The Hydrolysis of 5′-CAP Dinucleotide Analogs: Catalysis by Bi- and Terpyridine Complexes of Cu²⁺ and Zn²⁺ Ions

REFERENCES

• Shatkin , A. J. 1976 . Capping of eukaryotic mRNAs . Cell , 9 : 645 – 653 .
   PubMed Web of Science ®Google Scholar
• Darnell , J. E. 1979 . Transcription units for mRNA production in eukaryotic cells and their DNA viruses . Prog. Nucleic Acid Res. Mol. Biol. , 22 : 327 – 353 .
   PubMedGoogle Scholar
• Baker , B. F. 1993 . Decapitation of a 5′-capped oligoribonucleotide by o-phenanthroline: Cu(II) . J. Am. Chem. Soc. , 115 : 3378 – 3379 .
   Web of Science ®Google Scholar
• Baker , B. F. , Ramasamy , K. and Kiely , J. 1996 . Decapitation of a 5′ capped RNA by antysense copper complex conjugate . Bioorg. Med. Chem. Lett. , 6 : 1647 – 1652 .
   Web of Science ®Google Scholar
• Mikkola , S. , Salomäki , S. , Zhang , Z. , Mäkki , E. and Lönnberg , H. 2005 . Preparation and properties of mRNA 5′-cap structure . Current. Org. Chem. , 9 : 999 – 1022 .
   Web of Science ®Google Scholar
• Zhang , Z. , Lönnberg , H. and Mikkola , S. 2005 . Metal ion complexes of macrocyclic polyamines enhance both the phosphate hydrolysis and imidazole ring opening of RNA 5′-cap structure . Chem. Biodivers. , 2 : 92 – 103 .
   PubMed Web of Science ®Google Scholar
• Zoltewicz , J. A. , Clark , D. F. , Sharpless , T. W. and Grahe , G. 1970 . Kinetics and mechanism of the acid-catalyzed hydrolysis of some purine nucleosides . J. Am. Chem. Soc. , 92 : 1741 – 1749 .
   PubMed Web of Science ®Google Scholar
• Lahti , M. , Santa , H. , Darżynkiewicz , E. and Lönnberg , H. 1990 . pH-independent depurination of 7-alkylguanosines and their 5′-monophosphates . Acta Chem. Scand. , 44 : 636 – 638 .
   Google Scholar
• Chetsanga , C. J. , Bearie , B. and Makaroff , C. 1982 . Alkaline opening of imidazole ring of 7-methylguanosine. 1. Analysis of the resulting pyrimidine derivatives . Chem. Biol. Interact. , 41 : 217 – 233 .
   PubMed Web of Science ®Google Scholar
• Chetsanga , C. J. and Makaroff , C. 1982 . Alkaline opening of imidazole ring of 7-methylguanosine. 2. Further studies on reaction mechanisms and products . Chem. Biol. Interact. , 41 : 235 – 249 .
   PubMed Web of Science ®Google Scholar
• Darżynkiewicz , E. , Labadi , I. , Haber , D. , Burger , K. and Lönnberg , H. 1988 . 7-Methylguanine nucleotides and their structural analogues; protolytic equilibria, complexing with magnesium (II) ion and kinetics for alkaline opening of the imidazole ring . Acta Chem. Scand. B , 42 : 86 – 92 .
   PubMedGoogle Scholar
• Stachelska , A. and Wieczorek , Z. 2005 . Alkaline hydrolysis of the imidazole moiety in the dinucleotide cap analogs–is the stacking interaction important? . Collect. Symp. Ser. , 7 : 475 – 477 .
   Google Scholar
• Stachelska , A. , Wieczorek , Z. J. , Stępiński , J. , Jankowska-Anyszka , M. , Lönnberg , H. and Darżynkiewicz , E. 2006 . Kinetics of the imidazolium ring opening of mRNA 5′-cap analogs in aqueous alkali . Collect. Czech. Chem. Commun. , 71 : 567 – 578 .
   Web of Science ®Google Scholar
• Mikkola , S. 2004 . Hydrolytic reactions of diadenosine 5′,5′-triphosphate . Org. Biomol. Chem. , 2 : 770 – 776 .
   PubMed Web of Science ®Google Scholar
• Baker , B. F. , Khalili , H. , Wei , N. and Morrow , J. R. 1997 . Cleavage of the 5′ cap structure of mRNA by a europium (III) macrocyclic complex with pendant alcohol groups . J. Am. Chem. Soc. , 119 : 8749 – 8755 .
