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Volumn 50, Issue 14, 2007, Pages 3397-3401

New sst4/5-selective somatostatin peptidomimetics based on a constrained tryptophan scaffold

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOINDOLO[2,3 C]AZEPIN 2 ONE; AROMATIC COMPOUND; AZEPINE DERIVATIVE; DEXTRO AMINO ACID; LYSINE; PEPTIDOMINETIC AGENT; SOMATOSTATIN DERIVATIVE; SOMATOSTATIN RECEPTOR 4; SOMATOSTATIN RECEPTOR 5; TRYPTOPHAN; UNCLASSIFIED DRUG; CYCLIC AMP; SOMATOSTATIN;

EID: 34447532194     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070246f     Document Type: Article
Times cited : (22)

References (37)
  • 1
    • 0015914428 scopus 로고
    • Hypothalamic polypeptide that inhibits secretion of immunoreactive pituitary growth-hormone
    • Brazeau, P.; Vale, W.; Burgus, R.; Ling, N.; Butcher, M.; Rivier, J.; Guillemin, R. Hypothalamic polypeptide that inhibits secretion of immunoreactive pituitary growth-hormone. Science 1973, 179, 77-79.
    • (1973) Science , vol.179 , pp. 77-79
    • Brazeau, P.1    Vale, W.2    Burgus, R.3    Ling, N.4    Butcher, M.5    Rivier, J.6    Guillemin, R.7
  • 6
    • 0030837553 scopus 로고    scopus 로고
    • A refined model for the somatostatin pharmacophore: Conformational analysis of lanthionine-sandostatin analogs
    • Melacini, G.; Zhu, Q.; Osapay, G.; Goodman, M. A refined model for the somatostatin pharmacophore: Conformational analysis of lanthionine-sandostatin analogs. J. Med. Chem. 1997, 40, 2252-2258.
    • (1997) J. Med. Chem , vol.40 , pp. 2252-2258
    • Melacini, G.1    Zhu, Q.2    Osapay, G.3    Goodman, M.4
  • 7
    • 0002649780 scopus 로고
    • Peptides, chemistry and biology
    • and discovery in the development of peptide analogs, Smith, J. A, Rivier, J. E, Eds, ESCOM: Leiden, The Netherlands
    • Veber, D. F. Design and discovery in the development of peptide analogs. In Peptides, chemistry and biology, Proceedings of the 12th American Peptide Symposium, Cambridge, Massachusetts, June 16-21, 1991; Smith, J. A., Rivier, J. E., Eds.; ESCOM: Leiden, The Netherlands, 1992; pp 3-14
    • (1991) Proceedings of the 12th American Peptide Symposium, Cambridge, Massachusetts, June 16-21 , pp. 3-14
    • Veber, D.F.D.1
  • 8
    • 0020363575 scopus 로고
    • Sms 201-995 - A very potent and selective octapeptide analog of somatostatin with prolonged action
    • Bauer, W.; Briner, U.; Doepfner, W.; Haller, R.; Huguenin, R.; Marbach, P.; Petcher, T. J.; Pless, J. Sms 201-995 - A very potent and selective octapeptide analog of somatostatin with prolonged action. Life Sci. 1982, 31, 1133-1140.
    • (1982) Life Sci , vol.31 , pp. 1133-1140
    • Bauer, W.1    Briner, U.2    Doepfner, W.3    Haller, R.4    Huguenin, R.5    Marbach, P.6    Petcher, T.J.7    Pless, J.8
  • 10
    • 0024117485 scopus 로고
    • The role of somatostatin in the regulation of anterior-pituitary hormone-secretion and the use of its analogs in the treatment of human pituitary-tumors
    • Lamberts, S. W. J. The role of somatostatin in the regulation of anterior-pituitary hormone-secretion and the use of its analogs in the treatment of human pituitary-tumors. Endocr. Rev. 1988, 9, 417-436.
