Structure based drug design of angiotensin-i converting enzyme inhibitors

Current Medicinal Chemistry

Volumn 19, Issue 6, 2012, Pages 845-855

  Anthony, C S ^a   Masuyer, G ^b   Sturrock, E D ^a   Acharya, K R ^b  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b University of Bath   (United Kingdom)

Author keywords

Angiotensin I converting enzyme; Cardiovascular disease; Crystal structure; Domain selective inhibitors; Hypertension; Structurebased drug design; Zinc metallopeptidase

Indexed keywords

CHYMASE; CYANOCOBALAMIN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENDOTHELIN CONVERTING ENZYME; ENDOTHELIN CONVERTING ENZYME INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; NATURAL PRODUCT; OMAPATRILAT;

ANGIONEUROTIC EDEMA; ARTICLE; COUGHING; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG BINDING SITE; DRUG DESIGN; DRUG STRUCTURE; ESSENTIAL HYPERTENSION; GLYCOSYLATION; HUMAN; NEPHROTIC SYNDROME; NEUTROPENIA; RASH;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; ASPARTIC ACID ENDOPEPTIDASES; BIOLOGICAL AGENTS; DRUG DESIGN; HUMANS; HYPERTENSION; METALLOENDOPEPTIDASES; MOLECULAR STRUCTURE; PEPTIDYL-DIPEPTIDASE A;

EID: 84857520077     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712799034950     Document Type: Article

References (96)

1. Strong, K.; Mathers, C.; Leeder, S.; Beaglehole, R. Preventing chronic diseases: How many lives can we save? Lancet 2005, 366 (9496), 1578-1582. (Pubitemid 41540116)
2. Lim, S. S.; Gaziano, T. A.; Gakidou, E.; Reddy, K. S.; Farzadfar, F.; Lozano, R.; Rodgers, A. Prevention of cardiovascular disease in high-risk individuals in low-income and middle-income countries: Health effects and costs. Lancet 2007, 370 (9604), 2054-2062. (Pubitemid 50007974)
3. Ehlers, M. R.; Riordan, J. F. Angiotensin-converting enzyme: New concepts concerning its biological role. Biochemistry 1989, 28 (13), 5311-5318. (Pubitemid 19175737)
4. Turner, A. J.; Hooper, N. M. The angiotensin-converting enzyme gene family: Genomics and pharmacology. Trends Pharmacol. Sci. 2002, 23 (4), 177-183. (Pubitemid 34270600)
5. Unger, T. The role of the renin-Angiotensin system in the development of cardiovascular disease. Am. J Cardiol. 2002, 89 (2A), 3A-9A.
6. Eriksson, U.; Danilczyk, U.; Penninger, J. M. Just the beginning: Novel functions for angiotensin-converting enzymes. Curr. Biol. 2002, 12 (21), R745-R752. (Pubitemid 35273898)
7. Acharya, K. R.; Sturrock, E. D.; Riordan, J. F.; Ehlers, M. R. Ace revisited: A new target for structure-based drug design. Nat. Rev. Drug Discov. 2003, 2 (11), 891-902. (Pubitemid 37407795)
8. Watermeyer, J.; Kroger, W. L.; Sturrock, E. D.; Ehlers, M. R. Angiotensinconverting enzyme -New insights into structure, biological significance and prospects for domain-selective inhibitors. Curr. Enzyme. Inhib. 2010, 5 (3), 134-147.
9. Hooper, N. M.; Karran, E. H.; Turner, A. J. Membrane protein secretases. Biochem. J. 1997, 321 ( Pt 2), 265-279. (Pubitemid 27056469)
10. Soubrier, F.; Alhenc-Gelas, F.; Hubert, C.; Allegrini, J.; John, M.; Tregear, G.; Corvol, P. Two putative active centers in human angiotensin I-converting enzyme revealed by molecular cloning. Proc. Natl. Acad. Sci. U. S. A 1988, 85 (24), 9386-9390. (Pubitemid 19027137)
11. Hagaman, J. R.; Moyer, J. S.; Bachman, E. S.; Sibony, M.; Magyar, P. L.; Welch, J. E.; Smithies, O.; Krege, J. H.; O'Brien, D. A. Angiotensinconverting enzyme and male fertility. Proc. Natl. Acad. Sci. U. S. A 1998, 95 (5), 2552-2557.
