386
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Design and Facile Synthesis of New Dinucleotide Cap Analog Containing Both 2′ and 3′-OH Modification on M7Guanosine Moiety

, &
Pages 611-619 | Received 14 Jan 2015, Accepted 13 Apr 2015, Published online: 07 Aug 2015

REFERENCES

  • Furuichi, Y.; Shatkin, A.J. Viral and cellular mRNA capping: Past and prospects. Adv. Virus Res. 2000, 55, 135–184.
  • Kore, A.R.; Charles, I.; Shanmugasundaram, M.; Xiao, Z.; Conard, R.C. Recent developments in 5′-terminal cap analogs: Synthesis and biological ramifications. Mini. Rev. Org. Chem. 2008, 5, 179–192.
  • Kore, A.R.; Charles, I.; Shanmugasundaram, M. Organic synthesis and improved biological properties of modified mRNA cap analogs. Curr. Org. Chem. 2010, 14, 1083–1098.
  • Jemielity, J.; Kowalska, J.; Rydzik, A.M.; Darzynkiewicz, E. Synthetic mRNA cap analogs with modified triphosphate bridge – Synthesis, applications and prospects. New. J. Chem. 2010, 34, 829–844.
  • Niedzwiecka, A.; Marcotrigiano, J.; Stepinski, J.; Jankowska, M.-A.; Wyslouch, A.-C.; Dadlez, M.; Gingras, A.; Mak, P.; Darzynkiewicz, E.; Sonenberg, N.; Burlesy, S.; Stolarski, R. Biophysical studies of eIF4E cap-binding protein: Recognition of mRNA 5′ cap structure and synthetic fragments of eIF4E and 4E-BPJ protein. J. Mol. Biol. 2002, 319, 615–635.
  • Hu, G.; Gershon, P.D.; Hodel, A.E.; Quiocho, F.A. mRNA cap recognition: Dominant role of enhanced stacking interactions between methylated based and protein aromatic side chains. Proc. Natl. Acad. Sci. USA. 1999, 96, 7149–7154.
  • Mazza, C.; Segref, A.; Mattaj, I.W.; Cusack, S. Large-scale induced fit recognition of an m(7) GpppG cap analogue by the human nuclear cap-binding complex. EMBO J. 2002, 21, 5548–5557.
  • Pasquinelli, A.E.; Dahlberg, J.E.; Lund, E. Reverse 5′ caps in RNAs made in vitro by phage RNA polymerase. RNA. 1995, I, 957–967.
  • Coller, J.; Parker, R. Eukaryotic mRNA decapping. Annu. Rev. Biochem. 2004, 73, 861–890.
  • Stepinski, J.; Waddell, C.; Stolarski, R.; Darzynkiewicz, E.; Rhoads, R.E. Synthesis and properties of mRNAs containing the novel “anti-reverse” cap analogs 7-methyl(3′-O-methyl)GpppG and 7-methyl(3′-deoxy)GpppG. RNA. 2001, 7, 1486–1495.
  • Peng, Z.-H.; Sharma, V.; Singleton, S.F.; Gershon, P.D. Synthesis and application of a chain-terminating dinulceotide mRNA cao analog. Org. Lett. 2002, 4, 161–164.
  • Jemielity, J.; Fowler, T.; Zuberek, J.; Stepinski, J.; Lewdorowicz, M.; Niedzwiecka, A.; Stolarski, R.; Darzynkiewicz, E.; Rhoads, R.E. Novel “aniti-reverse” cap analogs with superior translational properties. RNA. 2003, 9, 1108–1122.
  • Kore, A.R.; Shanmugasundaram, M.; Charles, I.; Cheng, A.M.; Barta, T.J. Synthesis and application of 2′-fluoro-substituted cap analogs. Bioorg. Med. Chem. Lett. 2007, 17, 5295–5299.
  • Kore, A.R.; Charles, I.; Shanmugasundaram, M. Synthesis and application of 2′-ara-fluoroguanosine-substituted cap analog. Chem. Lett. 2009, 38, 652–653.
  • Kore, A.R.; Shanmugasundaram, M.; Charles, I.; Vlassov, A.V.; Barta, T.J. Locked nucleic acid (LNA)-modified dinucleotide mRNA cap analogue: Synthesis, enzymatic incorporation, and utilization. J. Am. Chem. Soc. 2009, 131, 6364–6365.
