Structure-based exploration of cyclic dipeptide chitinase inhibitors

Journal of Medicinal Chemistry

Volumn 47, Issue 23, 2004, Pages 5713-5720

  Houston, Douglas R ^a   Synstad, Bjørnar ^b   Eijsink, Vincent G H ^b   Stark, Michael J R ^a   Eggleston, Ian M ^a   Van Aalten, Daan M F ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b NORWEGIAN UNIVERSITY OF LIFE SCIENCES   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOSAMIDIN; ARGADIN; CHITINASE; CYCLO(ARGYNYL DEXTRO PROLINE); CYCLO(ARGYNYLPROLINE); CYCLO(GLYCERYLPROLINE); CYCLO(HISTIDYLPROLINE); CYCLO(TYROSYLPROLINE); DIPEPTIDE; GLYCOSIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BINDING; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; SACCHAROMYCES CEREVISIAE; SERRATIA MARCESCENS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

CHITINASE; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; PIPERAZINES; SACCHAROMYCES CEREVISIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 7544238813     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049940a     Document Type: Article

References (34)

1. Huber, M.; Cabib, E.; Miller, L. H. Malaria parasite chitinase and penetration of the mosquito peritrophic membrane. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2807-2810.
2. Vinetz, J. M.; Dave, S. K.; Specht, C. A.; Brameld, K. A.; Xu, B.; Hayward, R.; Fidock, D. A. The chitinase PfCHT1 from the human malaria parasite Plasmodium falciparum lacks proenzyme and chitin-binding domains and displays unique substrate preferences. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14061-14066.
3. Dickinson, K.; Keer, V.; Hitchcock, C. A.; Adams, D. J. Chitinase activity from candida-albicans and its inhibition by allosamidin. J. Gen. Microbiol. 1989, 735, 1417-1421.
4. Cohen, E. Chitin synthesis and degradation as targets for pesticide action. Arch. Insect Biochem. Physiol. 1993, 22, 245-261.
5. Arnold, K.; Brydon, L. J.; Chappell, L. H.; Gooday, G. W. Chitinolytic activities in heligmosomoides-polygyrus and their role in egg hatching. Mol. Biochem. Parasitol. 1993, 58, 317-323.
6. Villagomezcastro, J. C.; Calvomendez, C.; Lopezromero, E. Chitinase activity in encysting entamoeba-invadens and its inhibition by allosamidin. Mol. Biochem. Parasitol. 1992, 52, 53-62.
7. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K. The structure of allosamidin, a novel insect chitinase inhibitor produced by Streptomyces sp. Tetrahedron Lett. 1986, 27, 2475-2478.
8. VillagomezCastro, J. C.; LopezRomero, E. Identification and partial characterization of three chitinase forms in Entamoeba invadens with emphasis on their inhibition by allosamidin. Antonie Van Leeuwenhoek 1996, 70, 41-48.
9. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A. Search for microbial insect growth-regulators. 2. Allosamidin, a novel insect chitinase inhibitor. J. Antibiot. 1987, 40, 296-300.
10. Tsai, Y.-L.; Hayward, R. E.; Langer, R. C.; Fidock, D. A.; Vinetz, J. M. Disruption of Plasmodium falciparum chitinase markedly impairs parasite invasion of mosuito midgut. Infect. Immun. 2001, 69, 4048-4054.
11. Sakuda, S. Studies on the chitinase inhibitors, allosamidins, volume 2 of Chitin Enzymology; Atec Edizioni: 1996; p 203-212.
12. Berecibar, A.; Grandjean, C.; Siriwardena, A. Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: mannostatins, trehazolin, allosamidins and their analogues. Chem. Rev. 1999, 99, 779-844.
13. Arai, N.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Iwai, Y.; Turberg, A.; Koelbl, H.; Omura, S. Argadin, a new chitinase inhibitor, produced by Clonostachys sp. FO-7314. Chem. Pharm. Bull. 2000, 48, 1442-1446.
14. Shiomi, K.; Arai, N.; Iwai, Y.; Turberg, A.; Koelbl, H.; Omura, S. Structure of argifin, a new chitinase inhibitor produced by Gliocladium sp. Tetrahedron Lett. 2000, 41, 2141-2143.
15. Blattner, R.; Furneaux, R. H.; Lynch, G. P. Synthesis of allosamidin analogues. Carbohydrate Res. 1996, 296, 29-40.