    • (1988) Endocr. Rev , vol.9 , pp. 417-436
    • Lamberts, S.W.J.1
  • 11
    • 0029974510 scopus 로고    scopus 로고
    • Advances in the use of somatostatins in the management of endocrine tumors
    • Chaudhry, A.; Kvols, L. Advances in the use of somatostatins in the management of endocrine tumors. Curr. Opin. Oncol. 1996, 8, 44-48.
    • (1996) Curr. Opin. Oncol , vol.8 , pp. 44-48
    • Chaudhry, A.1    Kvols, L.2
  • 12
    • 33746674999 scopus 로고    scopus 로고
    • Novel sst(2)-selective somatostatin agonists. Three-dimensional consensus structure by NMR
    • Grace, C. R. R.; Erchegyi, J.; Koerber, S. C.; Reubi, J. C.; Rivier, J.; Riek, R. Novel sst(2)-selective somatostatin agonists. Three-dimensional consensus structure by NMR. J. Med. Chem. 2006, 49, 4487-4496.
    • (2006) J. Med. Chem , vol.49 , pp. 4487-4496
    • Grace, C.R.R.1    Erchegyi, J.2    Koerber, S.C.3    Reubi, J.C.4    Rivier, J.5    Riek, R.6
  • 14
    • 0018240568 scopus 로고
    • Inferences about the conformation of somatostatin at a biologic receptor based on NMR studies
    • Arison, B. H.; Hirschmann, R.; Veber, D. F. Inferences about the conformation of somatostatin at a biologic receptor based on NMR studies. Bioorg. Chem. 1978, 7, 447-451.
    • (1978) Bioorg. Chem , vol.7 , pp. 447-451
    • Arison, B.H.1    Hirschmann, R.2    Veber, D.F.3
  • 16
    • 0024600650 scopus 로고
    • Somatostatin analogs inhibit growth of pancreatic cancer by stimulating tyrosine phosphatase
    • Liebow, C.; Reilly, C.; Serrano, M.; Schally, A. V. Somatostatin analogs inhibit growth of pancreatic cancer by stimulating tyrosine phosphatase. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 2003-2007.
    • (1989) Proc. Natl. Acad. Sci. U.S.A , vol.86 , pp. 2003-2007
    • Liebow, C.1    Reilly, C.2    Serrano, M.3    Schally, A.V.4
  • 17
    • 0006497774 scopus 로고    scopus 로고
    • Non-peptide somatostatin receptor ligands
    • Yang, L. H. Non-peptide somatostatin receptor ligands. Annu. Rep. Med. Chem. 1999, 34, 209-218.
    • (1999) Annu. Rep. Med. Chem , vol.34 , pp. 209-218
    • Yang, L.H.1
  • 18
    • 0141869940 scopus 로고    scopus 로고
    • Clinically validated peptides as templates for de novo peptidomimetic drug design at G-protein-coupled receptors
    • Jones, R. M.; Boatman, P. D.; Semple, G.; Shin, Y. J.; Tamura, S. Y. Clinically validated peptides as templates for de novo peptidomimetic drug design at G-protein-coupled receptors. Curr. Opin. Pharmacol. 2003, 3, 530-543.
    • (2003) Curr. Opin. Pharmacol , vol.3 , pp. 530-543
    • Jones, R.M.1    Boatman, P.D.2    Semple, G.3    Shin, Y.J.4    Tamura, S.Y.5
  • 20
    • 0242266516 scopus 로고    scopus 로고
    • Application of a novel design paradigm to generate general nonpeptide combinatorial scaffolds mimicking beta turns: Synthesis of ligands for somatostatin receptors
    • Chianelli, D.; Kim, Y. C.; Lvovskiy, D.; Webb, T. R. Application of a novel design paradigm to generate general nonpeptide combinatorial scaffolds mimicking beta turns: Synthesis of ligands for somatostatin receptors. Bioorg. Med. Chem. 2003, 11, 5059-5068.
