Phage display screening for peptidic chitinase inhibitors

Journal of Molecular Recognition

Volumn 21, Issue 6, 2008, Pages 401-409

  Petter, Cordula ^a   Scholz, Christa ^a   Wessner, Helga ^a   Hansen, Gerd ^a   Henklein, Peter ^a   Watanabe, Takeshi ^b   Höhne, Wolfgang ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

^b NIIGATA UNIVERSITY   (Japan)

Author keywords

Affinity optimization; Chitinase; Peptide inhibitors; Peptide spot synthesis; Phage display

Indexed keywords

CHITINASE; ENZYME INHIBITOR; PEPTIDE LIBRARY;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; KINETICS;

CHITINASE; ENZYME INHIBITORS; KINETICS; PEPTIDE LIBRARY;

SERRATIA MARCESCENS;

EID: 56749168846     PISSN: 09523499     EISSN: 10991352     Source Type: Journal    
DOI: 10.1002/jmr.911     Document Type: Article

References (44)

1. van Aalten DMF, Synstad B, Bruberg MB, Hough E, Riise BW, Eijsink VGH, Wierenga RK. 2000. Structure of a two domain chitotriosidase from Serratia marcescens at 1.9Å resolution. Proc. Natl. Acad. Sci. 97: 5842-5847.
2. Andersen OA, Dixon MJ, Eggleston IM, van Aalten DM. 2005. Natural product family 18 chitinase inhibitors. Nat. Prod. Rep. 22: 563-579.
3. Arai N, Shiomi K, Yamaguchi Y, Masuma R, Iwai Y, Turberg A, Kölbl H, Omura S. 2000. Argadin, a new chitinase inhibitor, produced by Clonostachys sp. FO-7314. Chem. Pharm. Bull. 48: 1442-1446.
4. Brurberg MB, Nes IF, Eijsink GH. 1996. Comparative studies of chitinase A and B from Serratia marcescens. Microbiology 146: 1581-1589.
5. Choi EH, Zimmerman PA, Foster CB, Zhu S, Kumaraswami V, Nutman TB, Chanock SJ. 2001. Genetic polymorphisms in molecules of innate immunity and susceptibility to infection with Wuchereria bancrofti in south India. Genes Immun. 2: 248-253.
6. Donnelly LE, Barnes PJ. 2004. Acidic mammalian chitinase - a potential target for asthma therapy. Trends Pharmacol. Sci. 25: 509-511.
7. Dupont J, Tanwar MK, Thaler HT, Fleisher M, Kauff N, Hensley ML, Sabbatini P, Anderson S, Aghajanian C, Holland EC, Spriggs D. 2004. Early detection and prognosis of ovarian cancer using serum YKL-40. J. Clin. Oncol. 22: 3330-3339.
8. Elias JA, Homer RJ, Hamid Q, Lee CG. 2005. Chitinases and chitinase-like proteins in T(H)2 inflammation and asthma. J. Allergy Clin. Immunol. 116: 497-500.
9. Germer A, Mugge C, Peter M-G, Rottmann A, Kleinpeter E. 2003. Solutionand bound-state conformational study of N,N′,N″-triacetyl chitotriose and other analogous potential inhibitors of hevamine: application of trNOESY and STD NMR spectroscopy. Chem. Eur. J. 9: 1964-1973.
10. Giraldo P, Cenarro A, Alfonso P, Perez-Calvo JI, Rubio-Felix D, Giralt M, Pocovi M. 2001. Chitotriosidase genotype and plasma activity in patients with type 1 Gaucheŕs disease and their relatives (carriers and non-carriers). Haematol. 86: 977-984.
11. Hilpert K, Hansen G, Wessner H, Schneider-Mergener J, Höhne W. 2000. Characterizing and optimizing protease/peptide inhibitor interactions, a new application for spot synthesis. J. Biochem. (Japan) 128: 1051-1057.
12. Hollis T, Monzingo AF, Bortone K, Ernst S, Cox R, Robertus JD. 2000. The X-ray structure of a chitinase from the pathogenic fungus Coccidioides immitis. Protein Sci. 9: 544-551.
