Phosphorothioate analogs of m7GTP are enzymatically stable inhibitors of cap-dependent translation

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 7, 2009, Pages 1921-1925

  Kowalska, Joanna ^a   Lukaszewicz, Maciej ^a   Zuberek, Joanna ^a   Ziemniak, Marcin ^a   Darzynkiewicz, Edward ^a   Jemielity, Jacek ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

5 mRNA cap analogs; Decapping Scavenger DcpS; Inhibition of translation; Nucleotide synthesis; Phosphorothioate; Translation initiation factor eIF4E

Indexed keywords

7 METHYLGUANOSINE; 7 METHYLGUANOSINE 5' (1 THIOTRIPHOSPHATE); DECAPPING SCAVENGER PYROPHOSPHATASE; GUANOSINE TRIPHOSPHATE DERIVATIVE; INITIATION FACTOR 4E; INORGANIC PYROPHOSPHATASE; MESSENGER RNA; PHOSPHOROTHIOIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 7 METHYLGUANOSINE TRIPHOSPHATE; 7-METHYLGUANOSINE 5'-(1-THIOTRIPHOSPHATE); 7-METHYLGUANOSINE TRIPHOSPHATE; CAPPED RNA; DCPS PROTEIN, HUMAN; DRUG DERIVATIVE; GUANOSINE TRIPHOSPHATE; NUCLEOTIDE; PROTEIN SYNTHESIS INHIBITOR; RIBONUCLEASE;

ARTICLE; BINDING AFFINITY; DIASTEREOISOMER; DRUG POTENCY; DRUG STABILITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROLYSIS; RABBIT; RETICULOCYTE; TRANSLATION REGULATION; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; MOUSE; PROTEIN SYNTHESIS; STEREOISOMERISM; SYNTHESIS;

ORYCTOLAGUS CUNICULUS;

ANIMALS; ENDORIBONUCLEASES; EUKARYOTIC INITIATION FACTOR-4E; GUANOSINE TRIPHOSPHATE; HUMANS; MICE; PROTEIN BIOSYNTHESIS; PROTEIN SYNTHESIS INHIBITORS; RNA CAP ANALOGS; RNA CAPS; RNA, MESSENGER; STEREOISOMERISM; THIONUCLEOTIDES;

EID: 61849171926     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.053     Document Type: Article

References (20)

1. Furuichi Y., and Shatkin A.J. Adv. Virus. Res. 55 (2000) 135
2. Richter J.D., and Sonenberg N. Nature 433 (2005) 477
3. De Benedetti A., and Graff J.R. Oncogene 23 (2004) 3189
4. Herbert T.P., Fahraeus R., Prescott A., Lane D.P., and Proud C.G. Curr. Biol. 10 (2000) 793
5. Moerke N.J., Aktas H., Chen H., et al. Cell 128 (2007) 257
6. Graff J.R., Konicek B.W., and Vincent T.M. J. Clin. Invest. 117 (2007) 2638
7. Darzynkiewicz E., Ekiel I., Lassota P., and Tahara S.M. Biochemistry 26 (1987) 4372
8. Cai A., Jankowska-Anyszka M., Centers A., Chlebicka L., Stepinski J., Stolarski R., Darzynkiewicz E., and Rhoads R.E. Biochemistry 38 (1999) 8538
9. Jemielity J., Fowler T., Zuberek J., Stepinski J., Lewdorowicz M., Niedzwiecka A., Stolarski R., Darzynkiewicz E., and Rhoads R.E. RNA 9 (2003) 1108
10. Zuberek J., Jemielity J., Jablonowska A., Stepinsk J., Dadlez M., Stolarski R., and Darzynkiewicz E. Biochemistry 43 (2004) 5370
11. Kowalska J., Lewdorowicz M., Zuberek J., et al. RNA 14 (2008) 1119
12. Liu H., Rodgers N.D., Jiao X., and Kiledjian M. EMBO J. 21 (2002) 4699
13. Moran J.R., and Whitesides G.M. J. Org. Chem. 49 (1984) 704
14. 3S: 551.98.
15. Ludwig J., and Eckstein F. J. Org. Chem. 54 (1989) 631
16. Major D.T., Nahum V., Wang Y., Reiser G., and Fischer B. J. Med. Chem. 47 (2004) 4405
17. Li P., Xu Z., Liu H., Wennefors C.K., Dobrikov M.I., Ludwig J., and Shaw B.R. J. Am. Chem. Soc. 127 (2005) 16782
18. Niedzwiecka A., Marcotrigiano J., Stepinski J., et al. J. Mol. Biol. 319 (2002) 615
19. Rhoads R.E. Prog. Mol. Subcell. Biol. 9 (1985) 104
20. The synthesis was accomplished accordingly to the strategy described in Refs. 9a,b.