Exceptional and Selective Stabilization of A-T Rich DNA·DNA Duplexes by N-Methylpyrrole Carboxamide Peptides Conjugated to Oligodeoxynucleotides

Journal of the American Chemical Society

Volumn 117, Issue 17, 1995, Pages 4995-4996

  Sinyakov, Alexander N ^a   Lokhov, Sergey G ^b   Kutyavin, Igor V ^c   Gamper, Howard B ^c   Meyer, Rich B ^c  

^a STATE RESEARCH CENTER OF VIROLOGY AND BIOTECHNOLOGY VECTOR   (Russian Federation)

^b INSTITUTE OF CHEMICAL BIOLOGY AND FUNDAMENTAL MEDICINE   (Russian Federation)

^c Nanogen Inc USA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLPYRROLECARBOXAMIDE PEPTIDE DERIVATIVE; AMIDE; OLIGODEOXYRIBONUCLEOTIDE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; DNA PROTEIN COMPLEX; DNA STRUCTURE; THERMOSTABILITY;

EID: 0029005427     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00122a031     Document Type: Editorial

References (17)

1. For review, see: Zimmer, C.; Wähnert, U. Prog. Biophys. Mol. Biol. 1986, 47, 31 and references cited therein.
2. Luck, G.; Triebel, H.; Waring, M.; Zimmer, C. Nucleic Acids Res. 1974, 1, 503.
3. Wartell. R. M.; Larson, J. E.; Wells, R. D. J. Biol. Chem. 1974, 249, 6719.
4. Marky, L. A.; Breslauer, K. J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4359.
5. Isaacs, S. T.; Shen, C.-K.; Hearst, J. E.; Rapoport, H. Biochemistry 1977, 16, 1058.
6. Reinhardt, C. G.; Krugh, T. R. Biochemistry 1978, 17, 4845.
7. Hansen, J. B.; Koch, T.; Buchardt, O.; Nielsen, P. E.; Wirth, M.; Norden, B. Biochemistry 1983, 22, 4878.
8. Gursky, G. V.; Zasedatelev, A. S.; Zhuze, A. L.; Knorlin, A. A.; Grokhovsky, S. L.; Streltsov, S. A.; Surovaya, A. N.; Nikitin, S. M.; Krylov, A. S.; Retchinsky, V. O.; Mikhailov, M. V.; Beabealashvili, R. S.; Gottikh, B. P. Cold Spring Harbor Symp. Quant. Biol. 1983, 47, 367.
9. Zimmer, C.; Luck, G.; Thrum, H. Stud. Biophys. 1970, 24-25, 311.
10. Pullman, B. Specificity and Biological Interaction. International Symposium at the Pontifical Academy of Sciences; Chagas, C., Pullman, B., Eds.; Vatican Press: Vatican City, 1984; pp 1–20.
11. Hélène, C.; Toulmé, J.-J. In Topics in Molecular and Structural Biology. Oligodeoxynucleotides: antisense inhibitors of gene expression; Cohen, J. S., Eds.; CRC Press: Boca Raton, 1989; pp 137–172.
12. Grehn, L.; Ragnarsson, U. J. Org. Chem. 1981, 46, 3492.
13. The 3'-terminal phosphate of the cetyltrimethylammonium salt of an ODN in organic solution was activated using triphenylphosphine/dipyridyl disulfide using a previously described method (Godovikova, T. S.; Zarytova, V. F.; Maltzeva, T. V.; Khalimskaya, L. M. Bioorg. Khim. 1989, 15, 1246).
14. 19do not form triplexes in 0.2 M NaCl even when an A:T ratio of 1:2 is employed (Kibler-Herzog, L.; Kell, B.; Zon, G.; Shinozuka, K.; Mizan, S.; Wilson, W. D. Nucleic Acids Res. 1990, 18, 3545).
15. Free netropsin significantly destabilizes the poly(dT)·poly(dA)·poly(dT) triplex (Park, Y.-W.; Breslauer, K. J. Proc. Natl. Acad. Sci U.S.A. 1992, 89, 6653).
16. 8and minor groove binders do not form T-A-T triplexes with poly(dA) when the T:A ratio is 1:1 or 2:1.
17. The ODN-ethidium bromide conjugates used in this study were a gift of Dr. A. Koshkin (Novosibirsk, Russia). Their synthesis is described in the following: Koshkin, A. A.; Ivanova, T. M.; Bulychev, N. V.; Dobrikov, M. I.; Lebedev, A. V. Bioorg. Khim. 1993, 13, 570.