   Web of Science ®Google Scholar
• Andersson , S. , Lähde , M. , Mikkola , S. , Morris , G. , Stachelska , A. , Valakoski , S. and Williams , N. H. 2002 . Metal ion-promoted hydrolysis of mRNA 5′-cap models . Collect. Symp. Ser. Chem. , 5 : 373 – 375 .
   Google Scholar
• Valakoski , S. , Heiskanen , S. , Andersson , S. , Lähde , M. and Mikkola , S. 2002 . Metal ion-promoted cleavage of mRNA 5′-cap models: Hydrolysis of the triphosphate bridge and reactions of the N7-methyl guanine base . J. Chem. Soc., Perkin Trans. , 2 : 1 – 8 .
   Google Scholar
• McCue , K. P. and Morrow , J. R. 1999 . Hydrolysis of a model for the 5′-cap of mRNA by dinuclear copper (II) and zinc (II) complexes. Rapid hydrolysis by four copper (II) ions . Inorg. Chem. , 38 : 6136 – 6142 .
   PubMed Web of Science ®Google Scholar
• Wieczorek , Z. , Darżynkiewicz , E. , Kuusela , S. and Lönnberg , H. 1999 . The Cu2+-promoted cleavage of mRNA 5′-cap analogs: a kinetic study with P1-(7-methylguanosin-5′-yl) P3-(nucleosid-5′-yl) triphosphates and P1-(7-methylguanosin-5′-yl) P4-(guanosin-5′-yl) tetraphosphat . Nucleos. Nucleot. , 18 : 11 – 21 .
   Web of Science ®Google Scholar
• Stachelska-Wierzchowska , A. and Wieczorek , Z. J. 2011 . Hydrolysis of 5′,5′-tri- or tetraphosphate-mRNA 5′-cap analogs promoted by Cu2+ or Zn2+ metal ions . Nucleos. Nucleot. Nucl. , 30 : 1 – 14 .
   PubMed Web of Science ®Google Scholar
• Maanapää , L. , Taherpour , S. , Zhang , Z. , Guillaume , C. , Szilágy , I. , Mäki , E. and Mikkola , S. 2007 . Cu2+-terpyridine complexes as catalysts of the cleavage of the 5′-cap structure of mRNA . Nucleos. Nucleot. Nucl. , 26 : 1423 – 1426 .
   PubMed Web of Science ®Google Scholar
• Szilágyi , I. , Mikkola , S. , Lönnberg , H. , Labádi , I. and Pálinko , I. 2007 . Hydrolysis of dinucleoside phosphates–mRNA 5′ cap analogues–promoted by a binuclear copper (II)–zinc (II) complex . J. Inorg. Biochem. , 101 : 1400 – 1403 .
   PubMed Web of Science ®Google Scholar
• Linkletter , B. and Chin , J. 1995 . Rapid hydrolysis of RNA with a CuII complex . Angew. Chem. Int. Ed. Engl. , 34 ( 4 ) : 472 – 474 .
   Web of Science ®Google Scholar
• Darżynkiewicz , E. , Ekiel , I. , Tahara , S. M. , Seliger , L. S. and Shatkin , A. J. 1985 . Chemical synthesis and characterization of 7-methylguanosine cap analogues . Biochemistry , 24 : 1701 – 1707 .
   Web of Science ®Google Scholar
• Darżynkiewicz , E. , Stępiński , J. , Tahara , S. M. , Stolarski , R. , Ekiel , I. , Haber , D. , Neuvonen , K. , Lehikoinen , P. , Labadi , I. and Lönnberg , H. 1990 . Synthesis, conformation and hydrolytic stability of P1,P3-dinucleoside triphosphates related to mRNA 5′-cap, and comparative kinetic studies on their nucleoside and nucleoside monophosphate analogs . Nucleos. Nucleot. , 9 : 599 – 618 .
   Web of Science ®Google Scholar
• Roy , R. N. , Roy , L. N. , Tabor , B. J. , Himes , C. A. , Richards , S. J. , Simon , A. N. , Moore , A. C. , Seing , L. A. , Craig , H. D. and Robinson , K. T. 2004 . Buffer standards for the physiological pH of zwitterionic compounds, MOBS and TABS from 5 to 55°C . J. Solution Chem. , 33 ( 10 ) : 1199 – 1211 .
   Web of Science ®Google Scholar
• Gustafson , R. L. and Martel , A. E. 1959 . Hydrolytic tendencies of metal chelate compounds. V. Hydrolysis and dimerization of copper (II) chelates of 1,2-diamines . J. Am. Chem. Soc. , 81 ( 3 ) : 525 – 529 .
   Web of Science ®Google Scholar