Skip to main content

Raman and NMR Studies on the Molecular Interactions between Electrophilic Reagents and Nucleic Acids Constituents

  • Chapter
Spectroscopy of Inorganic Bioactivators

Part of the book series: NATO ASI Series ((ASIC,volume 280))

Abstract

The molecular interactions between nucleic acids bases (using nucleosides as a model molecule) and the methylating carcinogen dimethyl sulfate (DMS) as well as those between their methylation products and anticarcinogen cis-Pt(NH3)2Cl2 (cisplatin) have been studied by Raman, IR and NMR spectroscopies. The aim of this work is to contribute to the study of the molecular mechanism of the cancerogenesis and of the pharmacological action of cisplatin. Localized and delocalized (mispairing) molecular reactivities of 1-methyladenosine (1-MeAdo) and 7-methylguanosine (7-MeGuo) have been related to biological activity, while the interactions of the same molecules with cisplatin have been related to the anticarcinogenic activity of the drug.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.00
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. A.Bertoluzza ‘Molecular interaction between nucleic acids and alkylating agents by Raman spectroscopy’, in Spectroscopy of biological molecules, Vol.139, p.91, Ed. by C.Sandorfy and T.Theophanides, D.Reidel Publishing Company, Dordrecht (1984);

    Google Scholar 

  2. S.Mansy and S.Tobias ‘Heavy-metal nucleotide interactions. II.Binding of methylmercury (II) to purine nucleosides and nucleotides studied by Raman difference spectroscopy’, J.Am.Chem.Soc., 96(22), (1974) 6874;

    Article  PubMed  CAS  Google Scholar 

  3. S.Mansy, W.L.Peticolas and R.S.Tobias ‘Raman spectra of methylderivatives of 5′-adenosine monophosphate, tubercidin, inosine, uridine and cytidine. Perturbation of nucleosides vibrations by electrophilic attack at different sites’, Spectrochim.Acta, 35A, (1979) 315;

    CAS  Google Scholar 

  4. J.D.Watson and F.H.C.Crick ‘Genetical implications of the structure of deoxyribonucleic acid’. Nature, 171, (1953) 964;

    Article  PubMed  CAS  Google Scholar 

  5. A.Bertoluzza, C.Fagnano, M.R.Tosi, V.Tugnoli, M.A.Morelli and G.Barbarella ‘Molecular interactions between nucleic acids and antitumor substances by Raman and NMR spectroscopy’, Anticancer Research, 64, (1986) 1385;

    Google Scholar 

  6. W.Stadely, W. von Philipsborn, A.Wick and I.Kompis ‘N-15-NMR. Studies of aminopyridines, aminopyrimidines and of some diazine N-oxide’, Helv.Chim.Acta, 63, (1980) 504;

    Article  Google Scholar 

  7. N.C.Gonnella, H.Hakanishi, D.S.Holtwick, K.Kanamori, N.J.Leonard and J.D.Roberts ‘Studies of tautcmers and protonation of adenine and its derivatives by nitrogen-15 nuclear magnetic resonance spectroscopy’, J.Am.Chem.Soc., 105(7), (1983) 2050;

    Article  CAS  Google Scholar 

  8. G.C.Levy and R.L.Lichter ‘Nitrogen-15 nuclear magnetic resonance spectroscopy’, p.74, John Wiley, New York (1979);

    Google Scholar 

  9. A.Bertoluzza, C.Fagnano, M.R.Tosi, V.Tugnoli, M.A. Morelli and G.Barbarella ‘Raman and NMR spectroscopies of interactions of carcinogenic and anticarcinogenic substances with nucleic acids constituents’, in Spectroscopy of biological molecules, p.411, Ed. by E.D.Schmid, F.W.Schneider and F.Siebert, John Wiley, New York (1988);

    Google Scholar 

  10. A.Bertoluzza, C.Fagnano, M.R.Tosi, V.Tugnoli, M.A. Morelli and G.Barbarella ‘Carcinogenic and anticarcinogenic substances and nucleic acids constituents: their interaction mechanism by Raman and NMR spectroscopy’, Biochem. Pharmacol., 37(9), (1988) 1851;

