AT2-selective angiotensin II analogues containing tyrosine-functionalized 5,5-bicyclic thiazabicycloalkane dipeptide mimetics

Journal of Medicinal Chemistry

Volumn 47, Issue 24, 2004, Pages 6009-6019

  Johannesson, Petra ^a   Erdélyi, Máté ^a   Lindeberg, Gunnar ^a   Frändberg, Per Anders ^a   Nyberg, Fred ^a   Karlén, Anders ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANGIOTENSIN 1 RECEPTOR; ANGIOTENSIN 2 RECEPTOR; ANGIOTENSIN II DERIVATIVE; CYCLOALKANE DERIVATIVE; DIPEPTIDE DERIVATIVE; ANGIOTENSIN II; CROWN COMPOUND; DIMETHYL SULFOXIDE; DIPEPTIDE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; TYROSINE;

ANIMAL TISSUE; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; RECEPTOR AFFINITY; STRUCTURE ANALYSIS; SWINE; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; FEMALE; IN VITRO STUDY; LIVER; METABOLISM; MOLECULAR MIMICRY; RADIOASSAY; SOLUTION AND SOLUBILITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; UTERUS;

ANGIOTENSIN II; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CROWN COMPOUNDS; DIMETHYL SULFOXIDE; DIPEPTIDES; FEMALE; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; RADIOLIGAND ASSAY; RATS; RECEPTOR, ANGIOTENSIN, TYPE 1; RECEPTOR, ANGIOTENSIN, TYPE 2; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE; TYROSINE; UTERUS;

EID: 8644272445     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049651m     Document Type: Article

References (84)