  • Kore, A.R.; Charles, I. Synthesis and evaluation of 2′-O-allyl substituted dinucleotide cap analog for mRNA translation. Biorg. Med. Chem. 2010, 18, 8061–8065.
  • Kore, A.R.; Shanmugasundaram, M.; Vlassov, A.V. Synthesis and application of a new 2′, 3′-isopropylidene guanosine substituted cap analog. Bioorg. Med. Chem. Lett. 2008, 18, 4828–4832.
  • Warminski, M.; Kowalska, J.; Buck, J.; Zuberek, J.; Lukaszewicz, M.; Nicola, C.; Kuhn, A.N.; Sahin, U.; Darzynkiewicz, E.; Jemielity, J. The synthesis of isopropylidene mRNA cap analogs modified with phosphorothiolate moiety and their evaluation as promoters of mRNA translation. Bioorg. Med. Chem. Lett. 2013, 22, 3753–3758.
  • Kowalska, J.; Wypijewska del Nogal, A; Darzynkiewicz, Z.M.; Buck, J.; Nicola, C.; Kuhn, A.N.; Lukaszewicz, M.; Joanna Zuberek, J.; Malwina Strenkowska, M.; Marcin Ziemniak, M.; Maciej Maciejczyk, M.; Elzbieta Bojarska, E.; Rhoads, R.E.; Darzynkiewicz, E.; Sahin, U.; Jemielity, J. Synthesis, properties, and biological activity of boranophosphate analogs of the mRNA cap: Versatile tools for manipulation of therapeutically relevant cap-dependent processes. Nucelic Acids Res. 2014, 42, 10245–10264.
  • Kuhn, A.N.; Diken, M.; Kreiter, S.; Selmi, A.; Kowalska, J.; Jemielity, J.; Darzynkiewicz, E.; Huber, C.; Türeci, Ö.; Sahin, U. Phosphorothiolate cap analogs increase stability and translational efficiency of RNA vaccines in immature dendritic cells and induce superior immune responses in vivo. Gene Therapy. 2010, 17, 961–971.
  • Morse, M.A.; Nair, S.K.; Boczkowski, D.; Tyler, D.; Hurwitz, H.I.; Proia, A.; Clay, T.M.; Schlom, J.; Gilboa, E.; Lyerly, H.K. The feasibility and safety of immunotherapy with dendritic cells loaded with CEA mRNA following neoadjuvant chemoradiotherapy and resection of pancreatic cancer. Int. J. Gastrointest. Cancer 2002, 32, 1–6.
  • Tcherepanova, I.Y.; Adams, M.D.; Feng, X.; Hinohara, A.; Horvatinovich, J.; Calderhead, D.; Healey, D.; Nicolette, C.A. Ectopic expression of a truncated CD40L protein from synthetic post-transcriptionally capped RNA in dendritic cells induces high levels of IL-12 secretion. BMC Mol. Biol. 2008, 9, 90.
  • Ziemniak, M.; Strenkowska, M.; Kowalska, J.; Jemielity, J. Potential therapeutic applications of RNA cap analogs. Future Med. Chem. 2013, 5, 1141–1172.
  • Yoshikawa, M.; Kato, T.; Takenishi, T. A novel method for phosphorylation of nucleosides to 5′-nucleotides. Tetrahedron Lett. 1967, 8, 5065–5068.
  • Kore, A.R.; Parmar, G. An industrial process for selective synthesis of 7-methyl guanosine 5′-diphosphate: Versatile synthon for synthesis of mRNA cap analogues. Nucleosides Nucleotides Nucleic Acids 2006, 25, 337–340.
  • Sawai, H.; Shimazu, M.; Wakai, H.; Wakabayashi, H.; Shinozuka, K. Divalent metal ion-catalyzed pyrophosphate bond formations in aqueous solution. Synthesis of nucleotides containing polyphosphate. Nucleosides Nucleotides. 1992, 11, 773–785.
  • Kore, A.R.; Shanmugasundaram, M.; Charles, I. An efficient synthesis of highly functionalized dinucleotide cap analogs. Tetrahedron Lett. 2012, 52, 3518–3520.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.