12. Kondoh, G.; Tojo, H.; Nakatani, Y.; Komazawa, N.; Murata, C.; Yamagata, K.; Maeda, Y.; Kinoshita, T.; Okabe, M.; Taguchi, R.; Takeda, J. Angiotensin-converting enzyme is a GPI-Anchored protein releasing factor crucial for fertilization. Nat. Med. 2005, 11 (2), 160-166. (Pubitemid 40321351)
13. Fuchs, S.; Frenzel, K.; Hubert, C.; Lyng, R.; Muller, L.; Michaud, A.; Xiao, H. D.; Adams, J. W.; Capecchi, M. R.; Corvol, P.; Shur, B. D.; Bernstein, K. E. Male fertility is dependent on dipeptidase activity of testis ACE. Nat. Med. 2005, 11 (11), 1140-1142. (Pubitemid 43093652)
14. Leisle, L.; Parkin, E. T.; Turner, A. J.; Hooper, N. M. Angiotensinconverting enzyme as a GPIase: A critical reevaluation. Nat. Med. 2005, 11 (11), 1139-1140. (Pubitemid 43093651)
15. Ehlers, M. R.; Fox, E. A.; Strydom, D. J.; Riordan, J. F. Molecular cloning of human testicular angiotensin-converting enzyme: The testis isozyme is identical to the C-terminal half of endothelial angiotensin-converting enzyme. Proc. Natl. Acad. Sci. U. S. A 1989, 86 (20), 7741-7745. (Pubitemid 19265263)
16. Voronov, S.; Zueva, N.; Orlov, V.; Arutyunyan, A.; Kost, O. Temperatureinduced selective death of the C-domain within angiotensin-converting enzyme molecule. FEBS Lett. 2002, 522 (1-3), 77-82. (Pubitemid 34722501)
17. Sturrock, E. D.; Danilov, S. M.; Riordan, J. F. Limited proteolysis of human kidney angiotensin-converting enzyme and generation of catalytically active N-And C-terminal domains. Biochem. Biophys. Res. Commun. 1997, 236 (1), 16-19. (Pubitemid 27341830)
18. Wei, L.; Clauser, E.; Alhenc-Gelas, F.; Corvol, P. The two homologous domains of human angiotensin I-converting enzyme interact differently with competitive inhibitors. J. Biol. Chem. 1992, 267 (19), 13398-13405.
19. Jaspard, E.; Wei, L.; Alhenc-Gelas, F. Differences in the properties and enzymatic specificities of the two active sites of angiotensin I-converting enzyme (kininase II). Studies with bradykinin and other natural peptides. J Biol. Chem. 1993, 268 (13), 9496-9503. (Pubitemid 23146003)
20. Kost, O. A.; Balyasnikova, I. V.; Chemodanova, E. E.; Nikolskaya, I. I.; Albrecht, R. F.; Danilov, S. M. Epitope-dependent blocking of the angiotensin-converting enzyme dimerization by monoclonal antibodies to the N-terminal domain of ACE: Possible link of ACE dimerization and shedding from the cell surface. Biochemistry 2003, 42 (23), 6965-6976. (Pubitemid 36706479)
21. Rousseau, A.; Michaud, A.; Chauvet, M.-T.; Lenfant, M.; Corvol, P. The hemoregulatory peptide N-Acetyl-Ser-Asp-Lys-Pro is a natural and specific substrate of the N-terminal active site of human angiotensin-converting enzyme. Journal of Biological Chemistry 1995, 270 (8), 3656-3661.
