Screening-based discovery and structural dissection of a novel family 18 chitinase inhibitor

Journal of Biological Chemistry

Volumn 281, Issue 37, 2006, Pages 27278-27285

  Schüttelkopf, Alexander W ^a   Andersen, Ole A ^a   Rao, Francesco V ^a   Allwood, Matthew ^a   Lloyd, Clare ^b   Eggleston, Ian M ^a   Van Aalten, Daan M F ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CARBOHYDRATES; CELLS; X RAY CRYSTALLOGRAPHY;

CAFFEINE MOIETIES; CHEMOTHERAPEUTIC POTENTIAL; COMPLEX CHEMISTRY; STACKING INTERACTIONS; TRYPTOPHANS;

ENZYME INHIBITION;

1 [2 (THEOBROMIN 1 YL)ETHYL]THEOBROMINE; 3 METHYLXANTHINE; CAFFEINE; CAFFEINE DERIVATIVE; CHITINASE; CHITINASE INHIBITOR; ENZYME INHIBITOR; PENTOXIFYLLINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; DRUG BINDING; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

ALGORITHMS; ASPERGILLUS FUMIGATUS; BINDING SITES; BIOCHEMISTRY; CAFFEINE; CHITINASE; COMPUTATIONAL BIOLOGY; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; ESCHERICHIA COLI; MODELS, CHEMICAL; MODELS, MOLECULAR; TRYPTOPHAN;

MAMMALIA;

EID: 33748742696     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M604048200     Document Type: Article

References (37)

1. Thompson, J. D., Higgins, D. G., and Gibson, T. J. (1994) Nucleic Acids Res. 22, 4673-4680
2. Cabib, E., Silverman, S. J., and Shaw, J. A. (1992) J. Gen. Microbiol. 138, 97-102
3. Kuranda, M. J., and Robbins, P. W. (1991) J. Biol. Chem. 266, 19758-19767
4. Takaya, N., Yamazaki, D., Horiuchi, H., Ohta, A., and Takagi, M. (1998) Biosci. Biotechnol. Biochem. 62, 60-65
5. Hollak, C. E. M., van Weely, S., van Oers, M. H. J., and Aerts, J. M. F. G. (1994) J. Clin. Investig. 93, 1288-1292
6. Boot, R. G., Renkema, G. H., Verhoek, M., Strijland, A., Bliek, J., de Meulemeester, T. M. A. M. O., Mannens, M. M. A. M., and Aerts, J. M. F. G. (1998) J. Biol. Chem. 273, 25680-25685
7. Labadaridis, I., Dimitriou, E., Theodorakis, M., Kafalidis, G., Velegraki, A., and Michelakakis, H. (2005) Arch. Dis. Child. 90, F531-F532
8. Guo, Y., He, W., Boer, A. M., Wevers, R. A., de Bruijn, A. M., Groener, J. E., Hollak, C. E., Aerts, J. M., Galjaard, H., and van Diggelen, O. P. (1995) J. Inherit. Metab. Dis. 18, 717-722
9. Andersen, O. A., Dixon, M. J., Eggleston, I. M., and van Aalten, D. M. F. (2005) Nat. Prod. Rep. 22, 563-579
10. Izumida, H., Imamura, N., and Sano, H. (1996) J. Antibiot. 49, 76-80
11. Houston, D. R., Eggleston, I., Synstad, B., Eijsink, V. G. H., and van Aalten, D. M. F. (2002) Biochem. J. 368, 23-27
12. Arai, N., Shiomi, K., Yamaguchi, Y., Masuma, R., Iwai, Y., Turberg, A., Koelbl, H., and Omura, S. (2000) Chem. Pharm. Bull. 48, 1442-1446
13. Shiomi, K., Arai, N., Iwai, Y., Turberg, A., Koelbl, H., and Omura, S. (2000) Tetrahedron Lett. 41, 2141-2143
14. Houston, D. R., Shiomi, K., Arai, N., Omura, S., Peter, M. G., Turberg, A., Synstad, B., Eijsink, V. G. H., and van Aalten, D. M. F. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 9127-9132
15. Sakuda, S., Isogai, A., Matsumoto, S., Suzuki, A., and Koseki, K. (1986) Tetrahedron Lett. 27, 2475-2478
16. Terwisscha van Scheltinga, A. C., Armand, S., Kalk, K. H., Isogai, A., Henrissat, B., and Dijkstra, B. W. (1995) Biochemistry 34, 15619-15623
17. Rao, F. V., Houston, D. R., Boot, R. G., Aerts, J. M. F. G., Sakuda, S., and van Aalten, D. M. F. (2003) J. Biol. Chem. 278, 20110-20116
18. Rao, F. V., Houston, D. R., Boot, R. G., Aerts, J. M. F. G., Hodkinson, M., Adams, D. J., Shiomi, K., Omura, S., and van Aalten, D. M. F. (2005) Chem. Biol. 12, 65-76
19. Rao, F. V., Andersen, O. A., Vora, K. A., DeMartino, J. A., and van Aalten, D. M. F. (2005) Chem. Biol. 12, 973-980
20. Erlanson, D. A., McDowell, R. S., and O'Brien, T. (2004) J. Med. Chem. 47, 3463-3482
21. Carr, R. A. E., Congreve, M., Murray, C. W., and Rees, D. C. (2005) Drug Discov. Today 10, 987-992
22. Schüttelkopf, A. W., and van Aalten, D. M. F. (2004) Acta Crystallogr. Sect. D Biol. Crystallogr. 60, 1355-1363
23. Morris, G. M., Goodsell, D. S., Halliday, R., Huey, R., Hart, W. E., Belew, R. K., and Olson, A. J. (1998) J. Comp. Chem. 19, 1639-1662
24. Cavallaro, R. A., Filocamo, L., Galuppi, A., Galioni, A., Brufani, M., and Genazzani, A. A. (1999) J. Med. Chem. 42, 2527-2534
25. Leatherbarrow, R. J. (2001) GraFit, Version 5, Erithacus Software Ltd., Horley, UK
26. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
27. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. Sect. A 47, 110-119
28. Murshudov, G. N., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr. Sect. D Biol. Crystallogr. 53, 240-255
29. Hopkins, A. L., Groom, C. R., and Alex, A. (2004) Drug Discov. Today 9, 430-431
30. Gray, N., Detivaud, L., Doerig, C., and Meijer, L. (1999) Curr. Med. Chem. 6, 859-875
31. Chiosis, G., Lucas, B., Huezo, H., Solit, D., Basso, A., and Rosen, N. (2003) Curr. Cancer Drug Targets 3, 371-376
32. Braendvang, M., and Gundersen, L. L. (2005) Bioorg. Med. Chem. 13, 6360-6373
33. Vivet-Boudou, V., Didierjean, J., Isel, C., and Marquet, R. (2006) Cell. Mol. Life Sci. 63, 163-186
34. Fusetti, F., von Moeller, H., Houston, D., Rozeboom, H. J., Dijkstra, B. W., Boot, R. G., Aerts, J. M. F., and van Aalten, D. M. F. (2002) J. Biol. Chem. 277, 25537-25544
35. Perrakis, A., Tews, I., Dauter, Z., Oppenheim, A. B., Chet, I., Wilson, K. S., and Vorgias, C. E. (1994) Structure 2, 1169-1180
36. Kollman, P. (1993) Chem. Rev. 93, 2395-2417
37. Lipinski, C. A., Lombardo, F., Dominy, B. W., and Feeney, P. J. (1997) Adv. Drug Delivery Rev. 23, 3-25