1. Timmermans, P. B.; Wong, P. C.; Chiu, A. T.; Herblin, W. F.; Benfield, P.; Carini, D. J.; Lee, R. J.; Wexler, R. R.; Saye, J. A.; Smith, R. D. Angiotensin II Receptors and Angiotensin II Receptor Antagonists. Pharmacol. Rev. 1993, 45, 205-251.
2. De Gasparo, M.; Catt, K. J.; Inagami, T.; Wright, J. W.; Unger, T. International Union of Pharmacology. XXIII. The Angiotensin II Receptors. Pharmacol. Rev. 2000, 52, 415-472.
3. 2 Receptors: Regulation, Signaling and Function. Blood Pressure 2003, 12, 70-88.
4. Horiuchi, M. Functional Aspects of Angiotensin Type 2 Receptor. Adv. Exp. Med. Biol. 1996, 396, 217-224.
5. 1 receptors. J. Biol. Chem. 1986, 271, 22729-22735.
6. 2 Receptor. J. Hum. Hypertens. 1998, 12, 311-318.
7. 2 Receptor Signaling Pathway in NG108-15 Cells. J. Biol. Chem. 2003, 278, 3606-3614.
8. 2 Receptors: Cardiovascular Hope or Hype? Br. J. Pharmacol. 2003, 140, 809-824.
9. Samanen, J. M.; Peishoff, C. E.; Keenan, R. M.; Weinstock, J. Refinement of a Molecular Model of Angiotensin II (All) Employed in the Discovery of Potent Nonpeptide Antagonists. Bioorg. Med. Chem. Lett. 1993, 3, 909-914.
10. Nikiforovich, G. V.; Marshall, G. R. Three-Dimensional Recognition Requirements for Angiotensin Agonists: A Novel Solution for an Old Problem. Biochem. Biophys. Res. Commun. 1993, 195, 222-228.
11. Nikiforovich, G. V.; Kao, J. L.-F.; Plucinska, K.; Zhang, W. J.; Marshall, G. R. Conformational Analysis of Two Cyclic Analogues of Angiotensin: Implications for the Biologically Active Conformation. Biochemistry 1994, 33, 3591-3598.
12. Joseph, M.-P.; Maigret, B.; Scheraga, H. A. Proposals for the Angiotensin II Receptor-Bound Conformation by Comparative Computer Modeling of All and Cyclic Analogs. Int. J. Pept. Protein Res. 1995, 46, 514-526.
13. Balodis, J.; Golbraikh, A. Conformational Analysis of Cyclic Angiotensin II Analogues. Lett. Pept. Sci. 1996, 3, 195-199.
14. Carpenter, K. A.; Wilkes, B. C.; Schiller, P. W. The Octapeptide Angiotensin II Adopts a Well-Defined Structure in a Phospholipid Environment. Eur. J. Biochem. 1998, 251, 448-453.
15. Matsoukas, J. M.; Polevaya, L.; Ancans, J.; Mavromoustakos, T.; Kolocouris, A.; Roumelioti, P.; Vlahakos, D. V.; Yamdagni, R.; Wu, Q.; Moore, G. J. The Design and Synthesis of a Potent Angiotensin II Cyclic Analogue Confirms the Ring Cluster Receptor Conformation of the Hormone Angiotensin II. Bioorg. Med. Chem. 2000, 8, 1-10.
16. 1 Non-peptide Antagonists. Bioorg. Med. Chem. 2001, 9, 1639-1647.
17. 1 Receptor as a Ligand Contact Point: Receptor-Bound Angiotensin II Adopts an Extended Structure. Biochemistry 2000, 39, 9662-9670.
18. 2, Parallel to the Transmembrane Domains and in an Extended Form. Can. J. Physiol. Pharm. 2002, 80, 418-425.
19. Printz, M. P.; Nemethy, G.; Bleich, H. Conformational Analysis of Two Cyclic Analogues of Angiotensin: Implications for the Biologically Active Conformation. Nature 1972, 237, 135-140.
20. Spear, K. L.; Brown, M. S.; Reinhard, E. J.; McMahon, E. G.; Olins, G. M.; Palomo, M. A.; Patton, D. R. Conformational Restriction of Angiotensin II: Cyclic Analogues Having High Potency. J. Med. Chem. 1900, 33, 1935-1940.
21. 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: Leiden, 1990; pp 305-306.
22. 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. Multiple Binding Modes for the Receptor-Bound Conformations of Cyclic All Agonists. J. Med. Chem. 1993, 36, 1902-1913.
23. 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. Design, Synthesis, and Biological Activities of Four Angiotensin II Receptor Ligands with γ-Turn Mimetics Replacing Amino Acid Residues 3-5. J. Med. Chem. 1997, 40, 903-919.
24. Lindman, S.; Lindeberg, G.; Nyberg, F.; Karlén, A.; Hallberg, A. Comparison of Three γ-Turn Mimetic Scaffolds Incorporated into Angiotensin II. Bioorg. Med. Chem. 2000, 8, 2375-2383.
25. 1 Receptor. J. Med. Chem. 2002, 45, 1767-1777.
26. Samanen, J.; Aiyar, N.; Edwards, R. In Peptides, Proceedings of the Thirteenth American Peptide Symposium; Hodges, R. S., Smith, J. A., Eds.; ESCOM: Leiden, 1994; pp 640-642.
27. Cody, W. L.; He, J. X.; Lunney, E. A.; Humblet, C. C.; Lu, G. H.; Panek, R. L.; Dudley, D. T. Modifications of the C-terminal Dipeptide of Angiotensin II Yielded a Novel Series of Analogues with Type II (AT2) Receptor Selectivity. Protein Pept. Lett. 1996, 3, 107-112.
28. Miura, S.-I.; Karnik, S. S. Angiotensin II Type 1 and Type 2 Receptors Bind Angiotensin II Through Different Types of Epitope Recognition. J. Hypertens. 1999, 17, 397-404.