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 5059-5068
    • Chianelli, D.1    Kim, Y.C.2    Lvovskiy, D.3    Webb, T.R.4
  • 24
    • 0030063814 scopus 로고    scopus 로고
    • A non-peptide ligand for the somatostatin receptor having a benzodiazepinone structure
    • Papageorgiou, C.; Borer, X. A non-peptide ligand for the somatostatin receptor having a benzodiazepinone structure. Bioorg. Med. Chem. Lett. 1996, 6, 267-272.
    • (1996) Bioorg. Med. Chem. Lett , vol.6 , pp. 267-272
    • Papageorgiou, C.1    Borer, X.2
  • 25
    • 0033541091 scopus 로고    scopus 로고
    • Identification of a potent heterocyclic ligand to somatostatin receptor subtype 5 by the synthesis and screening of beta-turn mimetic libraries
    • Souers, A. J.; Virgilio, A. A.; Rosenquist, A.; Fenuik, W.; Ellman, J. A. Identification of a potent heterocyclic ligand to somatostatin receptor subtype 5 by the synthesis and screening of beta-turn mimetic libraries. J. Am. Chem. Soc. 1999, 121, 1817-1825.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 1817-1825
    • Souers, A.J.1    Virgilio, A.A.2    Rosenquist, A.3    Fenuik, W.4    Ellman, J.A.5
  • 27
    • 15444348498 scopus 로고    scopus 로고
    • Spiro[1H-indene- 1,4′-piperidine] derivatives as potent and selective non-peptide human somatostatin receptor subtype 2 (sst(2)) agonists
    • Yang, L. H.; Guo, L. Q.; Pasternak, A.; Mosley, R.; Rohrer, S.; Birzin, E.; Foor, F.; Cheng, K.; Schaeffer, J.; Patchett, A. A. Spiro[1H-indene- 1,4′-piperidine] derivatives as potent and selective non-peptide human somatostatin receptor subtype 2 (sst(2)) agonists. J. Med. Chem. 1998, 41, 2175-2179.
    • (1998) J. Med. Chem , vol.41 , pp. 2175-2179
    • Yang, L.H.1    Guo, L.Q.2    Pasternak, A.3    Mosley, R.4    Rohrer, S.5    Birzin, E.6    Foor, F.7    Cheng, K.8    Schaeffer, J.9    Patchett, A.A.10
  • 28
    • 13144306065 scopus 로고    scopus 로고
    • Yang, L. H.; Berk, S. C.; Rohrer, S. P.; Mosley, R. T.; Guo, L. Q.; Underwood, D. J.; Arison, B. H.; Birzin, E. T.; Hayes, E. C.; Mitra, S. W.; Parmar, R. M.; Cheng, K.; Wu, T. J.; Butler, B. S.; Foor, F.; Pasternak, A.; Pan, Y. P.; Silva, M.; Freidinger, R. M.; Smith, R. G.; Chapman, K.; Schaeffer, J. M.; Patchett, A. A. Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10836-10841.
    • Yang, L. H.; Berk, S. C.; Rohrer, S. P.; Mosley, R. T.; Guo, L. Q.; Underwood, D. J.; Arison, B. H.; Birzin, E. T.; Hayes, E. C.; Mitra, S. W.; Parmar, R. M.; Cheng, K.; Wu, T. J.; Butler, B. S.; Foor, F.; Pasternak, A.; Pan, Y. P.; Silva, M.; Freidinger, R. M.; Smith, R. G.; Chapman, K.; Schaeffer, J. M.; Patchett, A. A. Synthesis and biological activities of potent peptidomimetics selective for somatostatin receptor subtype 2. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10836-10841.
  • 29
    • 0030884435 scopus 로고    scopus 로고
    • Design of peptides, proteins, and peptidomimetics in chi space
    • Hruby, V. J.; Li, G. G.; HaskellLuevano, C.; Shenderovich, M. Design of peptides, proteins, and peptidomimetics in chi space. Biopolymers 1997, 43, 219-266.
