Octa-O-bis-(R,R)-tartarate ditellurane (SAS) - A novel bioactive organotellurium(IV) Compound: Synthesis, characterization, and protease inhibitory activity

ChemMedChem

Volumn 2, Issue 11, 2007, Pages 1601-1606

  Yosef, Sigal ^a   Brodsky, Miri ^a   Sredni, Benjamin ^a   Albeck, Amnon ^a   Albeck, Michael ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

Biological activity; Cysteine proteases; Enzyme inhibitors; Tellurium; Thiol oxidation

Indexed keywords

CYSTEINE PROTEINASE INHIBITOR; OCTA O BISTARTARATE DITELLURANE; OCTA-O-BISTARTARATE DITELLURANE; ORGANOMETALLIC COMPOUND; PEPTIDE HYDROLASE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HYDROLYSIS; MASS SPECTROMETRY; METABOLISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYSTEINE PROTEINASE INHIBITORS; HYDROLYSIS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PEPTIDE HYDROLASES; TARTRATES;

EID: 49649127680     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200700155     Document Type: Article

References (51)

1. H. A. Schroeder, J. Buckman, J. J. Balassa, J. Chronic. Dis. 1967, 20, 147-161.
2. A. J. Larner in The Bulletin of Selenium-Tellurium Development Association 1996.
3. A. P. Ordyntseva, I. D. Sivovolova, G. M. Abakarov, E. I. Sadekova, Khim.-Farm. Zh. 1988, 22, 1098-1100.
4. B. Deuticke, P. Lütkemeier, B. Poser, Biochim. Biophys. Acta Biomembr. 1992, 1109, 97-107, and references therein.
5. M. Albeck, T. Tamari, B. Sredni, Synthesis 1989, 635-636.
6. B. Sredni, R. R. Caspi, A. Klein, Y. Kalechman, Y. Danziger, M. Ben Ya'akov, T. Tamari, F. Shalit, M. Albeck, Nature 1987, 330, 173-176.
7. B. Sredni, R. H. Xu, M. Albeck, U. Gafter, R. Gal, A. Shani, T. Tichler, J. Shapira, I. Bruderman, R. Catane, B. Kaufman, J. K. Whisnant, K. L. Mettinger, Y. Kalechman, Int. J. Cancer 1996, 65, 97-103.
8. B. Sredni, R. Gal, I. J. Cohen, J. E. Dazard, D. Givol, U. Gafter, B. Motro, S. Eliyahu, M. Albeck, H. M. Lander, Y. Kalechman, FASEB J. 2004, 18, 400-402.
9. H. Rosenblatt-Bin, Y. Kalechman, A. Vonsover, R. H. Xu, J. P. Da, F. Shalit, M. Huberman, A. Klein, G. Strassmann, M. Albeck, B. Sredni, Cell. Immunol. 1998, 184, 12-25.
10. Y. Kalechman, U. Gafter, J. P. Da, M. Albeck, D. Alarcon-Segovia, B. Sredni, J. Immunol. 1997, 159, 2658-2667.
11. Y. Kalechman, U. Gafter, R. Gal, G. Rushkin, D. Yan, M. Albeck, B. Sredni, J. Immunol. 2002, 169, 384-392.
12. Y. Kalechman, U. Gafter, T. Weinstein, A. Chagnac, I. Freidkin, A. Tobar, M. Albeck, B. Sredni, J. Biol. Chem. 2004, 279, 24724-24732.
13. B. Sredni, R. Geffen, W. Duan, M. Albeck, S. Shalit, H. M. Lander, N. Kinor, O. Sagi, A. Albeck, S. Yosef, M. Brodsky, D. Sredni-Kenigsbuch, T. Sonino, D. L. Longo, M. P. Mattson, G. Yadid, FASEB J. 2007, 21, 1870-1883.
14. B. Sredni, M. Albeck, T. Tichler, A. Shani, J. Shapira, I. Bruderman, R. Catane, B. Kaufman, Y. Kalechman, J. Clin. Oncol. 1995, 13, 2342-2353.
15. B. Sredni, A. Shani, R. Catane, B. Kaufman, G. Strassmann, M. Albeck, Y. Kalechman, J. Natl. Cancer Inst. 1996, 88,1276-1284.
16. G. Strassmann, T. Kambayashi, C. O. Jacob, D. Sredni, Cell. Immunol. 1997, 176, 180-185.
17. A. Albeck, H. Weitman, B. Sredni, M. Albeck, Inorg. Chem. 1998, 37, 1704-1712.
18. M. Brodsky, S. Yosef, G. Rushkin, M. Albeck, D. L. Longo, A. Albeck, B. Sredni, J. Interferon Cytokine Res. 2007, 27, 453-462.
