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DOI: 10.1039/A606847B (Paper) Reference Section for: Chem. Commun., 1997, 121-122

Enhanced binding of a hexacyclic amidine analogue of Hoechst 33258 to the minor groove of DNA: 1H NMR and UV melting studies with the decamer duplex d(GGTAATTACC)2

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Clare E. Bostock-Smith, Kevin J. Embrey and Mark S. Searle

Abstract

NMR and UV melting studies with the decamer duplex d(GGTAATTACC)2 show that replacing the N-methylpiperazine ring of the DNA minor groove binding agent Hoechst 33258 with a hexacyclic amidine leads to both an increase in duplex stability (ΔTm ≈ 7 °C) and enhanced A–T specific recognition; the amidine NH exchanges slowly with the solvent and has a small temperature coefficient (<3 ppb/°C) supporting its involvement in intermolecular hydrogen bonding, however, the data suggest that the ring is flipping rapidly even at 278 K even though the interaction appears to contribute significantly to complex stability.

References

  1. J. Portugal and M. J. Waring, Biochim. Biophys. Acta, 1988, 949, 158 CrossRef CAS.
  2. M. S. Searle and K. J. Embrey, Nucl. Acids Res., 1990, 18, 3753 CAS.
  3. J. A. Parkinson, J. Barber, K. T. Douglas, J. Rosamond and D. Sharples, Biochemistry, 1990, 29, 10 181 CrossRef CAS.
  4. A. Fede, A. Labhardt, W. Bannwarth and W. Leupin, Biochemistry, 1991, 30, 11377 CrossRef CAS.
  5. K. J. Embrey, M. S. Searle and D. J. Craik, Eur. J. Biochem., 1993, 211, 437 CAS.
  6. A. Fede, M. Billeter, W. Leupin and K. Wuthrich, Structure, 1993, 1, 177 CrossRef CAS.
  7. P. E. Pjura, K. Grzeskowiak and R. E. Dickerson, J. Mol. Biol., 1987, 197, 257 CAS.
  8. M.-K. Teng, N. Usman, C. A. Frederick and A. H. J. Wang, Nucl. Acids. Res., 1988, 16, 2671 CAS.
  9. M. A. A. F. deC. T. Carrondo, M. Coll, J. Aymami, A. H. J. Wang, G. A. van der Marel, J. H. van Boom and A. Rich, Biochemistry, 1989, 28, 7849 CrossRef.
  10. J. R. Quintana, A. A. Lipanov and R. E. Dickerson, Biochemistry, 1991, 30, 10 294 CrossRef CAS.
  11. N. Spink, D. G. Brown, J. V. Skelly and S. Neidle, Nucl. Acids Res., 1994, 22, 1607 CrossRef CAS.
  12. M. C. Vega, I. Garcia Saez, J. Aymami, R. Eritja, G. A. van der Marel, J. H. van Boom, A. Rich and M. Coll, Eur. J. Biochem., 1994, 222, 721 CAS.
  13. A. A. Wood, C. M. Nunn, A. Czarny, D. W. Boykin and S. Neidle, Nucl. Acids. Res., 1995, 23, 3678 CrossRef CAS.
  14. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440 CrossRef CAS.
  15. A. Czarny, D. W. Boykin, A. A. Wood, C. M. Nunn, S. Neidle, M. Zhao and W. D. Wilson, J. Am. Chem. Soc., 1995, 117, 4716 CrossRef CAS.
  16. M. S. Searle, M. S. Westwell and D. H. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 141 RSC.
  17. G. J. Sharman, M. S. Searle, B. Benhamu, P. Groves and D. H. Williams, Angew. Chem., Int. Ed. Engl., 1995, 34, 1483 CrossRef CAS.
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