Identification and characterization of acidic mammalian chitinase inhibitors

Journal of Medicinal Chemistry

Volumn 53, Issue 16, 2010, Pages 6122-6128

  Cole, Derek C ^a   Olland, Andrea M ^a   Jacob, Jaison ^a,b   Brooks, Jon ^a   Bursavich, Matthew G ^a,c   Czerwinski, Robert ^a   Declercq, Charlene ^a   Johnson, Mark ^a   Joseph Mccarthy, Diane ^a,d   Ellingboe, John W ^a   Lin, Laura ^a   Nowak, Pawel ^a   Presman, Ella ^a   Strand, James ^a   Tam, Amy ^a   Williams, Cara M M ^a   Yao, Shihua ^a   Tsao, Désirée H H ^a   Fitz, Lori J ^a  

^a PFIZER INC   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^c Myriad Pharmaceuticals   (United States)

^d ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 [4 [2 (4 BROMOPHENOXY)ETHYL]PIPERAZINE 1 YL] 1H 1,2,4 TRIAZOL 3 AMINE; ACIDIC MAMMALIAN CHITINASE INHIBITOR; CHITINASE; ENZYME INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; FEMALE; IC 50; LUNG LAVAGE; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SURFACE PLASMON RESONANCE; X RAY CRYSTALLOGRAPHY;

ALLERGENS; ANIMALS; BRONCHOALVEOLAR LAVAGE FLUID; CATALYTIC DOMAIN; CHITINASE; CRYSTALLOGRAPHY, X-RAY; FEMALE; HYDROPHOBICITY; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED C57BL; MODELS, MOLECULAR; PIPERAZINES; PROTEIN BINDING; RESPIRATORY HYPERSENSITIVITY; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PLASMON RESONANCE; TRIAZOLES;

EID: 77955874353     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100533p     Document Type: Article

References (44)

