Phosphinic tripeptides as dual angiotensin-converting enzyme C-domain and endothelin-converting enzyme-1 inhibitors

Journal of Medicinal Chemistry

Volumn 53, Issue 1, 2010, Pages 208-220

  Jullien, Nicolas ^a,c   Makritis, Anastasios ^b   Georgiadis, Dimitris ^b   Beau, Fabrice ^a   Yiotakis, Athanasios ^b   Dive, Vincent ^a  

^a Institute Frederic Joliot   (France)

^b UNIVERSITY OF ATHENS   (Greece)

^c INSTITUT DE RADIOPROTECTION ET DE SÛRETÉ NUCLÉAIRE IRSN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN II; DIPEPTIDYL CARBOXYPEPTIDASE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENDOTHELIN 1; ENDOTHELIN CONVERTING ENZYME; ENDOTHELIN CONVERTING ENZYME INHIBITOR; ISOXAZOLE DERIVATIVE; MEMBRANE METALLOENDOPEPTIDASE; PHOSPHINIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITOR INTERACTION; HYPERTENSION; IC 50; MALE; MEAN ARTERIAL PRESSURE; NONHUMAN; RAT; REACTION ANALYSIS; SPONTANEOUSLY HYPERTENSIVE RAT; STEREOCHEMISTRY;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; ASPARTIC ACID ENDOPEPTIDASES; BLOOD PRESSURE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; MATRIX METALLOPROTEINASE 13; METALLOENDOPEPTIDASES; MOLECULAR CONFORMATION; NEPRILYSIN; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; RATS; RATS, INBRED SHR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74849136063     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9010803     Document Type: Article

References (39)

