Fluorogenic peptide substrates containing benzoxazol-5-yl-alanine derivatives for kinetic assay of cysteine proteases

Analytical Biochemistry

Volumn 342, Issue 1, 2005, Pages 20-27

  Szabelski, Mariusz ^a   Rogiewicz, Monika ^a   Wiczk, Wiesław ^a  

^a UNIVERSITY OF GDA SK   (Poland)

Author keywords

Benzoxazole; Cathepsin B; Fluorogenic peptide; Papain; Protease substrate

Indexed keywords

ENERGY TRANSFER; ENZYME ACTIVITY; FLUORESCENCE; HYDROLYSIS; KINETIC PARAMETERS; NITROGEN OXIDES; PAPAIN; PEPTIDES; SUBSTRATES;

ALANINE DERIVATIVES; BENZOXAZOLE; CATHEPSIN B; DONOR-ACCEPTOR PAIRS; ENZYMATIC PROCESS; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUOROGENICS; PEPTIDE SUBSTRATES;

AMINO ACIDS;

3 [2 (1 METHYOXYNAPHTHALEN 4 YL)BENZOXAZOL 5 YL]ALANINE; 3 [2 (2 BENZOFURANYL)BENZOXAZOL 5 YL]ALANINE; 3 [2 (4 PYRIDYL)BENZOXAZOL 5 YL]ALANINE; ALANINE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CARBOXYPEPTIDASE; CYSTEINE PROTEINASE; PAPAIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME SUBSTRATE; FLUORESCENCE RESONANCE ENERGY TRANSFER; HYDROLYSIS; PRIORITY JOURNAL; PROTEIN PROCESSING;

EID: 20444423312     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ab.2005.04.014     Document Type: Article

References (45)

