Comparison of three γ-turn mimetic scaffolds incorporated into angiotensin II

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 9, 2000, Pages 2375-2383

  Lindman, Susanna ^a   Lindeberg, Gunnar ^a   Nyberg, Fred ^a   Karlén, Anders ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN 1 RECEPTOR; ANGIOTENSIN II DERIVATIVE;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SPECIFICITY; DRUG SYNTHESIS; IN VITRO STUDY; LIVER MEMBRANE; MOLECULAR MODEL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

ANGIOTENSIN II; ANIMALS; BENZENE; BINDING, COMPETITIVE; DRUG DESIGN; ELECTROSTATICS; LIVER; MEMBRANES; MODELS, MOLECULAR; MOLECULAR MIMICRY; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; RATS; RECEPTOR, ANGIOTENSIN, TYPE 1; RECEPTOR, ANGIOTENSIN, TYPE 2; RECEPTORS, ANGIOTENSIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033869114     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00169-3     Document Type: Article

References (46)

1. Hruby V.J. Life Sci. 31:1982;189.
2. Giannis A., Kolter T. Angew. Chem. Int. Ed. Engl. 32:1993;1244.
3. Hölzemann, G. Kontakte (Darmstadt) 1991, 3.
4. Hölzemann, G. Kontakte (Darmstadt) 1991, 55.
5. Liskamp R.M.J. Recl. Trav. Chim. Pays-Bas. 113:1994;1.
6. Fairlie D.P., West M.L., Wong A.K. Curr. Med. Chem. 5:1998;29.
7. Schmidt B., Lindman S., Tong W., Lindeberg G., Gogoll A., Lai Z., Thörnwall M., Synnergren B., Nilsson A., Welch C.J., Sohtell M., Westerlund C., Nyberg F., Karlén A., Hallberg A. J. Med. Chem. 40:1997;903.
8. Spear K.L., Brown M.S., Reinhard E.J., McMahon E.G., Olins G.M., Palomo M.A., Patton D.R. J. Med. Chem. 33:1990;1935.
9. Alkorta I., Suarez M.L., Herranz R., González-Muñiz R., García-López M.T. J. Mol. Model. 2:1996;16.
10. Brickmann K., Yuan Z., Sethson I., Somfai P., Kihlberg J. Chem. Eur. J. 5:1999;2241.
11. Callahan J.F., Bean J.W., Burgess J.L., Eggleston D.S., Hwang S.M., Kopple K.D., Koster P.F., Nichols A., Peishoff C.E., Samanen J.M., Vasko J.A., Wong A., Huffman W.F. J. Med. Chem. 35:1992;3970.
12. Callahan J.F., Newlander K.A., Burgess J.L., Eggleston D.S., Nichols A., Wong A., Huffman W.F. Tetrahedron. 49:1993;3479.
13. Newlander K.A., Callahan J.F., Moore M.L., Tomaszek T.A., Huffman W.F. J. Med. Chem. 36:1993;2321.
14. Ferguson M.D., Meara J.P., Nakanishi H., Lee M.S., Kahn M. Tetrahedron Lett. 38:1997;6961.
15. Graf von Roedern E., Lohof E., Hessler G., Hoffmann M., Kessler H. J. Am. Chem. Soc. 118:1996;10156.
16. Kemp D.S., Carter J.S. J. Org. Chem. 54:1989;109.
17. Olson G.L., Cheung H.-C., Chiang E., Madison V.S., Sepinwall J., Vincent G.P., Winokur A., Gary K.A. J. Med. Chem. 38:1995;2866.
18. Sato M., Lee J.Y.H., Nakanishi H., Johnson M.E., Chrusciel R.A., Kahn M. Biochem. Biophys. Res. Commun. 187:1992;999.
19. Schmidt, B.; Kühn, C. Synlett 1998, 1240.
20. Printz M.P., Némethy G., Bleich H. Nature (London), New Biol. 237:1972;135.
