Pharmacological validation of trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness

Journal of Medicinal Chemistry

Volumn 54, Issue 23, 2011, Pages 8188-8194

  Bland, Nicholas D ^b   Wang, Cuihua ^a   Tallman, Craig ^a   Gustafson, Alden E ^b   Wang, Zhouxi ^a   Ashton, Trent D ^d   Ochiana, Stefan O ^a   McAllister, Gregory ^e   Cotter, Kristina ^b   Fang, Anna P ^b   Gechijian, Lara ^b   Garceau, Norman ^c   Gangurde, Rajiv ^c   Ortenberg, Ron ^c   Ondrechen, Mary Jo ^a   Campbell, Robert K ^b   Pollastri, Michael P ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b MARINE BIOLOGICAL LABORATORY   (United States)

^c Blue Sky Biotech Inc   (United States)

^d Boston University   (United States)

^e NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHODIESTERASE; PHOSPHODIESTERASE B1; PHOSPHODIESTERASE B2; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ARTICLE; BIOCHEMISTRY; BLOOD; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG TARGETING; HUMAN; IN VITRO STUDY; NONHUMAN; PARASITE; PROTEIN EXPRESSION; PROTEIN INTERACTION; PROTEIN PURIFICATION; TRYPANOSOMA BRUCEI;

3',5'-CYCLIC-AMP PHOSPHODIESTERASES; BENZAMIDES; CATALYTIC DOMAIN; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMIASIS, AFRICAN;

EID: 82555165572     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201148s     Document Type: Article

References (32)

