Development of potent and selective phosphinic peptide inhibitors of angiotensin-converting enzyme 2

Journal of Medicinal Chemistry

Volumn 51, Issue 7, 2008, Pages 2216-2226

  Mores, Andreas ^a   Matziari, Magdalini ^a   Beau, Fabrice ^b   Cuniasse, Philippe ^b   Yiotakis, Athanasios ^a   Dive, Vincent ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN CONVERTING ENZYME 2; CARBOXYPEPTIDASE A;

ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; NONHUMAN;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; PHOSPHINIC ACIDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41849126356     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701275z     Document Type: Article

References (35)

1. Erdos, E. G. Angiotensin I converting enzyme and the changes in our concepts through the years. Lewis K. Dahl memorial lecture. Hypertension 1990, 16, 363-70.
2. Barllo, M.; Jiao, X. Y.; Wojtowicz, H.; Rajan, P.; Verbuggen, C.; Augustyns, K.; Haemers, A. Convenient one-pot preparation of disubstituted phosphinic acids derived from simple amino acids and proline. Synthesis 1995, 1074-75.
3. Zaman, M. A.; Oparil, S.; Calhoun, D. A. Drugs targeting the renin-angiotensin-aldosterone system. Nat. Rev. Drug Discovery 2002, 1, 621-36.
4. Wong, J.; Patel, R. A.; Kowey, P. R. The clinical use of angiotensin-converting enzyme inhibitors. Prog. Cardiovasc. Dis. 2004, 47, 116-30.
5. Tipnis, S. R.; Hooper, N. M.; Hyde, R.; Karran, E.; Christie, G.; Turner, A. J. A human homolog of angiotensin-converting enzyme. Cloning and functional expression as a captopril-insensitive carboxypeptidase. J. Biol. Chem. 2000, 275, 33238-43.
6. Donoghue, M.; Hsieh, F.; Baronas, E.; Godbout, K.; Gosselin, M.; Stagliano, N.; Donovan, M.; Woolf, B.; Robison, K.; Jeyaseelan, R.; Breitbart, R. E.; Acton, S. A novel angiotensin-converting enzyme-related carboxypeptidase (ACE2) converts angiotensin I to angiotensin 1-9. Circ. Res. 2000, 87, E1-9.
7. Vickers, C.; Hales, P.; Kaushik, V.; Dick, L.; Gavin, J.; Tang, J.; Godbout, K.; Parsons, T.; Baronas, E.; Hsieh, F.; Acton, S.; Patane, M.; Nichols, A.; Tummino, P. Hydrolysis of biological peptides by human angiotensin-converting enzyme-related carboxypeptidase. J. Biol. Chem. 2002, 277, 14838-43.
8. Brosnihan, K. B.; Neves, L. A.; Chappell, M. C. Does the angiotensin-converting enzyme (ACE)/ACE2 balance contribute to the fate of angiotensin peptides in programmed hypertension. Hypertension 2005, 46, 1097-9.
9. Der Sarkissian, S.; Huentelman, M. J.; Stewart, J.; Katovich, M. J.; Raizada, M. K. ACE2: A novel therapeutic target for cardiovascular diseases. Prog. Biophys. Mol. Biol. 2006, 91, 163-98.
10. Oudit, G. Y.; Crackower, M. A.; Backx, P. H.; Penninger, J. M. The role of ACE2 in cardiovascular physiology. Trends Cardiovasc. Med. 2003, 13, 93-101.
11. Hamming, I.; Cooper, M. E.; Haagmans, B. L.; Hooper, N. M.; Korstanje, R.; Osterhaus, A. D.; Timens, W.; Turner, A. J.; Navis, G.; van Goor, H. The emerging role of ACE2 in physiology and disease. J. Pathol. 2007, 212, 1-11.
12. Crackower, M. A.; Sarao, R.; Oudit, G. Y.; Yagil, C.; Kozieradzki, I.; Scanga, S. E.; Oliveira-dos-Santos, A. J.; da Costa, J.; Zhang, L.; Pei, Y.; Scholey, J.; Ferrario, C. M.; Manoukian, A. S.; Chappell, M. C.; Backx, P. H.; Yagil, Y.; Penninger, J. M. Angiotensin-converting enzyme 2 is an essential regulator of heart function. Nature 2002, 417, 822-8.
13. Gurley, S. B.; Allred, A.; Le, T. H.; Griffiths, R.; Mao, L.; Philip, N.; Haystead, T. A.; Donoghue, M.; Breitbart, R. E.; Acton, S. L.; Rockman, H. A.; Coffman, T. M. Altered blood pressure responses and normal cardiac phenotype in ACE2-null mice. J. Clin. Invest. 2006, 116, 2218-25.
14. Ashley, E.; Chun, H. J.; Quertermous, T. Opposing cardiovascular roles for the angiotensin and apelin signaling pathways. J. Mol. Cell. Cardiol. 2006, 41, 778-81.
15. Ishida, J.; Hashimoto, T.; Hashimoto, Y.; Nishiwaki, S.; Iguchi, T.; Harada, S.; Sugaya, T.; Matsuzaki, H.; Yamamoto, R.; Shiota, N.; Okunishi, H.; Kihara, M.; Umemura, S.; Sugiyama, F.; Yagami, K.; Kasuya, Y.; Mochizuki, N.; Fukamizu, A. Regulatory roles for APJ, a seven-transmembrane receptor related to angiotensin-type 1 receptor in blood pressure in vivo. J. Biol. Chem. 2004, 279, 26274-9.
