De Novo Design and Synthesis of Somatostatin Non-Peptide Peptidomimetics Utilizing β-d-Glucose as a Novel Scaffolding

Journal of the American Chemical Society

Volumn 115, Issue 26, 1993, Pages 12550-12568

  Hirschmann, Ralph ^a   Nicolaou, K C ^a,e   Pietranico, Sherrie ^a,f   Leahy, Ellen M ^a,g   Salvino, Joseph ^a,h   Cichy, Maria A ^a   Spoors, P Grant ^a   Shakespeare, William C ^a   Sprengeler, Paul A ^a   Hamley, Peter ^a   Smith, Amos B ^a   Arison, Byron ^b   Cascieri, Margaret R ^b   Strader, Catherine D ^b   Reisine, Terry ^a   Raynor, Karen ^a   Maechler, Laurie ^c   Donaldson, Cindy ^d   Vale, Wylie ^d   Freidinger, Roger M ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c MDS Inc   (Canada)

^d SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f HOFFMANN LA ROCHE INC   (United States)

^g AFFYMAX RESEARCH INSTITUTE   (United States)

^h EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CGP 23996; CYCLO(PROLYLPHENYLALANYL DEXTRO TRYPTOPHYLLYSYLTHREONYLPHENYLALANYL); N ACETYLSEGLITIDE; OCTREOTIDE; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GROWTH HORMONE RELEASE; HYPOPHYSIS; MOUSE; NONHUMAN; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0027857964     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00079a039     Document Type: Article

References (76)

