A first QSAR model for galectin-3 glycomimetic inhibitors based on 3D docked structures

Medicinal Chemistry

Volumn 2, Issue 5, 2006, Pages 481-489

  Sirois, Suzanne ^a   Giguère, Denis ^a   Roy, René ^a  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

3D QSAR; Galectin 3; Glycomimetics; Neural network

Indexed keywords

GALECTIN 3; GALECTIN 3 INHIBITOR; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; ARTIFICIAL NEURAL NETWORK; BINDING AFFINITY; CORRELATION ANALYSIS; DRUG BINDING; DRUG DESIGN; DRUG TARGETING; GENETIC ALGORITHM; HYDROGEN BOND; HYDROPHOBICITY; MATHEMATICAL MODEL; MOLECULAR MODEL; PREDICTION; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; PROTEIN DATABASE; PROTEIN MODIFICATION; PROTEIN STRUCTURE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

BIOMIMETIC MATERIALS; ELECTROSTATICS; GALECTIN 3; GLUCOSE; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; HYDROPHOBICITY; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STATIC ELECTRICITY;

EID: 33748661710     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340606778250252     Document Type: Article

References (49)

1. Giguère, D.; Sato, S.; St-Pierre, C.; Sirois, S.; Roy, R. Bioorg: Med. Chem. Lett., 2006, 16, 1668.
2. Barondes, S. H.; Castronovo, V.; Cooper, D. N.; Cummings, R. D.; Drickamer, K.; Feizi, T.; Gitt, M. A.; Hirabayashi, J.; Hughes, C.; Kasai, K.; Leffler, H.; Liu, F.-T.; Lotan, R. M.; Monsigny, A.M.; Pillai, S.; Poirer, F.; Raz, A.; Rigby, P.W.J.; Rini, L.M.; Wang, J.L. Cell, 1994, 76, 597.
3. Almkvist, J.; Karlsson, A. Glycoconj. J., 2004, 19, 575.
4. Sato, S.; Nieminen, J. Glycoconj. J., 2004, 19, 583.
5. Rabinovich, G. A.; Baum, L. G.; Tinari, N.; Paganelli, R.; Natoli, C.; Liu, F. T.; Iacobelli, S. Trends Immunol., 2002, 23, 313.
6. Nakahara, S.; Oka, N.; Raz, A. Apoptosis, 2005, 10, 267.
7. Rabinovich, G. A.; Cumashi, A.; Bianco, G. A.; Ciavardelli, D.; Iurisci, I.; D'Egidio, M.; Piccolo, E.; Tinari, N.; Nifantiev, N.; Iacobelli, S. Glycobiology, 2005.
8. Hsu, D. K.; Liu, F. T. Glycoconj. J., 2004, 19, 507.
9. Morris, S.; Ahmad. N.; Andre, S.; Kaltner. H.; Gabius, H. J.; Brenowitz, M.; Brewer, F. Glycobiology, 2004, 14, 293.
10. Seetharaman, J.; Kanigsberg, A.; Slaaby, R.; Leffler, H.; Barondes, S. H.; Rini, J. M. J. Biol. Chem., 1998, 273, 13047.
11. Sorme, P.; Arnoux, P.; Kahl-Knutsson, B.; Leffler, H.; Rini, J. M.; Nilsson, U. J. J Am. Chem. Soc., 2005, 127, 1737.
12. Sorme, P.; Qian, Y.; Nyholm, P. G.; Leffler,. H.; Nilsson, U. J. Chembiochem., 2002, 3, 183.
13. Sorme, P.; Kahl-Knutsson, B.; Huflejt, M.; Nilsson, U. J.; Leffler, H. Anal. Biochem., 2004, 334, 36..
14. Sorme, P.; Kahl-Knutson, B.; Wellmar, U.; Nilsson, U. J.; Leffler, H. Methods Enzymol., 2003, 362, 504.
15. Tejler, J.; Leffler, H.; Nilsson, U. J. Bioorg. Med. Chem. Lett., 2005, 15, 2343.
16. Cumpstey, I.; Carlsson, S.; Leffler, H.; Nilsson, U. J. Org. Biomol. Chem., 2005, 3, 1922.
