A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 19, 2012, Pages 6190-6194

  Liu, Ligong ^a,b   Li, Caiping ^a   Cochran, Siska ^a   Feder, Daniel ^b   Guddat, Luke W ^b   Ferro, Vito ^a,b  

^a Progen Pharmaceuticals Limited   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Glycoconjugates; Growth factors; Heparan sulfate mimetics; Inhibitors; Ugi condensation

Indexed keywords

ANGIOGENIC FACTOR; FIBROBLAST GROWTH FACTOR 1; FIBROBLAST GROWTH FACTOR 2; GLYCOCONJUGATE; HEPARAN SULFATE; VASCULOTROPIN;

ANGIOGENESIS; ARTICLE; BINDING AFFINITY; BINDING SITE; CALCULATION; CHEMICAL REACTION; MOLECULAR DOCKING; MOLECULAR LIBRARY; PROTEIN INTERACTION; STEREOCHEMISTRY; SULFONATION; UGI REACTION;

BINDING SITES; FIBROBLAST GROWTH FACTOR 1; FIBROBLAST GROWTH FACTOR 2; GLYCOCONJUGATES; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; SMALL MOLECULE LIBRARIES; SULFATES; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 84866403093     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.08.001     Document Type: Article

References (48)

1. For recent reviews see A. Dömling, W. Wang, and K. Wang Chem. Rev. 112 2012 3083
2. M. Colombo, and I. Peretto Drug Discovery Today 13 2008 677
3. B. Ganem Acc. Chem. Res. 42 2009 463
4. L. Banfi, G. Guanti, R. Riva, and A. Basso Curr. Opin. Drug Discov. Devel. 10 2007 704
5. I. Akritopoulou-Zanze Curr. Opin. Chem. Biol. 12 2008 324
6. C. Hulme, and J. Dietrich Mol. Divers. 13 2009 195
7. A. Dömling Chem. Rev. 106 2006 17
8. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
9. A. Dömling Curr. Opin. Chem. Biol. 6 2002 306
10. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51
11. L. Weber Curr. Med. Chem. 9 2002 2085
12. P.V. Murphy, H. Bradley, M. Tosin, N. Pitt, G.M. Fitzpatrick, and W.K. Glass J. Org. Chem. 68 2003 5692
13. H. Bradley, G. Fitzpatrick, W.K. Glass, H. Kunz, and P.V. Murphy Org. Lett. 3 2001 2629
14. W.K.C. Park, M. Auer, H. Jaksche, and C.-H. Wong J. Am. Chem. Soc. 118 1996 10150
15. D.P. Sutherlin, T.M. Stark, R. Hughes, and R.W. Armstrong J. Org. Chem. 61 1996 8350
16. O. Lockhoff, and I. Frappa Comb. Chem. High Throughput Screening 5 2002 361
17. O. Lockhoff Angew. Chem., Int. Ed. 37 1998 3436
18. K. Bedjeguelal, H. Bienayme, A. Dumoulin, S. Poigny, P. Schmitt, and E. Tam Bioorg. Med. Chem. Lett. 16 2006 3998
19. M. ChapmanTimothy, G. DaviesIeuan, B. Gu, M. BlockTimothy, I.C. ScopesDavid, A. HayPhilip, M. CourtneyStephen, A. McNeillLuke, J. SchofieldChristopher, and G. DavisBenjamin J. Am. Chem. Soc. 127 2005 506
20. T.M. Chapman, I.G. Davies, B. Gu, T.M. Block, D.I.C. Scopes, P.A. Hay, S.M. Courtney, L.A. McNeill, C.J. Schofield, and B.G. Davis J. Am. Chem. Soc. 127 2005 506
