Selective targeting of lysosomal cysteine proteases with radiolabeled electrophilic substrate analogs

Chemistry and Biology

Volumn 7, Issue 1, 2000, Pages 27-38

  Bogyo, Matthew ^a   Verhelst, Steven ^b   Bellingard Dubouchaud, Valerie ^a   Toba, Sam ^a   Greenbaum, Doron ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Active site labeling; Cathepsins; Epoxides; Inhibitors; Vinyl sulfones

Indexed keywords

ANIMALIA;

EID: 0034054576     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(00)00061-2     Document Type: Article

References (41)

1. Chapman H.A., Reese R.J., Shi G.-P. Emerging roles for cysteine proteases in human biology. Annu. Rev. Physiol. 59:1997;63-88.
2. Chapman H.A. Endosomal proteolysis and MHC class II fundtion. Curr. Opin. Immunol. 10:1998;93-102.
3. Barrett A.J., Rawlings N.D., Woessner J.F. Handbook of Proteolytic Enzymes. 1998;Academic Press, London.
4. Sloane B.F., Moin K., Krepela E., Rozhin J. Cathepsin B and its endogenous inhibitors: the role in tumor malignancy. Cancer Metastasis Rev. 9:1990;333-352.
5. Werb Z. Proteinases and matrix degredation. Keller W.N., Harris E.D., Ruddy S., Sledge C.S. Textbook of Rheumatology. 1989;300-321 W.B. Saunder Co, Philadelphia.
6. Katunuma N., Kominami E. Abnormal expression of lysosomal cysteine proteinases in muscle wasting diseses. Rev. Physiol. Biochem. Pharmacol. 108:1987;1-20.
7. Otto H.-H., Schirmeister T. Cysteine proteases and their inhibitors. Chem. Rev. 97:1997;133-171.
8. Shaw E. Cysteinyl proteinases and their selective inactivation. Adv. Enzymol. Relat. Areas Mol. Biol. 63:1990;271-347.
9. Towatari T., Nikawa T., Murata M., Yokoo C., Tamai M., Hanada K., Katunuma N. Novel epoxysuccinyl peptides; a selective inhibitor of cathepsin B, in vivo. FEBS Lett. 280:1991;311-315.
10. Murata M., Katunuma N.et al. Novel epoxysuccinyl peptides; a selective inhibitor of cathepsin B, in vitro. FEBS Lett. 280:1991;307-310.
11. Turk D., Turk V.et al. Crystal structure of cathepsin B inhibited with CA-030 at 2.0 Å resolution: a basis for the design of specific epoxysuccinyl inhibitors. Biochemistry. 34:1995;4791-4797.
12. Illy C., Quraishi O., Wang J., Purisima E., Vernet T., Mort J.S. Role of the occluding loop in cathepsin activity. J. Biol. Chem. 272:1997;1197-1202.
13. Meara J.P., Rich D.H. Mechanistic studies on the inactivation of papain by epoxysuccinyl inhibitors. J. Med. Chem. 39:1996;3357-3366.
14. Matsunaga Y., Saibara T., Kido H., Katunuma N. Participation of cathepsin B in processing of antigen presentation to MHC class II. FEBS Lett. 324:1993;325-330.
15. Maekawa Y., Katunuma N.et al. Switch of CD4+ T cell differentiation from Th2 to Th1 by treatment with cathepsin B inhibitor in experiemental Leishmaniasis. J. Immunol. 161:1998;2120-2127.
16. Katunuma N., Kakiuchi T.et al. Novel physiological functions of cathepsins B and L on antigen processing and osteoclastic bone resorption. Adv. Enzyme Reg. 1998;235-251.
17. Buttle D.J., Murata M., Knight C.G., Barrett A.J. CA074 methyl ester: a proinhibitor for intracellular cathepsin B. Arch. Biochem. Biophys. 299:1992;377-380.
18. Barrett A.J. Introduction to proteinases. Barrett A.J., Salvesen G. Protease Inhibitors. 1986;3-22 Elsevier, Amsterdam.
19. Gour-Salin B.J., Lachance P., Plouffe C., Storer A.C., Ménard R. Epoxysuccinyl dipeptides as selective inhibitors of cathepsin B. J. Med. Chem. 36:1993;720-725.