22. Deddish, P. A.; Marcic, B.; Jackman, H. L.; Wang, H. Z.; Skidgel, R. A.; Erdos, E. G. N-domain-specific substrate and C-domain inhibitors of angiotensin-converting enzyme: Angiotensin-(1-7) and keto-ACE. Hypertension 1998, 31 (4), 912-917. (Pubitemid 28185567)
23. Oba, R.; Igarashi, A.; Kamata, M.; Nagata, K.; Takano, S.; Nakagawa, H. The N-terminal active centre of human angiotensin-converting enzyme degrades Alzheimer amyloid beta-peptide. Eur J Neurosci. 2005, 21 (3), 733-740. (Pubitemid 40363508)
24. Hemming, M. L.; Selkoe, D. J. Amyloid beta-protein is degraded by cellular angiotensin-converting enzyme (ACE) and elevated by an ACE inhibitor. J. Biol. Chem. 2005, 280 (45), 37644-37650. (Pubitemid 41642372)
25. Cushman, D. W.; Cheung, H. S.; Sabo, E. F.; Ondetti, M. A. Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids. Biochemistry 1977, 16 (25), 5484-5491. (Pubitemid 8254139)
26. Natesh, R.; Schwager, S. L.; Sturrock, E. D.; Acharya, K. R. Crystal structure of the human angiotensin-converting enzyme-lisinopril complex. Nature 2003, 421 (6922), 551-554. (Pubitemid 36168450)
27. Patchett, A. A.; Harris, E.; Tristram, E. W.; Wyvratt, M. J.; Wu, M. T.; Taub, D.; Peterson, E. R.; Ikeler, T. J.; ten, B. J.; Payne, L. G.; Ondeyka, D. L.; Thorsett, E. D.; Greenlee, W. J.; Lohr, N. S.; Hoffsommer, R. D.; Joshua, H.; Ruyle, W. V.; Rothrock, J. W.; Aster, S. D.; Maycock, A. L.; Robinson, F. M.; Hirschmann, R.; Sweet, C. S.; Ulm, E. H.; Gross, D. M.; Vassil, T. C.; Stone, C. A. A new class of angiotensin-converting enzyme inhibitors. Nature 1980, 288 (5788), 280-283. (Pubitemid 11165879)
28. Patchett, A. A.; Cordes, E. H. The design and properties of Ncarboxyalkyldipeptide inhibitors of angiotensin-converting enzyme. Adv. Enzymol. Relat Areas Mol. Biol. 1985, 57, 1-84.
29. Natesh, R.; Schwager, S. L.; Evans, H. R.; Sturrock, E. D.; Acharya, K. R. Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry 2004, 43 (27), 8718-8724. (Pubitemid 38880042)
30. Corradi, H. R.; Schwager, S. L.; Nchinda, A. T.; Sturrock, E. D.; Acharya, K. R. Crystal structure of the N domain of human somatic angiotensin Iconverting enzyme provides a structural basis for domain-specific inhibitor design. J. Mol. Biol. 2006, 357 (3), 964-974.
31. Vidt, D. G.; Bravo, E. L.; Fouad, F. M. Medical intelligence drug therapy: Captopril. N. Engl. J. Med. 1982, 306 (4), 214-219. (Pubitemid 12163110)
32. Todd, P. A.; Heel, R. C. Enalapril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension and congestive heart failure. Drugs 1986, 31 (3), 198-248. (Pubitemid 16184167)
33. Dusing, R.; Kayser, G.; Wagner, S.; Scherf, H.; Glanzer, K.; Predel, H. G.; Kramer, H. J. Baroreflex setting and sensitivity in normal subjects: Effects of pharmacologic inhibition of the angiotensin I converting enzyme. Am. J. Cardiol. 1987, 59 (10), 50D-54D. (Pubitemid 17071265)
34. Lund-Johansen, P.; Omvik, P. Long-term haemodynamic effects of enalapril (alone and in combination with hydrochlorothiazide) at rest and during exercise in essential hypertension. J. Hypertens. Suppl 1984, 2 (2), S49-S56.