21. L. Liu, C.P. Li, S. Cochran, and V. Ferro Bioorg. Med. Chem. Lett. 14 2004 2221
22. J. Zhang, G. Rivers, Y. Zhu, A. Jacobson, J. Peyers, G. Grundstrom, P. Burch, S. Hussein, A. Marolewski, W. Herlihy, and J. Rusche Bioorg. Med. Chem. 9 2001 825
23. For reviews see A. Bikfalvi Bull. Cancer 94 2007 F193
24. H.E. Conrad Heparin-binding Proteins 1998 Academic Press San Diego
25. Z. Galzie, A.R. Kinsella, and J.A. Smith Biochem. Cell Biol. 75 1997 669
26. For reviews see M. Rusnati, and M. Presta Curr. Pharm. Des. 13 2007 2025
27. J.M. Pluda Semin. Oncol. 24 1997 203
28. T. Kessler, F. Fehrmann, R. Bieker, W.E. Berdel, and R.M. Mesters Curr. Drug Targets 8 2007 257
29. L.M. Ellis, and D.J. Hicklin Nat. Rev. Cancer 8 2008 579
30. A.D. DiGabriele, I. Lax, D.I. Chen, C.M. Svahn, M. Jaye, J. Schlessinger, and W.A. Hendrickson Nature 393 1998 812
31. S. Faham, R.E. Hileman, J.R. Fromm, R.J. Linhardt, and D.C. Rees Science 271 1996 1116
32. L. Pellegrini, D.F. Burke, F. von Delft, B. Mulloy, and T.L. Blundell Nature 407 2000 1029
33. J. Schlessinger, A.N. Plotnikov, O.A. Ibrahimi, A.V. Eliseenkova, B.K. Yeh, A. Yayon, R.J. Linhardt, and M. Mohammadi Mol. Cell 6 2000 743
34. S. Cochran, C. Li, J.K. Fairweather, W.C. Kett, D.R. Coombe, and V. Ferro J. Med. Chem. 46 2003 4601
35. K.D. Johnstone, T. Karoli, L. Liu, K. Dredge, E. Copeman, C.P. Li, K. Davis, E. Hammond, I. Bytheway, E. Kostewicz, F.C. Chiu, D.M. Shackleford, S.A. Charman, W.N. Charman, J. Harenberg, T.J. Gonda, and V. Ferro J. Med. Chem. 53 2010 1686
36. L. Liu, I. Bytheway, T. Karoli, J.K. Fairweather, S. Cochran, C. Li, and V. Ferro Bioorg. Med. Chem. Lett. 18 2008 344
37. V. Ferro, K. Dredge, L. Liu, E. Hammond, I. Bytheway, C. Li, K. Johnstone, T. Karoli, K. Davis, E. Copeman, and A. Gautam Semin. Thromb. Hemost. 33 2007 557
38. C. Freeman, L.G. Liu, M.G. Banwell, K.J. Brown, A. Bezos, V. Ferro, and C.R. Parish J. Biol. Chem. 280 2005 8842
39. L. Liu, C. Li, S. Cochran, S. Jimmink, and V. Ferro ChemMedChem 7 2012 1267
40. V. Ferro, L. Liu, K.D. Johnstone, N. Wimmer, T. Karoli, P. Handley, J. Rowley, K. Dredge, C.P. Li, E. Hammond, K. Davis, L. Sarimaa, J. Harenberg, and I. Bytheway J. Med. Chem. 55 2012 3804
41. I. Capila, and R.J. Linhardt Angew. Chem., Int. Ed. 41 2002 390
42. N.J. Harmer Biochem. Soc. Trans. 34 2006 442
43. C. Biswas Trends Glycosci. Glycotechnol. 4 1992 53
44. C. Bernlind, S. Oscarson, and G. Widmalm Carbohydr. Res. 263 1994 173
45. S. Cochran, C.P. Li, and V. Ferro Glycoconjugate J. 26 2009 577
46. I. Bytheway, and S. Cochran J. Med. Chem. 47 2004 1683
47. R. Thomsen, and M.H. Christensen J. Med. Chem. 49 2006 3315
48. L. Huang, C. Fernandez, and R.J. Kerns Bioorg. Med. Chem. Lett. 17 2007 419