1. Nicolaou, K. C.; Salvino, J. M.; Raynor, Κ.; Pietranico, S.; Reisine, T.; Freidinger, R. M.; Hirschmann, R. In Peptides–Chemistry, Structure and Biology: Proceedings of the 11th American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds.; ESCOM: Leiden, 1990; p 881.
2. Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengeler, P. A.; Furst, G.; Smith, A. B., III; Strader, C. D.; Cascieri, M. A.; Candelore, M. R.; Donaldson, C.; Vale, W.; Maechler, L. J. Am. Chem. Soc. 1992, 114, 9217.
3. Hirschmann, R. In Peptide Chemistry 1992; Proceedings of the 2nd Japan Symposium on Peptide Chemistry; Yanaihara, N., Ed.; Escom: Leiden, 1993; p 466.
4. Hirschmann, R.; Sprengeler, P. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B. III J. Am. Chem. Soc. 1992, 114, 9699.
5. Hirschmann, R.; Sprengeler, P. A.; Kawasaki, T.; Leahy, J. W.; Shakespeare, W. C.; Smith, A. B., III Tetrahedron 1993, 49, 3665.
6. Smith, A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carrol, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1992, 114, 10672.
7. Freidinger, R. M. TIPS Rev. 1989, 10, 270.
8. Sherman, D. B.; Spatola, A. F. J. Am. Chem. Soc. 1990, 112, 433.
9. Hirschmann, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1278.
10. Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 42, 104.
11. Pelton, J. T.; Gulya, K.; Hruby, V.; Duckies, S. P.; Yamamura, H. I. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 236.
12. Thaisrivongs, S.; Pals, D. T.; Turner, S. R.; Kroll, L. T. J. Med. Chem. 1988, 31, 1369.
13. Bail, J. B.; Alewood, P. F. J. Mol. Recogn. 1990, 3, 55.
14. Williams, P. D.; Perlow, D. S.; Payne, L. S.; Holloway, M. K.; Siegl, P. K. S.; Schorn, T. W.; Lynch, R. J.; Doyle, J. J.; Strouse, J. F.; Vlasuk, G. P. J. Med. Chem. 1991, 34, 887.
15. Hruby, V. J.; Sharma, S. D. Current Opinion Biotech. 1991, 2, 599.
16. Schiller, P. W.; Nguyen, T.M.-D.; Weltrowska, G.; Wilkes, B. C.; Marsden, B. J.; Lemieux, C.; Chung, N. N. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 11871.
17. Veber, D. F.; Saperstein, R.; Nutt, R. F.; Freidinger, R. M.; Brady, S. F.; Curley, P.; Perlow, D. S.; Paleveda, W. J.; Colton, C. D.; Zacchei, A. G.; Tocco, D. J.; Hoff, D. R.; Vandlen, R. L.; Gerich, J. E.; Hall, L.; Mandarino, L.; Cordes, E. H.; Anderson, P. S.; Hirschmann, R. Life Sciences 1984, 34, 1371.
18. Veber, D. F.; Freidinger, R. M. TINS 1985, 392.
19. Bell, J.; Peters, G. E.; McMartin, C.; Thomas, N. W.; Wilson, C. G. J. Pharm. Pharmacol. 1984, 35, 88P.
20. Conradi, R. A.; Hilgers, A. R.; Ho, N. F. H.; Burton, P. S. Pharmaceutical Res. 1992, 9, 435.
21. Walter, R. Federation Proc. 1977, 36, 1872.
22. Gulland, J. M.; Robinson, R. Mem. Proc. Manchester Lit. Phil Soc. 1925, 69, 79.
23. Nagai, U.; Sato, K. Peptides—Structure and Function 1985, 465.
24. Feigel, M. J. Am. Chem. Soc. 1986, 108, 181.
25. Kemp, D. S.; Stites, W. E. Tetrahedron Lett. 1988, 29, 5057.
26. Hinds, M. G.; Richards, N. G. J.; Robinson, J. A. J. Chem. Soc., Chem. Commun. 1988, 1447.
27. Kahn, M.; Wilke, S.; Chen, B.; Fujita, K. J. Am. Chem. Soc. 1988, 110, 1638.
28. Kahn, M.; Wilke, S.; Chen, B.; Fujita, K.; Lee, Y.; Johnson, M. E. J. Mol. Recogn. 1988, 1, 75.
29. Kahn, M.; Bertenshaw, S. Tetrahedron Lett. 1989, 30, 2317.
30. Nagai, U.; Sato, K. Angew. Chem. 1989, 101, 466.
31. Olson, G. L.; Voss, M. E.; Hill, D. E.; Kahn, M.; Madison, V. S.; Cook, C. M. J. Am. Chem. Soc. 1990, 112, 323.
32. Ernest, I.; Kalvoda, J.; Rihs, G.; Mutter, M. Tetrahedron Lett. 1990, 31, 4011.
33. Diaz, H.; Espina, J. R.; Kelly, J. W. J. Am. Chem. Soc. 1992, 114, 8316.
34. Bélanger, P. C.; Dufresne, C. Can. J. Chem. 1986, 64, 1514.
35. Brazeau, P.; Vale, W.; Burgus, R.; Guillemin, R. Can. J. Biochem. 1974, 52, 1067.
