Structures of triacetyloleandomycin and mycalamide A bind to the large ribosomal subunit of Haloarcula marismortui

Antimicrobial Agents and Chemotherapy

Volumn 53, Issue 12, 2009, Pages 5010-5014

  Gürel, Güliz ^a   Blaha, Gregor ^a   Steitz, Thomas A ^a,b   Moore, Peter B ^a  

^a YALE UNIVERSITY   (United States)

^b HOWARD HUGHES MEDICAL INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MYCALAMIDE A; PEPTIDE; TRANSFER RNA; TROLEANDOMYCIN;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG BINDING; DRUG BINDING SITE; DRUG PROTEIN BINDING; DRUG STRUCTURE; GROWTH INHIBITION; HALOARCULA MARISMORTUI; LARGE RIBOSOMAL SUBUNIT; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS INHIBITION;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CRYSTALLOGRAPHY, X-RAY; HALOARCULA MARISMORTUI; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; PROTEIN BIOSYNTHESIS; PYRANS; RIBOSOME SUBUNITS, LARGE; TROLEANDOMYCIN;

EID: 71249162369     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00817-09     Document Type: Article

References (34)

1. Ban, N., B. Freeborn, P. Nissen, P. Penczek, R. A. Grassucci, R. Sweet, J. Frank, P. B. Moore, and T. A. Steitz. 1998. A 9 angstrom resolution X-ray crystallographic map of the large ribosomal subunit. Cell 93:1105-1115. (Pubitemid 28307416)
2. Ban, N., P. Nissen, J. Hansen, P. B. Moore, and T. A. Steitz. 2000. The complete atomic structure of the large ribosomal subunit at 2.4 angstrom resolution. Science 289:905-920. (Pubitemid 30659939)
3. Berisio, R., J. Harms, F. Schluenzen, R. Zarivach, H. A. S. Hansen, P. Fucini, and A. Yonath. 2003. Structural insight into the antibiotic action of telithromycin against resistant mutants. J. Bacteriol. 185:4276-4279. (Pubitemid 36835269)
4. Berisio, R., F. Schluenzen, J. Harms, A. Bashan, T. Auerbach, D. Baram, and A. Yonath. 2003. Structural insight into the role of the ribosomal tunnel in cellular regulation. Nat. Struct. Biol. 10:366-370.
5. Blaha, G., G. Gurel, S. J. Schroeder, P. B. Moore, and T. A. Steitz. 2008. Mutations outside the anisomycin-binding site can make ribosomes drug-resistant. J. Mol. Biol. 379:505-519.
6. Brunger, A. T., P. D. Adams, G. M. Clore, W. L. DeLano, P. Gros, R. W. Grosse-Kunstleve, J. S. Jiang, J. Kuszewski, M. Nilges, N. S. Pannu, R. J. Read, L. M. Rice, T. Simonson, and G. L. Warren. 1998. Crystallography & NMR system: a new software suite for macromolecular structure determination. Acta Crystallogr. D 54:905-921. (Pubitemid 28443603)
7. Bryskier, A. J., J.-P. Butzler, H. C. Neu, and P. M. Tulkens. 1993. Macrolides. Chemistry, pharmacology and clinical uses. Arnette Blackwell, Paris, France.
8. Burres, N. S., and J. J. Clement. 1989. Antitumor activity and mechanism of action of the novel marine natural products mycalamide-A and -B and onnamide. Cancer Res. 49:2935-2940.
9. DeLano, W. L. 2002. The Pymol molecular graphics system. De Lano Scientific, San Carlos, CA.
10. Evans, R. M. 1965. The chemistry of the antibiotics used in medicine. Pergamon Press, Oxford, United Kingdom.
11. Gürel, G., G. Blaha, P. B. Moore, and T. A. Steitz. 2009. U2504 determines the species specificity of the A-site cleft antibiotics: the structures of tiamulin, homoharringtonine, and bruceantin bound to the ribosome. J. Mol. Biol. 389:146-156.
12. Hansen, J. L., J. A. Ippolito, N. Ban, P. Nissen, P. B. Moore, and T. A. Steitz. 2002. The structures of four macrolide antibiotics bound to the large ribosomal subunit. Mol. Cell 10:117-128.
13. Hansen, J. L., P. B. Moore, and T. A. Steitz. 2003. Structures of five antibiotics bound at the peptidyl transferase center of the large ribosomal subunit. J. Mol. Biol. 330:1061-1075.
14. Ippolito, J. A., Z. F. Kanyo, D. P. Wang, F. J. Franceschi, P. B. Moore, T. A. Steitz, and E. M. Duffy. 2008. Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit. J. Med. Chem. 51:3353-3356.
