Novel β-amino acid derivatives as inhibitors of cathepsin A

Journal of Medicinal Chemistry

Volumn 55, Issue 17, 2012, Pages 7636-7649

  Ruf, Sven ^a   Buning, Christian ^a   Schreuder, Herman ^a   Horstick, Georg ^a,c   Linz, Wolfgang ^a   Olpp, Thomas ^a   Pernerstorfer, Josef ^a   Hiss, Katrin ^a   Kroll, Katja ^a   Kannt, Aimo ^a   Kohlmann, Markus ^a   Linz, Dominik ^b   Hübschle, Thomas ^a   Rütten, Hartmut ^a   Wirth, Klaus ^a   Schmidt, Thorsten ^a   Sadowski, Thorsten ^a  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

^c Evangelisches Krankenhaus Oberhausen   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2,4 DICHLOROPHENYL) 3 [[1 (2 FLUOROPHENYL) 5 (2 HYDROXY 3,3 DIMETHYLBUTOXY) 1H PYRAZOLE 3 CARBONYL]AMINO] PROPIONIC ACID; 3 (2,4 DICHLOROPHENYL) 3 [[5 (3,3 DIMETHYL 2 OXOBUTOXY) 1 (2 FLUOROPHENYL) 1H PYRAZOLE 3 CARBONYL]AMINO]PROPIONIC ACID; 3 [[1 (2 FLUOROPHENYL) 5 (2 HYDROXY 3,3 DIMETHYLBUTOXY) 1H PYRAZOLE 3 CARBONYL]AMINO] 3 O TOLYLPROPIONIC ACID; 3 [[1 (2 FLUOROPHENYL) 5 METHOXY 1H PYRAZOLE 3 CARBONYL]AMINO] 3 (2 METHYLPHENYL)PROPIONIC ACID; BETA AMINO ACID; CARBOXYPEPTIDASE C; EBELACTONE B; SERINE PROTEINASE INHIBITOR; SPIRONOLACTONE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; CHIRAL CHROMATOGRAPHY; COMPETITIVE INHIBITION; CONTROLLED STUDY; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; DRUG ABSORPTION; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG CONFORMATION; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG METABOLISM; DRUG SYNTHESIS; ENZYME ACTIVE SITE; GENOTOXICITY; GLOMERULUS FILTRATION RATE; HEART ATRIUM FIBRILLATION; HEART VENTRICLE HYPERTROPHY; HIGH THROUGHPUT SCREENING; LIGAND BINDING; LIPOPHILICITY; MALE; MAXIMUM PLASMA CONCENTRATION; MUTAGENICITY; NONHUMAN; PATHOPHYSIOLOGY; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CATHEPSIN A; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; PROTEASE INHIBITORS;

EID: 84866333904     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300663n     Document Type: Article

References (40)

