'3 + 1' mixed-ligand oxorhenium(V) complexes and their inhibition of the cysteine proteases cathepsin B and cathepsin K

Inorganica Chimica Acta

Volumn 359, Issue 9, 2006, Pages 2736-2750

  Baird, Ian R ^a   Mosi, Renee ^a   Olsen, Micki ^a   Cameron, Beth R ^a   Fricker, Simon P ^a   Skerlj, Renato T ^a  

^a GENZYME CORPORATION   (United States)

Author keywords

'3 + 1' mixed ligand complexes; Cathepsin B; Cathepsin K; Cysteine protease inhibitor; Oxorhenium(V) compounds

Indexed keywords

AMINO ACIDS; CHELATION; COMPLEXATION; DISEASES; LIGANDS; RHENIUM COMPOUNDS; SYSTEMS ENGINEERING;

CATHEPSIN B; CATHEPSIN K; CYSTEINE PROTEASE INHIBITORS; MIXED LIGAND COMPLEXES; OXORHENIUM(V) COMPOUNDS;

SYNTHESIS (CHEMICAL);

EID: 33646507652     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2005.10.058     Document Type: Article

References (68)

1. Bromme D. Drug News Perspect. 12 (1999) 73
2. Duffy M.J. Clin. Cancer Res. 2 (1996) 613
3. Szpaderska A.M., and Frankfater A. Cancer Res. 61 (2001) 3493
4. van Noorden C.J., Jonges T.G., Meade-Tollin L.C., Smith R.E., and Koehler A. Br. J. Cancer 82 (2000) 931
5. Kos J., and Lah T. Oncol. Rep. 5 (1998) 1349
6. Troen B.R. Drug News Perspect. 17 (2004) 19
7. Yasuda Y., Kaleta J., and Bromme D. Adv. Drug Delivery Rev. 57 (2005) 973
8. Wang D., Li W., Pechar M., Kopeckova P., Bromme D., and Kopecek J. Int. J. Pharmaceut. 277 (2004) 73
9. Biskobing D.M. Expert Opin. Invest. Drugs 12 (2003) 611
10. Berquin I.M., and Sloane B.F. Intracellular Prot. Catab. (1996) 281
11. Elliott E., and Sloane B.F. Perspect. Drug Discov. Des. 6 (1996) 12
12. Fernandez P., Farre X., Nadal A., Fernandez E., Peiro N., Sloane B.F., Sih G., Chapman H.A., Campo E., and Cardesa A. Int. J. Cancer 95 (2001) 51
13. Ishibashi O., Mori Y., Kurokawa T., and Kumegawa M. Cancer Biochem. Biophys. 17 (1999) 69
14. Osmak M., Svetic B., Gabrijelcic-Geiger D., and Skrk J. Anticancer Res. 21 (2001) 481
15. Satoh Y., Higashi T., Nouso K., Shiota T., Kinugasa N., Yoshida K., Uematsu S., Nakatsukasa H., Nishimura Y., and Tsuji T. Acta Med. Okayama 50 (1996) 305
16. Sloane B.F., Yan S., Podgorski I., Linebaugh B.E., Cher M.L., Mai J., Cavallo-Medved D., Sameni M., Dosescu J., and Moin K. Semin. Cancer Biol. 15 (2005) 149
17. Podgorski I., and Sloane B.F. Biochem. Soc. Symp. 70 (2003) 263
18. Leto G., Pizzolanti G., Tumminello F.M., and Gebbia N. In Vivo 8 (1994) 231
19. Navab R., Mort J.S., and Brodt P. Clin. Exp. Metastasis 15 (1997) 121
20. Redwood S.M., Liu B., Weiss R., Hodge D., and Droller M.J. Cancer 69 (1991) 1212
21. Falgueyret J.P., Oballa R.M., Okamoto O., Wesolowski G., Aubin Y., Rydzewski R.M., Prasit P., Riendeau D., Rodan S.B., and Percival M.D. J. Med. Chem. 44 (2001) 94
22. Cunha R.L.O.R., Urano M.E., Chagas J.R., Almeida P.C., Bincoletto C., Tersariol I.L.S., and Comasseto J.V. Bioorg. Med. Chem. Lett. 15 (2005) 755
23. Chircorian A., and Barrios A.M. Bioorg. Med. Chem. Lett. 14 (2004) 5113
