A new strategy for the destabilization of double-stranded nucleic acids by phenylalkylamine derivatives

Angewandte Chemie - International Edition

Volumn 37, Issue 21, 1998, Pages 3016-3019

  Ali, Anmar ^a   Gasiorek, Martin ^a   Schneider, Hans Jörg ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Amines; Intercalation; Nucleic acids; Stacking interactions; Supramolecular chemistry

Indexed keywords

AMINE; DNA; LIGAND; NUCLEIC ACID; PHENYL GROUP; PHENYLALKYLAMINE; POLYMER; RNA;

ARTICLE; MELTING POINT; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0032538766     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981116)37:21<3016::AID-ANIE3016>3.0.CO;2-V     Document Type: Article

References (31)

1. a) W. D. Wilson in Nucleic Acids in Chemistry and Biology (Eds.: M. Blackburn, M. Gait), IRL, Oxford, chap. 8, 1989;
2. b) J. W. Lown, Anti-Cancer Drug Des. 1988, 3, 25;
3. c) P. D. Dervan, Science 1986, 232, 464;
4. d) S. Neidle, Z. Abraham, CRC Crit. Rev. Biochem. 1984, 17, 73;
5. e) S. Neidle, T. Jenkins, Mol. Des. Model. Part B 1991, 203, 433;
6. f) for interactions of RNA with small ligands, see "Design and Analysis of Molecular Motifs for Specific Recognition of RNA": K. Li, M. Fernandez-Saiz, C. T. Rigl, A. Kumar, K. G. Ragunathan, A. W. McConnaughie, D. W. Boykin, H.-J. Schneider, W. D. Wilson in Bioorg. Med. Chem. 1997, Symposium Issue: Strategies for RNA Recognition, 1157.
7. G. L. Eichhorn, Nature 1962, 194, 474.
8. a) H.-P.Hsieh, J. G. Muller, C. J. Burrows, J. Am. Chem. Soc. 1994, 116, 1207;
9. b) H. R. Mahler, R. Goutarel, Q. Khuong-Huu, Biochemistry 1968, 7, 1568.
10. Double-strand destabilizations have also been reported with some intercalating reagents such as acridine orange, but with subsequent precipitations: J. Kapusdnsky, Z. Darzynkiewicz, Nucleic Acids Res. 1983, 11, 7555.
11. E. Kimura, T. Ikeda, M. Shionoya, Pure Appl Chem. 1997, 69, 2187.
12. D. W. Wilson, L. Ratmeyer, M. T. Cegla, J. Spychala, D. Boykin, M. Demeunynck, J. Homme, G. Krishnan, D. Kennedy, R. Vinayak, G. Zon, New J. Chem. 1994, 18, 419.
13. J.-L. Dimicoli, C. Hélène, Biochemistry 1974, 13, 724.
14. J. Sartorius, H.-J. Schneider, FEBS Lett. 1995, 374, 387;
15. H.-J. Schneider, J. Sartorius in Physical Supramolecular Chemistry (NATO ASI Ser. Ser. C 1996, 485), p. 11.
16. L. Kapciak, E. J. Gabbay, J. Am. Chem. Soc. 1975, 97, 403;
17. E. J. Gabbay, C. S. Baxter, J. Am. Chem. Soc. 1973, 95, 7850.
18. D. L. Ollis, S. W. White, Chem. Rev. 1987, 87, 981.
19. S. Chandrasekaran, S. Kusuma, D. W. Boykin, W. D. Wilson, Magn. Res. Chem. 1986, 24, 630;
20. for similar shifts in self-associating nucleoside derivatives, see K. H. Scheller, H. Sigel, J. Am. Chem. Soc. 1983, 105, 5891;
21. O. Yamauchi, A. Odani, H. Masuda, H. Sigel, Met. Ions Biol. Syst. 1996, 32, 207, and references therein.
22. W. Curtis Johnson, Jr., Circular Dichroism and the conformational analysis of biomolecules, Plenum, New York, 1996, pp. 433-468
23. C. Hélène, T. Montenay-Garestier, J. L. Dimicoli, Biochim. Biophys. Acta 1971, 254, 349.
24. R. J. Roberts, Cell 1995, 82, 9, and references therein.
25. M. Fernandez-Saiz, H.-J. Schneider, J. Sartorius, W. D. Wilson, J. Am. Chem. Soc., 1996, 18, 4739.
26. L. Strekowski, J. L. Mokrosz, W. D. Wilson, M. J. Mokroz, A. Strekowski, Biochemistry 1992, 57, 10802;
27. D. W. Wilson, L. Ratmeyer, M. T. Cegla, J. Spychala, D. Boykin, M. Demeunynck, J. Homme, G. Krishnan, D. Kennedy, R. Vinayak, G. Zon, New J. Chem. 1994, 18, 419.
28. a) A. Korolkovas in Essentials of Medicinal Chemistry, Wiley, New-York, 1988;
29. b) P. V. Scaria, J. C. Craig, R. H. Shafer, Biopolymers 1993, 33, 887;
30. c) J. Sartorius , H.-J. Schneider, J. Chem. Soc. Perkin Trans. 2 1997, 2319, and references therein.
31. The synthesis of the new ligands will be reported elsewhere. All new compounds showed satisfactory analytical data.