1. Hiraiwa, M. Cathepsin A/protective protein: an unusual lysosomal multifunctional protein Cell. Mol. Life Sci. 1999, 55, 894-907 (Pubitemid 30019209)
2. Itoh, K.; Takiyama, N.; Kase, R.; Kondoh, K.; Sanao, A.; Oshima, A. Purification and characterization of human lysosomal protective protein expressed in stably transformed Chinese hamster ovary cells J. Biol. Chem. 1993, 268, 1180-1186 (Pubitemid 23019758)
3. Jackman, H. J.; Tan, F.; Tamei, H.; Beurling-Harbury, C.; Li, X.-Y.; Skidgel, R. A. A deamidase in human platelets that deamidates tachykinins: probable identity with the lysosomal protective protein J. Biol. Chem. 1990, 265, 11265-11272
4. Jackman, H. J.; Morris, P. W.; Deddish, P. A.; Skidgel, R. A.; Erdös, E. G. Inactivation of endothelin I by deamidase (lysosomal protective protein) J. Biol. Chem. 1992, 267, 2872-2875
5. Itoh, K.; Kase, R.; Simmoto, M.; Satake, A.; Sakaruba, H.; Suzuki, Y. Protective protein as an endogenous endothelin degradation enzyme in human tissues J. Biol. Chem. 1995, 270, 515-518
6. d'Azzo, A.; Hoogeveen, A. T.; Reuser, J. J.; Robinson, H.; Galjaard, H. Molecular defect in combined β-galactosidase and neuraminidase deficiency in man Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 4535-4539
7. Zhou, X. Y.; Morreau, H.; Rottier, R.; Davis, D.; Bonten, E.; Gillemans, N. Mouse model for the lysosomal disorder galactosialidosis and correction of the phenotype with overexpressing erythroid precursor cells Genes Dev. 1995, 9, 2623-2634
8. Seyrantepe, V.; Hinek, A.; Junzheng, P.; Fedjaev, M.; Sheila, E.; Yoshito, K.; Canuel, M.; Itoh, K.; Morales, C. R.; Lavoie, J.; Tremblay, J.; Pshezhetsky, A. V. Enzymatic activity of lysosomal carboxypeptidase (cathepsin) A is required for proper elastic fiber formation an inactivation of endothelin-1 Circulation 2008, 117, 1973-1981 (Pubitemid 351543473)
9. Miller, J. J.; Changaris, D. G.; Levy, R. S. Conversion of angiotensin I to angiotensin II by cathepsin A isozymes of porcine kidney Biochem. Biophys. Res. Commun. 1988, 154, 1122-1129
10. Ito, H.; Majima, M.; Nakajima, S.-i.; Hayashi, I.; Katori, M.; Izumi, T. Effect of prolonged administration of a urinary kininase inhibitor ebelactone B on the development of deoxycorticosterone acetate-salt hypertension in rats Br. J. Pharmacol. 1999, 126, 613-620 (Pubitemid 29087839)
11. Hayashi, I.; Majima, M.; Fujita, T.; Okumura, T.; Kumagai, Y.; Tomita, N. In vivo transfer of antisense oligonucleotide against urinary kininase blunts deoxycorticosterone acetate-salt hypertension in rats Br. J. Pharmacol. 2000, 131, 820-826
12. Cuervo, A. M.; Mann, L.; Bonten, E. J.; d'Azzo, A.; Dice, J. F. Cathepsin A regulates chaperone-mediated autophagy through cleavage of the lysosomal receptor EMBO J. 2003, 22, 47-59 (Pubitemid 36091268)
13. Westermann., D.; Schultheiss, H. P.; Tschöpe, C. New perspective on the tissue kallikrein-kinin system in myocardial infarction: role of angiogenesis and cardiac regeneration Int. Immunopharmacol 2008, 8, 148-154
14. Kam, J.-D. Dual ACE/NEP inhibitors-more than playing the ACE card J. Hum. Hypertens. 2006, 20, 478-481
15. Weiner, B.; Szymanski, W.; Jansen, D. B.; Minnard, A. J.; Ferninga, B. L. Recent advances in the catalytic asymmetric synthesis of β-amino acids Chem. Soc. Rev. 2010, 39, 1656-1691
16. Montalbetti, C. A. G. N.; Falque, V. Amide bond formation and peptide coupling Tetrahedron 2005, 61, 10827-10852 (Pubitemid 41447509)
17. Oprea, T. I.; Davis, M.; Teague, S. J.; Leeson, P. D. Is there a difference between leads and drugs? A historical perspective J. Chem. Inf. Comput. Sci. 2001, 41, 1308-1315
