Angiotensin analogues palmitoylated in positions 1 and 4

Journal of Medicinal Chemistry

Volumn 40, Issue 20, 1997, Pages 3271-3279

  Maletínská, Lenka ^a   Neugebauer, Witold ^a   Pérodin, Jacqueline ^a   Lefebvre, Marie ^a   Escher, Emanuel ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN 1 RECEPTOR; ANGIOTENSIN ANTAGONIST; ANGIOTENSIN DERIVATIVE;

ADRENAL CORTEX; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AORTA STRIP; ARTICLE; BIOASSAY; BLOOD PRESSURE MEASUREMENT; CATTLE; CONTROLLED STUDY; CORONARY ARTERY DILATATION; CORONARY ARTERY OBSTRUCTION; DRUG RECEPTOR BINDING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; LIPOLYSIS; MALE; MOLECULAR WEIGHT; NONHUMAN; PALMITOYLATION; PEPTIDE SYNTHESIS; PROTEIN DEGRADATION; RABBIT; RAT; RESTENOSIS; STRUCTURE ACTIVITY RELATION;

ADRENAL CORTEX; ANGIOTENSIN II; ANIMALS; AORTA; BLOOD PRESSURE; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LIPOLYSIS; MODELS, CHEMICAL; PALMITIC ACID; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030880713     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9608669     Document Type: Article

References (60)