35. Dunn, F. G.; Oigman, W.; Ventura, H. O.; Messerli, F. H.; Kobrin, I.; Frohlich, E. D. Enalapril improves systemic and renal hemodynamics and allows regression of left ventricular mass in essential hypertension. Am. J. Cardiol. 1984, 53 (1), 105-108. (Pubitemid 14217516)
36. Simon, A. C.; Levenson, J. A.; Bouthier, J.; Maarek, B.; Safar, M. E. Effects of acute and chronic angiotensin-converting enzyme inhibition on large arteries in human hypertension. J. Cardiovasc. Pharmacol. 1985, 7 Suppl 1, S45-S51. (Pubitemid 15174502)
37. Ajayi, A. A.; Campbell, B. C.; Meredith, P. A.; Kelman, A. W.; Reid, J. L. The effect of captopril on the reflex control heart rate: Possible mechanisms. Br. J. Clin. Pharmacol. 1985, 20 (1), 17-25. (Pubitemid 15229451)
38. Hanif, K.; Bid, H. K.; Konwar, R. Reinventing the ACE inhibitors: Some old and new implications of ACE inhibition. Hypertens. Res. 2010, 33 (1), 11-21.
39. Skidgel, R. A.; Defendini, R.; Erdos, E. G. Angiotensin I converting enzyme and its role in neuropeptide metabolism. In Neuropeptides and their peptidases, Turner, A. J., Ed.; Ellis Horwood Ltd.: Chichester, UK, 1987; pp 165-182.
40. Hecker, M.; Blaukat, A.; Bara, A. T.; Muller-Esterl, W.; Busse, R. ACE inhibitor potentiation of bradykinin-induced venoconstriction. Br. J. Pharmacol. 1997, 121 (7), 1475-1481. (Pubitemid 27317563)
41. Minshall, R. D.; Erdos, E. G.; Vogel, S. M. Angiotensin I-converting enzyme inhibitors potentiate bradykinin's inotropic effects independently of blocking its inactivation. Am. J. Cardiol. 1997, 80 (3A), 132A-136A. (Pubitemid 27377486)
42. Minshall, R. D.; Tan, F.; Nakamura, F.; Rabito, S. F.; Becker, R. P.; Marcic, B.; Erdos, E. G. Potentiation of the actions of bradykinin by angiotensin Iconverting enzyme inhibitors. The role of expressed human bradykinin B2 receptors and angiotensin I-converting enzyme in CHO cells. Circ. Res. 1997, 81 (5), 848-856. (Pubitemid 27467220)
43. Kohlstedt, K.; Busse, R.; Fleming, I. Signaling via the angiotensinconverting enzyme enhances the expression of cyclooxygenase-2 in endothelial cells. Hypertension 2005, 45 (1), 126-132. (Pubitemid 40066426)
44. Kohlstedt, K.; Shoghi, F.; Muller-Esterl, W.; Busse, R.; Fleming, I. CK2 phosphorylates the angiotensin-converting enzyme and regulates its retention in the endothelial cell plasma membrane. Circ. Res. 2002, 91 (8), 749-756. (Pubitemid 35204958)
45. Israili, Z. H.; Hall, W. D. Cough and angioneurotic edema associated with angiotensin-converting enzyme inhibitor therapy. A review of the literature and pathophysiology. Ann. Intern. Med. 1992, 117 (3), 234-242.
46. Warren, S. E.; O'Connor, D. T. Hyperkalemia resulting from captopril administration. JAMA 1980, 244 (22), 2551-2552. (Pubitemid 11250848)
47. Textor, S. C.; Bravo, E. L.; Fouad, F. M.; Tarazi, R. C. Hyperkalemia in azotemic patients during angiotensin-converting enzyme inhibition and aldosterone reduction with captopril. Am. J. Med. 1982, 73 (5), 719-725. (Pubitemid 13234228)
48. Burnakis, T. G.; Mioduch, H. J. Combined therapy with captopril and potassium supplementation. A potential for hyperkalemia. Arch. Intern. Med. 1984, 144 (12), 2371-2372. (Pubitemid 15214235)
49. DiBianco, R. Adverse reactions with angiotensin converting enzyme (ACE) inhibitors. Med. Toxicol. 1986, 1 (2), 122-141. (Pubitemid 16024503)
50. Napoli, C.; Bruzzese, G.; Ignarro, L. J.; Crimi, E.; de, N. F.; Williams-Ignarro, S.; Libardi, S.; Sommese, L.; Fiorito, C.; Mancini, F. P.; Cacciatore, F.; Liguori, A. Long-term treatment with sulfhydryl angiotensin-converting enzyme inhibition reduces carotid intima-media thickening and improves the nitric oxide/oxidative stress pathways in newly diagnosed patients with mild to moderate primary hypertension. Am. Heart J. 2008, 156 (6), 1154-1158.
51. Urata, H.; Boehm, K. D.; Philip, A.; Kinoshita, A.; Gabrovsek, J.; Bumpus, F. M.; Husain, A. Cellular localization and regional distribution of an angiotensin II-forming chymase in the heart. J. Clin. Invest 1993, 91 (4), 1269-1281. (Pubitemid 23127321)
52. Wei, C. C.; Hase, N.; Inoue, Y.; Bradley, E. W.; Yahiro, E.; Li, M.; Naqvi, N.; Powell, P. C.; Shi, K.; Takahashi, Y.; Saku, K.; Urata, H.; Dell'italia, L. J.; Husain, A. Mast cell chymase limits the cardiac efficacy of Ang Iconverting enzyme inhibitor therapy in rodents. J. Clin. Invest 2010, 120 (4), 1229-1239.
53. Sadhukhan, R.; Sen, I. Different glycosylation requirements for the synthesis of enzymatically active angiotensin-converting enzyme in mammalian cells and yeast. J Biol. Chem. 1996, 271 (11), 6429-6434. (Pubitemid 26095455)
54. Gordon, K.; Redelinghuys, P.; Schwager, S. L.; Ehlers, M. R.; Papageorgiou, A. C.; Natesh, R.; Acharya, K. R.; Sturrock, E. D. Deglycosylation, processing and crystallization of human testis angiotensin-converting enzyme. Biochem. J 2003, 371 (Pt 2), 437-442. (Pubitemid 36547627)
55. Yu, X. C.; Sturrock, E. D.; Wu, Z.; Biemann, K.; Ehlers, M. R.; Riordan, J. F. Identification of N-linked glycosylation sites in human testis angiotensinconverting enzyme and expression of an active deglycosylated form. J Biol. Chem. 1997, 272 (6), 3511-3519. (Pubitemid 27066852)
56. Watermeyer, J. M.; Sewell, B. T.; Schwager, S. L.; Natesh, R.; Corradi, H. R.; Acharya, K. R.; Sturrock, E. D. Structure of testis ACE glycosylation mutants and evidence for conserved domain movement. Biochemistry 2006, 45 (42), 12654-12663. (Pubitemid 44630850)
57. Akif, M.; Schwager, S. L.; Anthony, C. S.; Czarny, B.; Beau, F.; Dive, V.; Sturrock, E. D.; Acharya, K. R. Novel mechanism of inhibition of human Angiotensin-I converting enzyme (ACE) by a highly specific phosphinic tripeptide. Biochem. J 2011, 36 (1), 53-59.
58. Anthony, C. S.; Corradi, H. R.; Schwager, S. L.; Redelinghuys, P.; Georgiadis, D.; Dive, V.; Acharya, K. R.; Sturrock, E. D. The N domain of human angiotensin-I-converting enzyme: The role of N-glycosylation and the crystal structure in complex with an N domain-specific phosphinic inhibitor, RXP407. J. Biol. Chem. 2010, 285 (46), 35685-35693.
