Studies toward the unique pederin family member psymberin: Structure-activity relationships, biochemical studies, and genetics identify the mode-of-action of psymberin

Journal of the American Chemical Society

Volumn 134, Issue 46, 2012, Pages 18998-19003

  Wu, Cheng Yang ^a   Feng, Yu ^a   Cardenas, Eduardo R ^a   Williams, Noelle ^a   Floreancig, Paul E ^b   De Brabander, Jef K ^a,c   Roth, Michael G ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^c UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE SIDE CHAIN; ARCHAEAL; BIOCHEMICAL STUDIES; CAENORHABDITIS ELEGANS; CELL UPTAKE; CELL-FREE; CYTOTOXIC ACTIVITIES; DIASTEREOMERS; GENETIC SCREENS; IN-VITRO ASSAYS; MOLECULAR TARGETS; MUTANT STRAIN; NATURAL PRODUCTS; PEDERIN; POINT MUTATIONS; PROTEIN SYNTHESIS; PROTEIN TRANSLATION; RIBOSOMAL PROTEINS; SIDE-CHAINS; STRUCTURAL MODIFICATIONS; STRUCTURE ACTIVITY RELATIONSHIPS;

AMIDES; GENE ENCODING; MOLECULAR PHYSICS; PROTEINS; STEREOCHEMISTRY;

CYTOTOXICITY;

DIHYDROISOCOUMARIN; ISOCOUMARIN DERIVATIVE; MYCALAMIDE A; PEDERIN; PSYMBERIN; RIBOSOME PROTEIN; TRANSLATION TERMINATION FACTOR; UNCLASSIFIED DRUG;

ARTICLE; CAENORHABDITIS ELEGANS; CONTROLLED STUDY; GENETIC SCREENING; HUMAN; HUMAN CELL; IN VITRO STUDY; MUTANT; NONHUMAN; POINT MUTATION; PROTEIN BINDING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

HELA CELLS; HUMANS; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84869467008     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3057002     Document Type: Article

References (26)

1. Feng, Y.; Jiang, X.; De Brabander, J. K. J. Am. Chem. Soc. 2012, 134, 17083
2. Cichewicz, R. H.; Valeriote, F. A.; Crews, P. Org. Lett. 2004, 6, 1951
3. Narquizian, R.; Kocienski, P. J. In The role of Natural Products in Drug Discovery; Mulzer, J.; Bohlmann, R.; Eds.; Ernst Schering Research Foundation Workshop 32; Springer: New York, 2000; pp 25-56.
4. Mosey, R. A.; Floreancig, P. E. Nat. Prod. Rep. 2012, 29, 980
5. Fisch, K. M.; Gurgui, C.; Heycke, N.; van der Sar, S. A.; Anderson, S. A.; Webb, V. L.; Taudien, S.; Platzer, M.; Rubio, B. K.; Robinson, S. J.; Crews, P.; Piel, J. Nat. Chem. Biol. 2009, 5, 494
6. Piel, J.; Butzke, D.; Fusetani, N.; Hui, D.; Platzer, M.; Wen, G.; Matsunaga, S. J. Nat. Prod. 2005, 68, 472
7. Brega, A.; Falaschi, A.; De Carli, L.; Pavan, M. J. Cell Biol. 1986, 36, 485
8. Burres, N. S.; Clement, J. J. Cancer Res. 1989, 49, 2935
9. Richter, A.; Kocienski, P.; Raubo, P.; Davies, D. A. Anticancer Drug Des. 1997, 12, 217
10. Wan, S.; Wu, F.; Rech, J. C.; Green, M. E.; Balachandran, R.; Horne, W. S.; Day, B. W.; Floreancig, P. E. J. Am. Chem. Soc. 2011, 133, 16668
11. We gratefully acknowledge a gift of natural mycalamide A from Peter Northcote (Victoria University of Wellington). For a reference, see: West, L. M.; Northcote, P. T.; Hood, K. A.; Miller, J. H.; Page, M. J. J. Nat. Prod. 2000, 63, 707
12. Jiang, X.; Williams, N.; De Brabander, J. K. Org. Lett. 2007, 9, 227
13. Dang, Y.; Schneider-Poetsch, T.; Eyler, D. E.; Jewett, J. C.; Bhat, S.; Rawal, V. H.; Green, R.; Liu, J. O. RNA 2011, 17, 1578
14. Baliga, B. S.; Pronczuk, A. W.; Munro, H. N. J. Biol. Chem. 1969, 244, 4480
15. Huang, X.; Shao, N.; Huryk, R.; Palani, A.; Aslanian, R.; Seidel-Dugan, C. Org. Lett. 2009, 11, 867
16. Watanabe, T.; Imaizumi, T.; Chinen, T.; Nagumo, Y.; Shibuya, M.; Usui, T.; Kanoh, N.; Iwabuchi, Y. Org. Lett. 2010, 12, 1040
17. Thompson, A. M.; Blunt, J. W.; Munro, M. H. G.; Perry, N. B. J. Chem. Soc. Perkin Trans. 1 1992, 1335
18. Thompson, A. M.; Blunt, J. W.; Munro, M. H. G.; Clark, B. M. J. Chem. Soc. Perkin Trans. 1 1994, 1025
19. Thompson, A. M.; Blunt, J. W.; Munro, M. H. G.; Perry, N. B. J. Chem. Soc. Perkin Trans. 1 1995, 1233
20. Kaletta, T.; Hengartner, M. O. Nat. Rev. Drug Discovery 2006, 5, 387
21. Ben-Shem, A.; Garreau de Loubresse, N.; Melnikov, S.; Jenner, L.; Yusupova, G.; Yusupov, M. Science 2011, 334, 1524
22. Gurel, G.; Blaha, G.; Steitz, T. A.; Moore, P. B. Antimicrob. Agents Chemother. 2009, 53, 5010
23. Chandramouli, P.; Topf, M.; Menetret, J. F.; Eswar, N.; Cannone, J. J.; Gutell, R. R.; Sali, A.; Akey, C. W. Structure 2008, 16, 535
24. Gad, S. C. Toxicology 1994, 93, 33
25. Stewart, I.; Seawright, A. A.; Schluter, P. J.; Shaw, G. R. BMC Dermatol. 2006, 6, 5
26. One of the reviewers suggested we perform a parallel DARTS assay to detect any protein binding partner(s) of psymberin in mammalian cells. We performed a DARTS assay of psymberin in HeLa cells twice without detecting any protein protection by psymberin as determined by silver staining. For a description of the DARTS assay, see: Lemonick Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 6811