24. van Zutphen S., Kraus M., Driessen C., van der Marel G.A., Overkleeft H.S., and Reedijk J. J. Inorg. Biochem. 99 (2005) 1384
25. Maresca K.P., Femia F.J., Babich J.W., and Zubieta J. Inorg. Chem. Commun. 1 (1998) 209
26. Spies H., Fietz T., Pietzsch H.-J., Johansen B., Leibnitz P., Reck G., Scheller D., and Klostermann K. J. Chem. Soc., Dalton Trans. 13 (1995) 2277
27. Papadopoulos M.S., Pirmettis I.C., Pelecanou M., Raptopoulou C.P., Terzis A., Stassinopoulou C.I., and Chiotellis E. Inorg. Chem. 35 (1996) 7377
28. Maresca K.P., Femia F.J., Bonavia G.H., Babich J.W., and Zubieta J. Inorg. Chim. Acta 297 (2000) 98
29. Zablotskaya A., Segal I., Kemme A., Germane S., Popelis J., Lukevics E., Berger R., and Spies H. Chem. Heterocycl. Compd. 38 (2002) 477
30. Friebe M., Spies H., Seichter W., Leibnitz P., and Johansen B. J. Chem. Soc., Dalton Trans. (2000) 2471
31. Femia F.J., Chen X., Maresca K.P., Shoup T.M., Babich J.W., and Zubieta J. Inorg. Chim. Acta 306 (2000) 30
32. Papadopoulos M.S., Tsoukalas C., Pirmettis I.C., Nock B.A., Maina T., Abedin Z., Raptopoulou C.P., Terzis A., and Chiotellis E. Inorg. Chim. Acta 285 (1999) 97
33. Syhre R., Seifert S., Spies H., Gupta A., and Johansen B. Eur. J. Nucl. Med. 25 (1998) 793
34. Nock B.A., Maina T., Yannoukakos D., Pirmettis I.C., Papadopoulos M.S., and Chiotellis E. J. Med. Chem. 42 (1999) 1066
35. Mastrostamatis S.G., Papadopoulos M.S., Pirmettis I.C., Paschali E., Varvarigou A.D., Stassinopoulou C.I., Raptopoulou C.P., Terzis A., and Chiotellis E. J. Med. Chem. 37 (1994) 3212
36. Papagiannopoulou D., Pirmettis I.C., Maina T., Pelecanou M., Nikolopoulou A., Chiotellis E., Raptopoulou C.P., Vlahos A.T., Terzis A., Papadopoulos M.S., and Chiotellis E. J. Biol. Inorg. Chem. 6 (2001) 256
37. Johansen B., Berger R., Brust P., Pietzsch H.-J., Scheunemann M., Seifert S., Spies H., and Syhre R. Eur. J. Nucl. Med. 24 (1997) 316
38. Johansen B., Scheunemann M., Spies H., Brust P., Wober J., Syhre R., and Pietzsch H.-J. Nucl. Med. Biol. 23 (1996) 429
39. Maresca K.P., Shoup T.M., Femia F.J., Burker M.A., Fischman A., Babich J.W., and Zubieta J. Inorg. Chim. Acta 338 (2002) 149
40. Friebe M., Mahmood A., Spies H., Berger R., Johansen B., Mohammed A., Eisenhut M., Bolzati C., Davison A., and Jones A.G. J. Med. Chem. 43 (2000) 2745
41. Chi D.Y., O'Neil J.P., Anderson C.J., Welch M.J., and Katzenellenbogen J.A. J. Med. Chem. 37 (1994)
42. Hasnain S., Hirama T., Tam A., and Mort J.S. J. Biol. Chem. 267 (1992) 4713
43. Nock B.A., Maina T., Tsortos A., Pelecanou M., Raptopoulou C.P., Papadopoulos M.S., Pietzsch H.-J., Stassinopoulou C.I., Terzis A., Spies H., Nounesis G., and Chiotellis E. Inorg. Chem. 39 (2000) 4433
44. Pelecanou M., Pirmettis I.C., Nock B.A., Papadopoulos M.S., Chiotellis E., and Stassinopoulou C.I. Inorg. Chim. Acta 281 (1998) 148
45. Fietz T., Spies H., Pietzsch H.-J., and Leibnitz P. Inorg. Chim. Acta 231 (1995) 233
