Structure-dependent effects of minor groove binders on the DNA triple helix motif poly(dA)·2poly(dT): Influence of antitumoractive nonintercalative bisquaternary ammonium heterocycles

Anti-Cancer Drug Design

Volumn 13, Issue 5, 1998, Pages 417-429

  Förtsch, Ingo ^a   Baguley, Bruce ^b   Zimmer, Christoph ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Bisquaternary ammonium heterocycles; DNA binding; Triple helix

Indexed keywords

AMMONIUM DERIVATIVE; ANTINEOPLASTIC AGENT; DNA; HETEROCYCLIC COMPOUND; NSC 101327; PENTAMIDINE; SN 16814; SN 18071; SN 6113; SN 6131; SN 6132; SN 6999; SODIUM ION; SPERMINE; UNCLASSIFIED DRUG;

ARTICLE; CIRCULAR DICHROISM; DNA DENATURATION; DRUG DNA INTERACTION; DRUG STRUCTURE; IONIC STRENGTH; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TRIPLE HELIX;

ANTINEOPLASTIC AGENTS; CIRCULAR DICHROISM; DNA; HETEROCYCLIC COMPOUNDS; LIGANDS; NUCLEIC ACID DENATURATION; POLYDEOXYRIBONUCLEOTIDES; QUATERNARY AMMONIUM COMPOUNDS; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE;

