Synthesis of 6″-triazole-substituted α-GalCer analogues as potent iNKT cell stimulating ligands

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 24, 2012, Pages 7149-7154

  Pauwels, Nora ^a   Aspeslagh, Sandrine ^b   Elewaut, Dirk ^b   Calenbergh, Serge Van ^a  

^a GHENT UNIVERSITY   (Belgium)

^b GHENT UNIVERSITY HOSPITAL   (Belgium)

Author keywords

GalCer; CD1d; Click chemistry; IL 2; iNKT cell; Triazole

Indexed keywords

1 O [6 DEOXY 6 (4 BENZYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 1 O [6 DEOXY 6 (4 BUTYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 1 O [6 DEOXY 6 (4 ETHYLPHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 1 O [6 DEOXY 6 (4 PHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 1 O [6 DEOXY 6 (4 PROPYLPHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 1 O [6 DEOXY 6 (TRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O (2,3,4 TRI O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL) 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O (6 AZIDO 2,3,4 TRI O BENZYL 6 DEOXY ALPHA DEXTRO GALACTOPYRANOSYL) 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (4 BENZYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (4 BUTYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (4 ETHYLPHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (4 PHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (4 PROPYLPHENYLTRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; 3,4 DI O BENZYL 1 O [2,3,4 TRI O BENZYL 6 DEOXY 6 (TRIAZOL 1 YL) ALPHA DEXTRO GALACTOPYRANOSYL] 2 HEXACOSYLAMINOOCTADECANE 1,3,4 TRIOL; ALPHA GALACTOSYLCERAMIDE; ALPHA GALACTOSYLCERAMIDE DERIVATIVE; GLYCOLIPID; INTERLEUKIN 2; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ALPHA-GALACTOSYLCERAMIDE; GALACTOSYLCERAMIDE; IMMUNOLOGICAL ADJUVANT; LIGAND;

ANIMAL CELL; ANTIGENICITY; ARTICLE; CONTROLLED STUDY; CYCLOADDITION; CYTOKINE RELEASE; DEPROTECTION REACTION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IMMUNOSTIMULATION; IN VITRO STUDY; INVARIANT NATURAL KILLER T CELL; MOUSE; NATURAL KILLER T CELL; NONHUMAN; STRUCTURE ACTIVITY RELATION; ANIMAL; BONE MARROW CELL; CHEMISTRY; DENDRITIC CELL; DRUG EFFECT; IMMUNOLOGY; SYNTHESIS;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; BONE MARROW CELLS; DENDRITIC CELLS; GALACTOSYLCERAMIDES; LIGANDS; MICE; NATURAL KILLER T-CELLS; TRIAZOLES;

EID: 84870065738     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.063     Document Type: Article

References (29)

1. D.I. Godfrey, H.R. MacDonald, M. Kronenberg, M.J. Smyth, and L. Van Kaer Nat. Rev. Immunol. 4 2004 231
2. M. Kronenberg Annu. Rev. Immunol. 26 2005 877
3. M. Sköld, and S.M. Behar Infect. Immun. 71 2003 10
4. A. Bendelac, P.B. Savage, and L. Teyton Annu. Rev. Immunol. 25 2007 297
5. M.J. Smyth, N.Y. Crowe, Y. Hayakawa, K. Takeda, H. Yagita, and D. Godfrey Curr. Opin. Immunol. 14 2002 165
6. K.J.L. Hammond, and D.I. Godfrey Tissue Antigens 59 2002 353
7. T. Natori, M. Morita, K. Akimoto, and Y. Koezuka Tetrahedron 50 1994 2771
8. M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima J. Med. Chem. 38 1995 2176
9. K.O.A. Yu, and S.A. Porcelli Immunol. Lett. 100 2005 42
10. C. Carnaud, D. Lee, O. Donnars, S.-H. Park, H. Beavis, Y. Koezuka, and A. Bendelac J. Immunol. 163 1999 4647
11. G. Galli, S. Nuti, S. Tavarini, L. Galli-Stampino, C. De Lalla, G. Casorati, P. Dellabona, and S. Abrignani Vaccine 21 2003 48
12. C.R. Berkers, and H. Ovaa Trends Pharmacol. Sci. 26 2005 252
13. A. Banchet-Cadeddu, E. Henon, M. Dauchez, J.-H. Renault, F. Monneaux, and A. Haudrechy Org. Biomol. Chem. 9 2011 3080
14. K. Miyamoto, S. Miyake, and T. Yamamura Nature 413 2001 531
15. J. Schmieg, G. Yang, R.W. Franck, and M. Tsuji J. Exp. Med. 198 2003 1631
16. X.T. Zhou, C. Forestier, R.D. Goff, C. Li, L. Teyton, A. Bendelac, and P.B. Savage Org. Lett. 4 2002 1267
17. Y. Liu, R.D. Goff, D. Zhou, J. Mattner, B.A. Sullivan, A. Khurana, C. Cantu III, E.V. Ravkov, C.C. Ibegbu, J.D. Altman, L. Teyton, A. Bendelac, and P.B. Savage J. Immunol. Methods 312 2006 34
18. T. Ebensen, C. Link, P. Riese, K. Schulze, M. Morr, and C.A. Guzmán J. Immunol. 179 2007 2065
19. T. Tashiro, R. Nakagawa, S. Inoue, M. Shiozaki, H. Watarai, M. Taniguchi, and K. Mori Tetrahedron Lett. 49 2008 6827
20. S. Aspslagh, Y. Li, E.D. Yu, N. Pauwels, M. Trappeniers, E. Girardi, T. Decruy, K. Van Beneden, K. Venken, M. Drennan, L. Leybaert, J. Wang, R.W. Frank, S. Van Calenbergh, D.M. Zajonc, and D. Elewaut EMBO J. 30 2011 2294
21. G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, and A.A. Genazzani Med. Res. Rev. 28 2008 278
22. M. Trappeniers, K. Van Beneden, T. Decruy, U. Hillaert, B. Linclau, D. Elewaut, and S. Van Calenbergh J. Am. Chem. Soc. 130 2008 16468
23. P.J. Jervis, M. Moulis, J.-P. Jukes, H. Ghadbane, L.R. Cox, V. Cerundolo, and G.S. Besra Carbohydr. Res. 356 2012 152
24. P.J. Jervis, L.M. Graham, E.L. Foster, L.R. Cox, S.A. Porcelli, and G.S. Besra Bioorg. Med. Chem. Lett. 22 2012 4348
25. N. Pauwels, S. Aspeslagh, G. Vanhoenacker, K. Sandra, E.D. Yu, D.M. Zajonc, D. Elewaut, B. Linclau, and S. Van Calenbergh Org. Biomol. Chem. 9 2011 8413
26. I. Carvalho, P. Andrade, V.L. Campo, P.M.M. Guedes, R. Sesti-Costa, J.S. Silva, S. Schenkman, S. Dedola, L. Hill, M. Rejzek, S.A. Nepogodiev, and R.A. Field Bioorg. Med. Chem. 18 2010 2412
27. S.G. Hansen, and H.H. Jensen Synlett 2009 3275
28. N.M.O. O'Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, and G.R. Hutchison J. Cheminformatics 3 2011 33
29. http://www.pymol.org.