29. 2 Receptor Affinity. Bioorg. Med. Chem. 2003, 11, 2947-2954.
30. 2 Receptor Ligand with a γ-Turn-Like Mimetic Replacing the Amino Acid Residues 4-5 of Angiotensin II. J. Med. Chem. 2004, 47, 859-870.
31. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Turns in Peptides and Proteins. Adv. Protein Chem. 1985, 37, 1-109.
32. Ball, J. B.; Alewood, P. F. Conformational Constraints: Non-peptide β-Turn Mimics. J. Mol. Recognit. 1990, 3, 55-64.
33. Hölzemann, G. Peptide Conformation Mimetics. Part 1. Kontakte (Darmstadt) 1991, 3-12.
34. Hölzemann, G. Peptide Conformation Mimetics. Part 2. Kontakte (Darmstadt) 1991, 55-63.
35. Giannis, A.; Kolter, T. Peptidomimetics for Receptor Ligands: Discovery, Development, and Medicinal Perspectives. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
36. Liskamp, R. M. J. Conformationally Restricted Amino Acids and Dipeptides, (Non)peptidomimetics and Secondary Structure Mimetics. Recl. Trau. Chim. Pays-Bas 1994, 113, 1-19.
37. Fairlie, D. P.; West, M. L.; Wong, A. K. Towards Protein Surface Mimetics. Curr. Med. Chem. 1998, 5, 29-62.
38. Souers, A. J.; Ellman, J. A. β-Turn Mimetic Library Synthesis: Scaffolds and Applications. Tetrahedron 2001, 57, 7431-7448.
39. Burgess, K. Solid-Phase Syntheses of β-Turn Analogues to Mimic or Disrupt Protein-Protein Interactions. Acc. Chem. Res. 2001, 34, 826-835.
40. MacDonald, M.; Aubé, J. Approaches to Cyclic Peptide β-Turn Mimics. Curr. Org. Chem. 2001, 5, 417-438.
41. Kee, S.; Jois, S. D. S. Design of β-turn Based Therapeutic Agents. Curr. Pharm. Design 2003, 9, 1209-1224.
42. Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Design and Synthesis of Conformationally Constrained Amino Acids as Versatile Scaffolds and Peptide Mimetics. Tetrahedron 1997, 53, 12789-12854 and references therein.
43. Baures, P. W.; Ojala, W. H.; Costain, W. J.; Ott, M. C.; Pradhan, A.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. Design, Synthesis, and Dopamine Receptor Modulating Activity of Diketopiperazine Peptidomimetics of L-Prolyl-L-Leucylglycinamide. J. Med. Chem. 1997, 40, 3594-3600.
44. Gillespie, P.; Cicariello, J.; Olson, G. L. Conformational Analysis of Dipeptide Mimetics. Biopolymers 1997, 43, 191-217.
45. Siddiqui, M. A.; Préville, P.; Tarazi, M.; Warder, S. E.; Eby, P.; Gorseth, E.; Puumala, K.; DiMaio, J. Synthesis of Constrained Bicyclic Dipeptide Mimetics. Tetrahedron Lett. 1997, 38, 8807-8810.
46. Subasinghe, N. L.; Khalil, E. M.; Johnson, R. L. Stereospecific Synthesis of 2-substituted Bicyclic Thiazolidine Lactams. Tetrahedron Lett. 1997, 38, 1317-1320.
47. Witter, D. J.; Famiglietti, S. J.; Cambier, J. C.; Castelhano, A. L. Design and Synthesis of SH3 Domain Binding Ligands: Modifications of the Consensus Sequence XPpXP. Bioorg. Med. Chem. Lett. 1998, 8, 3137-3142.
48. Geyer, A.; Bockelmann, D.; Weissenbach, K.; Fischer, H. Synthesis and Structure of a Hydrophilic β-turn Mimetic. Tetrahedron Lett. 1999, 40, 477-478.
49. Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. Design, Synthesis, and Dopamine Receptor Modulating Activity of Spiro Bicyclic Peptidomimetics of L-Prolyl-L-Leucyl- Glycinamide. J. Med. Chem. 1999, 42, 628-637.
50. Khalil, E. M.; Pradhan, A.; Ojala, W. H.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. Synthesis and Dopamine Receptor Modulating Activity of Substituted Bicyclic Thiazolidine Lactam Peptidomimetics of L-Prolyl-L-Leucyl- Glycinamide. J. Med. Chem. 1999, 42, 2977-2987.
51. Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Stereoselective Synthesis of Conformationally Constrained Reverse Turn Dipeptide Mimetics. Tetrahedron Lett. 2001, 42, 145-148.
52. Gu, X.; Qiu, W.; Ying, J.; Ndungu, J. M.; Hruby, V. J. In Peptides, The Wave of the Future, Proceedings of the Seventeenth American Peptide Symposium; Lebl, M., Houghten, R. A., Eds.; American Peptide Society: San Diego, 2001; pp 602-603.
53. 2. J. Med. Chem. 1993, 36, 2356-2361.
54. Johannesson, P.; Lindeberg, G.; Tong, W.; Gogoll, A.; Karlén, A.; Hallberg, A. Bicyclic Tripeptide Mimetics with Reverse Turn Inducing Properties. J. Med. Chem. 1999, 42, 601-608.
55. Johannesson, P.; Lindeberg, G.; Tong, W.; Gogoll, A.; Synnergren, B.; Nyberg, F.; Karlén, A.; Hallberg, A. Angiotensin II Analogues Encompassing 5,9-and 5,10-Fused Thiazabicycloalkane Tripeptide Mimetics. J. Med. Chem. 1999, 42, 4524-4537.
56. Baldwin, J. E.; Lee, V.; Schofield, C. J. Synthesis of a Bicyclic γ-Lactam Dipeptide Analog. Heterocydes 1992, 34, 903-906.