EID: 0031854969     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. AGAZIE, Y.M., LEE, J.S. & BURKHOLDER, G.D. (1994). Characterization of a new monoclonal antibody to triplex DNA and immunofluorescent staining of mammalian chromosomes. Journal of Biological Chemistry, 269, 7019.
2. AGAZIE, Y.M., BURKHOLDER, G.D. & LEE, J.S. (1996). Triplex DNA in the nucleus: direct binding of triplex-specific antibodies and their effect on transcription, replication and cell growth. Biochemical Journal, 316, 461.
3. BAGULEY, B.C. (1982). Nonintercalative DNA-binding antitumour compounds. Molecular and Cellular Biochemistry, 43, 167.
4. BARAWKAR, D.A., & GANESH, K.N. (1995). Fluorescent d(CGCGHAATTCGCG): characterization of major groove polarity and study of minor groove interactions through a major groove semantophore conjugate. Nucleic Acid Research, 23, 159.
5. BURCKHARDT, G., ZIMMER, CH. & BAGULEY, B.C. (1987). Binding of nonintercalative antitumor drugs to DNA-polymers: structural effects of bisquaternary ammonium heterocycles, Journal of Biomolecular Structure & Dynamics, 4, 813.
6. BURKHOLDER, G.D., LATIMER, J.P. & LEE, J.S. (1991). Immunofluorescent localization of triplex DNA in polytene chromosomes of Chironomus and Drosophila. Chromosoma, 101, 11.
7. CAIN, B.F., BAGULEY, B.C. & DENNY, W.A. (1978). Potenial antitumor agents. 28. Deoxyribonucleic acid polyintercalating agents. Journal of Medicinal Chemistry, 21, 658.
8. CHALIKIAN, T.V., PLUM, G.E., SARVAZYAN, A.P. & BRESLAUER, K.J. (1994). Influence of drug binding on DNA hydration: acoustic and densimetric characterizations of netropsin binding to the poly(dAdT)-poly(dAdT) and poly(dA)-poly(dT) duplexes and the poly(dT)-poly(dT)-poly(dT) triplex at 25 degrees C. Biochemistry, 33, 8629.
9. DENNY, W.A., ATWELL, G.J., BAGULEY, B.C. & CAIN, B.F (1979). Potential antitumor agents. Part 29. Quantitative structure-activity relationships for the antileukemic bisquaternary ammonium heterocycles. Journal of Medicinal Chemistry, 22, 134.
10. DURAND, M & MAURIZOT, J.C. (1996). Distamycin A complexation with a nucleic acid triple helix. Biochemistry, 35, 9133.
11. DURAND, M., THUONG, N.T. & MAURIZOT. J.C. (1992). Binding of netropsin to a DNA triple helix. Journal of Biological Chemistry, 267, 24394.
12. DURAND, M., THUONG, N.T. & MAURIZOT, J.C (1994a). Interaction of Hoechst 33258 with a DNA triple helix. Biochimie, 76, 181.
13. DURAND, M., THUONG, N.T. & MAURIZOT, J.C. (1994b). Berenil complexation with a nucleic acid triple helix. Journal of Biomolecular Structure & Dynamics, 11, 1191.
14. FORTSCH, I., BIRCH-HIRSCHFELD, E., SCHÜTZ, H. & ZIMMER, C.H. (1996). Different effects of nonintercalative antitumor drugs on DNA triple helix stability: SN-18071 promotes triple helix formation. Journal of Biomolecular Structure & Dynamics, 14, 317.
15. HAMPEL, K.J. & LEE, J.S. (1993). Two-dimensional pulsed-field gel electrophoresis of yeast chromosomes: evidence for triplex-mediated DNA condensation. Biochemical Cell Biology, 71, 190.
16. HAMPEL, K.J., CROSSON, P. & LEE, J.S. (1991). Polyamines favor DNA triplex formation at neutral pH. Biochemistry, 30, 4455.
17. HAMPEL, K.J., ASHLEY, C. & LEE, J.S. (1994). Kilobase-range communication between polypurine-polypyrimidine tracts in linear plasmids mediated by triplex formation: a braided knot between two linear duplexes. Biochemistry, 33, 5674.
18. HÉLENE, C. (1991). The anti-gene strategy: control of gene expression by triplex-forming oligonucleotides. Anti-Cancer Drug Design, 6, 569.
19. HELÈNE, C. & TOULMÉ, J.-J. (1990). Specific regulation of gene expression by antisense, sense and antigene nucleic acids. Biochimica et Biophysica Acta, 1049, 99.
20. HORWITZ, E.M., MALONEY, K.A. & LEY, TJ (1994). A human protein containing a 'cold shock' domain binds specifically to H-DNA upstream from the human gamma-globin genes. Journal of Biological Chemistry, 269, 14130.
21. 2 studied by CD, LD, and normal absorption. Biochemistry, 35, 1187.
22. KITTLER, L., WÄHNERT, U., BAGULEY, B.C., BAILLY, C., WARING, M.J. & LÖBER, G. (1996). Sequence-Specific binding of antitumor bisquaternary ammonium heterocycles to DNA and inhibition of polymerase activity in vitro. Anti-Cancer Drug Design, 11, 101.
