New chromogenic substrates of human neutrophil cathepsin G containing non-natural aromatic amino acid residues in position P1 selected by combinatorial chemistry methods

Molecular Diversity

Volumn 11, Issue 2, 2007, Pages 93-99

  Wysocka, Magdalena ^a   Łȩgowska, Anna ^a   Bulak, Elzbieta ^a   Jaśkiewicz, Anna ^a   Miecznikowska, Hanna ^a   Lesner, Adam ^a   Rolka, Krzysztf ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Cathepsin G; Chromogenic substrates; Peptidomimetics

Indexed keywords

AROMATIC AMINO ACID; CATHEPSIN G; CHROMOGENIC SUBSTRATE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; COMBINATORIAL CHEMISTRY; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; NEUTROPHIL; PRIORITY JOURNAL; SYNTHESIS;

AMINO ACIDS, AROMATIC; BIOMIMETICS; CATHEPSINS; CHROMOGENIC COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; HUMANS; MODELS, BIOLOGICAL; NEUTROPHILS; PEPTIDE LIBRARY; SERINE ENDOPEPTIDASES; SUBSTRATE SPECIFICITY;

EID: 36148992208     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-007-9063-7     Document Type: Article

References (25)

1. Wa̧torek W, Farley D, Salvasen G and Travis J (1988). Neutrophil elastase and cathepsin G: structure, function and biological control. Adv Exp Med Biol 240: 23-31
2. Campbell EJ, Silverman EK and Campbell MA (1989). Elastase and cathepsin G of human monocytes. Quantification of cellular content, release in response to stimuli, and heterogeneity in elastase-mediated proteolytic activity. J Immunol 143: 2961-2968
3. Shafer WM, Katzif S, Bowers S, Fallon M, Hubalek M, Reed MS, Veprek P and Pohl J (2002). Tailoring an antibacterial peptide of human lysosomal cathepsin G to enhance its broad-spectrum action against antibiotic-resistant bacterial pathogens. Curr Pharm Des 8: 695-702
4. Yamazaki T and Aoki Y (1998). Cathepsin G enhances human natural killer cytotoxicity. Immunology 93: 115-121
5. Schechter NM, Wang ZM, Blacher RW, Lessin SR, Lazarus GS and Rubin H (1994). Determination of the primary structures of human skin chymase and cathepsin G from cutaneous mast cells of urticaria pigmentosa lesions. J Immunol 152: 4062-4069
6. Duranton J, Adam C and Bieth JG (1998). Kinetic mechanism of the inhibition of cathepsin G by alpha 1-antichymotrypsin and alpha 1-proteinase inhibitor. Biochemistry 37: 11239-11245
7. Zamolodchikova TS, Vorotyntseva TI and Antonov VK (1995). Duodenase, a new serine protease of unusual specificity from bovine duodenal mucosa. Purification and properties. Eur J Biochem 227: 866-872
8. Tsu CA, Perona JJ, Schellenberger V, Turck CW and Craik CS (1996). The substrate specificity of Uca pugilator collagenolytic serine protease 1 correlates with the bovine type I collagen cleavage sites. J Biol Chem 269: 19565-16572
9. Hof P, Mayr I, Huber R, Korzus E, Potempa J, Travis J, Powers JC and Bode W (1996). The 1.8 A crystal structure of human cathepsin G in complex with Suc-Val-Pro-PheP-(OPh)2: a Janus-faced proteinase with two opposite specificities. EMBO J 15: 5481-5491
10. Hojo K, Maeda M, Iguchi S, Smith T, Okamoto H and Kawasaki K (2000). Amino acids and peptides. XXXV. Facile preparation of p-nitroanilide analogs by the solid-phase method. Chem Pharm Bull 48: 1740-1745
11. Zabłlotna E, Dysasz H, Lesner A, Jaśkiewicz A, Kaźmierczak K, Miecznikowska H and Rolka K (2004). A simple method for selection of trypsin chromogenic substrates using combinatorial chemistry approach. Biochem Biophys Res Commun 319: 185-188
12. Kaźmierczak K, Zabłlotna E, Jaśkiewicz A, Miecznikowska H and Rolka K (2003). Selection of low-molecular-mass trypsin and chymotrypsin inhibitors based on the binding loop of CMTI-III using combinatorial chemistry methods. Biochem Biophys Res Commun 310: 811-814
13. Sole NA and Barany G (1992). Optimization of solid-phase synthesis of [Ala8]-dynorphin A. J Org Chem 57: 5399-5403
14. Hougten RH, Pinilla C, Blondelle SE, Appel JR, Dooley CT and Cuervo JH (1991). Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery. Nature 354: 84-90
15. Furka A, Sebestyn F, Asgedom M and Dib G (1991). General method for rapid synthesis of multicomponent peptide mixtures. Int J Pept Protein Res 37: 487-494
16. Wysocka M, Kwiatkowska B, Rzadkiewicz M, Lesner A and Rolka K. (2007). Selection of new chromogenic substrates of serine proteinases using combinatorial chemistry methods. Comb Chem High Trough S 3: 171-180
17. Ostresh JM, Blondelle SE, Dorner B and Houghten RA (1996). Generation and use of nonsupport-bound peptide and peptidomimetic combinatorial libraries. Methods Enzymol 267: 220-228
18. Baugh RJ and Travis J (1976). Human leukocyte granule elastase: rapid isolation and characterization. Biochemistry 15: 836-841
19. Furlong ST, Mauger RC, Strimpler AM, Liu YP, Morris FX and Edwards PD (2002). Synthesis and physical characterization of a P1 arginine combinatorial library, and its application to the determination of the substrate specificity of serine peptidases. Bioorg Med Chem 10: 3637-3650
20. Lesner A, Brzozowski K, Kupryszewski G and Rolka K (2000). Design, chemical synthesis and kinetic studies of trypsin chromogenic substrates based on the proteinase binding loop of Cucurbita maxima trypsin inhibitor (CMTI-III). Biochem Biophys Res Commun 269: 81-85
21. Lesner A, Kupryszewski G and Rolka K (2001). Chromogenic substrates of bovine beta-trypsin: the influence of an amino acid residue in P1 position on their interaction with the enzyme. Biochem Biophys Res Commun 285: 1350-1354
22. Tanaka T, Minematsu Y, Reilly CF, Travis J and Powers JC (1985). Human leukocyte cathepsin G. Subsite mapping with 4-nitroanilides, chemical modification, and effect of possible cofactors. Biochemistry 24: 2040-2047
23. Powers JC, Tanaka T, Harper JW, Minematsu Y, Barker L, Lincoln D, Crumley KV, Fraki JE, Schechter NM and Lazarus GG (1985). Mammalian chymotrypsin-like enzymes. Comparative reactivities of rat mast cell proteases, human and dog skin chymases, and human cathepsin G with peptide 4-nitroanilide substrates and with peptide chloromethyl ketone and sulfonyl fluoride inhibitors. Biochemistry 24: 2048-2058
24. Polanowska J, Krokoszynska I, Czapinska H, Watorek W, Dadlez M and Otlewski J (1998). Specificity of human cathepsin G. Biochim Biophys Acta 1386: 189-198
25. Gosalia DN, Salisbury CM, Ellman JA and Diamond SL (2005). High throughput substrate specificity profiling of serine and cysteine proteases using solution-phase fluorogenic peptide microarrays. Mol Cell Proteomics 4: 626-636