Conformational constraints in angiotensin IV to probe the role of Tyr 2, Pro 5 and Phe 6

Journal of Peptide Science

Volumn 17, Issue 8, 2011, Pages 545-553

  Lukaszuk, Aneta ^a   Demaegdt, Heidi ^a   van den Eynde, Isabelle ^a   Vanderheyden, Patrick ^a   Vauquelin, Georges ^a   Tourwé, Dirk ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Aminopeptidase N; Angiotensin IV; AT 4 receptor; Conformational constraints; Insulin regulated aminopeptidase

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; ANGIOTENSIN I; ANGIOTENSIN II [3-8]; CANDESARTAN; PHENYLALANINE; PROLINE; TYROSINE; VALSARTAN;

AMINO ACID SYNTHESIS; ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; CONFORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; HUMAN; HUMAN CELL; MOLECULAR PROBE; PRIORITY JOURNAL;

AMINOPEPTIDASES; ANGIOTENSIN II; ANIMALS; BIOCATALYSIS; CELL MEMBRANE; CELLS, CULTURED; CHO CELLS; CRICETINAE; CRICETULUS; HEK293 CELLS; HUMANS; MOLECULAR STRUCTURE; PHENYLALANINE; PROLINE; PROTEIN CONFORMATION; SPECTROPHOTOMETRY, ATOMIC; SUBSTRATE SPECIFICITY; TYROSINE;

EID: 79960408853     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1365     Document Type: Article

References (60)