1. Petrillo, E. W., Jr.; Ondetti, M. A. Angiotensin-converting enzyme inhibitors: medicinal chemistry and biological actions. Med. Res. Rev. 1982, 2, 1-41.
2. Roques, B. P.; Noble, F.; Dauge, V.; Fournie-Zaluski, M. C.; Beaumont, A. Neutral endopeptidase 24.11: structure, inhibition, and experimental and clinical pharmacology. Pharmacol. Rev. 1993, 45, 87-146.
3. Jeng, A. Y. Utility of endothelin-converting enzyme inhibitors for the treatment of cardiovascular diseases. Curr. Opin. Investig. Drugs 2003, 4, 1076-1081.
4. Cerdeira, A. S.; Bras-Silva, C.; Leite-Moreira, A. F. Endothelin-converting enzyme inhibitors: their application in cardiovascular diseases. Rev. Port. Cardiol. 2008, 27, 385-408.
5. Elijovich, F.; Laffer, C. A role for single-pill triple therapy in hypertension. Ther. Adv. Cardiovasc. Dis. 2009, 3, 231-240.
6. Worthley, M. I.; Corti, R.; Worthley, S. G. Vasopeptidase inhibitors: will they have a role in clinical practice? Br. J. Clin. Pharmacol. 2004, 57, 27-36.
7. Daull, P.; Jeng, A. Y.; Battistini, B. Towards triple vasopeptidase inhibitors for the treatment of cardiovascular diseases. J. Cardiovasc. Pharmacol. 2007, 50, 247-256.
8. Campbell, D. J. Vasopeptidase inhibition: a double-edged sword? Hypertension 2003, 41, 383-389.
9. Oefner, C.; D'Arcy, A.; Hennig, M.; Winkler, F. K.; Dale, G. E. Structure of human neutral endopeptidase (Neprilysin) complexed with phosphoramidon. J. Mol. Biol. 2000, 296, 341-349.
10. Schulz, H.; Dale, G. E.; Karimi-Nejad, Y.; Oefner, C. Structure of human endothelin-converting enzyme I complexed with phosphoramidon. J. Mol. Biol. 2009, 385, 178-187.
11. Sturrock, E. D.; Natesh, R.; van Rooyen, J. M.; Acharya, K. R. Structure of angiotensin I-converting enzyme. Cell. Mol. Life Sci. 2004, 61, 2677-2686.
12. Georgiadis, D.; Beau, F.; Czarny, B.; Cotton, J.; Yiotakis, A.; Dive, V. Roles of the two active sites of somatic angiotensin-converting enzyme in the cleavage of angiotensin I and bradykinin: insights from selective inhibitors. Circ. Res. 2003, 93, 148-154.
13. Georgiadis, D.; Cuniasse, P.; Cotton, J.; Yiotakis, A.; Dive, V. Structural determinants of RXPA380, a potent and highly selective inhibitor of the angiotensin-converting enzyme C-domain. Biochemistry 2004, 43, 8048-8054.
14. van Esch, J. H.; Tom, B.; Dive, V.; Batenburg, W. W.; Georgiadis, D.; Yiotakis, A.; van Gool, J. M.; de Bruijn, R. J.; de Vries, R.; Danser, A. H. Selective angiotensin-converting enzyme C-domain inhibition is sufficient to prevent angiotensin I-induced vasocon-striction. Hypertension 2005, 45, 120-125.
15. Dive, V.; Cotton, J.; Yiotakis, A.; Michaud, A.; Vassiliou, S.; Jiracek, J.; Vazeux, G.; Chauvet, M. T.; Cuniasse, P.; Corvol, P. RXP 407, a phosphinic peptide, is a potent inhibitor of angiotensin I converting enzyme able to differentiate between its two active sites. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4330-4335.
16. Kroger, W. L.; Douglas, R. G.; O'Neill, H. G.; Dive, V.; Sturrock, E. D. Investigating the domain specificity of phosphinic inhibitors RXPA380 and RXP407 in angiotensin-converting enzyme. Biochemistry 2009, 48, 8405-8412.
17. Yiotakis, A.; Vassiliou, S.; Jiracek, J.; Dive, V. Protection of the Hydroxyphosphinyl Function of Phosphinic Dipeptides by Adamantyl. Application to the Solid-Phase Synthesis of Phosphinic Peptides. J. Org. Chem. 1996, 61, 6601-6605.
18. Makaritis, A.; Georgiadis, D.; Dive, V.; Yiotakis, A. Diastereoselective solution and multipin-based combinatorial array synthesis of a novel class of potent phosphinic metalloprotease inhibitors. Chemistry 2003, 9, 2079-2094.
19. Caramella, P.; Grunanger, P. Nitrile Oxides and Imines;Wiley: New York, 1984, Vol. 1.
20. Lee, G. A. A simplified synthesis of unsaturated nitrogen-hetero-cycles using nitrile bataines. Synthesis 1982, 508-509.
21. Christl, M.; Huisgen, R. Chem. Ber. 1973, 3345-3367.