15. Jones, T. A., J. Y. Zou, S. W. Cowan, and M. Kjeldgaard. 1991. Improved methods for building protein models in electron-density maps and the location of errors in these models. Acta Crystallogr. A 47:110-119.
16. Lee, B., and F. M. Richards. 1971. The interpretation of protein structures: estimation of static accessibility. J. Mol. Biol. 55:379-400.
17. Mankin, A. S. 2008. Macrolide myths. Curr. Opin. Microbiol. 11:414-421.
18. Nishimura, S., S. Matsunaga, M. Yoshida, H. Hirota, S. Yokoyama, and N. Fusetani. 2005. 13-Deoxytedanolide, a marine sponge-derived antitumor macrolide, binds to the 60S large ribosomal subunit. Bioorg. Med. Chem. 13:449-454.
19. Otwinowski, Z., and W. Minor. 1997. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 276:307-326. (Pubitemid 27085611)
20. Schlunzen, F., J. M. Harms, F. Franceschi, H. A. S. Hansen, H. Bartels, R. Zarivach, and A. Yonath. 2003. Structural basis for the antibiotic activity of ketolides and azalides. Structure 11:329-338. (Pubitemid 36287695)
21. Schlunzen, F., E. Pyetan, P. Fucini, A. Yonath, and J. M. Harms. 2004. Inhibition of peptide bond formation by pleuromutilins: the structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin. Mol. Microbiol. 54:1287-1294.
22. Schlunzen, F., R. Zarivach, J. Harms, A. Bashan, A. Tocilj, R. Albrecht, A. Yonath, and F. Franceschi. 2001. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 413:814-821. (Pubitemid 33026843)
23. Schmeing, T. M., K. S. Huang, D. E. Kitchen, S. A. Strobel, and T. A. Steitz. 2005. Structural insights into the roles of water and the 2′ hydroxyl of the P site tRNA in the peptidyl transferase reaction. Mol. Cell 20:437-448.
24. Schmeing, T. M., K. S. Huang, S. A. Strobel, and T. A. Steitz. 2005. An induced-fit mechanism to promote peptide bond formation and exclude hydrolysis of peptidyl-tRNA. Nature 438:520-524.
25. Schmeing, T. M., P. B. Moore, and T. A. Steitz. 2003. Structures of deacylated tRNA mimics bound to the E site of the large ribosomal subunit. RNA 9:1345-1352. (Pubitemid 37310865)
26. Schroeder, S. J., G. Blaha, and P. B. Moore. 2007. Negamycin binds to the wall of the nascent chain exit tunnel of the 50S ribosomal subunit. Antimicrob. Agents Chemother. 51:4462-4465.
27. Schroeder, S. J., G. Blaha, J. Tirado-Rives, T. A. Steitz, and P. B. Moore. 2007. The structures of antibiotics bound to the E site region of the 50 S ribosomal subunit of Haloarcula marismortui: 13-deoxytedanolide and girodazole. J. Mol. Biol. 367:1471-1479.
28. Selmer, M., C. M. Dunham, F. V. Murphy, A. Weixlbaumer, S. Petry, J. R. Weir, A. C. Kelley, and V. Ramakrishnan. 2006. Structure of the Thermus thermophilus 70S ribosome complexed with mRNA and tRNA. Science 313:1935-1942.
29. Sohn, J. H., N. Waizumi, H. M. Zhong, and V. H. Rawal. 2005. Total synthesis of mycalamide A. J. Am. Chem. Soc. 127:7290-7291.
30. Tenson, T., M. Lovmar, and M. Ehrenberg. 2003. The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome. J. Mol. Biol. 330:1005-1014.
31. Thompson, J., C. A. Pratt, and A. E. Dahlberg. 2004. Effects of a number of classes of 50S inhibitors on stop codon readthrough during protein synthesis. Antimicrob. Agents Chemother. 48:4889-4891.
32. Tu, D., G. Blaha, P. B. Moore, and T. A. Steitz. 2005. Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell 121:257-270. (Pubitemid 40546393)
33. Wilson, D. N., J. M. Harms, K. H. Nierhaus, F. Schlunzen, and P. Fucini. 2005. Species-specific antibiotic-ribosome interactions: implications for drug development. Biol. Chem. 386:1239-1252.
34. Wilson, D. N., F. Schluenzen, J. M. Harms, A. L. Starosta, S. R. Connell, and P. Fucini. 2008. The oxazolidinone antibiotics perturb the ribosomal peptidyl-transferase center and effect tRNA positioning. Proc. Natl. Acad. Sci. USA 105:13339-13344.