1. Chai SY, Fernando R, Peck G, Ye SY, Mendelsohn FA, Jenkins TA, Albiston AL. The angiotensin IV/AT4 receptor. Cell. Mol. Life. Sci. 2004; 61: 2728-2737.
2. Delorenzi A, Locatelli F, Romano A, Nahmod V, Maldonado H. Angiotensin II (3-8) induces long-term memory improvement in the crab Chasmagnathus. Neurosci. Lett. 1997; 226: 143-146.
3. Delorenzi A, Maldonado H. Memory enhancement by the angiotensinergic system in the crab Chasmagnathus is mediated by endogenous angiotensin II. Neurosci. Lett. 1999; 266: 1-4.
4. 1-angiotensin IV and LVV-hemorphin 7, on spatial learning in rats. Neuroscience 2004; 124: 341-349.
5. Pederson ES, Krishnan R, Harding JW, Wright JW. A role for the angiotensin AT4 receptor subtype in overcoming scopolamine-induced spatial memory deficits. Regul. Pept. 2001; 102: 147-156.
6. Wright JW, Miller-Wing AV, Shaffer MJ, Higginson C, Wright DE, Hanesworth JM, Harding JW. Angiotensin II(3-8) (ANG IV) hippocampal binding: potential role in the facilitation of memory. Brain Res. Bull. 1993; 32: 497-502.
7. Wright JW, Stubley L, Pederson ES, Kramar EA, Hanesworth JM, Harding JW. Contributions of the brain angiotensin IV-AT4 receptor subtype system to spatial learning. J. Neurosci. 1999; 19: 3952-3961.
8. Hall KL, Venkateswaran S, Hanesworth JM, Schelling ME, Harding JW. Characterization of a functional angiotensin IV receptor on coronary microvascular endothelial cells. Regul. Pept. 1995; 58: 107-115.
9. 4 and their functions. Regul. Pept. 1995; 59: 269-295.
10. Wright JW, Yamamoto BJ, Harding JW. Angiotensin receptor subtype mediated physiologies and behaviors: new discoveries and clinical targets. Prog. Neurobiol. 2008; 84: 157-181.
11. Swanson GN, Hanesworth JM, Sardinia MF, Coleman JK, Wright JW, Hall KL, Miller-Wing AV, Stobb JW, Cook VI, Harding EC, Harding JW, Discovery of a distinct binding site for angiotensin II (3-8), a putative angiotensin IV receptor. Regul. Pept. 1992; 40:409-419.
12. 4 receptor is insulin-regulated membrane aminopeptidase: potential mechanisms of memory enhancement. Trends Endocrinol. Metab. 2003; 14: 72-77.
13. 4) receptor is the enzyme insulin-regulated aminopeptidase. J. Biol. Chem. 2001; 276: 48623-48626.
14. Herbst JJ, Ross SA, Scott HM, Bobin SA, Morris NJ, Lienhard GE, Keller SR. Insulin stimulates cell surface aminopeptidase activity toward vasopressin in adipocytes. Am. J. Physiol. 1997; 272: E600-E606.
15. 4 ligands are potent, competitive inhibitors of insulin regulated aminopeptidase (IRAP). J. Neurochem. 2003; 86: 344-350.
16. Matsumoto H, Nagasaka T, Hattori A, Rogi T, Tsuruoka N, Mizutani S, Tsujimoto M. Expression of placental leucine aminopeptidase/oxytocinase in neuronal cells and its action on neuronal peptides. Eur. J. Biochem. 2001; 268: 3259-3266.
17. Vauquelin G, Michotte Y, Smolders I, Sarre S, Ebinger G, Dupont A, Vanderheyden P. Cellular targets for angiotensin II fragments: pharmacological and molecular evidence. J. Renin Angiotensin Aldosterone Syst. 2002; 3: 195-204.
18. Garreau I, Chansel D, Vandermeersch S, Fruitier I, Piot JM, Ardaillou R. Hemorphins inhibit angiotensin IV binding and interact with aminopeptidase N. Peptides 1998; 19: 1339-1348.
19. Moeller I, Allen AM, Chai SY, Zhuo J, Mendelsohn FAO. Bioactive angiotensin peptides. J. Hum. Hypertens. 1998; 12: 289-293.
20. Santos AN, Langner J, Herrmann M, Riemann D. Aminopeptidase N/CD13 is directly linked to signal transduction pathways in monocytes. Cell. Immunol. 2000; 201: 22-32.
21. Shipp MA, Look AT. Hematopoietic differentiation antigens that are membrane-associated enzymes-cutting is the key. Blood 1993; 82: 1052-1070.
22. 3H]AL-11. Mol. Cell Endocrinol. 2009; 311: 77-86.
23. Demaegdt H, Smitz L, De Backer JP, Le MT, Bauwens M, Szemenyei E, Tóth G, Michotte Y, Vanderheyden P, Vauquelin G. Translocation of the insulin-regulated aminopeptidase to the cell surface: detection by radioligand binding. Br. J. Pharmacol. 2008; 154: 872-881.