1. Holgate, S. T. Pathogenesis of asthma Clin. Exp. Allergy 2008, 38, 872-897
2. van Aalten, D. M.; Komander, D.; Synstad, B.; Gaseidnes, S.; Peter, M. G.; Eijsink, V. G. Structural insights into the catalytic mechanism of a family 18 exo-Chitinase Proc. Natl. Acad. Sci. U.S.A 2001, 98, 8979-8984
3. Zhu, Z.; Zheng, T.; Homer, R. J.; Kim, Y. K.; Chen, N. Y.; Cohn, L.; Hamid, Q.; Elias, J. A. Acidic mammalian chitinase in asthmatic Th2 inflammation and IL-13 pathway activation Science 2004, 304, 1678-1682
4. Homer, R. J.; Zhu, Z.; Cohn, L.; Lee, C. G.; White, W. I.; Chen, S.; Elias, J. A. Differential expression of chitinases identify subsets of murine airway epithelial cells in allergic inflammation Am. J. Physiol. Lung. Cell Mol. Physiol. 2006, 291, L502-L511
5. Follettie, M. T.; Ellis, D. K.; Donaldson, D. D.; Hill, A. A.; Diesl, V.; DeClercq, C.; Sypek, J. P.; Dorner, A. J.; Wills-Karp, M. Gene expression analysis in a murine model of allergic asthma reveals overlapping disease and therapy dependent pathways in the lung Pharmacogenomics J. 2006, 6, 141-152
6. Rao, F. V.; Houston, D. R.; Boot, R. G.; Aerts, J. M.; Sakuda, S.; van Aalten, D. M. Crystal structures of allosamidin derivatives in complex with human macrophage chitinase J. Biol. Chem. 2003, 278, 20110-20116
7. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A. Search for microbial insect growth regulators. II. Allosamidin, a novel insect chitinase inhibitor J. Antibiot. (Tokyo) 1987, 40, 296-300
8. Reese, T. A.; Liang, H. E.; Tager, A. M.; Luster, A. D.; Van Rooijen, N.; Voehringer, D.; Locksley, R. M. Chitin induces accumulation in tissue of innate immune cells associated with allergy Nature 2007, 447, 92-96
9. Chou, Y. T.; Yao, S.; Czerwinski, R.; Fleming, M.; Krykbaev, R.; Xuan, D.; Zhou, H.; Brooks, J.; Fitz, L.; Strand, J.; Presman, E.; Lin, L.; Aulabaugh, A.; Huang, X. Kinetic characterization of recombinant human acidic mammalian chitinase Biochemistry 2006, 45, 4444-4454
10. Olland, A. M.; Strand, J.; Presman, E.; Czerwinski, R.; Joseph-McCarthy, D.; Krykbaev, R.; Schlingmann, G.; Chopra, R.; Lin, L.; Fleming, M.; Kriz, R.; Stahl, M.; Somers, W.; Fitz, L.; Mosyak, L. Triad of polar residues implicated in pH specificity of acidic mammalian Chitinase Protein Sci. 2009, 18, 569-578
11. Fox, S.; Farr-Jones, S.; Sopchak, L.; Boggs, A.; Comley, J. High-throughput screening: searching for higher productivity J. Biomol. Screening 2004, 9, 354-358
12. Fox, S.; Farr-Jones, S.; Sopchak, L.; Boggs, A.; Nicely, H. W.; Khoury, R.; Biros, M. High-throughput screening: update on practices and success J. Biomol. Screening 2006, 11, 864-869
13. Keseru, G. M.; Makara, G. M. The influence of lead discovery strategies on the properties of drug candidates Nature Rev. Drug Discovery 2009, 8, 203-212
14. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nature Rev. Drug Discovery 2007, 6, 881-890
15. Hajduk, P. J.; Greer, J. A decade of fragment-based drug design: strategic advances and lessons learned Nature Rev. Drug Discovery 2007, 6, 211-219
16. Congreve, M.; Chessari, G.; Tisi, D.; Woodhead, A. J. Recent developments in fragment-based drug discovery J. Med. Chem. 2008, 51, 3661-3680
17. Fink, T.; Bruggesser, H.; Reymond, J. L. Virtual exploration of the small-molecule chemical universe below 160 Da Angew. Chem., Int. Ed. Engl. 2005, 44, 1504-1508
18. Hann, M. M.; Oprea, T. I. Pursuing the leadlikeness concept in pharmaceutical research Curr. Opin. Chem. Biol. 2004, 8, 255-263
19. Rees, D. C.; Congreve, M.; Murray, C. W.; Carr, R. Fragment-based lead discovery Nature Rev. Drug Discovery 2004, 3, 660-672
20. Wyss, D.; Eaton, H. L. Fragment-Based Approaches to Lead Discovery Front. Drug Des. Discovery 2007, 3, 171-202
21. Schade, M. NMR fragment screening: Advantages and applications IDrugs 2006, 9, 110-113
