Deoxynojirimycin and its hexosaminyl derivatives bind to natural killer cell receptors rNKR-P1A and hCD69

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 15, 2010, Pages 4645-4648

  Catelani, Giorgio ^a   D'Andrea, Felicia ^a   Griselli, Alessio ^a   Guazzelli, Lorenzo ^a   Nmcová, Petra ^c   Bezouka, Karel ^b,c   Kenek, Karel ^b,c   Ken, Vladimír ^b  

^a UNIVERSITY OF PISA   (Italy)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

d ManNAc (1 4) DNJ; d TalNAc (1 4) DNJ; Deoxynojirimycin; NK cells; rNKR P1A and hCD69 receptors

Indexed keywords

1 DEOXYNOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; BETA DEXTRO MANNAC (1-4); BETA DEXTRO TALNAC (1-4); CD69 ANTIGEN RECEPTOR; LYMPHOCYTE ANTIGEN RECEPTOR; LYMPHOCYTE RECEPTOR; NATURAL KILLER CELL RECEPTOR NKR P1A; UNCLASSIFIED DRUG;

AGONIST; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; GLYCOSYLATION; HUMAN; HUMAN CELL; IMMUNOREACTIVITY; NATURAL KILLER CELL; NONHUMAN; PILOT STUDY; RAT; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

1-DEOXYNOJIRIMYCIN; ANIMALS; ANTIGENS, CD; ANTIGENS, DIFFERENTIATION, T-LYMPHOCYTE; DISACCHARIDES; GLUCOSAMINE; GLYCOSYLATION; HEXOSAMINES; HUMANS; LECTINS, C-TYPE; MONOSACCHARIDES; OXIDATION-REDUCTION; RATS; RECEPTORS, IMMUNOLOGIC;

RATTUS;

EID: 77955431936     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.05.109     Document Type: Article

References (31)

1. A. Santoni, A. Zingoni, C. Cerboni, and A. Gismondi Am. J. Reprod. Immunol. 58 2007 280
2. P. Krist, E. Herkommerová-Rajnochová, J. Rauvolfová, T. Semeuk, P. Vavruková, J. Pavlíek, K. Bezouka, L. Petru, and V. Ken Biochem. Biophys. Res. Commun. 287 2001 11
3. K. Bezouka, J. Sklená, J. Dvoáková, V. Havlíek, M. Pospíil, J. Thiem, and V. Ken Biochem. Biophys. Res. Commun. 238 1997 149
4. E. Attolino, F. Bonaccorsi, G. Catelani, F. D'Andrea, K. Kenek, K. Bezouka, and V. Ken J. Carbohydr. Chem. 27 2008 156
5. A. Stütz, Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond 1999 Wiley-VHC New York
6. P. Compain, O.R. Martin, Iminosugars - From Synthesis to Therapeutic Applications 2007 Wiley Chichester
7. L.A.G.M. Van den Broek, M.W.P. Kat-van den Nieuwenhof, T.D. Butters, and C.A.A. van Boeckel J. Pharm. Pharmacol. 48 1996 172
8. X.-L. Zhang, Min. Liu, P. Xie, S. Wan, J.T. Ye, X. Zhou, and J. Wu Bioorg. Med. Chem. Lett. 14 2004 3789
9. X.-S. Ye, F. Sun, M. Liu, Q. Li, Y. Wang, G. Zhang, L.-H. Zhang, and X.-L. Zhang J. Med. Chem. 48 2005 3688
10. L. Zhang, F. Sun, Y. Li, X. Sun, X. Liu, Y. Huang, L.-H. Zhang, X.-S. Ye, and J. Xiao ChemMedChem 2 2007 1594
11. J. Zhou, Y. Zhang, X. Zhou, J. Zhou, L.-H. Zhang, X.-S. Ye, and X.-L. Zhang Bioorg. Med. Chem. 16 2008 1605
12. L. Zhang, F. Sun, Q. Wang, J. Zhou, L.-H. Zhang, X.-L. Zhang, and X.-S. Ye ChemMedChem 4 2009 756
13. N. Asano, R.J. Nash, R.J. Molyneux, and G.W. Fleet Tetrahedron: Asymmetry 11 2000 1645
14. E. Attolino, G. Catelani, F. D'Andrea, and M. Nicolardi J. Carbohydr. Chem. 23 2004 179
15. F. D'Andrea, G. Catelani, M. Mariani, and B. Vecchi Tetrahedron Lett. 42 2001 1139
16. A.J. Steiner, and A.E. Stütz Carbohydr. Res. 339 2004 2615
17. J. Spreitz, and A.E. Stütz Carbohydr. Res. 339 2004 1923
18. A.J. Steiner, G. Schitter, A.E. Stütz, T.M. Wrodnigg, C.A. Tarling, S.G. Whithers, K. Fantur, D. Mahuran, E. Pashke, and M. Tropak Bioorg. Med. Chem. 16 2008 10216
19. S. David, and S. Hanessian Tetrahedron 41 1985 643
20. D -21.8 (c 1.04, MeOH).
21. C.R.R. Matos, R.S.C. Lopes, and S.C. Lopes Synthesis 4 1999 571
22. R.V. Stevens Acc. Chem. Res. 17 1984 289
23. 2O, 62.9 MHz): δ 176.0 (CO), 101.1 (C-1′), 78.7 (C-5′), 78.4 (C-4), 76.2 (C-3), 73.9 (C-3′), 68.4 (C-2), 68.2 C-4′), 61.9 (C-6′), 60.3 (C-5), 58.3 (C-6), 54.5 (C-2′), 47.0 (C-1), 22.8 (MeCON).
24. + = 14233.99. The thermal and long-term biochemical stability of the protein was investigated using spectral techniques and mass spectrometry, and the protein proved stable for at least 7 days at 30 C or 37 °C.
25. O. Vank, M. Nálezková, D. Kavan, I. Boroviková, P. Pompach, P. Novák, V. Kumar, L. Vannucci, J. Hudeek, K. Hofbauerová, J. Brynda, V. Kopecký Jr., P. Kolenko, J. Dohnálek, P. Kadeávek, J. Chmelík, L. Gorík, L. ídek, V. Sklená, and K. Bezouka FEBS J. 275 2008 5589
26. 50 values were calculated from at least three independent experiments.
27. K. Kenek, M. Kuldová, K. Hulíková, I. Stibor, P. Lhoták, M. Dudi, J. Budka, H. Pelantová, K. Bezouka, A. Fierová, and V. Ken Carbohydr. Res. 342 2007 1781
28. K. Bezouka, V. Ken, C. Kieburg, and T.K. Lindhorst FEBS Lett. 426 1998 243
29. J. Pavlíek, B. Sopko, R. Ettrich, V. Kopecký, V. Baumruk, P. Novák, K. Havlíková, M. Vrbacký, L. Martínková, V. Ken, M. Pospíil, and K. Bezouka Biochemistry 42 2003 9295
30. C.E. Andoniou, D.M. Andrews, and M.A. Degli-Esposti Immunol. Rev. 214 2006 239
31. S.L. Van Dommelen, and M.A. Degli-Esposti Immunol. Cell Biol. 82 2004 332