16. Nishimoto, Y.; Sakuda, S.; Takayama, S.; Yamada, Y. Isolation and characterization of new allosamidins. J. Antibiot. 1991, 44, 716-722.
17. Kato, T.; Shizuri, Y.; Izumida, H.; Yokoyama, A.; Endo, M. Styloguanidines, new chitinase inhibitors from the marine sponge Stylotella aurantium. Tetrahedron Lett. 1995, 36, 2133-2136.
18. Izumida, H.; Imamura, N.; Sano, H. A novel chitinase inhibitor from a marine bacterium Pseudomonas sp. J. Antibiot. 1996, 49, 76-80.
19. Takadera, T.; Nomoto, A.; Izumida, H.; Nishijima, M.; Sano, H. The effect of chitinase inhibitors, cyclo(Arg-Pro) against cell separation of Saccharomyces cerevisiae and the morphological change of Candida albicans. J. Antibiot. 1996, 49, 829-831.
20. Terwisscha, A.; van Scheltinga, C.; Armand, S.; Kalk, K. H.; Isogai, A.; Henrissat, B.; Dijkstra, B. W. Stereochemistry of chitin hydrolysis by a plant Chitinase/lysozyme and X-ray structure of a complex with allosamidin. Biochemistry 1995, 34, 15619-15623.
21. Tews, I.; Terwisscha van Scheltinga, A. C.; Perrakis, A.; Wilson, K. S.; Dijkstra, B. W. Substrate-assisted catalysis unifies two families of chitinolytic enzymes. J. Am. Chem. Soc. 1997, 119, 7954-7959.
22. Brameld, K. A.; Goddard, W. A. Substrate distortion to a boat conformation at subsite - 1 is critical in the mechanism of family 18 chitinases. J. Am. Chem. Soc. 1998, 120, 3571-3580.
23. van Aalten, D. M. F.; Komander, D.; Synstad, B.; GÅseidnes, S.; Peter, M. G.; Eijsink, V. G. H. Structural insights into the catalytic mechanism of a family 18 exo-chitinase. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 8979-8984.
24. Houston, D. R.; Eggleston, I.; Synstad, B.; Eijsink, V. G. H.; van Aalten, D. M. F. The cyclic dipeptide CI-4 inhibits family 18 chitinases by structural mimicry of a reaction intermediate. Biochem. J. 2002, 368, 23-27.
25. Houston, D. R.; Shiomi, K.; Arai, N.; Omura, S.; Peter, M. G.; Turberg, A.; Synstad, B.; Eijsink, V. G. H.; van Aalten, Ü. M. F. High-resolution structures of a chitinase complexed with natural product cyclopentapeptide inhibitors: Mimicry of carbohydrate substrate. Proc. Natl. Acad. Sci., U.S.A. 2002, 99, 9127-9132.
26. Kuranda, M. J.; Robbins, P. W. Chitinase is required for cell-separation during growth of Saccharomyces ceremsiae. J. Biol. Chem. 1991, 266, 19758-19767.
27. Sakuda, S.; Nishimoto, Y.; Ohi, M.; Watanabe, M.; Takayama, S.; Isogai, A.; Yamada, Y. Effects of demethylallosamidin, a potent yeast chitinase inhibitor, on the cell-division of yeast. Agr. Biol. Chem. Tokyo 1990, 54, 1333-1335.
28. Takaya, N.; Yamazaki, D.; Horiuchi, H.; Ohta, A.; Takagi, M. Cloning and characterization of a chitinase-encoding gene chiA from Aspergillus nidulans, disruption of which decreases germination frequency and hyphal growth. Biosci. Biotechnol. Biochem. 1998, 62, 60-65.
29. Brurberg, M. B.; Nes, I. F.; Eijsink, V. G. H. Comparative studies of chitinases A and B from Serratia marcescens. Microbiology 1996, 142, 1581-1589.
30. van Aalten, D. M. F.; Synstad, B.; Brurberg, M. B.; Hough, E.; Riise, B. W.; Eijsink, V. G. H.; Wierenga, R. K. Structure of a two-domain chitotriosidase from Serratia marcescens at 1.9 Å resolution. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 5842-5847.
31. Brunger, A. T.; Adams, P. D.; Clore, G. M.; 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 and NMR system: A new software system for macromolecular structure determination. Acta Crystallogr. 1998, D54, 905-921.
32. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron density maps and the location of errors in these models. Acta Crystallogr. 1991, A47, 110-119.
33. Kleywegt, G. J.; Henrick, K.; Dodson, E. J.; van Aalten, D. M. F. Pound-wise but penny-foolish: How well do micromolecules fare in macromolecular refinement? Structure 2003, 11, 1051-1059.
34. Schuettelkopf, A. W.; van Aalten, D. M. F. PRODRG: A tool for high-throughput crystallography. Acta Crystallogr. 2004, D60, 1355-1363.