22. Neumann, T.; Junker, H. D.; Schmidt, K.; Sekul, R. SPR-based fragment screening: advantages and applications Curr. Top. Med. Chem. 2007, 7, 1630-1642
23. Perspicace, S.; Banner, D.; Benz, J.; Muller, F.; Schlatter, D.; Huber, W. Fragment-based screening using surface plasmon resonance technology J. Biomol. Screening 2009, 14, 337-349
24. Ockey, D. A.; Dotson, J. L.; Struble, M. E.; Stults, J. T.; Bourell, J. H.; Clark, K. R.; Gadek, T. R. Structure-activity relationships by mass spectrometry: identification of novel MMP-3 inhibitors Bioorg. Med. Chem. 2004, 12, 37-44
25. Nienaber, V. L.; Richardson, P. L.; Klighofer, V.; Bouska, J. J.; Giranda, V. L.; Greer, J. Discovering novel ligands for macromolecules using X-ray crystallographic screening Nature Biotechnol. 2000, 18, 1105-1108
26. Muegge, I. Synergies of virtual screening approaches Mini-Rev. Med. Chem. 2008, 8, 927-933
27. Joseph-McCarthy, D.; Baber, J. C.; Feyfant, E.; Thompson, D. C.; Humblet, C. Lead optimization via high-throughput molecular docking Curr. Opin. Drug Discovery Dev. 2007, 10, 264-274
28. Nair, M. G.; Gallagher, I. J.; Taylor, M. D.; Loke, P.; Coulson, P. S.; Wilson, R. A.; Maizels, R. M.; Allen, J. E. Chitinase and Fizz family members are a generalized feature of nematode infection with selective upregulation of Ym1 and Fizz1 by antigen-presenting cells Infect. Immun. 2005, 73, 385-394
29. Zhao, J.; Yeong, L. H.; Wong, W. S. Dexamethasone alters bronchoalveolar lavage fluid proteome in a mouse asthma model Int. Arch. Allergy Immunol. 2007, 142 (3) 219-229
30. Tomcufcik, A. S.; Meyer, W. E.; Dusza, J. P. 2-(Substituted-1- piperazinyl)-[1,2,4]triazolo[1,5- a ]pyrimidines. U.S. Patent 4,582,833, 1986.
31. Thunus, L.; Lapiere, C. L. 3-Disubstituted 2-(4-methyl-1-piperazinyl) pyridines Eur. J. Med. Chem. 1974, 9, 55-58
32. Joseph-McCarthy, D.; Thomas, B. E. t.; Belmarsh, M.; Moustakas, D.; Alvarez, J. C. Pharmacophore-based molecular docking to account for ligand flexibility Proteins 2003, 51, 172-188
33. Joseph-McCarthy, D.; Alvarez, J. C. Automated generation of MCSS-derived pharmacophoric DOCK site points for searching multiconformation databases Proteins 2003, 51, 189-202
34. Joseph-McCarthy, D. M., I. J.; Zou, J.; Walker, G.; Alvarez, J. C. Pharmacophore-Based Molecular Docking: A Practical Guide; Marcel Dekker: New York, 2005; pp 327 - 347.
35. Ewing, T. J.; Makino, S.; Skillman, A. G.; Kuntz, I. D. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases J. Comput.-Aided Mol. Des. 2001, 15, 411-428
36. Rush, T.; I., E.S. Manas; Tawa, G.J.; Alvarez, J.C. Solvation-Based Scoring for High Throughput Docking; Marcel Dekker: New York, 2005; pp 249 - 278.
37. Thompson, D. C.; Humblet, C.; Joseph-McCarthy, D. Investigation of MM-PBSA rescoring of docking poses J. Chem. Inf. Model. 2008, 48, 1081-1091
38. Mayer, M.; Meyer, B. Characterization of ligand binding by saturation transfer difference NMR spectroscopy Angew. Chem., Int. Ed. Engl. 1999, 38, 1784-1788
39. Myszka, D. G. Survey of the 1998 optical biosensor literature J. Mol. Recognit. 1999, 12, 390-408
40. Frostell-Karlsson, A.; Remaeus, A.; Roos, H.; Andersson, K.; Borg, P.; Hamalainen, M.; Karlsson, R. Biosensor analysis of the interaction between immobilized human serum albumin and drug compounds for prediction of human serum albumin binding levels J. Med. Chem. 2000, 43, 1986-1992
41. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode Methods Enzymol. 1997, 276, 307-326
42. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Crystallography & NMR system: aA new software suite for macromolecular structure determination Acta. Crystallogr., Sect. D: Biol. Crystallogr. 1998, 54, 905-921
43. CCP4 The CCP4 suite: programs for protein crystallography Acta. Crystallogr., Sect. D: Biol. Crystallogr. 1994, 50, 760-763
44. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta. Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132