1. Regoli, D.; Park, W. K.; Rioux, F. Pharmacology of Angiotensin. Pharmacol. Rev. 1974, 26, 69-123.
2. Khosla, M. C.; Smeby, R. R.; Bumpus, F. M. Structure-Activity Relationship in Angiotensin II Analogs. Handbk. Exp. Pharma-col. 1974, 37, 126-161.
3. Pérodin, J.; Bossé, R.; Gagnon, S.; Zhou, L.-M.; Bouley, R.; Ledue, R.; Escher, E. Structure-activity Relationship of the Agonist-antagonist Transition on the Type 1 Angiotensin II Receptor, the Search for Inverse Agonists. In Recent Advances in Cellular and Molecular Aspects of Angiotensin Receptors; Raizada, M. K., Phillips, M. I., Summers, C., Eds.; Plenum Press: New York 1996; Vol. 358, pp 131-143.
4. Pals, D. T.; Denning, G. S.; Keenan, R. E. Historical Development of Saralasin. Kidney Int. 1979, 15, S7-S10.
5. Leduc, R.; Bernier, M.; Escher, E. Angiotensin-II Analogues. I: Synthesis and Incorporation of the Halogenated Amino Acids 3-(4′-Iodophenyl)alanine, 3-(3′,5′-Dibromo-4′-chlorophenyl)alanine, 3-(3′,4′,5′-Tribromophenyl)alanine, and 3-(2′,3′,4′,5′,6′-Pent-abromophenyl)alanine. Helv. Chim. Acta 1983, 66, 960-970.
6. Bossé, R.; Gerold, M.; Fischli, W.; Hoick, M.; Escher, E. An Angiotensin with Prolonged Action and Blood Pressure-Lowering Properties. J. Cardiovasc. Pharmacol. 1990, 16, S50-S55.
7. Regoli, D.; Park, W. K. The Pressor and Myotropic Effects and the Antagonistic Properties of Several Analogues of Angiotensin II. Can. J. Physiol. Pharmacol. 1972, 5, 99-112.
8. Regoli, D.; Rioux, F.; Park, W. K.; Choi, C. Role of the N-terminal Amino Acid for the Biological Activities of Angiotensin and Inhibitory Analogues. Can. J. Physiol. Pharmacol. 1974, 52, 39-49.
9. Samanen, J.; Cash, T.; Narindray, D.; Brandeis, E.; Yellin, T.; Regoli, D. The Role of Position 4 in Angiotensin II Antagonism: A Structure-Activity Study. J. Med. Chem. 1989, 32, 1366-1370.
10. Guillemette, G.; Bernier, M.; Parent, P.; Leduc, R.; Escher, E. Angiotensin II Dependence of Hormone Affinity on the Electronegativity of a Single Side Chain. J. Med. Chem. 1984, 27, 315-320.
11. 3)Phe. Helv. Chim. Acta 1983, 66, 1355-1365.
12. 4]angiotensin II (Sarmesin). J Med. Chem. 1986, 29, 1121-1124.
13. Christen, Y.; Waeber, B.; Nussberger, J.; Porchet, M.; Borland, R. M.; Lee, R. J.; Maggon, K.; Shum, L.; Timmermans, P. B.; Brunner, H. R. Oral Administration of DuP 753, a Specific Angiotensin II Receptor Antagonist, to Normal Male Volunteers. Inhibition of Pressor Response to Exogenous Angiotensin I and II. Circulation 1991, 83, 1333-1342.
14. Whitebread, S.; Mele, M.; Kamber, B.; De Gasparo, M. Preliminary Biochemical Characterization of Two Angiotensin II Receptor Subtypes. Biochem. Biophys. Res. Commun. 1989, 163, 284-291.
15. Chiu, A. T.; Herblin, W. F.; McCall, D. E.; Ardecky, R. J.; Carini, D. J.; Duncia, J. V.; Pease, L. J.; Wong, P. C.; Wexler, R. R.; Johnson, A. L.; Timmermans, P. B. M. W. M. Identification of Angiotensin II Receptor Subtypes. Biochem. Biophys. Res. Commun. 1989, 165, 196-203.
16. Sasaki, K.; Yamano, Y.; Bardhan, S.; Iwai, N.; Murray, J.; Hasegawa, M.; Matsuda, Y.; Inagami, T. Cloning and Expression of Complementary DNA Encoding a Bovine Adrenal Angiotensin II Type-1 Receptor. Nature 1991, 351, 230-233.
17. Tsuzuki, S.; Ichiki, T.; Nakakubo, H.; Kitami, Y.; Guo, D. F.; Shirai, H.; Inagami, T. Molecular Cloning and Expression of the Gene Encoding Human Angiotensin II Type 2 Receptor. Biochem. Biophys. Res. Commun. 1994, 200, 1449-1454.
18. 1 Receptor: Gain-of-function Study Using Gene Transfer. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 10663-10667.