    • (1997) Biopolymers , vol.43 , pp. 219-266
    • Hruby, V.J.1    Li, G.G.2    HaskellLuevano, C.3    Shenderovich, M.4
  • 31
    • 0034622296 scopus 로고    scopus 로고
    • A convenient and scaleable procedure for removing the Fmoc group in solution
    • Sheppeck, J. E.; Kar, H.; Hong, H. A convenient and scaleable procedure for removing the Fmoc group in solution. Tetrahedron Lett. 2000, 41, 5329-5333.
    • (2000) Tetrahedron Lett , vol.41 , pp. 5329-5333
    • Sheppeck, J.E.1    Kar, H.2    Hong, H.3
  • 32
    • 0034033495 scopus 로고    scopus 로고
    • Affinity profiles for human somatostatin receptor subtypes SST1-SST5 of somatostatin radiotracers selected for scintigraphic and radiotherapeutic use
    • Reubi, J. C.; Schar, J. C.; Waser, B.; Wenger, S.; Heppeler, A.; Schmitt, J. S.; Mäcke, H. R. Affinity profiles for human somatostatin receptor subtypes SST1-SST5 of somatostatin radiotracers selected for scintigraphic and radiotherapeutic use. Eur. J. Nucl. Med. 2000, 27, 273-282.
    • (2000) Eur. J. Nucl. Med , vol.27 , pp. 273-282
    • Reubi, J.C.1    Schar, J.C.2    Waser, B.3    Wenger, S.4    Heppeler, A.5    Schmitt, J.S.6    Mäcke, H.R.7
  • 33
    • 0037027926 scopus 로고    scopus 로고
    • A new peptidic somatostatin agonist with high affinity to all five somatostatin receptors
    • Reubi, J. C.; Eisenwiener, K. P.; Rink, H.; Waser, B.; Mäcke, H. R. A new peptidic somatostatin agonist with high affinity to all five somatostatin receptors. Eur. J. Pharmacol. 2002, 456, 45-49.
    • (2002) Eur. J. Pharmacol , vol.456 , pp. 45-49
    • Reubi, J.C.1    Eisenwiener, K.P.2    Rink, H.3    Waser, B.4    Mäcke, H.R.5
  • 35
    • 0027085885 scopus 로고
    • Main chain and side-chain chiral methylated somatostatin analogs - Syntheses and conformational analyses
    • Huang, Z. W.; He, Y. B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. Main chain and side-chain chiral methylated somatostatin analogs - Syntheses and conformational analyses. J. Am. Chem. Soc. 1992, 114, 9390-9401.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 9390-9401
    • Huang, Z.W.1    He, Y.B.2    Raynor, K.3    Tallent, M.4    Reisine, T.5    Goodman, M.6
  • 36
    • 33745851855 scopus 로고    scopus 로고
    • Synthesis and evaluation of the beta-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative
    • Van Rompaey, K.; Ballet, S.; Tomboly, C.; De Wachter, R.; Vanommeslaeghe, K.; Biesemans, M.; Willem, R.; Tourwé, D. Synthesis and evaluation of the beta-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative. Eur. J. Org. Chem. 2006, 2899-2911.
    • (2006) Eur. J. Org. Chem , pp. 2899-2911
    • Van Rompaey, K.1    Ballet, S.2    Tomboly, C.3    De Wachter, R.4    Vanommeslaeghe, K.5    Biesemans, M.6    Willem, R.7    Tourwé, D.8
  • 37
    • 0033551723 scopus 로고    scopus 로고
    • Synthesis of novel proline and gamma-lactam derivatives as non-peptide mimics of somatostatin/sandostatin (R)
    • Damour, D.; Herman, F.; Labaudiniere, R.; Pantel, G.; Vuilhorgne, M.; Mignani, S. Synthesis of novel proline and gamma-lactam derivatives as non-peptide mimics of somatostatin/sandostatin (R). Tetrahedron 1999, 55, 10135-10154.
    • (1999) Tetrahedron , vol.55 , pp. 10135-10154
    • Damour, D.1    Herman, F.2    Labaudiniere, R.3    Pantel, G.4    Vuilhorgne, M.5    Mignani, S.6


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