19. G. M. Frei, I. Lebenthal, M. Albeck, A. Albeck, B. Sredni, Biochem. Pharm. 2007, 74, 712-722.
20. H. Gottlieb, S. Hoz, I. Eliashiv, M. Albeck, Inorg. Chem. 1994, 33, 808-811.
21. K. J. Irgolic in Organotellurium Compounds (Vol. E12b of Methods of Organic Chemistry (Houben-Weyl) Additional and Supplementary Volumes of the 4th edition), (Ed.: D. Klamann), Georg Thieme, Stuttgart, 1990.
22. The Chemistry of Organic Selenium and Tellurium Compounds, Vol. 1 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1986.
23. E. A. Stukalo, E. M. Yur'eva, L. N. Markovskii, Zh. Org. Khim. 1983, 19, 343-346 (Engl. 301-303).
24. W. Mazurek, A. G. Moritz, M. J. O'connor, Inorg. Chim. Acta 1986, 113, 143-146.
25. R. Kitz, I. B. Wilson, J. Biol. Chem. 1962, 237, 3245-3249.
26. E. Im, A. Venkatakrishnan, A. Kazlauskas, Mol. Biol. Cell 2005, 16, 3488-3500.
27. S. S. Lakka, C. S. Gondi, N. Yanamandra, W. C. Olivero, D. H. Dinh, M. Gujrati, J. S. Rao, Oncogene 2004, 23, 4681-4689.
28. B. F. Sloane, Semin. Cancer Biol. 1990, 1, 137-152.
29. B. F. Sloane, J. R. Dunn, K. V. Honn, Science 1981, 212, 1151-1153.
30. T. Yamashima, Cell Calcium 2004, 36, 285-293.
31. T. Yamashima, Prog. Neurobiol. 2000, 62, 273-295.
32. R. E. Esser, R. A. Angelo, M. D. Murphey, L. M. Watts, L. P. Thornburg, J. T. Palmer, J. W. Talhouk, R. E. Smith, Arthritis Rheum. 1994, 37, 236-247.
33. D. J. Buttle, C. J. Handley, M. Z. Ilic, J. Saklatvala, M. Murata, A. J. Barrett, Arthritis Rheum. 1993, 36, 1709-1717.
34. N. Katunuma, E. Kominami, Rev. Physiol. Biochem. Pharmacol. 1987, 108, 1-20.
35. N. Teich, H. Bödeker, W. Keim, BMC Gastroenterol. 2002, 2, 16-19.
36. L. Foghsgaard, D. Wissing, D. Mauch, U. Lademann, L. Bastholm, M. Boes, F. Elling, M. Leist, M. Jäättelä, J. Cell Biol. 2001, 153, 999-1010.
37. M. E. Guicciardi, H Miyoshi, S. F. Bronk, G. Gores, Am. J. Pathol. 2001, 159, 2045-2054.
38. B. Zhivotovsky, D. H. Burgess, D. M. Vanags, S. Orrenius, Biochem. Biophys. Res. Commun. 1997, 230, 481-488.
39. A. Albeck, S. Fluss, R. Persky, J. Am. Chem. Soc. 1996, 118, 3591-3596.
40. Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.
41. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
42. S. Mackay, C. J. Gilmore, C. Edwards, M. Tremayne, N. Stuart, K. Shankland, "maXus": A computer program for the solution and refinement of crystal structures from diffraction data, University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and Macscience Co. Ltd., Yokohama , Japan, 1998.
43. G. M. Sheldrick, SHELXL97. Program for the refinement of crystal structures, University of Gottingen, Germany, 1997.
44. Molecular Structure Corporation. ORTEP. TEXRAY Structure Analysis Package. MSC. 3200 Research Forest Drive, The Woodlands, TX 77381, USA, 1997.
45. B. C. W. Hummel, Can. J. Biochem. Physiol. 1959, 37, 1393-1399.
46. E. G. DelMar, C. Langman, J. W. Brodrick, M. C. Gekas, Anal. Biochem. 1979, 99, 316-320.
47. J. Bieth, B. Spiess, C. G. Wermuth, Biochem. Med. 1974, 11, 350-357.
48. G. W. Schwert, Y. Takenaka, Biochim. Biophys. Acta 1955, 16, 570-575.
49. J. E. Folk, E. W. Schirmer, J. Biol. Chem. 1963, 238, 3884-3894.
50. J. Tang, Methods Enzymol. 1970, 19, 406-421.
51. C. Giordano, C. Gallina, V. Consalvi, R. Scandurra, Eur. J. Med. Chem. 1990, 25, 479-487.