59. Zou, K.; Maeda, T.; Watanabe, A.; Liu, J.; Liu, S.; Oba, R.; Satoh, Y.; Komano, H.; Michikawa, M. Abeta42-to-Abeta40-And angiotensinconverting activities in different domains of angiotensin-converting enzyme. J. Biol. Chem. 2009, 284 (46), 31914-31920.
60. Rice, G. I.; Thomas, D. A.; Grant, P. J.; Turner, A. J.; Hooper, N. M. Evaluation of angiotensin-converting enzyme (ACE), its homologue ACE2 and neprilysin in angiotensin peptide metabolism. Biochem. J. 2004, 383 (Pt 1), 45-51. (Pubitemid 39389449)
61. Bonnet, D.; Lemoine, F. M.; Khoury, E.; Pradelles, P.; Najman, A.; Guigon, M. Reversible inhibitory effects and absence of toxicity of the tetrapeptide acetyl-N-Ser-Asp-Lys-Pro (AcSDKP) in human long-term bone marrow culture. Exp. Hematol. 1992, 20 (10), 1165-1169.
62. Sharma, U.; Rhaleb, N. E.; Pokharel, S.; Harding, P.; Rasoul, S.; Peng, H.; Carretero, O. A. Novel anti-inflammatory mechanisms of N-Acetyl-Ser-Asp-Lys- Pro in hypertension-induced target organ damage. Am. J. Physiol Heart Circ. Physiol 2008, 294 (3), H1226-H1232. (Pubitemid 351468718)
63. Liu, Y. H.; D'Ambrosio, M.; Liao, T. D.; Peng, H.; Rhaleb, N. E.; Sharma, U.; Andre, S.; Gabius, H. J.; Carretero, O. A. N-Acetyl-seryl-Aspartyl- lysylproline prevents cardiac remodeling and dysfunction induced by galectin-3, a mammalian adhesion/growth-regulatory lectin. Am. J. Physiol Heart Circ. Physiol 2009, 296 (2), H404-H412.
64. Castoldi, G.; di Gioia, C. R.; Bombardi, C.; Perego, C.; Perego, L.; Mancini, M.; Leopizzi, M.; Corradi, B.; Perlini, S.; Zerbini, G.; Stella, A. Prevention of myocardial fibrosis by N-Acetyl-seryl-Aspartyl-lysyl-proline in diabetic rats. Clin. Sci. (Lond) 2010, 118 (3), 211-220.
65. Peng, H.; Carretero, O. A.; Liao, T. D.; Peterson, E. L.; Rhaleb, N. E. Role of N-Acetyl-seryl-Aspartyl-lysyl-proline in the antifibrotic and antiinflammatory effects of the angiotensin-converting enzyme inhibitor captopril in hypertension. Hypertension 2007, 49 (3), 695-703.
66. Azizi, M.; Rousseau, A.; Ezan, E.; Guyene, T. T.; Michelet, S.; Grognet, J. M.; Lenfant, M.; Corvol, P.; Menard, J. Acute angiotensin-converting enzyme inhibition increases the plasma level of the natural stem cell regulator N-Acetyl-seryl-Aspartyl-lysyl-proline. J. Clin. Invest 1996, 97 (3), 839-844. (Pubitemid 26060543)
67. Azizi, M.; Ezan, E.; Nicolet, L.; Grognet, J. M.; Menard, J. High plasma level of N-Acetyl-seryl-Aspartyl-lysyl-proline: A new marker of chronic angiotensin-converting enzyme inhibition. Hypertension 1997, 30 (5), 1015-1019. (Pubitemid 27476151)
68. Fuchs, S.; Xiao, H. D.; Cole, J. M.; Adams, J. W.; Frenzel, K.; Michaud, A.; Zhao, H.; Keshelava, G.; Capecchi, M. R.; Corvol, P.; Bernstein, K. E. Role of the N-terminal catalytic domain of angiotensin-converting enzyme investigated by targeted inactivation in mice. J. Biol. Chem. 2004, 279 (16), 15946-15953. (Pubitemid 38509282)
69. 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 (8), 4330-4335. (Pubitemid 29190336)