19. Kambayashi, Y.; Bardhanm, S.; Takahashi, K.; Tsuzuki, S.; Inui, H.; Hamakubo, T.; Inagami, T. Molecular Cloning of a Novel Angiotensin II Receptor Isoform Involved in Phosphotyrosine Phosphatase Inhibition. J. Biol. Chem. 1993, 268, 24543-24546.
20. Giasson, E.; Meloche, S. Role of p70 S6 Protein Kinase in Angiotenisn II-induced Protein Synthesis in Vascular Smooth Muscle Cells. J. Biol. Chem. 1995, 270, 5225-5231.
21. Tsuda, T.; Kawahara, Y.; Shii, K.; Koide, M.; Ishida, Y.; Yokoyama, M. Vasoconstrictor-induced Protein-tyrosine Phosphorylation in Cultured Vascular Smooth Muscle Cells. FEBS Lett. 1991, 285, 44-48.
22. Servant, M. J.; Giasson, E.; Meloche, S. Inhibition of Growth Factor-induced Protein Synthesis by a Selective MEK Inhibitor in Aortic Smooth Muscle Cells. J. Biol. Chem. 1996,271, 16047-16052.
23. Molloy, C. J.; Taylor, D. S.; Weber, H. Angiotensin II Stimulation of Rapid Protein Tyrosine Phosphorylation and Protein Kinase Activation in Rat Aortic Smooth Muscle Cells. J. Biol. Chem. 1993, 268, 7338-7345.
24. Leduc, I.; Haddad, P.; Giasson, E.; Meloche, S. Involvement of a Tyrosine Kinase Pathway in the Growth-promoting Effects of Angiotensin II on Aortic Smooth Muscle Cells. Mol. Pharmacol. 1995, 48, 582-592.
25. Weber, H.; Taylor, D. S.; Molloy, C. J. Angiotensin II Induces Delayed Mitogenesis and Cellular Proliferation in Rat Aortic Smooth Muscle Cells: Correlation with the Expression of Specific Growth Factors and Reversal by Suramin. J. Clin. Invest. 1994, 93, 788-798.
26. McBride, W.; Lange, R. A.; Hillis, L. D. Restenosis after Successful Coronary Angioplasty: Pathophysiology and Prevention. N. Engl. J. Med. 1988, 318, 1734-1737.
27. Deamen, M. J.; Lombardi, D. M.; Bosman, F. T.; Schwartz, S. M. Angiotensin II Induces Smooth Muscle Cell Proliferation in the Normal and Injured Rat Arterial Wall. Circ. Res. 1991, 68, 450-456.
28. Naftilan, A. J.; Pratt, R. E.; Dzau, V. J. Induction of Platelet-derived Growth Factor A-chain and c-myc Gene Expression by Angiotensin II in Cultured Rat Vascular Smooth Muscle Cells. J. Clin. Invest. 1989, 83, 1419-1424.
29. Powell, J. S.; Clozel, J. P.; Muller, R. K. M.; Kuhn, H.; Hefti, F.; Hosang, M.; Baumgartner, H. R. Inhibitors of Angiotensin-Converting Enzyme Prevent Myointimal Proliferation after Vascular Injury. Science 1989, 245, 186-188.
30. Schmitt, R.; Clozel, J. P.; Iberg, N.; Buhler, F. R. Prevention of Neointima Formation by Mibefradil After Vascular Injury in Rats - Comparision with ACE Inhibition. Cardiovasc. Drugs Ther. 1996, 10, 101-105.
31. Huber, K. C.; Schwartz, R. S.; Edwards, W. D.; Camrud, A. R.; Bailey, K. R.; Jorgenson, M. A.; Holmes, D. R., Jr. Effects of Angiotensin-converting Enzyme Inhibition on Neointimal Proliferation in Porcine Coronary Injury Model. Am. Heart J. 1993, 125, 695-701.
32. Sung, C. P.; Arleth, A. J.; Storer, B. L.; Ohlstein, E. H. Angiotensin Type 1 Receptors Mediate Smooth Muscle Proliferation and Endothelin Biosynthesis in Rat Vascular Smooth Muscle. J. Pharmacol. Exp. Ther. 1994, 271, 429-437.
33. Laporte, S.; Escher, E. Neointima Formation after Vascular Injury is Angiotensin II Mediated. Biochem. Biophys. Res. Commum. 1992, 187, 1510-1516.
34. Pham, D.; Laporte, S.; Pérodin, J.; Bourgeois, R.; Escher, E. What Can Angiotensin Antagonists Do that Converting Enzyme Inhibition Can't: The Case of Post-Angioplastic Restenosis. Can. J. Physiol. Pharmacol. 1996, 74, 867-877.
35. Zhang, W. J.; Nikiforovich, G. V.; Pérodin, J.; Richard, D. E.; Escher, E.; Marshall, G. R. Novel Cyclic Analogs of Angiotensin II with Cyclization between Positions 5 and 7: Conformational and Biological Implications. J. Med. Chem. 1996, 39, 2738-2744.
