Synthesis and binding properties of oligonucleotides covalently linked to an acridine derivative: New study of the influence of the dye attachment site

Bioconjugate Chemistry

Volumn 7, Issue 3, 1996, Pages 369-379

  Asseline, Ulysse ^a   Bonfils, Edwige ^b   Dupret, Daniel ^b   Thuong, Nguyen T ^a  

^a CNRS   (France)

^b Appligene Oncor   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; BINDING ENERGY; CHAINS;

ACRIDINE DERIVATIVES; BINDING PROPERTIES; DEOXYURIDINE; DIASTEREOISOMERS; INTERCALATING AGENTS; NEW STUDY; OLIGONUCLEOTIDE CHAINS; POLYMETHYLENE;

OLIGONUCLEOTIDES;

9 AMINO 6 CHLORO 2 METHOXYACRIDINE; 9-AMINO-6-CHLORO-2-METHOXYACRIDINE; AMINOACRIDINE DERIVATIVE; ANTIMETABOLITE; DEOXYURIDINE; FLUORESCENT DYE; INTERCALATING AGENT; OLIGONUCLEOTIDE;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY;

AMINOACRIDINES; ANTIMETABOLITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYURIDINE; FLUORESCENT DYES; HYDROLYSIS; INTERCALATING AGENTS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; OLIGONUCLEOTIDES; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE;

EID: 0030135321     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc960024o     Document Type: Article

References (19)

1. J. S. Cohen Ed. (1989) Oligodeoxynucleotides. Antisense Inhibitors of Gene Expression. In Topics in Molecular and Structural Biology: Mac Millan Press, London.
2. Hélène, C., Montenay-Garestier, T., Saison, T., Takasugi, M., Toulmé, J. J., Asseline, U., Lancelot, G., Maurizot, J. C., Toulmé, F., and Thuong, X. T. (1985) Oligodeoxynucleotides covalently linked to intercalating agents: new class of gene regulatory substances. Biochimie 67, 773-783.
3. Nguyen, T., Thuong, N. T., and Hélène, C. (1993) Sequence-specific recognition and modification of double-helical DNA by oligonucleotides. Angew. Chem., Int. Ed Engl. 32, 666-690.
4. Asseline, U., Toulmé, P., Thuong, N. T. Delarue, M., Montenay-Garestier, T. and Hélène, C. (1984) Oligodeoxynucleotides covalently linked to intercalating dyes as base sequence-specific ligands. Influence of dye attachment site EMBO J. 3, 795-800.
5. Asseline, U., Delarue, M., Lancelot, G., Toulmé, F., Thuong, N. T., Montenay-Garestier, T., and Hélène, C. (1984) Nucleic acid-binding molecules with high affinity and sequences specificity: intercalating agents covalently linked to oligodeoxynucleotides. Proc. Natl. Acad. Sci. U.S.A. 81, 3297-3301.
6. Mann, J. S., Shibata, Y., and Meehan, T. (1992) Synthesis and properties of an oligonucleotide modified with a pyrene derivative at the 5′-phosphate. Bioconjugate Chem. 3, 554-558.
7. Yamana, K., and Letsinger, R. L. (1985) Synthesis and properties of oligonucleotides bearing a pendant pyrene group. Nucleic Acids Symp. Ser. 16, 169-172.
8. Ono, A., Dan, A., and Matsuda, A. (1993) Nucleosides and nucleotides. 121. Synthesis of oligonucleotides carrying linker groups at the 1′-position of sugar residues. Bioconjugate Chem. 4, 499-508.
9. Telser, J., Cruickshank, K. A., Morrison, L. E., and Netzel, T. L. (1989) Synthesis and characterization of DNA oligomers and duplexes containing covalently attached molecular labels: comparison of biotin, fluorescein and pyrene labels by thermodynamic and optical spectroscopic measurements. J. Am. Chem. Soc. 111, 6966-6976.
10. Pieles, U., Sproat, B. S., Neuner, P., and Cramer, F. (1989) Preparation of a novel psoralen containing deoxyadenosine building block for the facile solid-phase synthesis of psoralen-modified oligonucleotides for a sequence specific crosslink, to a given target sequence. Nucleic Acids Res. 17, 8967-8978.
11. Vu, H., and Hirschbein, B. L. (1991) Internucleotide phosphite sulfurization with tetraethylthiuram disulfide: Phosphorothioate oligonucleotide synthesis via phosphoramidite chemistry. Tetrahedron Lett. 32, 3005-3008
12. Conway, N. E., Fidanza, J. A., O'Donnell, M. J., Narekian, N. D., Ozaki, H., and Me Laughlin, L. W. (1991) Site-specific attachment of labels to the DNA backbone. In Oligonucleotides and Analogues: A Practical Approach (F. Eckstein, Ed.,) pp 211-239, IRL Press, Oxford.
13. Connolly, B. A., Potter, B. V. L., Eckstein, F., Pingould, A., and Grotjahn, L. (1984) Synthesis and characterization of an octanucleotide containing the EcoR1 recognition sequence with a phosphorothioate group at the cleavage site. Biochemistry 23, 3443-3453.
14. Wilk, A., and Stec, W. J. (1995) Analysis of oligo(deoxynucleoside phosphorothioate)s and their diastereoisomeric composition. Nucleic Acids Res. 23, 530-534.
15. Pieles, U., Zürcher, W., Schär, M. K. L. and Moser, H. E. (1993) Matrix-assisted laser desorption ionization time-of-flight mass-spectromerty: a powerful tool for the mass and sequence analysis of natural and modified oligonudeotides. Nucleic Acids Res. 21, 3191-3196.
16. Nordhoff, E., Cramer, R., Karas, M., Hillenkamp, F., Kirpeckar, F., Kristiansen, K., and Roepstroff, P. (1993) Ion stability of nucleic acids in infrared matrix-assisted laser desorption ionization mass spectrometry. Nucleic Acids Res. 21, 3347-3357.
17. Hashimoto, H. Nelson, M. G. and Switzer, C. (1993) Zwitterionic DNA. J. Am. Chem. Soc. 115, 7128-7134.
18. Lancelot, G., and Thuong, N. T. (1986) Nuclear magnetic resonance studies of complex formation between the oligonucleotide d(TATC) covalently linked to an acridine derivative and its complementary sequence d(GATA). Biochemistry 25, 5357-5363.
19. 2, derived from diastereomeric O-ethylphosphorothioates. Nucleic Acids Res. 14, 9081-9093.