Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Tetrahedron

Volumn 71, Issue 39, 2015, Pages 7344-7353

  Campo, Vanessa L ^a   Ivanova, Irina M ^b   Carvalho, Ivone ^a   Lopes, Carla D ^a   Carneiro, Zumira A ^a   Saalbach, Gerhard ^b   Schenkman, Sergio ^c   Da Silva, João Santana ^a   Nepogodiev, Sergey A ^b   Field, Robert A ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b NORWICH RESEARCH PARK   (United Kingdom)

^c FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Click chemistry; Macrophage invasion; Pseudo glycomacrocycles; Triazole linked oligomers; Trypanosoma cruzi

Indexed keywords

2 [2 (2 AZIDOETHOXY)ETHOXY]ETHYL 6 O (PROP 2 YNYL) BETA D GALACTOPYRANOSIDE; ALKYNE; GALACTOSE; MACROCYCLIC COMPOUND; OLIGOMER; SIALIDASE; TRIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CELL SURFACE; CLICK CHEMISTRY; CYCLOADDITION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MACROPHAGE; NONHUMAN; OLIGOMERIZATION; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS; TRYPANOSOMA CRUZI;

TRYPANOSOMA CRUZI;

EID: 84939254785     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.04.085     Document Type: Article

References (43)

1. D.V. Andrade, K.J. Gollob, and W.O. Dutra PLoS Negl. Trop. Dis. 8 2014 e3010
2. F.S. Buckner Adv. Parasitol. 75 2011 89 119
3. G. Rivera, V. Bocanegra-Garcia, C. Ordaz-Pichardo, B. Nogueda-Torres, and A. Monge Curr. Med. Chem. 16 2009 3286 3293
4. A. Varki Glycobiology 3 1993 97 130
5. L.L. Kiessling, and R.A. Splain Annu. Rev. Biochem. 79 2010 619 653
6. J.E. Turnbull, and R.A. Field Nat. Chem. Biol. 3 2007 74 77
7. B. Ernst, and J.L. Magnani Nat. Rev. Drug Discov. 8 2009 661 677
8. R.M. de Lederkremer, and R. Agusti Adv. Carbohydr. Chem. Biochem. 62 2009 311 366
9. C.A. Buscaglia, V.A. Campo, A.C.C. Frasch, and J.M. Di Noia Nat. Rev. Microbiol. 4 2006 229 236
10. M.E. Giorgi, and R.M. de Lederkremer Carbohydr. Res. 346 2011 1389 1393
11. S.S. Dc-Rubin, and S. Schenkman Cell. Microbiol. 14 2012 1522 1530
12. B.R. Miller, and A.E. Roitberg Future Med. Chem. 5 2013 1889 1900
13. L. Freire-de-Lima, I.A. Oliveira, J.L. Neves, L.L. Penha, F. Alisson-Silva, W.B. Dias, and A.R. Todeschini Front. Immun. 3 2012 10.3389/fimmu.2012.00356
14. J. Neres, R.A. Bryce, and K.T. Douglas Drug. Discov. Today 13 2008 110 117
15. V.L. Campo, T.B. Riul, I. Carvalho, and M.D. Baruffi ChemBioChem 15 2014 1495 1507
16. B.L. Silva, J.D.S. Filho, P. Andrade, I. Carvalho, and R.J. Alves Bioorg. Med. Chem. Lett. 24 2014 4529 4532
17. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
18. V. Aragao-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475 9492
19. A. Dondoni Chem. - Asian. J. 2 2007 700 708
20. S. Dedola, S.A. Nepogodiev, and R.A. Field Org. Biomol. Chem. 5 2007 1006 1017
21. V.L. Campo, R. Sesti-Costa, Z.A. Carneiro, J.S. Silva, S. Schenkman, and I. Carvalho Bioorg. Med. Chem. 20 2012 145 156
22. 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 2427
23. G.G. Junqueira, M.R. Carvalho, P. de Andrade, C.D. Lopes, Z.A. Carneiro, R. Sesti-Costa, J.S. Silva, and I. Carvalho J. Braz. Chem. Soc. 25 2014 1872 1884
24. E. Galante, C. Geraci, S. Sciuto, V.L. Campo, I. Carvalho, R. Sesti-Costa, P.M.M. Guedes, J.S. Silva, L. Hill, S.A. Nepogodiev, and R.A. Field Tetrahedron 67 2011 5902 5912
25. A. Bernardi, J. Jimenez-Barbero, A. Casnati, C. De Castro, T. Darbre, F. Fieschi, J. Finne, H. Funken, K.E. Jaeger, M. Lahmann, T.K. Lindhorst, M. Marradi, P. Messner, A. Molinaro, P.V. Murphy, C. Nativi, S. Oscarson, S. Penades, F. Peri, R.J. Pieters, O. Renaudet, J.L. Reymond, B. Richichi, J. Rojo, F. Sansone, C. Schaffer, W.B. Turnbull, T. Velasco-Torrijos, S. Vidal, S. Vincent, T. Wennekes, H. Zuilhof, and A. Imberty Chem. Soc. Rev. 42 2013 4709 4727
26. S. Bhatia, M. Dimde, and R. Haag MedChemComm 5 2014 862 878
27. K. Kempe, A. Krieg, C.R. Becer, and U.S. Schubert Chem. Soc. Rev. 41 2012 176 191
28. J. Xie, and N. Bogliotti Chem. Rev. 114 2014 7678 7739
29. L. Xu, Y. Li, and Y. Li Asian J. Org. Chem. 3 2014 582 602
30. A. Pathigoolla, and K.M. Sureshan Chem. Commun. 2014 317 319
31. K.D. Bodine, D.Y. Gin, and M.S. Gin J. Am. Chem. Soc. 126 2004 1638 1639
32. S. Muthana, H. Yu, H.Z. Cao, J.S. Cheng, and X. Chen J. Org. Chem. 74 2009 2928 2936
33. V.L. Campo, I. Carvalho, C.H.T.P. Da Silva, S. Schenkman, L. Hill, S.A. Nepogodiev, and R.A. Field Chem. Sci. 1 2010 507 514
34. A. Pathigoolla, R.G. Gonnade, and K.M. Sureshan Angew. Chem., Int. Ed. 51 2012 4362 4366
35. A. Pathigoolla, and K.M. Sureshan Angew. Chem., Int. Ed. 52 2013 8671 8675
36. D.M. Fidalgo, A.A. Kolender, and O. Varela Mater. Today Commun. 2 2015 e70 e83
37. C.E. Butler, T.M.U. de Carvalho, E.C. Grisard, R.A. Field, and K.M. Tyler Traffic 14 2013 853 869
38. S.F. Chen, L.Y. Li, C. Zhao, and J. Zheng Polymer 51 2010 5283 5293
39. A. Dondoni, and A. Marra J. Org. Chem. 71 2006 7546 7557
40. J.A. Harrison, K.P.R. Kartha, E.J.L. Fournier, T.L. Lowary, C. Malet, U.J. Nilsson, O. Hindsgaul, S. Schenkman, J.H. Naismith, and R.A. Field Org. Biomol. Chem. 9 2011 1653 1660
41. S.G. Lee, D.H. Shin, and B.G. Kim Enzyme Microb. Technol. 31 2002 742 746
42. S. Schenkman, M.S. Jiang, G.W. Hart, and V. Nussenzweig Cell 65 1991 1117 1125
43. F.M. Marim, T.N. Silveira, D.S. Lima, and D.S. Zamboni PLoS One 5 2010 e15263