1. Hotez, P. J.; Molyneux, D. H.; Fenwick, A.; Kumaresan, J.; Sachs, S. E.; Sachs, J. D.; Savioli, L. Control of neglected tropical diseases N. Engl. J. Med. 2007, 357, 1018-1027
2. Croft, S. L.; Barrett, M. P.; Urbina, J. A. Chemotherapy of trypanosomiases and leishmaniasis Trends Parasitol. 2005, 21, 508-512
3. Pollastri, M. P.; Campbell, R. K. Target repurposing for neglected diseases Future Med. Chem. 2011, 3, 1307-1315
4. Gupta, R.; Kumar, G.; Kumar, R. S. An update on cyclic nucleotide phosphodiesterase (PDE) inhibitors: phosphodiesterases and drug selectivity Methods Find. Exp. Clin. Pharmacol. 2005, 27, 101-118
5. Lugnier, C. Cyclic nucleotide phosphodiesterase (PDE) superfamily: a new target for the development of specific therapeutic agents Pharmacol. Ther. 2006, 109, 366-398
6. Martin, H.; Christopher, K. In Chemogenomics in Drug Discovery; Kubinyi, H.; Müller, G., Ed.; Wiley-VCH: New York, 2005; pp 243-288.
7. Menniti, F. S.; Faraci, W. S.; Schmidt, C. J. Phosphodiesterases in the CNS: targets for drug development Nature Rev. Drug. Discovery 2006, 5, 660-670
8. Gould, M. K.; de Koning, H. P. Cyclic-nucleotide signalling in protozoa FEMS Microbiol. Rev. 2011, DOI: 10.1111/j.1574-6976.2010.00262.x.
9. Oberholzer, M.; Marti, G.; Baresic, M.; Kunz, S.; Hemphill, A.; Seebeck, T. The Trypanosoma brucei cAMP phosphodiesterases TbrPDEB1 and TbrPDEB2: flagellar enzymes that are essential for parasite virulence FASEB J. 2007, 21, 720-731
10. Shakur, Y.; de Koning, H. P.; Ke, H.; Kambayashi, J.; Seebeck, T. Therapeutic potential of phosphodiesterase inhibitors in parasitic diseases Handb. Exp. Pharmacol 2011, 487-510
11. Rascon, A.; Soderling, S. H.; Schaefer, J. B.; Beavo, J. A. Cloning and characterization of a cAMP-specific phosphodiesterase (TbPDE2B) from Trypanosoma brucei Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4714-4719
12. Zoraghi, R.; Seebeck, T. The cAMP-specific phosphodiesterase TbPDE2C is an essential enzyme in bloodstream form Trypanosoma brucei Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4343-4348
13. Beghyn, T. B.; Charton, J.; Leroux, F.; Laconde, G.; Bourin, A.; Cos, P.; Maes, L.; Deprez, B. Drug to Genome to Drug: Discovery of New Antiplasmodial Compounds J. Med. Chem. 2011, 54, 3222-3240
14. Laxman, S.; Rascon, A.; Beavo, J. A. Trypanosome cyclic nucleotide phosphodiesterase 2B binds cAMP through its GAF-A domain J. Biol. Chem. 2005, 280, 3771-3779
15. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice Nucleic Acids Res. 1994, 22, 4673-4680
16. Chappie, T. A.; Humphrey, J. M.; Allen, M. P.; Estep, K. G.; Fox, C. B.; Lebel, L. A.; Liras, S.; Marr, E. S.; Menniti, F. S.; Pandit, J.; Schmidt, C. J.; Tu, M.; Williams, R. D.; Yang, F. V. Discovery of a series of 6,7-dimethoxy-4-pyrrolidylquinazoline PDE10A inhibitors J. Med. Chem. 2007, 50, 182-185
17. Dyke, H. J.; Montana, J. G. Update on the therapeutic potential of PDE4 inhibitors Expert Opin. Invest. Drugs 2002, 11, 1-13
18. Montana, J. G.; Dyke, H. J. Phosphodiesterase 4 inhibitors Annu. Rep. Med. Chem. 2001, 36, 41-56
19. Pages, L.; Gavalda, A.; Lehner, M. D. PDE4 inhibitors: a review of current developments (2005-2009) Expert Opin. Ther. Pat. 2009, 19, 1501-1519
20. Wang, H.; Yan, Z.; Geng, J.; Kunz, S.; Seebeck, T.; Ke, H. Crystal structure of the Leishmania major phosphodiesterase LmjPDEB1 and insight into the design of the parasite-selective inhibitors Mol. Microbiol. 2007, 66, 1029-1038
21. Card, G. L.; England, B. P.; Suzuki, Y.; Fong, D.; Powell, B.; Lee, B.; Luu, C.; Tabrizizad, M.; Gillette, S.; Ibrahim, P. N.; Artis, D. R.; Bollag, G.; Milburn, M. V.; Kim, S.-H.; Schlessinger, J.; Zhang, K. Y. J. Structural Basis for the Activity of Drugs that Inhibit Phosphodiesterases Structure 2004, 12, 2233-2247
22. Ashton, M. J.; Cook, D. C.; Fenton, G.; Karlsson, J.-A.; Palfreyman, M. N.; Raeburn, D.; Ratcliffe, A. J.; Souness, J. E.; Thurairatnam, S.; Vicker, N. Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs J. Med. Chem. 1994, 37, 1696-1703
23. Seebeck, T.; Sterk, G. J.; Ke, H. Phosphodiesterase inhibitors as a new generation of antiprotozoan drugs: exploiting the benefit of enzymes that are highly conserved between host and parasite Future Med. Chem. 2011, 3, 1289-1306
24. Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Sildenafil (Viagra), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824
25. Hirumi, H.; Martin, S.; Hirumi, K.; Inoue, N.; Kanbara, H.; Saito, A.; Suzuki, N. Cultivation of bloodstream forms of Trypanosoma brucei and T. evansi in a serum-free medium Trop. Med. Int. Health 1997, 2, 240-244
26. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res. 1997, 25, 3389-3402
27. Krieger, E.; Joo, K.; Lee, J.; Raman, S.; Thompson, J.; Tyka, M.; Baker, D.; Karplus, K. Improving physical realism, stereochemistry, and side-chain accuracy in homology modeling: four approaches that performed well in CASP8 Proteins 2009, 77 (Suppl. 9) 114-122
28. Laskowski, R. A.; Macarthur, M. W.; Moss, D. S.; Thornton, J. M. PROCHECK: A program to check the stereochemical quality of protein structures J. Appl. Crystallogr. 1993, 26, 283-291
29. Chen, V. B.; Arendall, W. B.; Headd, J. J.; Keedy, D. A.; Immormino, R. M.; Kapral, G. J.; Murray, L. W.; Richardson, J. S.; Richardson, D. C. MolProbity: all-atom structure validation for macromolecular crystallography Acta Crystallogr., Sect. D: Biol. Crystallogr. 2010, 66, 12-21
30. Eisenberg, D.; Luthy, R.; Bowie, J. U. VERIFY3D: Assessment of protein models with three-dimensional profiles Macromol. Crystallogr., Part B 1997, 277, 396-404
31. Braeunlich, G.; Fischer, R.; Es-sayed, M.; Henning, R.; Sperzel, M.; Schlemmer, K.-H.; Nielsch, U.; Tudhope, S.; Sturton, G.; Preparation of N -(3-benzofuranyl) ureas as antiinflammatory agents. Patent EP731099A1, 1996.
32. Gruenman, V.; Hoffer, M. 4-Benzyl-2-imidazolidinones from N -[(1-cyano-2-phenyl) ethyl] carbamates. US Patent US3923833A, 1975.