70. Kröger, 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 (35), 8405-8412.
71. Fuchs, S.; Xiao, H. D.; Hubert, C.; Michaud, A.; Campbell, D. J.; Adams, J. W.; Capecchi, M. R.; Corvol, P.; Bernstein, K. E. Angiotensin-converting enzyme C-terminal catalytic domain is the main site of angiotensin I cleavage in vivo. Hypertension 2008, 51 (2), 267-274. (Pubitemid 351159938)
72. Ehlers, M. R. Safety issues associated with the use of angiotensin-converting enzyme inhibitors. Expert. Opin. Drug Saf 2006, 5 (6), 739-740. (Pubitemid 44669486)
73. Nchinda, A. T.; Chibale, K.; Redelinghuys, P.; Sturrock, E. D. Synthesis and molecular modeling of a lisinopril-tryptophan analogue inhibitor of angiotensin I-converting enzyme. Bioorg. Med. Chem. Lett. 2006, 16 (17), 4616-4619. (Pubitemid 44094069)
74. Watermeyer, J. M.; Kroger, W. L.; O'Neill, H. G.; Sewell, B. T.; Sturrock, E. D. Characterization of domain-selective inhibitor binding in angiotensin converting enzyme using a novel derivative of lisinopril. Biochem. J. 2010, 428 (1), 67-74.
75. Cotton, J.; Hayashi, M. A.; Cuniasse, P.; Vazeux, G.; Ianzer, D.; De Camargo, A. C.; Dive, V. Selective inhibition of the C-domain of angiotensin I converting enzyme by bradykinin potentiating peptides. Biochemistry 2002, 41 (19), 6065-6071. (Pubitemid 34498912)
76. 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 (25), 8048-8054. (Pubitemid 38808259)
77. 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 (18), 5473-5478. (Pubitemid 46717270)
78. Bernstein, K. E.; Shen, X. Z.; Gonzalez-Villalobos, R. A.; Billet, S.; Okwan-Duodu, D.; Ong, F. S.; Fuchs, S. Different in vivo functions of the two catalytic domains of angiotensin-converting enzyme (ACE). Curr. Opin. Pharmacol. 2011, 11 (2), 105-111.
79. Petrillo, E. W., Jr.; Ondetti, M. A. Angiotensin-converting enzyme inhibitors: Medicinal chemistry and biological actions. Med. Res. Rev. 1982, 2 (1), 1-41.
80. 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 (1), 87-146. (Pubitemid 23108243)
81. Jeng, A. Y. Utility of endothelin-converting enzyme inhibitors for the treatment of cardiovascular diseases. Curr. Opin. Investig. Drugs 2003, 4 (9), 1076-1081. (Pubitemid 37321401)
82. Cerdeira, A. S.; Bras-Silva, C.; Leite-Moreira, A. F. Endothelin-converting enzyme inhibitors: Their application in cardiovascular diseases. Rev. Port. Cardiol. 2008, 27 (3), 385-408. (Pubitemid 351631807)
83. Dive, V.; Chang, C. F.; Yiotakis, A.; Sturrock, E. D. Inhibition of zinc metallopeptidases in cardiovascular disease-from unity to trinity, or duality? Curr. Pharm. Des 2009, 15 (31), 3606-3621.
84. Antonios, T. F.; MacGregor, G. A. Angiotensin converting enzyme inhibitors in hypertension: Potential problems. J. Hypertens. Suppl 1995, 13 (3), S11-S16.