20. Shi G.-P., Munger J.S., Meara J.P., Rich D.H., Chapman H.A. Molecular cloning and expression of human aveolar macrophage cathepsin S, an elastinolytic cysteine protease. J. Biol. Chem. 267:1992;7258-7262.
21. Palmer J.T., Rasnick D., Klaus J.L., Bromme D. Vinyl sulfones as mechanism-based cysteine protease inhibitors. J. Med. Chem. 38:1995;3193-3196.
22. Brömme D., Klaus J.L., Okamoto K., Rasnick D., Palmer J.T. Peptidyl vinyl sulfones: a new class of potent and selective cysteine protease inhibitors. Biochem J. 1996;85-89.
23. Riese R.J., Chapman H.A.et al. Cathepsin S activity regulates antigen presentation and immunity. J. Clin. Invest. 101:1998;2351-2363.
24. Damsky C.H., Fisher S.J. Trophoblast pseudo-vasculogenesis: faking it with endothelial adhesion receptors. Curr. Opin. Cell Biol. 10:1998;660-666.
25. Librach C.L., Fisher S.J.et al. 92-kD type IV collagenase mediates invasion of human cytotrophoblasts. J. Cell Biol. 113:1991;437-449.
26. Damsky C.H., Fisher S.J.et al. Integrin switching regulates normal trophoblast invasion. Development. 120:1994;3657-3666.
27. Zhou Y., Damsky C.H.et al. Human cytotrophoblasts adopt a vascular phenotype as they differentiate. J. Clin. Invest. 99:1997;2139-2151.
28. Xing R., Wu F., Mason R. Control of breast tumor cell growth using a targeted cysteine protease inhibitor. Cancer Res. 58:1998;904-909.
29. Xing R., Mason R. Design of a transferrin-proteinase inhibitor conjugate to probe for active cysteine proteinases in endosomes. Biochem. J. 336:1998;667-673.
30. Mason R.W., Wilcox D., Wilkstrom P., Shaw E.N. The identification of active forms of cysteine proteinases in Kirsten-virus-transformed mouse fibroblasts by use of a specific radiolabeled inhibitor. Biochem. J. 257:1989;125-129.
31. Xing R., Addington A.K., Mason R.W. Quantification of cathepsin B and L in cells. Biochem. J. 332:1998;499-505.
32. Fisher S.J., Damsky C.H.et al. Adhesive and degradative properties of human placental cytotrophoblast cells in vitro. J. Cell Biol. 109:1989;891-902.
33. Bogyo M., Shin S., McMaster J.S., Ploegh H. Substrate binding and sequence preference of the proteasome revealed by active-site-directed affinity probes. Chem. Biol. 5:1998;307-320.
34. Tripos Associates. 1999.
35. Cornell W.D., Kollman P.A.et al. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules. J. Am. Chem. Soc. 117:1995;5179-5197.
36. Gasteiger J., Marsili M. Iterative partial equilization of orbital electronegativity - a raid access to atomic charges. Tetrahedron. 36:1980;3219-3228.
37. Ewing T., Kuntz I.D. DOCK. 1998;UCSF, San Francisco.
38. Zou X., Sun Y., Kuntz I.D. Inclusion of solvation in ligand binding free energy calculations using the generalized-born model. J. Am. Chem. Soc. 121:1999;8033-8043.
39. Charbonneau H., Walsh K.A.et al. Human placenta protein-tyrosine-phosphatase: amino acid sequence and relationship to a family of receptor-like proteins. Proc. Natl Acad. Sci. USA. 86:1989;5252-5256.
40. Bogyo M., McMaster J.S., Gaczynska M., Tortorella D., Goldberg A.L., Ploegh H.L. Covalent modification of the active site Thr of proteasomal β-subunits and the E. coli homolog HslV by a new class of inhibitors. Proc. Natl Acad. Sci. USA. 94:1997;6629-6634.
41. Monaco J.J., McDevitt H.O. The LMP antigens: a stable MHC-controlled protein complex. Hum. Immunol. 15:1986;416-426.