17. Sirois, S.; Wei, D. Q.; Tsoukas, C. M.; Chou, K.-C.; Hatzakis, G.E. Med. Chem., 2005, 1, 173.
18. MOE, Molecular Operating Environment version 2005.04, CCG Chemical Computing Group, Montréal, QC, Canada H3A 2R7.
19. Lippmann, R. P.; Shahian, D. M. Ann. Thorac. Surg., 1997, 63, 1635.
20. Bang, S. Y.; Hwang, Y. S. Neural. Netw, 1997, 10, 1495-1503.
21. Mosier, P. D.; Jurs, P. C. J Chem. Inf. Comput. Sci., 2002, 42, 1460-70.
22. Cumpstey, I.; Sundin, A.; Leffler, H.; Nilsson, U. J. Angew. Chem. Int. Ed. Engl., 2005, 44, 5110.
23. Labute, P. J. Mol. Graph. Model., 2000, 18, 464.
24. Leo, A.; Hansch, C.; Church, C. J. Med. Chem., 1969, 12, 766.
25. Fabricius, J.; Englesen, S. B.; Rasmussen, K. J. Carbo. Chem., 1997, 16, 751.
26. Gasteiger, M.; Marsili, J. Tetrahedron, 1980, 36, 3219.
27. Li, A. P. Drug Discov. Today, 2001, 6, 357.
28. Hansch, C.; Leo, A.; Mekapati, S. B:; Kurup, A. Bioorg. Med. Chem., 2004, 12, 3391.
29. Ohtaka, H.; Velazquez-Campoy, A.; Xie, D.; Freire, E. Protein Sci., 2002, 11, 1908.
30. Sirois, S.; Hatzakis, G.; Wei, D.; Du, Q.; Chou, K. C. Comput. Biol. Chem., 2005, 29, 55.
31. Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science, 2003, 302, 613.
32. Blanchard, J.E.; Elowe, N. H.; Huitema, C.; Fortin, P. D.; Cechetto, J. D.; Eltis, L. D.; Brown, E. D. Chem. Biol., 2004, 11, 1445.
33. Kevorkov, D.; Makarenkov, V. J. Biomol. Screen., 2005, 10, 557.
34. Verma, R. P.; Hansch, C. Bioorg. Med. Chem., 2005.
35. Hansch, C.; Steinmetz, W. E.; Leo, A. J.; Mekapati, S. B.; Kurup, A.; Hoekman, D. J. Chem. Inf. Comput. Sci., 2003, 43, 120.
36. Hansch, C.; Hoekman, D.; Leo, A.; Weininger, D.; Selassie, C. D. Chem. Rev., 2002, 102, 783.
37. Verma, R. P.; Mekapati, S. B.; Kurup, A.; Hansch, C. Bioorg. Med. Chem., 2005, 13, 5508.
38. Hansch, C.; Verma, R. P.; Kurup, A.; Mekapati, S. B. Bioorg. Med. Chem. Lett., 2005, 15, 2149.
39. CPI, Critical Path Initiative http://www.fda.gov/oc/initiatives/ criticalpath/.
40. Wei, D. Q.; Zhang, R.; Du, Q.-S.; Gao, W.-N.; Li, Y.; Gao, H.; Wang, S.-Q.; Zhang, X.; Li, A.-X.; Sirois, S.; Chou, K.-C. Amino Acids, 2006, 1-8.
41. Sirois, S.; Sing, T.; Chou, K. C. Protein Pept. Sci., 2005, 6, 413.
42. Sirois, S.; Wei, D. Q.; Du, Q.; Chou, K. C. J Chem. Inf. Comput. Sci., 2004, 44, 1111.
43. Wei, D. Q.; Du, Q. S.; Sun, H.; Chou, K. C. Biochem. Biophys. Res. Commun., 2006.
44. Chou, K. C. Curr. Med. Chem., 2004, 11, 2105.
45. Chou, K. C.; Wei, D. Q.; Zhong, W. Z. Biochem. Biophys. Res. Commun., 2003, 308, 148-51.
46. Du, Q.; Wang, S.; Wei, D.; Sirois, S.; Chou, K. C. Anal. Biochem., 2005, 337, 262-70.
47. Du, Q. S.; Wang, S. Q.; Zhu, Y.; Wei, D. Q.; Goo, H.; Sirois, S.; Chou, K. C. Peptides, 2004, 25, 1857-64.
48. Chou, K. C. Biochem. Biophys. Res. Commun., 2004, 319, 433-8.
49. Cherkasov, A.; Shi, Z.; Fallahi, M.; Hammond, G. L. J. Med. Chem., 2005, 48, 3203-13.