36. Brazeau, P.; Vale, W.; Burgus, R.; Ling, N.; Butcher, M.; Rivier, J.; Guillemin, R. Science 1973, 179, 78.
37. Veber, D. F.; Holly, F. W.; Paleveda, W. J.; Nutt, R. F.; Bergstrand, S. J.; Torchiana, M.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 2636.
38. Arison, B. H.; Hirschmann, R.; Veber, D. F. Biorg. Chem. 1978, 7, 447.
39. Arison, B. H.; Hirschmann, R.; Paleveda, W. J.; Brady, S. F.; Veber, D. F. Biochem. Biophys. Res. Commun. 1981, 100, 1148.
40. Veber, D. F.; Freidinger, R. M.; Perlow, D. S.; Paleveda, W. J.; Holly, F. W.; Strachan, R. G.; Nutt, R. F.; Arison, B. H.; Homnick, C.; Randall, W. C.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. Nature 1981, 292, 55.
41. Vale, W.; Rivier, J.; Ling, N.; Brown, M. Metabolism 1978, 27, 1391.
42. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Henderickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
43. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
44. Jeremias, C. G.; Lucas, G. B.; Mackenzie, C. A. J. Am. Chem. Soc. 1948, 70, 2598.
45. Magus, V. Carbohydr. Res. 1979, 76, 261.
46. Binkley, R. W.; Ambrose, M. G. J. Carbohydr. Chem. 1984, 3, 1.
47. Zarytova, V. F.; Ivanova, E. M.; Kutyavin, I. V.; Segeev, D. S.; Sil'nikov, V. N.; Shishkin, G. V. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 1989, 3.
48. Lokhov, S. G.; Podyminogin, M. A.; Sergeev, D. S.; Sil'nikov, V. N.; Kutyavin, I. V.; Shishkin, G. V.; Zarytova, V. P. Bioconjugate Chem. 1992, 3, 414.
49. Barker, R.; Olsen, K. W.; Shaper, J. H.; Hill, R. L. J. Biol. Chem. 1972, 247, 7135.
50. Chipowsky, S.; Lee, Y. C. Carbohydr. Res. 1973, 31, 339.
51. Wojcik, B.; Adkins, H. J. Am. Chem. Soc. 1934, 56, 2419.
52. Fernandez, S.; Menendez, E.; Vicente, G. Synthesis 1991, 713.
53. Iacono, S.; Rasmussen, J. R. Org. Synth. 1985, 64, 57.
54. RajanBabu, T. V. J. Org. Chem. 1988, 53, 4522.
55. Blackburne, I. D.; Fredericks, P. M.; Buthrie, R. D. Aust. J. Chem. 1976, 29, 381.
56. Danishefsky, S. J.; Halcomb, R. L. J. Am. Chem. Soc. 1989, 111, 6661.
57. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans 1 1975, 1574.
58. Williams, J. M.; Richardson, A. C. Tetrahedron 1967, 23, 1369.
59. Street, I. P.; Armstrong, C. R.; Withers, S. G. Biochemistry 1986, 25, 6021.
60. Bhattacharjee, S. S.; Gorin, P. A. J. Can. J. Chem. 1969, 47, 1195.
61. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990.
62. Papageorgiou, C.; Haltiner, R.; Bruns, C.; Petcher, T. J. Biorg. Med. Chem. Lett. 1992, 2, 135.
63. Sreedharan, S. P.; Kodama, K. T.; Peterson, K. E.; Goetzl, E. J. J. Biol. Chem. 1989, 264, 949.
64. He, H.-T.; Johnson, Κ.; Thermos, K.; Reisine, T. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 1480.
65. Kimura, N.; Hayafuji, C.; Kimura, N. J. Biol. Chem. 1989, 264, 7033.
66. Rens-Domiano, S.; Law, S. F.; Yamada, Y.; Seino, S.; Bell, G. I.; Reisine, T. Mol. Pharmacol. 1992, 42, 28.
67. Brown, P. J.; Schonbrann, A. J. Biol. Chem. 1993, 268, 6668.
68. Smith, R. G.; Cheng, Κ.; Schoen, W. R.; Pong, S.-S.; Hickey, G.; Jacks, T.; Butler, B.; Chan, W.W.-S.; Chaung, L.-Y.P.; Judith, F.; Taylor, J.; Wyvratt, M. J.; Fisher, M. H. Science 1993, 260, 1643.
69. Vale, W.; Rivier, J.; Ling, N.; Brown, M. Metabolism 1978, 27, 1391.
70. Nutt, R. F.; Veber, D. F.; Curley, P. E.; Saperstein, R.; Hirschmann, R. Int. J. Peptide Protein Res. 1983, 21, 66.
71. Arison, B. H.; Hirschmann, R.; Veber, D. F. Biorg. Chem. 1978, 7, 447.
72. Strader, C. D.; Sigal, I. S.; Register, R. B.; Candelore, M. R.; Rands, E.; Dixon, R. A. F. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4384.
73. Pratt, J. W.; Richtmyer, N. K. J. Am. Chem. Soc. 1957, 79, 2597.
74. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
75. Raynor, Κ.; Reisine, T. J. Pharmacol. Exp. Ther. 1989, 251, 510.
76. Raynor, Κ.; Reisine, T. J. Pharmacol. Exp. Ther. 1993, 264, 110.