1. A.J. Barrett Classification of peptidases Methods Enzymol. 244 1994 1 15
2. B.S. Hartley Proteolytic enzymes Annu. Rev. Biochem. 29 1960 45 72
3. P.J. Berti, and A.C. Storer Alignment/Phylogeny of the papain superfamily of cysteine proteases J. Mol. Biol. 246 1995 273 283
4. H. Kirschke, A.J. Barrett, and N.D. Rawlings Proteinases 1: Lysosomal cysteine proteinases Protein Profile 2 1995 1581 1643
5. F. Authier, B.I. Posner, and J.J. Bergeron Endosomal proteolysis of internalized proteins FEBS Lett. 389 1996 55 60
6. H. Kakegawa, T. Nikawa, K. Tagami, H. Kamioka, K. Sumitani, T. Kawata, M. Drobnic-Kosorok, B. Lenarcic, V. Turk, and N. Katunuma Participation of cathepsin L on bone resorption FEBS Lett. 321 1993 247 250
7. R.E. Esser, R.A. Angelo, M.D. Murphey, L.M. Watt, L.P. Thornburg, J.T. Palmer, J.W. Talhouk, and R.E. Smith Cysteine proteinase inhibitors decrease articular cartilage and bone destruction in chronic inflammatory arthritis Arthritis Rheum. 37 1994 236 247
8. M.J. Duffy Inhibiting tissue invasion and metastasis as targets for cancer therapy Biotherapy 4 1992 45 52
9. E. Kominami, I. Kunio, and N. Katunuma Activation of the intramyofibral autophagic-lysosomal system in muscular dystrophy Am. J. Pathol. 127 1987 461 466
10. A.A. Gershkovich, and V.V. Kholodovych Fluorogenic substrates for proteases based on intramolecular fluorescence energy transfer (IFETS) J. Biochem. Biophys. Methods 33 1996 135 162
11. P.M.St. Hilaire, M. Willert, M.A. Juliano, L. Juliano, and M. Meldal Fluorescence-quenched solid phase combinatorial libraries in the characterization of cysteine protease substrate specificity J. Comb. Chem. 1 1999 509 523
12. D.K. Nägler, W. Tam, A.C. Storer, J.C. Krupa, J.S. Mort, and R. Ménard Interdependency of sequence and positional specificities for cysteine proteases of the papain family Biochemistry 38 1999 4868 4874
13. S.S. Cotrin, L. Puzer, W.A. Judice, L. Juliano, A.K. Carmona, and M.A. Juliano Positional-scanning combinatorial libraries of fluorescence resonance energy transfer peptides to define substrate specificity of carboxydipeptidases: Assays with human cathepsin B Anal. Biochem. 335 2004 244 252
14. W.A.S. Judice, L. Puzer, S.S. Cotrin, A.K. Carmona, G.H. Coombs, L. Juliano, and M.A. Juliano Carboxydipeptidase activities of recombinant cysteine peptidases cruzain of Trypanosoma cruzi and CPB of Leishmania mexicana Eur. J. Biochem. 271 2004 1046 1053
15. K. Stachowiak, M. Tokmina, A. Karpiñska, R. Sosnowska, and W. Wiczk Fluorogenic peptide substrates for carboxydipeptidase activity of cathepsin B Acta Biochim. Pol. 51 2004 81 92
16. C. Garcia-Echeverria, and D.H. Rich New intramolecularly quenched fluorogenic peptide substrates for the study of the kinetic specificity of papain FEBS Lett. 297 1992 100 102
17. 2SO and incubation time on papain activity studied using fluorogenic substrates Acta Biochim. Pol. 48 2001 995 1002
18. B.M. Krasovitskii, and B.M. Bolotin Organic luminescent materials 1988 VCH Weinheim, Germany
19. J.K. Dey, and S.K. Dogra Spectral characteristics of three different isomeric 2-(aminophenyl)benzoxazoles: Effect of solvent and acid concentration Chem. Phys. 143 1990 97 107
20. Y. Kanegae, K. Peariso, and S.S. Martinez Class of photostable, highly efficient UV dyes: 2-Phenylbenzoxazoles Appl. Spectrosc. 50 1996 316 319
21. S.G. Kim, and M.K. Cho Expression of glutathione S-transferases Ya, Yb1, Yb2, Yc1, and Yc2 and microsomal epoxide hydrolase genes by thiazole, benzothiazole, and benzothiadiazole Biochem. Pharmacol. 52 1996 1831 1841
22. D-F. Shi, D. Bradshow, S. Wrigley, C.J. McCall, P. Leliveld, I. Fichtner, and M.F.G. Stevens Antitumor benzothiazoles: III. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo J. Med. Chem. 39 1996 3375 3384
23. Y. Bathini, K.E. Rao, R.G. Shea, and J.W. Lown Molecular recognition between ligands and nucleic acids: Novel pyridine- and benzoxazole-containing agents related to Hoechst 33258 that exhibit altered DNA sequence specificity deduced from footprinting analysis and spectroscopic studies Chem. Res. Toxicol. 3 1990 268 280
24. M.R. DeLuca, K.E. Rao, and S.M. Kervin The total synthesis of UK-1 Tetrahedron Lett. 38 1997 199 202
25. 3 receptor partial agonists in the gut J. Med. Chem. 41 1998 3015 3021
26. 1′ compounds-Correlation between lipophilicity and cytotoxicity J. Med. Chem. 39 1996 1991 2007
27. 1′ subsite: Tripeptide transition state analogues based on a heterocycle-activated carbonyl group J. Med. Chem. 39 1996 3039 3043
28. 2- antagonistic activities J. Med. Chem. 40 1997 1049 1062
29. J. Catalan, E. Mena, and F. Fabero The role of the torsion of the phenyl moiety in the mechanism of stimulated ultraviolet light generation in 2-phenylbenzazoles J. Chem. Phys. 96 1992 2005 2016
30. A. Pla-Dalmau 2-(2′-Hydroxyphenyl)benzothiazoles, -benzoxazoles, and -benzimidazoles for plastic scintillation applications J. Org. Chem. 60 1995 5468 5473
31. M. Segala, N.S. Dominiques Jr., P.R. Livotto, and V. Stefani Heterocyclic dyes displaying excited-state intramolecular proton-transfer reactions (ESIPT): Computational study of the substitution effect on the electronic absorption spectra of 2-(2′-hydroxyphenyl)-1,3-benzoxazole derivatives J. Chem. Soc. Perkin Trans. 2 1999 1123 1127
32. R. Passerini The near-ultra-violet absorption spectra of some heterocyclic compounds: I. Benzoxazoles J. Chem. Soc. 1954 2256 2261
33. K. Guzow, M. Szabelski, J. Malicka, J. Karolczak, and W. Wiczk Synthesis and photophysical properties of 3-[2-(pyridyl)benzoxazol-5-yl]-l-alanine derivatives Tetrahedron 58 2002 2201 2209
34. A. Rzeska, J. Malicka, K. Guzow, M. Szabelski, and W. Wiczk New highly fluorescent amino-acid derivatives: Substituted 3-[2-(phenyl)benzoxazol-5-yl]- alanines-Synthesis and photophysical properties J. Photochem. Photobiol. A 146 2001 9 18
35. K. Guzow, M. Szabelski, J. Malicka, and W. Wiczk Synthesis of a new, highly fluorescent amino acid derivative: N-[(tert-Butoxy)carbonyl]-3-[2-(1H- indol-3-yl)benzoxazol-5-yl]-l-alanine methyl ester Helv. Chim. Acta 84 2001 1086 1092
36. K. Guzow, K. Mazurkiewicz, M. Szabelski, R. Ganzynkowicz, J. Karolczak, and W. Wiczk Influence of an aromatic substituent in position 2 on photophysical properties of benzoxazol-5-yl-alanine derivatives Chem. Phys. 295 2003 119 130
37. M.J. Adams, J.G. Highfield, and G.F. Kirkbright Determination of absolute fluorescence quantum efficiency of quinine bisulfate in aqueous medium by optoacoustic spectrometry Anal. Chem. 49 1977 1850 1852
38. M. Szabelski, K. Stachowiak, and W. Wiczk Influence of organic solvents on papain kinetics Acta Biochim. Pol. 48 2001 1197 1201
39. W. Wiczk, and L. Łankiewicz Average distance and distance distribution estimation by steady-state energy transfer measurements Wiadomości chemiczne 50 1996 99 124
40. 3 variations in extended substrates Biochem. J. 347 2000 123 129
41. D.K. Nägler, A.C. Storer, F.C.V. Portaro, E. Carmona, L. Juliano, and R. Ménard Major increase in endopeptidase activity of human cathepsin B upon removal of occluding loop contacts Biochemistry 36 1997 12608 12615
42. F. Lecaille, C. Serveau, F. Gauthier, and G. Lalmanach Revisiting the S2 specificity of papain by structural analogs of Phe FEBS Lett. 445 1999 311 314
43. L. Puzer, S.S. Cotrin, M.F.M. Alves, T. Egborge, M.S. Araújo, M.A. Juliano, L. Juliano, D. Brömme, and A.K. Carmona Comparative substrate specificity analysis of recombinant human cathepsin V and cathepsin L Arch. Biochem. Biophys. 430 2004 274 283
44. 1′ subsite of cysteine proteases FEBS Lett. 328 1993 107 110
45. K. Guzow, M. Szabelski, A. Rzeska, J. Karolczak, H. Sulowska, and W. Wiczk Photophysical properties of tyrosine at low pH range Chem. Phys. Lett. 362 2002 519 526