZOATES; IMMUNITY, CELLULAR; IMMUNITY, HUMORAL; IMMUNOGLOBULIN G; MICE; MICE, INBRED C57BL; SAPONINS;

EID: 84908400092     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.09.016     Document Type: Article

References (37)

1. P.M. Moyle, and I. Toth ChemMedChem 8 2013 360
2. W.C. Koff, D.R. Burton, P.R. Johnson, B.D. Walker, C.R. King, G.J. Nabel, R. Ahmed, M.K. Bhan, and S.A. Plotkin Science 340 2013 1232910
3. R.L. Coffman, A. Sher, and R.A. Seder Immunity 33 2010 492
4. G. Leroux-Roels Vaccine 28 2010 C25
5. E.B. Lindblad Immunol. Cell Biol. 82 2004 497
6. P. Marrack, A.S. McKee, and M.W. Munks Nat. Rev. Immunol. 9 2009 287
7. G. Mutwiri, V. Gerdts, S. van Drunen Littel-van den Hurk, G. Auray, N. Eng, S. Garlapati, L.A. Babiuk, and A. Potter Expert Rev. Vaccines 10 2011 95
8. N. Garcon, P. Chomez, and M. Van Mechelen Expert Rev. Vaccines 6 2007 723
9. J. Paavonen, P. Naud, J. Salmerón, C.M. Wheeler, S.N. Chow, D. Apter, H. Kitchener, X. Castellsague, J.C. Teixeira, S.R. Skinner, J. Hedrick, U. Jaisamrarn, G. Limson, S. Garland, A. Szarewski, B. Romanowski, F.Y. Aoki, T.F. Schwarz, W.A. Poppe, F.X. Bosch, D. Jenkins, K. Hardt, T. Zahaf, D. Descamps, F. Struyf, M. Lehtinen, G. Dubin HPV PATRICIA Study Group Lancet 374 2009 301
10. C.R. Kensil, U. Patel, M. Lennick, and D. Marciani J. Immunol. 146 1991 431
11. G. Ragupathi, J.R. Gardner, P.O. Livingston, and D.Y. Gin Exp. Rev. Vaccines 10 2011 463
12. The RTS,S Clinical Trials Partnership. New Engl. J. Med. 2011, 365, 1863.
13. C.R. Kensil, and R. Kammer Expert Opin. Invest. Drugs 7 1998 1475
14. S. Soltysik, D.A. Bedore, and C.R. Kensil Ann. N Y Acad. Sci. 690 1993 392
15. N.E. Jacobsen, W.J. Fairbrother, C.R. Kensil, A. Lim, D.A. Wheeler, and M.F. Powell Carbohydr. Res. 280 1996 1
16. S. Kamstrup, R. San Martin, A. Doberti, H. Grande, and K. Daalsgard Vaccine 18 2000 2244
17. J.L. Cleland, C.R. Kensil, A. Lim, N.E. Jacobsen, L. Basa, M. Spellman, D.A. Wheeler, D.A. Wheeler, J.-Y. Wu, and M.F. Powell J. Pharm. Sci. 85 1996 22
18. J.R. Pink, and M.-P. Kieny Vaccine 22 2004 2097
19. P. Wang, Y.-J. Kim, M. Navarro-Villalobos, B.D. Rohde, and D.Y. Gin J. Am. Chem. Soc. 127 2005 3256
20. Y.J. Kim, P. Wang, M. Navarro-Villalobos, B.D. Rohde, J. Derryberry, and D.Y. Gin J. Am. Chem. Soc. 128 2006 11906
21. K. Deng, M.M. Adams, P. Damani, P.O. Livingston, G. Ragupathi, and D.Y. Gin Angew. Chem., Int. Ed. 47 2008 6395
22. M.M. Adams, P. Damani, N. Perl, A. Won, F. Hong, P.O. Livingston, G. Ragupathi, and D.Y. Gin J. Am. Chem. Soc. 2010 1939 132
23. E.K. Chea, A. Fernández-Tejada, P. Damani, M.M. Adams, J.R. Gardner, P.O. Livingston, G. Ragupathi, and D.Y. Gin J. Am. Chem. Soc. 134 2012 13448
24. A. Fernández-Tejada, E.K. Chea, C. George, N. Pillarsetty, J.R. Gardner, P.O. Livingston, G. Ragupathi, J.S. Lewis, D.S. Tan, and D.Y. Gin Nat. Chem. 6 2014 635
25. J. Rhodes J. Immun. 143 1989 1482
26. X.-M. Gao, and J. Rhodes J. Immun. 144 1990 2883
27. J. Rhodes J. Immun. 145 1990 463
28. J. Rhodes, H. Chen, S.R. Hall, J.E. Beesley, D.C. Jenkins, P. Collins, and B. Zheng Nature 377 1995 71
29. H. Chen, and J. Rhodes J. Mol. Med. 74 1996 497
30. J. Rhodes Clin. Exp. Immunol. 130 2002 363
31. J. Charo, M. Sundbäck, K. Wasserman, A.-M.T. Ciupitu, B. Mirzai, R. van der Zee, and R. Kiessling Infect. Immun. 70 2002 6652
32. A. Gori, D. Trabattoni, A. Bandera, M. Saresella, G. Marchetti, L. Gazzola, M. Biasin, J. Rhodes, H. McDade, R. Panebianco, M. Galli, M. Moroni, P. Ferrante, N. Thomas, F. Franzetti, D. Bray, and M. Clerici Antiviral Ther. 9 2004 603
33. D.J. Marciani Drug Discovery Today 8 2003 934
34. K.C. Collins, J.E. Schlosburg, J.W. Lockner, P.T. Bremer, B.A. Ellis, and K.D. Janda Chem. Commun. 2014 4079
35. B. Zacharie, G. Attardo, N. Barriault, and C. Penney J. Chem. Soc., Perkin Trans. 1 1997 2925
36. F. Nimmerjahn, and J.V. Ravetch Science 310 2005 1510
37. T. Gilewski, R. Adluri, G. Ragupathi, S. Zhang, T.-J. Yao, K. Panageas, M. Moynahan, A.N. Houghton, L. Norton, and P.O. Livingston Clin. Cancer Res. 6 2000 1693