Natural product based inhibitors of the thioredoxin-thioredoxin reductase system

Organic and Biomolecular Chemistry

Volumn 2, Issue 11, 2004, Pages 1651-1658

  Wipf, Peter ^a   Lynch, Stephen M ^a   Birmingham, Anne ^b   Tamayo, Giselle ^c,d   Jiménez, Allan ^c   Campos, Nefertiti ^c   Powis, Garth ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c INSTITUTO NACIONAL DE BIODIVERSIDAD   (Costa Rica)

^d UNIVERSIDAD DE COSTA RICA   (Costa Rica)

Author keywords

[No Author keywords available]

Indexed keywords

ATTENUATION; CHEMICAL BONDS; DRUG PRODUCTS; ENZYMES; ETHERS; METABOLITES; POLYAMIDEIMIDES; REDUCTION; TOXICITY;

CYTOTOXICITY; REDOX CONTROL SYSTEMS; STILLE COUPLING REACTIONS;

AROMATIC COMPOUNDS;

MINK CELL FOCUS-FORMING VIRUS;

ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; NAPHTHOQUINONE; SPIRO COMPOUND; THIOREDOXIN; THIOREDOXIN REDUCTASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG SCREENING; HUMAN; IC 50; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NAPHTHOQUINONES; SPIRO COMPOUNDS; THIOREDOXIN; THIOREDOXIN REDUCTASE (NADPH);

EID: 2942700238     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402431a     Document Type: Article

References (41)