23. KOPKA, M.L. & LARSEN, T.A. (1992). Netropsin and the lexitropsins. The search for sequence-specific minor-groove-binding ligands. In Nucleic Acid Targeted Drug Design. Propst, C.L. & Perun, T.J. (eds), p. 304. Marcel Dekker, Inc.: New York.
24. LEE, J.S., LATIMER, L.J. & HAMPEL, K.J. (1993). Coralyne binds tightly to both T·A·T- and C·G·C(+)-containing DNA triplexes. Biochemistry, 32, 5591.
25. LUCK, G., ZIMMER, CH. & BAGULEY, B.C. (1984). Interaction of nucleic acids with a non-intercalative anti-leukemic compound containing bisquarternary heterocycles. Biochimica et Biophysica Acta, 782, 41.
26. LUCK, G, REINERT, K.-E., BAGULEY, B.C. & ZIMMER, CH. (1987). Interaction of the antitumor drugs SN-6999 and SN-18071 with DNA: influence of ligand structure on the binding specifity. Journal of Biomolecular Structure & Dynamics, 4, 1079.
27. LUCK, G., STȮRL, J., BAGULEY, B. &. ZIMMER, CH. (1992). DNA Binding of the nonintercalative ligands SN-6132, SN-6131 and SN-6113: minor variations of the ligand structure may cause changes in the base pair preferences. Journal of Biomolecular Structure & Dynamics, 10, 551.
28. MERGNY, J.L., DUVAL-VALENTIN, G., NGUYEN, C.H, PERROUAULT, L., FAUCON, B., ROUGÉE, M., MONTENAY-GARESTIER, T., BISAGNI, E. & HÉLÈNE, C. (1992). Triple helix-specific ligands. Science, 256, 1681.
29. PARK, Y.W. & BRESLAUER, K.J. (1992). Drug binding to higher ordered DNA structures: netropsin complexation with a nucleic acid triple helix. Proceedings of the National Academy of Sciences, USA, 89, 6653.
30. PILCH, D.S. & BRESLAUER, K.J. (1994). Ligand-induced formation of nucleic acid triple helices. Proceedings of the National Academy of Sciences, USA, 91, 9332.
31. PILCH, D.S., WARING, M.J., SUN, J.S., ROUGEE, M., NGUYEN, C.H., BISAGNI, E., GARESTIER, T. & HÉLÈNE, C. (1993). Characterization of a triple helix-specific ligand. BePI (3-methoxy-7H-8-methyl-11-[(3'-amino)-propylamino]-benzo[e]pyrido[4,3-b]indole) intercalates into both double-helical and triple-helical DNA. Journal of Molecular Biology, 232, 926.
32. PILCH, D.S. KIROLOS, M.A. & BRESLAUER, K.J. (1995). Berenil binding to higher ordered nucleic acid structures: complexation with a DNA and RNA triple helix. Biochemistry, 34, 16107.
33. RADHAKRISHNAN, I. & PATEL, D.J. (1994a). Hydration sites in purine:purine:pyrimidme and pyrimidine: purine:pyrimidine DNA triplexes in aqueous solution. Structure, 2, 395.
34. RADHAKRISHNAN, I. & PATEL, D.J. (1994b). Solution structure and hydration patterns of a pyrimidine: purine: pyrimidine DNA triplex containing a novel T-CG base-triple. Journal of Molecular Biology, 241, 600.
35. RENTZEPERIS, D. & MARKY, L.A (1995). Ligand binding to the Hoogsteen-WC groove of TAT base triplets: thermodynamic contribution of the thymine methyl group. Journal of the American Chemical Society, 117, 5423.
36. SOYFER, V.N. & POTAMAN, V.N. (EDS) (1995). Triple-Helical Nucleic Acids. Springer-Verlag: New York.
37. STONEHOUSE, T.J. & FOX, K.R. (1994). DNase I footprinting of triple helix formation at polypurine tracts by acridine-linked oligopyrimidines: stringency, structural changes and interaction with minor groove binding ligands. Biochimica et Biophysica Acta, 1218, 322.
38. THOMAS,T. & THOMAS, T.J. (1993). Selectivity of polyamines in triplex DNA stabilization. Biochemistry, 32, 14068.
39. THUONG, N.T. & HÉLÈNE, C. (1993). Sequence-specific recognition and modification of double-helical DNA by oligonucleotides. Angewandte Chemie International Edition English, 32, 666.
40. 6 and its complex of a minor groove binding drug. Journal of the American Chemical Society, 112, 4539.
41. WELLS, R.D., COLLIER, D.A., HANVEY, J.C., SHIMIZU, M. & WOHLRAB, c. (1988). The chemistry and biology of unusual DNA structures aopted by oligopurine-oligopyrimidine sequences. FASEB Journal, 2, 2939.
42. ZAKRZEWSKA, K. & PULLMAN, B. (1983). A theoretical evaluation of the effect of netropsin binding on the reactivity of the DNA towards alkylating agents. Nucleic Acid Research, 24, 8841.
43. ZIMMER, CH. & WĀHNERT, U. (1986). Nonintercalating DNA-binding ligands: specificity of the interaction and their use as tools in biophysical, biochemical and biological investigations of the genetic material. Progress in Biophysics and Molecular Biology, 47, 31.