57. Ben-Ishai, D. Reaction of Acylamino Acids with Paraformaldehyde. J. Am. Chem. Soc. 1957, 79, 5736-5738.
58. Pappo, R.; Allen, D. S., Jr.; Lemieux, R. U.; Johnson, W. S. Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds. J. Org. Chem. 1956, 21, 478-479.
59. Carpino, L. A.; Sadat-Aalaee, D.; Guang Chao, H.; DeSelms, R. H. [(9-Fluorenylmethyl)oxy]carbonyl (FMOC) Amino Acid Fluorides. Convienient New Peptide Coupling Reagents Applicable to the FMOC/tert-butyl Strategy for Solution and Solid-Phase Syntheses. J. Am. Chem. Soc. 1990, 112, 9651-9652.
60. Bertho, J. N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G. Amino-Acid Fluorides - Their Preparation and Use in Peptide-Synthesis. Tetrahedron Lett. 1991, 32, 1303-1306.
61. Kunz, H.; Waldmann, H. Synthesis of the Glycopeptide Partial Sequence A80-A84 of Human Fibroblast Interferon. Helv. Chim. Acta 1985, 68, 618-622.
62. Kunz, H.; Dombo, B. Solid-Phase Synthesis of Peptide and Glycopeptide Polymers with Allylic Anchor Groups. Angew. Chem. 1988, 100, 732-734.
63. Åkerblom, E. B. Six New Photolabile Linkers for Solid-Phase Synthesis. 2. Coupling of Various Building Blocks and Photolytic Cleavage. Mol Divers. 1998, 4, 53-69.
64. Åkerblom, E. B.; Nygren, A. S.; Agback, K. H. Six New Photolabile Linkers for Solid-Phase Synthesis. 1. Methods of Preparation. Mol. Divers. 1998, 3, 137-148.
65. Wokaun, A.; Ernst, R. R. Selective Detection of Multiple Quantum Transitions in NMR by Two-Dimensional Spectroscopy. Chem. Phys. Lett. 1977, 52, 407-412.
66. Piantini, U.; Soørensen, O. W.; Ernst, R. R. Multiple Quantum Filters for Elucidating NMR Coupling Networks. J. Am. Chem. Soc. 1982, 104, 6800-6801.
67. Shaka, A. J.; Freeman, R. Simplification of NMR Spectra by Filtration through Multiple-Quantum Coherence. J. Magn. Reson. 1983, 51, 169-173.
68. Kumar, A.; Ernst, R. R.; Wüthrich, K. A Two-Dimensional Nuclear Overhauser Enhancement (2D NOE) Experiment for the Elucidation of Complete Proton-Proton Cross-Relaxation Networks in Biological Macromolecules. Biochem. Biophys. Res. Commun. 1980, 95, 1-6.
69. Bodenhausen, G.; Kogler, H.; Ernst, R. R. Selection of Coherence-Transfer Pathways in NMR Pulse Experiments. J. Magn. Reson. 1984, 58, 370-388.
70. Bothner-By, A. A.; Stephens, R. L.; Lee, J.-M.; Warren, C. D.; Jeanloz, R. W. Structure Determination of a Tetrasaccharide: Transient Nuclear Overhauser Effects in the Rotating Frame. J. Am. Chem. Soc. 1984, 106, 811-813.
71. Braunschweiler, L.; Ernst, R. R. Coherence Transfer by Isotropic Mixing: Application to Proton Correlation Spectroscopy. J. Magn. Reson. 1983, 53, 521-528.
72. Müller, L. Sensitive Enhanced Detection of Weak Nuclei Using Heteronuclear Multiple Quantum Coherence. J. Am. Chem. Soc. 1979, 101, 4481-4484.
73. Bax, A.; Subramanian, S. Sensitivity-Enhanced Two-Dimensional Heteronuclear Shift Correlation NMR-Spectroscopy. J. Magn. Reson. 1986, 67, 565-569.
74. Parella, T. Pulsed Field Gradients: A New Tool for Routine NMR. Magn Reson Chem 1998, 36, 467-495.
75. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
76. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. Macromodel - an Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
77. Dudley, D. T.; Panek, R. L.; Major, T. C.; Lu, G. H.; Bruns, R. F.; Klinkefus, B. A.; Hodges, J. C.; Weishaar, R. E. Subclasses of Angiotensin-II Binding-Sites and Their Functional Significance. Mol. Pharmacol. 1990, 38, 370-377.
78. 1 Receptors are Down-Regulated During Gestation. Clin. Exp. Pharmacol. Physiol. 1997, 24, 309-314.
79. Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. Conformational Analysis of Azabicycloalkane Amino Acid Scaffolds as Reverse-Turn Inducer Dipeptide Mimics. Eur. J. Org. Chem. 2000, 2563-2569.
80. 2 Receptor. Eur. J. Pharmacol. 1998, 343, 323-331.
81. Gallinat, S.; Busche, S.; Raizada, M. K.; Sumners, C. The Angiotensin II Type 2 Receptor: an Enigma With Multiple Variations. Am. J. Physiol. 2000, 278, E357-E374.
82. 2 Receptor in High-Affinity Binding to Different Peptide Ligands. Peptides 2001, 22, 2145-2149.
83. Rosenström, U.; Sköld, C.; Lindeberg, G.; Botros, M.; Nyberg, F.; Hallberg, A.; Karlén, A. Synthesis and AT2 receptor-binding properties of angiotensin II analogues. J. Peptide Res., 2004, in press.
84. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Angiotensin II Receptor Binding Inhibitors. Drugs Future 1992, 17, 575-593 and references therein.