36. Pallai, P. V.; Richman, S.; Struthers, R. S.; Goodman, M. Approaches to the Synthesis of Retro-inverso Peptides. Int. J. Pept. Protein Res. 1983, 21, 84-92.
37. 1]angiotensin II as a Pressor Agent in Rats. Brain Res. 1990, 514, 5-10.
38. Maletínská, L.; Neugebauer, W.; Paré, M. C.; Pérodin, J.; Pham, D.; Escher, E. Lipid Masking and Reactivation of Angiotensin Analogues. Helv. Chim. Acta 1996, 79, 2023-2034.
39. Barlos, K.; Gatos, D.; Koutsogianni, S.; Scḧfer, W.; Stavropoulos, G.; Wenging, Y. Darstellung und Einsatz von N-Fmoc-O-Trt-Hydrozyaminosäuren zur "Solid Phase" Synthese von Peptiden. Tetrahedron Lett. 1991, 32, 471-474.
40. Bodor, N.; Prokai, L.; Wu, W.-M.; Farag, H.; Jonalagadda, S.; Kawamura, M.; Simpkins, J. A Strategy for Delivering Peptides into the Central Nervous System by Sequential Metabolism. Science 1992, 257, 1698-1700.
41. Branton, W. D.; Fields, C. G.; VanDrisse, V. L.; Fields, G. B. Solid-Phase Synthesis of O-Palmitoylated Peptides. Tetrahedron Lett. 1993, 31, 4885-4888.
42. Sieber, P. An Improved Method for Anchoring of 9-fluorenylmethoxycarbonyl-amino Acids to 4-alkoxybenzyl Alcohol Resins. Tetrahedron Lett. 1987, 28, 6147-6150.
43. 1 Antagonism. J. Pharmacol. Exp. Ther. 1995, 273, 753-761.
44. Holck, M.; Bossé, R.; Fischli, W.; Gerold, H.; Escher, E. An Angiotensin II Antagonist with Strongly Prolonged Action. Biochem. Biophys. Res. Commun. 1989, 160, 1350-1356.
45. 1 Receptor Antagonist. Eur. J. Pharmacol. 1995, 283, 63-72.
46. 1 Receptor Antagonist. Br. J. Pharmacol. 1992, 107, 1173-1180.
47. Waldman, H.; Sebastian, D. Enzymatic Protecting Group Techniques. Chem. Rev. 1994, 94, 911-937.
48. Sweers, H. M.; Wong, C.-H. Enzyme-Catalyzed Regioselective Deacylation of Protected Sugars in Carbohydrate Synthesis. J. Am. Chem. Soc. 1986, 108, 6421-6422.
49. Gisin, B. F. The Preparation of Merrifield-Resins Through Total Esterification with Cesium Salts. Helv. Chim. Acta 1973, 56, 1476-1482.
50. Merrifield, R. B.; Vizioli, L. D.; Boman, H. G. Synthesis of the Antibacterial Peptide Cecropin A(1-33). Biochemistry 1982, 21, 5020-5031.
51. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color Test for Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides. Anal. Biochem. 1970, 34, 595-598.
52. Meienhofer, J.; Waki, M.; Heimer, E. P.; Lambros, T. J.; Makofske, R. C.; Chang, C. D. Solid Phase Synthesis Without Repetitive Acidolysis. Int. J. Pept. Protein Res. 1979, 13, 35-42.
53. Fields, G. B.; Noble, R. L. Solid Phase Peptide Synthesis Utilizing 9-Fluorenylmethoxycarbonyl Amino Acids. Int. J. Pept. Protein Res. 1990, 35, 161-214.
54. Krebs, K. G.; Heusser, D.; Wimmer, H. Spray Reagents. In Thin-Layer Chromatography; Stahl, E., Ed.; Springer-Verlag: Berlin, 1969; pp 854-905.
55. Perkin-Elmer. Removal of Dnp Protection from Boc-His(Dnp). In Introduction to Cleavage Techniques, 2nd ed.; 1995; pp 22-23.
56. Glossmann, H.; Baukal, A. J.; Catt, K. J. Properties of Angiotensin II Receptors in the Bovine and Rat Adrenal Cortex. J. Biol. Chem. 1974, 249, 825-834.
57. Fraker, P. J.; Speck, J. C. Protein and Cell Membrane Iodinations with a Sparingly Soluble Chloroamide, 1,3,4,6-Tetrachloro-3a,6a-diphenylglycoluril. Biochem. Biophys. Res. Commun. 1978, 80, 849-857.
58. Furchgott, R. F.; Bhadrakom, S. Reactions of Strips of Rabbit Aorta to Epinephrine, Isopropylarterenol, Sodium Nitrite and Other drugs. J. Pharmacol. Exp. Ther. 1953, 108, 129-143.
59. Arunlakshana, O.; Schild, H. O. Some Quantitative Uses of Drug Antagonists. Br. J. Pharmacol. 1959, 14, 48-58.
60. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1978, 22, 3099-3108.