13. Honda Y, Kitaoka M, Tokuyasu K, Sasaki C, Fukamizo T, Hayashi K. 2003. Kinetic studies on the hydrolysis of N-acetylated and N-deacetylated derivatives of 4!methylumbelliferyl chitobioside by the family 18 chitinases ChiA and ChiB from Serratia marcescens. J. Biochem. (Japan) 133: 253-258.
14. Houston DR, Shiomi K, Arai N, Omura S, Peter MP, Turberg A, Synstad B, Eijsink VGH, van Aalten DMF. 2002. High-resolution structures of a chitinase complexed with natural product cyclopentapeptide inhibitors: mimicry of carbohydrat substrate. Proc. Natl. Acad. Sci. U.S.A. 99: 9127-9132.
15. Houston DR, Synstad B, Eijsink VGH, Stark MJR, Eggleston IM, van Aalten DMF. 2004. Structure-based exploration of cyclic dipeptide chitinase inhibitors. J. Med. Chem. 47: 5713-5720.
16. Izumida H, Nishijima M, Takadera T, Nomoto AM, Sano H. 1996a. The effect of chitinase inhibitors, cyclo(Arg-Pro) against cell separation of Saccharomyces cerevisiae and the morphological change of Candida albicans. J. Antibiot. (Tokyo) 49: 829-831.
17. Izumida H, Imamura N, Sano H. 1996b. A novel chitinase inhibitor from a marine bacterium, Pseudomonas sp. J. Antibiot. 49: 76-80.
18. Johnson MA, Pinto BM. 2002. Molecular mimicry of carbohydrates by peptides. Aust. J. Chem. 55: 13-25.
19. Kramer A, Schuster A, Reinecke U, Malin R, Volkmer-Engert R, Landgraf C, Schneider-Mergener J. 1994. Combinatorial cellulose-bound peptide libraries: screening tools for the identification of peptides that bind ligands with predefined specificity. Comp. Methods Enzymol. 6: 388-395.
20. Kramer A, Schneider-Mergener J. 1998. Synthesis and screening of peptide libraries on continuous cellulose membrane supports. Methods Mol. Biol. 87: 25-39.
21. Ladner RC, Sato AK, Gorzelany J, de Souza M. 2004. Phage display derived peptides as therapeutic alternatives to antibodies. Drug Discov. Today 9: 525-529.
22. Loiseau PM, Bories C, Sanon A. 2002. The chitinase system from Trichomonas vaginalis as a potential target for antimicrobial therapy of urogenital trichomoniasis. Biomed. Pharmacother. 56: 503-510.
23. Malaguarnera L, Simpore J, Prodi DA, Angius A, Sassu A, Persico I, Barone R, Musumeci S. 2003. A 24-bp duplication in exon 10 of human chitotriosidase gene from the sub-Saharan to the Mediterranean area; role of parasitic diseases and environmental conditions. Genes Immun. 4: 570-574.
24. Malaguarnera L, Rosa MD, Zambito AM, dell'Ombra N, Marco RD, Malaguarnera M. 2006. Potential role of chitotriosidase gene in nonalcoholic fatty liver disease evolution. Am. J. Gastroenterol. 101: 2060-2069.
25. Molano J, Duran A, Cabib E. 1977. A rapid and sensitive assay for chitinase using tritiated chitin. Anal. Biochem. 83: 648-656.
26. Omura S, Arai N, Yamaguchi Y, Masuma R, Iwai Y, Namkoshi M, Turberg A, Kölbl H, Shiomi K. 2000. Argifin, a new chitinase inhibitor, produced by Gliocladium sp. FTD-0668, I. Taxonomy, fermentation, and biological activities. J. Antibiot. 53: 603-608.
27. Perrakis A, Wilson KS, Chet I, Oppenheim AB, Vorgias CE. 1993. Phylogenetic relationchips of chitinases. RRA, Editor, Chitin Enzymology. European Chitin Society, Ancona. Italy; 217-232.
28. Perrakis A, Tews I, Dauter Z, Oppenheim AB, Chet I, Wilson KS, Vorgias CE. 1994. Crystal structure of a bacterial chitinase at 2.3 Å resolution. Structure 2: 1169-1180.