46. Rima G., Stage J., Fatome M., Laval J., Sentenac-Roumanou H., Lion C., and Lazraq M. Eur. J. Med. Chem. 26 (1991) 291
47. Banerjee S.R., Maresca K.P., Stephenson K.A., Valliant J.F., Babich J.W., Graham W.A., Barzana M., Dong Q., Fischman A.J., and Zubieta J. Bioconjug. Chem. 16 (2005) 885
48. Glaser M., Spies H., Berger R., Hahn F.E., Lugger T., and Johansen B. Inorg. Chim. Acta 257 (1997) 143
49. Nock B.A., Pietzsch H.-J., Tisato F., Maina T., Leibnitz P., Spies H., and Chiotellis E. Inorg. Chim. Acta 301 (2000) 26
50. Kuhelj R., Dolinar M., Pungercar J., and Turk V. Eur. J. Biochem. 229 (1995) 533
51. V. Annastassov, J. Cox, R. Mosi, G. Lau, J. Labrecque, S. Fricker, Cysteine proteases as a therapeutic target: cloning, expression and purification of Cathepsin B and Cathepsin L, in: 85th Canadian Chemistry Society Conference and Exhibition, 2002, Abstract #909.
52. D'Alessio K.J., McQueney M.S., Brun K.A., Orsini M.J., and Debouck C.M. Protein Expr. Purif. 15 (1999) 213
53. R. Leatherbarrow, grafit 4.09, Erithacus Software, Staines, UK, 1989.
54. Altomare A., Burla M.C., Cammalli G., Cascarano M., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna A. J. Appl. Cryst. 32 (1999) 115
55. Beurskens P.T., Admiraal G., Beurskens G., Bosman W.P., de Gelder R., Israel R., and Smits J.M.M. The dirdif-94 Program System, Technical Report of the Crystallography Laboratory (1994), University of Nijmegen, The Netherlands
56. Fietz T., Leibnitz P., Spies H., and Johansen B. Polyhedron 18 (1999) 1793
57. Kniess T., Noll B., and Spies H. Forschungszentrum Rossendorf e.V., [Bericht] FZR FZR-122 (1996) 136
58. Addison A.W., Rao T.N., Reedijk J., van Rijn J., and Verschoor G.C. J. Chem. Soc., Dalton Trans. (1984) 1349
59. Jackson T., Kojima M., and Lambrecht R.M. Aust. J. Chem. 46 (1993) 1093
60. Konno T., Shimazaki Y., Kawai M., and Hirotsu M. Inorg. Chem. 40 (2001) 4250
61. B.R. Cameron, I.R. Baird, L. Wang, R. Mosi, S. Fricker, R. Skerlj (in preparation).
62. R. Mosi, I. Baird, J. Cox, V. Anasstassora, B. Cameron, R. Skerlj, S. Fricker (in preparation).
63. Beynon R.J., and Salvesen G. In: Beynon R.J., and Bond J.S. (Eds). Proteolytic Enzymes: A Practical Approach (1989), IRL Press, Oxford, England
64. Pietzsch H.-J., Sheunemann M., Kretzschmar M., Elz S., Pertz H.H., Seifert S., Brust P., Spies H., Syhre R., and Johansen B. Nucl. Med. Biol. 26 (1999) 865
65. Meegala S., Plossl K., Kung M.-P., Stevenson A.D., Liable-Sands L.M., Rheingold A.L., and Kung K.F. J. Am. Chem. Soc. 117 (1995)
66. Meegala S., Plossl K., Kung M.-P., Chumpradit S., Stevenson A.D., Liable-Sands L.M., Rheingold A.L., and Kung K.F. Bioconjug. Chem. 7 (1996) 421
67. Turk D., Podobnik T., Popovic T., Katunuma N., Bode W., Huber R., and Turk V. Biochemistry 34 (1995)
68. Yamamoto A., Hara T., Tomoo K., Ishida T., Fujii T., Hata Y., Murata M., and Kitamura K. J. Biochem. 121 (1997)