1. (a) D. J. Newman, G. M. Cragg and K. M. Snader, J. Nat. Prod., 2003, 66, 1022-1037;
2. (b) R. Breinbauer, I. R. Vetter and H. Waldmann, Angew. Chem., Int. Ed., 2002, 41, 2878-2890;
3. (c) P. Wipf, J. T. Reeves, R. Balachandran and B. W. Day, J. Med. Chem., 2002, 45, 1901-1917.
4. P. Wipf, T. D. Hopkins, J.-K. Jung, S. Rodriguez, A. Birmingham, E. C. Southwick, J. S. Lazo and G. Powis, Bioorg. Med. Chem. Lett., 2001, 11, 2637-2641.
5. For a review on natural products derived from naphthalenoid precursors, see: K. Krohn, Progr. Chem. Org. Nat. Prod., 2003, 85, 1-49.
6. T. M. Grogan, C. Fenoglio-Prieser, R. Zeheb, W. Bellamy, Y. Frutiger, E. Vela, G/ Stemmerman, J. MacDonald, L. Richter, A. Gallegos and G. Powis, Hum. Pathol., 2000, 31, 475-481.
7. M. Berggren, A. Gallegos, J. R. Gasdaska, P. Y. Gasdaska, J. Warneke and G. Powis, Anticancer Res., 1996, 16, 3459-3466.
8. A. Gallegos, J. Raffel, A. K. Bhattacharyya and G. Powis, Proc. Am. Assoc. Cancer Res., 2000, 41, 189.
9. S. Kakolyris, A. Giatromanolaki, M. Koukourakis, G. Powis, J. Souglakos, E. Sivridis, K. C. Gatter and A. L. Harris, Clin. Cancer Res., 2001, 7, 3087-3091.
10. J. E. Oblong, M. Berggren, P. Y. Gasdaska and G. Powis, J. Biol. Chem., 1994, 269, 11714-11720.
11. S. J. Welsh, W. T. Bellamy, M. M. Briehl and G. Powis, Cancer Res., 2002, 62, 5089-5095.
12. B. Husbeck, D. E. Stringer, E. W. Gerner and G. Powis, Biochem. Biophys. Res. Commun., 2003, 306, 469-475.
13. E. Meuillet, D. Mahadevan, M. Berggren, A. Coon and G. Powis, Arch. Biochem. Biophys., 2004, in press.
14. M. I. Berggren, B. Husbeck, B. Samulitis, A. F. Baker, A. Gallegos and G. Powis, Arch. Biochem. Biophys., 2001, 392, 103-109.
15. S. Gromer, S. Urig and K. Becker, Med. Res. Rev., 2004, 24, 40-89.
16. K. U. Schallreuter, F. K. Gleason and J. M. Wood, Biochim. Biophys. Acta. 1990, 1054, 14-20.
17. S. J. Welsh, R. R. Williams, A. Birmingham, D. J. Newman, D. L. Kirkpatrick and G. Powis, Mol. Cancer Ther., 2003, 2, 235-243.
18. S. Gromer, L. D. Arscott, C. H. Williams Jr., R. H. Schirmer and K. Becker, J. Biol. Chem., 1998, 273, 20096-20101.
19. M. W. Kunkel, D. L. Kirkpatrick, J. I. Johnson and G. Powis, Anti-Cancer Drug Des., 1997, 12, 659-670.
20. P. Wipf and S. M. Lynch, Org. Lett., 2003, 5, 1155-1158.
21. (a) K. Maruoka, K. Nonoshita and H. Yamamoto, Tetrahedron Lett., 1987, 28, 5723-5726;
22. (b) A. J. Stern, J. J. Rohde and J. S. Swenton, J. Org. Chem., 1989, 54, 4413-4419.
23. Y. M. Choi-Sledeski, D. G. McGarry, D. M. Green, H. J. Mason, M. R. Becker, R. S. Davis, W. R. Ewing, W. P. Dankulich, V. E. Manetta, R. L. Morris, A. P. Spada, D. L. Cheney, K. D. Brown, D. J. Colussi, V. Chu, C. L. Heran, S. R. Morgan, R. G. Bentley, R. J. Leadley, S. Maignan, J.-P. Guilloteau, C. T. Dunwiddie and H. W. Pauls, J. Med. Chem., 1999, 42, 3572-3587.
24. R. L. Hannan, R. B. Barber and H. Rapoport, J. Org. Chem., 1979, 44, 2153-2158.
25. (a) P. Wipf and J.-K. Jung, J. Org. Chem., 2000, 65, 6319-6337;
26. (b) P. Wipf, J.-K. Jung, S. Rodriguez and J. S. Lazo, Tetrahedron, 2001, 57, 283-296.
27. N. G. Tregub, A. P. Knyazev and V. V. Mezheritskii, J. Org. Chem. USSR, 1990, 26, 143-146.
28. G. E. Boswell and J. F. Licause, J. Org. Chem., 1995, 60, 6592-6594.
29. S. Hanessian, D. Delorme and Y. Dufresne, Tetrahedron Lett., 1984, 25, 2515-2518.
30. Natural products transferred with the Material Transfer Agreement number BP-001-03.
31. Current molecular and morphological studies are being carried out to assess the taxonomy of both, the anamorph and teleomorph of the original isolate and will be published shortly. Both anamorph and teleomorph specimens are preserved at IN Bio's laboratories for future reference, under accession number 3352.
32. Collection permit number 005-96-VUI.
33. 13C-NMR, HSQC, DEPT, COSY and HMBC experiments and MS data. MK3018 was originally reported in H. Ogishi, N. Chiba, T. Mikawa, T. Sasaki, S. Miyagi and M. Sezaki, JP 01.294,686,1989; Chem. Abstr., 1990, 113, 38906q.
34. 5. Full assignments and farther data will be published shortly.
35. 13C-NMR. HSQC and HMBC experiments and MS data. Compared with spectroscopic data reported in A. G. M. Barrett, F. Blaney, A. D. Campbell, D. Hemprecht, T. Meyer, A. J. P. White, D. Witty and D. J. Williams, J. Org. Chem., 2002, 67, 2735-2750 Originally reported in S. Sakemi, T. Inagaki, K. Kaneda, H. Hirai, E. Iwata, T. Sakakibara, Y. Yamauchi, M. Norcia, L. M. Wondrack and J. A. Sutcliffe, J. Antibiot., 1995, 48, 134.
36. 13C-NMR. HSQC and HMBC experiments and MS data. Compared with spectroscopic data reported in A. G. M. Barrett, F. Blaney, A. D. Campbell, D. Hemprecht, T. Meyer, A. J. P. White, D. Witty and D. J. Williams, J. Org. Chem., 2002, 67, 2735-2750 Originally reported in S. Sakemi, T. Inagaki, K. Kaneda, H. Hirai, E. Iwata, T. Sakakibara, Y. Yamauchi, M. Norcia, L. M. Wondrack and J. A. Sutcliffe, J. Antibiot., 1995, 48, 134.
37. 13C-NMR. HSQC and HMBC experiments and MS data, and compared with published spectroscopic information in Barrett et al., ref. 31. Originally reported in K. Krohn, A. Michel, U. Floerke, H.-J. Aust, S. Draeger and B. Schulz, Annalen, 1994, 1093-1097 and 1099-1108.
38. P. Y. Gasdaska, J. E. Oblong, I. A. Cotgreave and G. Powis, Biochim. Biophys. Acta, 1994, 1218, 292-296.
39. D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czenvinski, D. L. Fine, B. J. Abbott, J. G. Mayo, R. H. Shoemaker and M. R. Boyd, Cancer Res., 1988, 48, 589-601.
40. All synthetic intermediates and products were fully characterized spectroscopically. See supplementary material for experimental details.
41. G. E. Boswell and J. F. Licause, J. Org. Chem., 1995, 60, 6592-6594.