18. Artursson, P. Epithelial transport of drug in cell culture: a model for studying the passive diffusion of drugs over intestinal absorbtive (Caco-2) cells J. Pharm. Sci. 1990, 79, 476-482 (Pubitemid 20221389)
19. Rudenko, G.; Bonten, E.; d'Azzo, A.; Hol, W. G. J. Three-dimensional structure of the human protective protein: structure of the precursor form suggests a complex activation mechanism Structure 1995, 3, 1249-1259 (Pubitemid 3001423)
20. Rudenko, G.; Bonten, E.; d'Azzo, A.; Hol, W. G. J. Structure determination of the human protective protein: twofold averaging reveals the three-dimensional structure of a domain, which was entirely absent in the initial model Acta Crystallogr. 1996, D52, 923-936 (Pubitemid 27064194)
21. Stella, V. J.; Himmelstein, J. Prodrugs and site-specific drug delivery J. Med. Chem. 1980, 23, 1275-1282 (Pubitemid 11164092)
22. Verdonk, M. L.; Cole, J. C.; Taylor, R. SuperStar: a knowledge-based approach for identifying interaction sites in proteins J. Mol. Biol. 1999, 289 (4) 1093-108 (Pubitemid 29306672)
23. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy J. Med. Chem. 2004, 47, 1739
24. See www.cerep.fr for more details.
25. Katori, M.; Majima, M. The renal kallikrein-kinin system: its role as a safety valve for excess sodium intake, and its attenuation as a possible etiologic factor in salt-sensitive hypertension Crit. Rev. Clin. Lab. Sci. 2003, 40, 43-115 (Pubitemid 36253643)
26. Linz, W.; Schoelkens, B. A. A specific B2-bradykinin receptor antagonist HOE 140 abolishes the antihypertrophic effect of ramipril Br. J. Pharmacol. 1992, 105, 771-772
27. Jackman, H. L.; Massad, M. G.; Sekosan, M.; Tan, F.; Brovkovych, V.; Marcic, B. M.; Erdös, E. G. Angiotensin 1-9 and 1-7 release in human heart. Role of cathepsin A Hypertension 2002, 39, 976-981 (Pubitemid 34547796)
28. Kitts, P. A.; Possee, R. D. A method for producing recombinant baculovirus expression vectors at high frequency BioTechniques 1993, 14, 810-817
29. Patent applications EP1144666, WO0112829, and AU6460800.
30. Vaughn, J. L.; Goodwin, R. H.; Tompkins, G. J.; McCawley, P. The establishment of two cell lines from the insect Spodoptera frugiperda (Lepidoptera; Noctuidae) In Vitro 1977, 13, 213-7
31. Brown, M; Faulkner, P. A plaque assay for nuclear polyhedrosis viruses using a solid overlay J. Gen. Virol. 1977, 36, 361-364 (Pubitemid 8150881)
32. Hochuli, E.; Bannwarth, W.; Döbeli, H.; Gentz, R.; Stüber, D. Genetic approach to facilitate purification of recombinant proteins with a novel metal chelate adsorbent Nat. Biotechnol. 1988, 6, 1321-1325 (Pubitemid 18266749)
33. Laemmli, U. K. Cleavage of structural proteins during assembly of the head of bacteriophage T4 Nature 1970, 227, 680-685
34. Kabsch, W. XDS Acta Crystallog. 2010, D66, 125-132
35. Kroemer, M.; Dreyer, M. K.; Wendt, K. U. APRV-a program for automated data processing, refinement and visualization Acta Crystallogr. 2004, D60, 1679-1682 (Pubitemid 41103555)
36. McCoy, A. J.; Grosse-Kunstleve, R. W.; Adams, P. D.; Winn, M. D.; Storoni, L. D.; Read, R. J. Phaser crystallographic software J. Appl. Crystallog. 2007, 40, 658-674 (Pubitemid 47080256)
37. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallog D 2004, 60, 2126-2132 (Pubitemid 41742764)
38. Bricogne, G.; Blanc, E.; Brandl, M.; Flensburg, C.; Keller, P.; Paciorek, W.; Roversi, P; Sharff, A.; Smart, O. S.; Vonrhein, C.; Womack, T. O. BUSTER; Global Phasing Ltd.: Cambridge, U.K., 2011.
39. Shelley, J. C.; Choletti, A.; Frye, L. L.; Greenwood, J. R.; Timlin, M. R.; Uchimaya, M. Epik: a software program for pKa prediction and protonation state generation for drug-like molecules J. Comput.-Aided Mol. Des. 2007, 21, 681-691
40. Sybyl 8.0; Tripos (1699 South Hanley Road, St. Louis, MO, U.S.).