85. Elijovich, F.; Laffer, C. A role for single-pill triple therapy in hypertension. Ther. Adv. Cardiovasc. Dis. 2009, 3 (3), 231-240.
86. Gros, C.; Noel, N.; Souque, A.; Schwartz, J. C.; Danvy, D.; Plaquevent, J. C.; Duhamel, L.; Duhamel, P.; Lecomte, J. M.; Bralet, J. Mixed inhibitors of angiotensin-converting enzyme (EC 3.4.15.1) and enkephalinase (EC 3.4.24.11): Rational design, properties, and potential cardiovascular applications of glycopril and alatriopril. Proc. Natl. Acad. Sci. U. S. A 1991, 88 (10), 4210-4214. (Pubitemid 21914509)
87. Worthley, M. I.; Corti, R.; Worthley, S. G. Vasopeptidase inhibitors: Will they have a role in clinical practice? Br. J. Clin. Pharmacol. 2004, 57 (1), 27-36. (Pubitemid 38067947)
88. Daull, P.; Jeng, A. Y.; Battistini, B. Towards triple vasopeptidase inhibitors for the treatment of cardiovascular diseases. J. Cardiovasc. Pharmacol. 2007, 50 (3), 247-256. (Pubitemid 47428971)
89. Campbell, D. J. Vasopeptidase inhibition: A double-edged sword? Hypertension 2003, 41 (3), 383-389. (Pubitemid 36314604)
90. Jullien, N.; Makritis, A.; Georgiadis, D.; Beau, F.; Yiotakis, A.; Dive, V. Phosphinic tripeptides as dual angiotensin-converting enzyme C-domain and endothelin-converting enzyme-1 inhibitors. J. Med. Chem. 2010, 53 (1), 208-220.
91. Yamato, M.; Koguchi, T.; Okachi, R.; Yamada, K.; Nakayama, K.; Kase, H.; Karasawa, A.; Shuto, K. K-26, a novel inhibitor of angiotensin I converting enzyme produced by an actinomycete K-26. J. Antibiot. (Tokyo) 1986, 39 (1), 44-52. (Pubitemid 16174636)
92. Ohuchio, S.; Kurihara, K.; Shinohara, A. T.; Takei, T.; Yoshida, J.; Amano, S.; Miyadoh, S.; Matsushida, Y.; Somura, T.; Sezaki, M. Studies on new angiotensin converting enzyme inhibitors, SF2513 A, B, C produced by Streptosporangium nondiastaticum. Sci. Rep. Meji Seika Kaisha 1988, 27, 46-54.
93. Ntai, I.; Bachmann, B. O. Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26. Bioorg. Med. Chem. Lett. 2008, 18 (10), 3068-3071. (Pubitemid 351680387)
94. Akif, M.; Ntai, I.; Sturrock, E. D.; Isaac, R. E.; Bachmann, B. O.; Acharya, K. R. Crystal structure of a phosphonotripeptide K-26 in complex with angiotensin converting enzyme homologue (AnCE) from Drosophila melanogaster. Biochem. Biophys. Res. Commun. 2010, 398 (3), 532-536.
95. Mukherjee, R.; McCaddon, A.; Smith, C. A.; Brasch, N. E. Synthesis, synchrotron X-ray diffraction, and kinetic studies on the formation of a novel thiolatocobalamin of captopril: Evidence for cis-trans isomerization in the beta-Axial ligand. Inorg. Chem. 2009, 48 (19), 9526-9534.
96. Hayashi, M. A.; Murbach, A. F.; Ianzer, D.; Portaro, F. C.; Prezoto, B. C.; Fernandes, B. L.; Silveira, P. F.; Silva, C. A.; Pires, R. S.; Britto, L. R.; Dive, V.; Camargo, A. C. The C-type natriuretic peptide precursor of snake brain contains highly specific inhibitors of the angiotensin-converting enzyme. J. Neurochem. 2003, 85 (4), 969-977. (Pubitemid 36578628)