    Article  PubMed  CAS  Google Scholar 

  11. F.Pochon, Y.Pascal, P.Pitha and A.M.Michelson ‘Photochimie des polynucleotides. IV.Photochimie de quelques nucleosides puriques methyles’, Biochim.Biophys.Acta, 213, (1970) 273;

    PubMed  CAS  Google Scholar 

  12. S.M.Hecht, B.L.Adams and J.W.Kozarich ‘Chemical transformation of 7,9-disubstituted purines and related heterocycles. Selective reduction of imine and immonium salts’, J.Org.Chem., 41(13), (1976) 2303;

    Article  PubMed  CAS  Google Scholar 

  13. G.Barbarella, A.Bertoluzza and V.Tugnoli ‘Nitrgen-15 characterization of 7-methylguanosine and its base-pair with cytidine in dimethyl sulfoxide’, Magn.Res.Chem., 25, (1987) 864;

    Article  CAS  Google Scholar 

  14. S.Mansy and W.L.Peticolas ‘Detection of the sites of alkylation in DNA and polynucleotides by laser Raman spectroscopy’, Biochemistry, 15(12), (1976) 2650;

    Article  PubMed  CAS  Google Scholar 

  15. G.Barbarella, A.Bertoluzza and V.Tugnoli ‘Nitrogen-15 NMR characterization of the neutral form of 7-methylguanosine’, Nucleic Acids Research, 16(14), (1988) 7202;

    Article  PubMed  CAS  Google Scholar 

  16. not yet published;

    Google Scholar 

  17. J.A.Haines, C.B.Reese and Lord Todd ‘The methylation of guanosine and related compounds with diazomethane’, J.Chem.Soc., (1962) 5281;

    Google Scholar 

  18. J. W. Jones and R. K. Robins ‘Purine nuceosides. III.Methylation studies of certain naturally occuring purine nucleosides’, J.Am.Chem.Soc., 85, (1963);

    Google Scholar 

  19. P.D.Lawley and P.Brookes ‘Further studies on the alkylation of nucleic acids and their constituent nucleotides’, Biochem.J., 89, (1963);

    Google Scholar 

  20. C.J.Chetsanga, B.Bearie and C.Makaroff ‘Alkaline opening of imidazole ring of 7-methylguanosine. 1.Analysis of the resulting pyrimidine derivatives’, Chem.-Biol.Interact., 41, (1982) 217;

    Article  PubMed  CAS  Google Scholar 

  21. C.J.Chetsanga and C.Makaroff ‘Alkaline opening of imidazole ring of 7-methylguanosine. 2.Further studies on reaction mechanism and products’, Chem.-Biol.Interact., 41, (1982) 235;

    Article  PubMed  CAS  Google Scholar 

  22. S.Boiteux, J.Belleney, B.P.Roques and J.Laval ‘Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides’. Nucleic Acids Research, 12(13), (1984) 5429;

    Article  PubMed  CAS  Google Scholar 

  23. T.R.O’Connor, S.Boiteux and J.Laval ‘Ring-opened 7-methylguanine residues in DNA are a block to in vitro DNA synthesis’, Nucleic Acids Research, 16(13), (1988) 5879;

    Article  PubMed  Google Scholar 

  24. G.Barbarella, A.Bertoluzza, M.A.Morelli and V.Tugnoli ‘Ring-opening of 7-methylguanosine in water at physiological pH. A C-13 magnetic resonance study’, Abstracts of the Second International Conference of Anticancer Research, October 11–15, 1988, Saronis, Greece;

    Google Scholar 

  25. M.D.Topal and J.R.Fresco ‘Complementary base pairing and the origin of substitution mutations’. Nature, 263, (1976) 285.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Kluwer Academic Publishers

About this chapter

Cite this chapter

Morelli, M.A., Bertoluzza, A., Fagnano, C., Tugnoli, V., Tosi, M.R., Barbarella, G. (1989). Raman and NMR Studies on the Molecular Interactions between Electrophilic Reagents and Nucleic Acids Constituents. In: Theophanides, T. (eds) Spectroscopy of Inorganic Bioactivators. NATO ASI Series, vol 280. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2409-3_11

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-2409-3_11

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-7585-5

  • Online ISBN: 978-94-009-2409-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics