Cyclic glycopeptidomimetics through a versatile sugar-based scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3841-3844

  Altamura, Maria ^a   Dragoni, Elisa ^b   Infantino, Angela Simona ^b   Legnani, Laura ^c   Ludbrook, Steve B ^d   Menchi, Gloria ^b   Toma, Lucio ^c   Nativi, Cristina ^b  

^a Menarini Ricerche SpA   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

^c UNIVERSITY OF PAVIA   (Italy)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Glycopeptides; Integrins; Peptidomimetics; Sugar aminoacids; Tachykinins

Indexed keywords

CARBOHYDRATE; CYCLIC GLYCOPEPTIDOMIMETIC AGENT; GLYCOPEPTIDE; INTEGRIN; IODINE 125; NEUROKININ 2 RECEPTOR; NEUROKININ A; PEPTIDOMIMETIC AGENT; SUGAR; TACHYKININ; UNCLASSIFIED DRUG; VERY LATE ACTIVATION ANTIGEN 4;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHO CELL; CYCLOADDITION; DIASTEREOISOMER; HUMAN; NONHUMAN; PEPTIDE SYNTHESIS; RECEPTOR BINDING;

CARBOHYDRATES; GLYCOPEPTIDES; INTEGRIN ALPHA4BETA1; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 67649644640     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.04.008     Document Type: Article

References (26)

1. Hanessian S., McNaughton-Smith G., Lombart H.-G., and Lubell W.D. Tetrahedron 53 (1997) 12789
2. Hanessian S., and Auzzas L. Acc. Chem. Res. 41 (2008) 1241 and references cited therein
3. Graf von Roedern E., Lohof E., Hessler G., Hoffmann M., and Kessler H. J. Am. Chem. Soc. 118 (1996) 10156
4. For recent reviews see:. Gruner S.A.W., Locardi E., Lohorf E., and Kessler H. Chem. Rev. 102 (2002) 491
5. Schweizer F. Angew. Chem., Int. Ed. 41 (2002) 231
6. Cipolla L., Peri F., La Ferla B., Redaelli C., and Nicotra F. Curr. Org. Synth. 2 (2005) 153
7. Lohof E., Plaker E., Mang C., Burkhart F., Dechantsreiter M.A., Haubner R., Wester H.J., Schwaiger M., Holzemann G., Goodman S.L., and Kessler H. Angew. Chem., Int. Ed. 39 (2000) 2761
8. Locardi E., Stockle M., Gruner S., and Kessler H. J. Am. Chem. Soc. 123 (2001) 8189
9. van Well R.M., Marinelli L., Altona C., Erkelens K., Siegal G., van Raaij M., Llamas-Saiz A.L., Kessler H., Novellino E., Lavecchia A., van Boom J.H., and Overhand M. J. Am. Chem. Soc. 125 (2003) 10822
10. El Oualid F., Burm B.E.A., Leroy I.M., Cohen L.H., van Boom J.H., van den Elst H., Overkleeft H.S., van der Marel G.A., and Overhand M. J. Med. Chem. 47 (2004) 3920
11. Chakraborty T.K., Srinivasu P., Tapadar S., and Mohan B.K. Glycoconjugate J. 22 (2005) 83
12. Haubner R., Finsinger D., and Kessler H. Angew. Chem., Int. Ed. 36 (1997) 1374
13. Burgess K., and Feng Y. Chemtracts: Org. Chem. 10 (1997) 1054
14. Venturi F., Venturi C., Liguori F., Cacciarini M., Montalbano M., and Nativi C. J. Org. Chem. 69 (2004) 6153
15. van den Bos L.J., Codée J.D.C., Van der Toorn J.C., Boltje T.J., van Boom J.H., Overkleeft H.S., and van der Marel G.A. Org. Lett. 6 (2004) 2165
16. Capozzi G., Giannini S., Menichetti S., Nativi C., Giolitti A., Patacchini R., Perrotta E., Altamura M., and Maggi C.A. Bioorg. Med. Chem. Lett. 12 (2002) 2263
17. Giannotti D., Perrotta E., Di Bugno C., Nannicini R., Harmat N.J.S., Giolitti A., Patacchini R., Renzetti A.R., Rotondaro L., Giuliani S., Altamura M., and Maggi C.A. J. Med. Chem. 43 (2000) 4041
18. Quartara L., and Altamura M. Curr. Drug Targets 7 (2006) 975
19. See Ref. 11 and references cited therein.
20. Siahaan T.J., and Lutz K. J. Pharm. Biomed. Anal. 12 (1994) 65
21. Modeling studies were performed through the exploration of the conformational space with a random search approach at an empirical level. All the located conformations were re-optimized within the density functional approach at the B3LYP/6-31G(d) level. Then, the energy was recalculated using a continuum solvent model (PCM) to take into account the effect of water.
22. Lin K.-C., and Castro A.C. Curr. Opin. Chem. Biol. 2 (1998) 453
23. Belvisi L., Bernardi A., Colombo M., Manzoni L., Potenza D., Scolastico C., Giannini G., Marcellini M., Riccioni T., Castorina M., LoGiudice P., and Pisano M. Bioorg. Med. Chem. 14 (2006) 169
24. Owen R.M., Carlson C.B., Xu J., Mowery P., Fasella E., and Kiessling L.L. Chem BioChem 8 (2007) 68
25. Green P.M., Ludbrook S.B., Miller D.D., Horgan C.M.T., and Barry S.T. FEBS Lett. 503 (2001) 75
26. The computational approach described for 15 was also applied to virtual cyclo(SAA5-Arg-Gly-Asp), that contains the RGD motif usually known to confer affinity for the αvβ3 integrin receptor when the tripeptide moiety assumes a kinked conformation. Calculations showed that the desired conformation is largely populated though this analog exhibits a certain degree of conformational freedom.