24. Lukaszuk A, Demaegdt H, Szemenyei E, Tóth G, Tymecka D, Misicka A, Karoyan P, Vanderheyden P, Vauquelin G, Tourwé D. Beta-homo-amino acid scan of angiotensin IV. J. Med. Chem. 2008; 51: 2291-2296.
25. Lukaszuk A, Demaegdt H, Feytens D, Vanderheyden P, Vauquelin G, Tourwé D. The replacement of His(4) in angiotensin IV by conformationally constrained residues provides highly potent and selective analogues. J. Med. Chem. 2009; 52: 5612-5618.
26. 4 receptor. J. Pept. Sci. 2007; 13: 434-444.
27. 4 receptor ligands. J. Pept. Sci. 2006; 12: 705-713.
28. 4 receptor: analysis of position two- and three-modified angiotensin IV analogs. Peptides 1999; 20: 915-920.
29. 4 receptor binding characteristics: D-amino acid- and glycine-substituted peptides. Peptides 1993; 14: 949-954.
30. 4 receptor structure-binding relationship: N-terminal-modified angiotensin IV analogues. Peptides 1994; 15: 1399-1406.
31. Ballet S, Frycia A, Piron J, Chung NN, Schiller PW, Kosson P, Lipkowski AW, Tourwé D. Synthesis and biological evaluation of constrained analogues of the opioid peptide H-Tyr-D-Ala-Phe-Gly-NH2 using the 4-amino-2-benzazepin-3-one scaffold. J. Pept. Res. 2005; 66: 222-230.
32. Ballet S, Mayorov AV, Cai M, Tymecka D, Chandler KB, Palmer ES, Rompaey KV, Misicka A, Tourwé D, Hruby VJ. Novel selective human melanocortin-3 receptor ligands: use of the 4-amino-1, 2, 4, 5-tetrahydro-2-benzazepin-3-one (Aba) scaffold. Bioorg. Med. Chem. Lett. 2007; 17: 2492-2498.
33. Kazmierski W, Hruby VJ. A new approach to receptor ligand design: synthesis and conformation of a new class of potent and highly selective μ opioid antagonists utilizing tetrahydroisoquinoline carboxylic acid. Tetrahedron 1988; 44: 697-710.
34. Kazmierski W, Wire WS, Lui GK, Knapp RJ, Shook JE, Burks TF, Yamamura HI, Hruby VJ. Design and synthesis of somatostatin analogues with topographical properties that lead to highly potent and specific mu opioid receptor antagonists with greatly reduced binding at somatostatin receptors. J. Med. Chem. 1988; 31: 2170-2177.
35. Kazmierski WM, Yamamura HI, Hruby VJ. Topographic design of peptide neurotransmitters and hormones on stable backbone templates-relation of conformation and dynamics to bioactivity. J. Am. Chem. Soc. 1991; 113: 2275-2283.
36. Kyle DJ, Martin JA, Farmer SG, Burch RM. Design and conformational analysis of several highly potent bradykinin receptor antagonists. J. Med. Chem. 1991; 34: 1230-1233.
37. Manning M, Cheng LL, Stoev S, Klis W, Nawrocka E, Olma A, Sawyer WH, Wo NC, Chan WY. Position three in vasopressin antagonist tolerates conformationally restricted and aromatic amino acid substitutions: a striking contrast with vasopressin agonists. J. Pept. Sci. 1997; 3: 31-46.
38. Mantey SA, Coy DH, Entsuah LK, Jensen RT. Development of bombesin analogs with conformationally restricted amino acid substitutions with enhanced selectivity for the orphan receptor human bombesin receptor subtype 3. J. Pharmacol. Exp. Ther. 2004; 310: 1161-1170.
39. Tóth G, Darula Z, Peter A, Fülop F, Tourwé D, Jaspers H, Verheyden P, Bocskey Z, Tóth Z, Borsodi A. Conformationally constrained deltorphin analogs with 2-aminotetralin-2-carboxylic acid in position 3. J. Med. Chem. 1997; 40: 990-995.
40. Tourwé D, Verschueren K, Frycia A, Davis P, Porreca F, Hruby VJ, Toth G, Jaspers H, Verheyden P, Van BG. Conformational restriction of Tyr and Phe side chains in opioid peptides: information about preferred and bioactive side-chain topology. Biopolymers 1996; 38: 1-12.
41. Laszlo SE, Bush BL, Doyle JJ, Greenlee WJ, Hangauer DG, Halgren TA, Lynch RJ, Schorn TW, Siegl PK. Synthesis and use of 3-amino-4-phenyl-2-piperidones and 4-amino-2-benzazepin-3-ones as conformationally restricted phenylalanine isosteres in renin inhibitors. J. Med. Chem. 1992; 35: 833-846.
