Structure-based pharmacophore design and virtual screening for novel Angiotensin Converting Enzyme 2 inhibitors

Journal of Chemical Information and Modeling

Volumn 46, Issue 2, 2006, Pages 708-716

  Rella, Monika ^a   Rushworth, Christopher A ^a   Guy, Jodie L ^a   Turner, Anthony J ^a   Langer, Thierry ^b   Jackson, Richard M ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CARDIOLOGY; DRUG PRODUCTS; ENZYME INHIBITION; ENZYMES; SCREENING; VIRTUAL REALITY;

ANGIOTENSIN CONVERTING ENZYME (ACE); METALLOPEPTIDASE; STRUCTURE-BASED PHARMACOPHORE DESIGN; VIRTUAL SCREENING;

PHARMACODYNAMICS;

ANGIOTENSIN CONVERTING ENZYME 2; DIPEPTIDYL CARBOXYPEPTIDASE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; LIGAND; LISINOPRIL;

ARTICLE; BIOLOGICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; METHODOLOGY; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; COMPUTER SIMULATION; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; LIGANDS; LISINOPRIL; MODELS, BIOLOGICAL; MODELS, MOLECULAR; PEPTIDYL-DIPEPTIDASE A; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646256792     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci0503614     Document Type: Conference Paper

References (28)

1. Tipnis, S. R.; Hooper, N. M.; Hyde, R.; Karran, E.; Christie, G.; Turner, A. J. A human homologue of angiotensin-converting enzyme. Cloning and functional expression as a captopril-insensitive carboxypeptidase. J. Biol. Chem. 2000, 275, 33238-33243.
2. 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 Discovery 2003, 2, 891-902.
3. Turner, A. J.; Hiscox, J. A.; Hooper, N. M. ACE2: From vasopeptidase to SARS virus receptor. Trends. Pharmacol. Sci. 2004, 25, 291-294.
4. 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, 14838-14843.
5. 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, 17996-18007.
6. Guy, J. L.; Jackson, R. M.; Jensen, H. A.; Hooper, N. M.; Turner, A. J. Identification of critical active-site residues in angiotensin-converting enzyme-2 (ACE2) by site-directed mutagenesis. FEBS J. 2005, 272, 3512-3520.
7. Shoichet, B. K. Virtual screening of chemical libraries. Nature 2004, 432, 862-865.
8. Oprea, T. I.; Matter, H. Integrating virtual screening in lead discovery. Curr. Opin. Chem. Biol. 2004, 8, 349-358.
9. Kitchen, D. B.; Decornez, H.; Furr, J. R.; Bajorath, J. Docking and scoring in virtual screening for drug discovery: methods and applications. Nat. Rev. Drug Discovery 2004, 3, 935-949.
10. Lengauer, T.; Lemmen, C.; Rarey, M.; Zimmermann, M. Novel technologies for virtual screening. Drug Discovery Today 2004, 9, 27-34.
11. Guner, O. F. History and evolution of the pharmacophore concept in computer-aided drug design. Curr. Top. Med. Chem. 2002, 2, 1321-1332.
12. Wermuth, C. G.; Ganellin, C. R.: Lindberg, P.; Mitscher, L. A. Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1997). Ann. Rep. Med. Chem. 1998, 33, 385-395.
13. Pirard, B.; Brendel, J.; Peukert, S. The discovery of Kv 1.5 blockers as a case study for the application of virtual screening approaches. J. Chem. Inf. Model. 2005, 45, 477-485.
14. Steindl, T.; Langer, T. Influenza virus neuraminidase inhibitors: generation and comparison of structure-based and common feature pharmacophore hypotheses and their application in virtual screening. J. Chem. Inf. Comput. Sci. 2004, 44, 1849-1856.
15. Wolber G.; Langer, T. LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. J. Chem. Inf. Comput. Sci. 2005, 45, 160-169.
16. LigandScout, Version 1.0; Inte:Ligand GmbH, Clemens-Maria-Hofbauer-G. 6, 2344 Maria Enzersdorf, Austria, http://www.inteligand.com.
17. Catalyst, Version 4.9; Accelrys Inc., 9685 Scranton Road, San Diego, CA 92121-3752, U.S.A., 2001. http://www.accelrys.com.
18. Derwent World Drug Index, http://www.derwent.com.
19. 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, 45-51.
20. Smellie, A.; Teig, S. L.; Towbin, P. Poling: Promoting conformational variation. J. Comput. Chem. 1995, 16, 171-187.
21. Zsoldos, Z.; Szabo, I.: Szabo, Z.; Johnson, A. P. Software tools for structure based rational drug design. J. Mol. Struct. (THEOCHEM), 2003, 666-667, 659-665.
22. Jackson, R. M. Q-fit: A probabilistic method for docking molecular fragments by sampling low energy conformational space. J. Comput. Aided. Mol. Des. 2002, 16, 43-57.
23. Oledzki, P.; Lyon, P.; Jackson, R. M. Manuscript in preparation.
24. 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, 11852-11853.
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, 5484-5491.
26. Laggner, C.; Schieferer, C.; Fiechtner, B.; Poles, G.; Hoffmann, R. D.; Glossmann, H.; Langer, T.; Moebius, F. F. Discovery of high-affinity ligands of sigmal receptor, ERG2, and emopamil binding protein by pharmacophore modelling and virtual screening. J. Med. Chem. 2005, 48, 4754-4764.
27. Interbioscreen Database; Moscow, http://www.ibscreen.com.
28. Hu, X.; Balaz, S.; Shelver, W. H. A practical approach to docking of zinc metalloproteinase inhibitors. J. Mol. Graphics Modell. 2004, 22, 293-307.