29. Rao FV, Houston DR, Boot RG, Aerts JMFG, Sakuda S, van Aalten DMF. 2003. Crystal structures of allosamidin derivatives in complex with human macrophage chitinase. J. Biol. Chem. 278: 20110-20116.
30. Rao FV, Houston DR, Boot RG, Aerts JMFG, Hodkinson M, Adams DJ, Shiomi K, Omura S, van Aalten DMF. 2005. Specificity and affinity of natural product cyclopentapeptide inhibitors against A. fumigatus, human, and bacterial chitinases. Chem. Biol. 12: 65-76.
31. Sakuda S, Isogai A, Matsumoto S, Suzuki A. 1986. The structure of allosamidin, a novel insect chitinase inhibitor, produced by Streptomyces sp. Tetrahedron Lett. 27: 2475-2478.
32. Sakuda S, Nishimoto Y, Ohi M, Watanabe M, Takayama S, Isogai A, Yamada Y. 1990. Effects of demethylallosamidin, a potent yeast chitinase inhibitor, on cell division of yeast. Arig. Biol. Chem. 54: 1333-1335.
33. Shahabuddin M, Toyoshima T, Aikawa M, Kaslow DC. 1993. Transmission-blocking activity of a chitinase inhibitor and activation of malarial parasite chitinase by mosquito protease. Proc. Natl. Acad. Sci. USA 90: 4266-4270.
34. Sidhu SS. 2001. Engineering M13 for phage display. Biomol. Eng. 18: 57-63.
35. Smith GP. 1985. Filamentous fusion phage: novel expression vectors that display cloned antigens on the virion surface. Science 228: 1315-1317.
36. Smith GP, Petrenko VA. 1997. Phage display. Chem. Rev. 97: 391-410.
37. Spindler K-D, Spindler-Barth M. 1999. Inhibitors of chitinases. In Chitin and Chitinases, Jolles P, Muzzarelli RAA (eds). Birkhäuser Verlag: Basel; 201-209.
38. van Steijn GJ, Amerongen AV, Veerman EC, Kasanmoentalib S, Overdijk B. 2002. Effect of periodontal treatment on the activity of chitinase in whole saliva of periodontitis patients. J. Periodontal Res. 37: 245-249.
39. Suzuki K, Taiyoji M, Sugawara N, Nikaidou N, Henrissat B, Watanabe T. 1999. The third chitinase gene (chiC) of Serratia marcescens 2170 and the relationship of its product to other bacterial chitinases. Biochem. J. 343: 587-596.
40. Suzuki K, Sugawara N, Suzuki M, Uchiyama T, Ktouno F, Nikaidou N, Watanabe T. 2002. Chitinases A, B, and C1 of Serratia marcescens 2170 produced by recombinant Escherichia coli: enzymatic properties and synergism on chitin degradation. Biosci. Biotechnol. Biochem. 66: 1075-1083.
41. Uchiyama T, Katouno F, Nikaidou N, Nonaka T, Sugiyama J, Watanabe T. 2001. Roles of exposed residues in crystalline chitin hydrolysis by chitinase A from Serratia marcescens 2170. J. Biol. Chem. 276: 41343-41349.
42. Vaaje-Kolstad G, Vasella A, Peter MG, Netter C, Houston DR, Westereng B, Synstad B, Eisink VG, van Aalten DM. 2004. Interactions of a family 18 chitinase with the designed inhibitor HM508 and its degradation product, chitobiono-delta-lactone. J. Biol. Chem. 279: 3612-3619.
43. Vos K, Steenbakkers P, Miltenburg AM, Bos E, van den Heuvel MW, van Hogezand RA, De Vries RRP, Breedveld FC, Boots AMH. 2000. Raised human cartilage glycoprotein-39 plasma levels in patients with rheumatoid arthritis and other inflammatory conditions. Ann. Rheum. Dis. 59: 544-548.
44. Zhu Z, Zheng T, Homer RJ, Kim Y, Chen NY, Hamid Q, Elias JA. 2004. Acidic mammalian chitinase in asthmatic Th2 inflammation and IL-13 pathway activation. Science 304: 1678-1682.