42. Darula Z, Kover KE, Monory K, Borsodi A, Mako E, Ronai A, Tourwe D, Peter A, Toth G. Deltorphin II analogues with 6-hydroxy-2-aminotetralin-2-carboxylic acid in position 1. J. Med. Chem. 2000; 43: 1359-1366.
43. 5]Enkephalin. J. Med. Chem. 1991; 34: 1823-1830.
44. Tourwé D, Mannekens E, Diem TN, Verheyden P, Jaspers H, Tóth G, Peter A, Kertesz I, Torok G, Chung NN, Schiller PW. Side chain methyl substitution in the δ-opioid receptor antagonist TIPP has an important effect on the activity profile. J. Med. Chem. 1998; 41: 5167-5176.
45. Ornstein PL, Arnold MB, Augenstein NK, Paschal JW. Syntheses of 6-oxodecahydroisoquinoline-3-carboxylates. Useful intermediates for the preparation of conformationally defined excitatory amino acid antagonists. J. Org. Chem. 1991; 56: 4388-4392.
46. Verschueren K, Toth G, Tourwé D, Lebl M, Van Binst G, Hruby V. A facile synthesis of 1, 2, 3, 4-Tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue. Synthesis 1992; 1992: 458-460.
47. Schiller PW, Weltrowska G, Nguyen TM, Lemieux C, Chung NN, Marsden BJ, Wilkes BC. Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: effects on receptor selectivity and stereospecificity. J. Med. Chem. 1991; 34: 3125-3132.
48. Mosberg HI, Lomize AL, Wang C, Kroona H, Heyl DL, Sobczyk-Kojiro K, Ma W, Mousigian C, Porreca F. Development of a model for the delta opioid receptor pharmacophore. 1. Conformationally restricted Tyr1 replacements in the cyclic delta receptor selective tetrapeptide Tyr-c[D-Cys-Phe-D-Pen]OH (JOM-13). J. Med. Chem. 1994; 37: 4371-4383.
49. Fülöp F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem. Rev. 2001; 101: 2181-2204.
50. srcPTK: effective acylation conditions for Htc residues. Lett. Pept. Sci. 2000; 7: 79-83.
51. Ruzza P, Cesaro L, Tourwé D, Calderan A, Biondi B, Maes V, Menegazzo I, Osler A, Rubini C, Guiotto A, Pinna LA, Borin G, Donella-Diana A. Spatial conformation and topography of the tyrosine aromatic ring in substrate recognition by protein tyrosine kinases. J. Med. Chem. 2006; 49: 1916-1924.
52. Johansen TE, Scholler MS, Tolstoy S, Schwartz TW. Biosynthesis of peptide precursors and protease inhibitors using new constitutive and inducible eukaryotic expression vectors. FEBS Lett. 1990; 267: 289-294.
53. Olsen J, Cowell GM, Konigshofer E, Danielsen EM, Moller J, Laustsen L, Hansen OC, Welinder KG, Engberg J, Hunziker W, Spiess M, Sjostrom H, Noren O. Complete amino acid sequence of human intestinal aminopeptidase N as deduced from cloned cDNA. FEBS Lett. 1988; 238: 307-314.
54. 125I]Ang IV binding and catalytic activity. Biochem. Pharmacol. 2004; 68: 885-892.
55. Vanderheyden PML, Fierens FLP, De Backer JP, Fraeyman N, Vauquelin G. Distinction between surmountable and insurmountable selective AT1 receptor antagonists by use of CHO-K1 cells expressing human angiotensin II AT1 receptors. Br. J. Pharmacol. 1999; 126: 1057-1065.
56. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973; 22: 3099-3108.
57. 125I]Angiotensin IV only binds to the cystinyl aminopeptidase apo-enzyme. Eur. J. Pharmacol. 2006; 546:19-27.
58. Irons DW, Davison JM, Baylis PH. Evaluation of enzyme inhibitors of cystinyl aminopeptidase and application to the measurement of immunoreactive atrial natriuretic peptide in human pregnancy. Clin. Chim. Acta. 1994; 231: 185-191.
59. Gasparo de M, Catt KJ, Inagami T, Wright JW, Unger T. International union of pharmacology. XXIII. The angiotensin II receptors. Pharmacol. Rev. 2000; 52: 415-472.
60. Andersson H, Demaegdt H, Vauquelin G, Lindeberg G, Karlén G, Hallberg M, Erdélyi M, Hallberg A. Disulfide cyclized tripeptide analogues of Angiotensin IV as potent and selective inhibitors of insulin-regulated aminopeptidase (IRAP). J. Med. Chem. 2010; 53: 8059-8071.