22. Chen, H.; Noble, F.; Mothe, A.; Meudal, H.; Coric, P.; Danascimento, S.; Roques, B. P.; George, P.; Fournie-Zaluski, M. C. Phosphinic derivatives as new dual enkephalin-degrading enzyme inhibitors: synthesis, biological properties, and antinociceptive activities. J. Med. Chem. 2000, 43, 1398-1408.
23. De Lombaert, S.; Blanchard, L.; Stamford, L. B.; Tan, J.; Wallace, E. M.; Satoh, Y.; Fitt, J.; Hoyer, D.; Simonsbergen, D.; Moliterni, J.; Marcopoulos, N.; Savage, P.; Chou, M.; Trapani, A. J.; Jeng, A. Y. Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action. J. Med. Chem. 2000, 43, 488-504.
24. Vazeux, G.; Cotton, J.; Cuniasse, P.; Dive, V. Potency and selectivity of RXP407 on human, rat, and mouse angiotensin-converting enzyme. Biochem. Pharmacol. 2001, 61, 835-841.
25. Yiotakis, A.; Dive, V. Synthetic active site-directed inhibitors of metzincins: achievement and perspectives. Mol. Aspects Med. 2008, 29, 329-338.
26. Lloyd, J.; Schmidt, J. B.; Hunt, J. T.; Barrish, J. C.; Little, D. K.; Tymiak, A. Solid phase synthesis of phosphinic acid endothelin converting enzyme inhibitors. Bioorg. Med. Chem. Lett. 1996, 6, 1323-1326.
27. McKittrick, B. A.; Stamford, A. W.; Weng, X.; Ma, K.; Chackalamannil, S.; Czarniecki, M.; Cleven, R. C.; Fawzi, A. B. Design and syntheis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11. Bioorg. Med. Chem. Lett. 1996, 6, 1629-1634.
28. Umekawa, K.; Hasegawa, H.; Tsutsumi, Y.; Sato, K.; Matsumura, Y.; Ohashi, N. Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme. Jpn. J. Pharmacol. 2000, 84, 7-15.
29. Muller, D. N.; Mullally, A.; Dechend, R.; Park, J. K.; Fiebeler, A.; Pilz, B.; Loffler, B. M.; Blum-Kaelin, D.; Masur, S.; Dehmlow, H.; Aebi, J. D.; Haller, H.; Luft, F. C. Endothelin-converting enzyme inhibition ameliorates angiotensin II-induced cardiac damage. Hypertension 2002, 40, 840-846.
30. Inguimbert, N.; Coric, P.; Poras, H.; Meudal, H.; Teffot, F.; Fournie-Zaluski, M. C.; Roques, B. P. Toward an optimal joint recognition of the S1′ subsites of endothelin converting enzyme-1 (ECE-1), angiotensin converting enzyme (ACE), and neutral endopeptidase (NEP). J. Med. Chem. 2002, 45, 1477-1486.
31. Hanessian, S.; Guesne, S.; Riber, L.; Marin, J.; Benoist, A.; Mennecier, P.; Rupin, A.; Verbeuren, T. J.; De Nanteuil, G. Targeting ACE and ECE with dual acting inhibitors. Bioorg. Med. Chem. Lett. 2008, 18, 1058-1062.
32. Bohlender, J.; Gerbaulet, S.; Kramer, J.; Gross, M.; Kirchengast, M.; Dietz, R. Synergistic effects of AT(1) and ET(A) receptor blockade in a transgenic, angiotensin II-dependent, rat model. Hypertension 2000, 35, 992-997.
33. Nelson, J.; Bagnato, A.; Battistini, B.; Nisen, P. The endothelin axis: emerging role in cancer. Nat. Rev. Cancer 2003, 3, 110-116.
34. Fujita, M.; Hayashi, I.; Yamashina, S.; Fukamizu, A.; Itoman, M.; Majima, M. Angiotensin type 1a receptor signaling-dependent induction of vascular endothelial growth factor in stroma is relevant to tumor-associated angiogenesis and tumor growth. Carcinogenesis 2005, 26, 271-279.
35. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMRChemical Shifts of Common Laboratory Solvents as Trace Impurities. J. Org. Chem. 1997, 62, 7512-7515.
36. Horovitz, A.; Levitzki, A. An accurate method for determination of receptor - ligand and enzyme - inhibitor dissociation constants from displacement curves. Proc. Natl. Acad. Sci. U.S.A 1987, 84, 6654-6658.
37. Jullien, N. D.; Cuniasse, P.; Georgiadis, D.; Yiotakis, A.; Dive, V. Combined use of selective inhibitors and fluorogenic substrates to study the specificity of somatic wild-type angiotensin-converting enzyme. FEBS J. 2006, 273, 1772-1781.
38. Cornish-Bowden, A.; Eisenthal, R. Estimation of Michaelis constant and maximum velocity from the direct linear plot. Biochim. Biophys. Acta 1978, 523, 268-272.
39. Vassiliou, S.; Mucha, A.; Cuniasse, P.; Georgiadis, D.; Lucet-Levannier, K.; Beau, F.; Kannan, R.; Murphy, G.; Knauper, V.; Rio, M. C.; Basset, P.; Yiotakis, A.; Dive, V. Phosphinic pseudotripeptides as potent inhibitors of matrix metalloproteinases: a structure - activity study. J. Med. Chem. 1999, 42, 2610-2620.