21. Nikiforovich G.V., Marshall G.R. Biochem. Biophys. Res. Commun. 195:1993;222.
22. Nikiforovich G.V., Kao J.L.-F., Plucinska K., Zhang W.J., Marshall G.R. Biochemistry. 33:1994;3591.
23. Plucinska K., Kataoka T., Yodo M., Cody W.L., He J.X., Humblet C., Lu G.H., Lunney E., Major T.C., Panek R.L., Schelkun P., Skeean R., Marshall G.R. J. Med. Chem. 36:1993;1902.
24. Samanen J.M., Peishoff C.E., Keenan R.M., Weinstock J. Bioorg. Med. Chem. Lett. 3:1993;309.
25. Joseph M.-P., Maigret B., Scheraga H.A. Int. J. Pept. Protein Res. 46:1995;514.
26. Sugg, E. E.; Dolan, C. A.; Patchett, A. A.; Chang, R. S. L.; Faust, K. A.; Lotti, V. J. In Peptides: Chemistry, Structure and Biology: Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E.; Marshall, G. R., Eds.; ESCOM Science Publishers: Leiden, 1990, pp 305-306.
27. Johannesson P., Lindeberg G., Tong W., Gogoll A., Karlén A., Hallberg A. J. Med. Chem. 42:1999;601.
28. Johannesson P., Lindeberg G., Tong W., Gogoll A., Synnergren B., Nyberg F., Karlén A., Hallberg A. J. Med. Chem. 42:1999;4524.
29. Hassner A., Alexanian V. Tetrahedron Lett. 46:1978;4475.
30. Blatt, A. H. In Organic Reactions; Adams, R., Ed.; Wiley & Sons, Inc.: New York, 1942; Vol. 1, pp 342-369.
31. Gerecs, A. In Friedel Crafts and Related Reactions; Olah, G. A., Ed.; Wiley & Sons, Inc.: New York, 1964; Vol. 3, pp 499-533.
32. Hidai M., Hikita T., Wada Y., Fujikura Y., Uchida Y. Bull. Chem. Soc. Jpn. 48:1975;2075.
33. Schoenberg A., Bartoletti I., Heck R.F. J. Org. Chem. 39:1974;3318.
34. dppp=1,3-bis(Diphenylphosphino)propane.
35. Sieber P. Helv. Chim. Acta. 60:1977;2711.
36. Tschaen D.M., Desmond R., King A.O., Fortin M.C., Pipik B., King S., Verhoeven T.R. Synth. Commun. 24:1994;887.
37. Augustine, R. L. Catalytic Hydrogenation. Marcel Dekker: New York, 1965, p 83.
38. Milner-White E.J., Ross B.M., Ismail R., Belhadj-Mostefa K., Poet R. J. Mol. Biol. 204:1988;777.
39. Milner-White E.J. J. Mol. Biol. 216:1990;385.
40. Rose G.D., Gierasch L.M., Smith J.A. Adv. Protein Chem. 37:1985;1.
41. Smith J.A., Pease L.G. CRC Crit. Rev. Biochem. 8:1980;315.
42. The inverse γ-turn was obtained from the crystal structure of rat oncomodulin (PDB code name 1RRO) between Ile-50 and Asn-52. The classic γ-turn was obtained from chemotaxis protein Che-Y-Escherichia coli (PDB code name 3CHY) between residues Pro-61 and Met-63.
43. Huffman, W. F.; Callahan, J. F.; Codd, E. E.; Eggleston, D. S.; Lemieux, C.; Newlander, K. A.; Schiller, P. W.; Takata, D. T.; Walker, R. F. In Synthetic Peptides: Approaches to Biological Problems; Tam, J. P.; Kaiser, E. T., Eds.; Alan R. Liss, Inc.: New York, 1989; Vol. 86, pp 257-266.
44. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902.
45. SYBYL Molecular Modeling Software, Version 6.6; Tripos Associates Inc.: St Louis, MO 63144.
46. Dudley D.T., Panek R.L., Major T.C., Lu G.H., Bruns R.F., Klinkefus B.A., Hodges J.C., Weishaar R.E. Mol. Pharmacol. 38:1990;370.