16. Lee, D. K.; George, S. R.; O'Dowd, B. F. Unravelling the roles of the apelin system: prospective therapeutic applications in heart failure and obesity. Trends Pharmacol. Sci. 2006, 27, 190-4.
17. El Messari, S.; Iturrioz, X.; Fassot, C.; De Mota, N.; Roesch, D.; Llorens-Cortes, C. Functional dissociation of apelin receptor signaling and endocytosis: implications for the effects of apelin on arterial blood pressure. J. Neurochem. 2004, 90, 1290-301.
18. Dales, N. A.; Gould, A. E.; Brown, J. A.; Calderwood, E. F.; Guan, B.; Minor, C. A.; Gavin, J. M.; Hales, P.; Kaushik, V. K.; Stewart, M.; Tummino, P. J.; Vickers, C. S.; Ocain, T. D.; Patane, M. A. Substrate-based design of the first class of angiotensin-converting enzyme-related carboxypeptidase (ACE2) inhibitors. J. Am. Chem. Soc. 2002, 124, 11852-3.
19. Towler, P.; Staker, B.; Prasad, S. G.; Menon, S.; Tang, J.; Parsons, T.; Ryan, D.; Fisher, M.; Williams, D.; Dales, N. A.; Patane, M. A.; Pantoliano, M. W. ACE2 X-ray structures reveal a large hinge-bending motion important for inhibitor binding and catalysis. J. Biol. Chem. 2004, 279, 17996-8007.
20. Ye, M.; Wysocki, J.; William, J.; Soler, M. J.; Cokic, I.; Batlle, D. Glomerular localization and expression of angiotensin-converting enzyme 2 and angiotensin-converting enzyme: Implications for albuminuria in diabetes. J. Am. Soc. Nephrol. 2006, 17, 3067-75.
21. 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, 148-54.
22. Dive, V.; Georgiadis, D.; Matziari, M.; Makaritis, A.; Beau, F.; Cuniasse, P.; Yiotakis, A. Phosphinic peptides as zinc metalloproteinase inhibitors. Cell. Mol. Life Sci. 2004, 61, 2010-9.
23. Dive, V.; Andarawewa, K. L.; Boulay, A.; Matziari, M.; Beau, F.; Guerin, E.; Rousseau, B.; Yiotakis, A.; Rio, M. C. Dosing and scheduling influence the antitumor efficacy of a phosphinic peptide inhibitor of matrix metalloproteinases. Int. J. Cancer 2005, 113, 775-81.
24. Grams, F.; Dive, V.; Yiotakis, A.; Yiallouros, I.; Vassiliou, S.; Zwilling, R.; Bode, W.; Stocker, W. Structure of astacin with a transition-state analogue inhibitor. Nat. Struct. Biol. 1996, 3, 671-5.
25. Gall, A. L.; Ruff, M.; Kannan, R.; Cuniasse, P.; Yiotakis, A.; Dive, V.; Rio, M. C.; Basset, P.; Moras, D. Crystal structure of the stromelysin-3 (MMP-11) catalytic domain complexed with a phosphinic inhibitor mimicking the transition-state. J. Mol. Biol. 2001, 307, 577-86.
26. Corradi, H. R.; Chitapi, I.; Sewell, B. T.; Georgiadis, D.; Dive, V.; Sturrock, E. D.; Acharya, K. R. The structure of testis angiotensin-converting enzyme in complex with the C domain-specific inhibitor RXPA380. Biochemistry 2007, 46, 5473-8.
27. Tochowicz, A.; Maskos, K.; Huber, R.; Oltenfreiter, R.; Dive, V.; Yiotakis, A.; Zanda, M.; Bode, W.; Goettig, P. Crystal structures of MMP-9 complexes with five inhibitors: contribution of the flexible Arg424 side-chain to selectivity. J. Mol. Biol. 2007, 371, 989-1006.
28. Rella, M.; Rushworth, C. A.; Guy, J. L.; Turner, A. J.; Langer, T.; Jackson, R. M. Structure-based pharmacophore design and virtual screening for novel angiotensin converting enzyme 2 inhibitors. J. Chem. Inf. Model. 2006, 46, 708-16.
29. Huentelman, M. J.; Zubcevic, J.; Hernandez Prada, J. A.; Xiao, X.; Dimitrov, D. S.; Raizada, M. K.; Ostrov, D. A. Structure-based discovery of a novel angiotensin-converting enzyme 2 inhibitor. Hypertension 2004, 44, 903-6.
30. Huang, L.; Sexton, D. J.; Skogerson, K.; Devlin, M.; Smith, R.; Sanyal, I.; Parry, T.; Kent, R.; Enright, J.; Wu, Q. L.; Conley, G.; DeOliveira, D.; Morganelli, L.; Ducar, M.; Wescott, C. R.; Ladner, R. C. Novel peptide inhibitors of angiotensin-converting enzyme 2. J. Biol. Chem. 2003, 278, 15532-40.
31. 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.
32. Baylis, E. K.; Cambell, M.; Dingwall, J. G. 1-aminoalkylphosphonous acids, part 1. isosteres of the protein aminoacids. J. Chem. Soc., Perkin. Trans. 1 1984, 2845-853.
33. Stetter, H.; Kuhlman, H. Eine einfache Herstellung von α-alkyl-acrysäure-ester. Synthesis 1979, 20-30.
34. Nomura, Y.; Ogawa, K.; Takeuchi, Y.; Tomoda, S. One-step synthesis and structural confirmation of 1-pyrroline trimer. Chem. Lett. 1977, 693-96.
35. 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, 6654-8.