Synthesis and properties of an oligonucleotide modified with an acridine derivative at the artificial abasic site

Bioconjugate Chemistry

Volumn 7, Issue 3, 1996, Pages 349-355

  Fukui, Keijiro ^a   Morimoto, Minoru ^a,b   Segawa, Hiroshi ^a   Tanaka, Kazuyoshi ^a   Shimidzu, Takeo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; QUANTUM YIELD;

ACRIDINE DERIVATIVES; COMPLEMENTARY STRAND; DESTABILIZATION EFFECTS; FLUORESCENCE QUANTUM YIELD; METHOXY; OLIGODEOXYNUCLEOTIDES; PHOSPHORAMIDITES; POSTSYNTHETIC MODIFICATION; PROPERTY; SYNTHESISED;

OLIGONUCLEOTIDES;

9 AMINO 6 CHLORO 2 METHOXYACRIDINE; 9-AMINO-6-CHLORO-2-METHOXYACRIDINE; ACRIDINE DERIVATIVE; AMINOACRIDINE DERIVATIVE; FLUORESCENT DYE; MEPACRINE; OLIGONUCLEOTIDE; THREONINE;

ARTICLE; CHEMISTRY; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROFLUOROMETRY; TEMPERATURE; ULTRAVIOLET SPECTROPHOTOMETRY;

ACRIDINES; AMINOACRIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENT DYES; HEAT; MAGNETIC RESONANCE SPECTROSCOPY; OLIGONUCLEOTIDES; QUINACRINE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE; THREONINE;

EID: 0030135721     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc960019k     Document Type: Article

References (22)

1. Cohen, J. S., Ed. (1989) Oligodeoxynucleotides: Antisense Inhibitors of Gene Expression. CRC Press. Boca Raton, FL.
2. Symon, R H., Ed. (1989) Nucleic Acid Probes. CRC Press. Boca Raton. FL.
3. François, J.-C., Saison-Behmoaras. T., Barbier. C., Chassignol, M., Thuong. N. T., and Héléne. C. (1989) Sequence-specific recognition and cleavage of duplex DNA via triplehelix formation by oligonucleotides covalently linked to a phenanthroline-copper chelate. Proc. Natl. Acad. Sci. U.S.A. 86, 9702-9706.
4. Lee, B. L., Murakami, A., Blake, K. R., Lin, S.-B., and Miller. P. S. (1988) Interaction of psoralen-derivatized oligodeaxyri-bonucleoside methylphosphonates with single-stranded DNA. Biochemistry 27, 3197-3203.
5. Connolly. B. A. (1987) The synthesis of oligonucleotides containing a primary ammo group at the 5′-terminus. Nucleic Acids Res. 15, 3131-3139.
6. Sinha, N. D., and Cook. R. M. (1988) The preparation and application of functionalised synthetic oligonucleotides: III. Use of H-pbosphonate derivatives of protected amino-hexanol and mercapto-propanol or -hexanol. Nucleic Acids Res. 16, 2659-2669.
7. Nielsen, J., Taagaard, M., Marugg, J. E., Boom, J. H. v., and Dahl. O. (1986) Application of 2-cyanoethyl N N N′ N′-tetraisopropylphosphorodiainidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of ligodeoryribonucleotides Nucleic Acids Res. 14, 7391-7403.
8. Hébert, N., Davis, P. W., DeBaets, E. L., and Acevedo. O. L. (19974) Synthesis of N-substituted hydroxyprolinol phosphoramidites for the preparation of combinatorial libraries. Tetrahedron Lett. 35, 9509-9512.
9. 35-S]dithiobis-(succinimidyl propionate). J. Mol. Biol. 104, 243
10. Brinkley, M. (1992) brief survey of methods for preparing protein conjugates with dyes, haptens. and cross-linking reagents. Bioconjugate Chem. 3, 2-13.
11. Doan, T. L., Perrouault, L., Praseuth, D., Habhoub, N., Decout, J.-L., Thuong, N. T., Lhomme, J., and Héléne, C. (1987) Sequence-specific recognition, photo-cross-linking and cleavage of the DNA double helix by an oligo-[α]-thymidylate covalently linked to an azidoproflavine derivative. Nucleic Acids Res 15, 7749-7760.
12. Asseline, U., Hau, J.-F., Czernecki, S., Diguarher, T. L., Perlai. M.-C., Valery, J-M., and Thuong, N. T. (1991) Synthesis and physicochemical properties of oligonucleotides built with either α-L or β-L nucleaotides units and covalently linked to an acridine derivative. Nucleic Acids Res 19, 4067-4074.
13. Sarma, R. H., Ed. (1979) Nucleic Acid Geometry and Dynamics, pp 289-323. Pergamon Press. Oxford. U. K.
14. Steck, E A. (1972) Chemotherapy of Protozoan Disease. pp 77-123. U-S. Government Printing Office. Washington. DC.
15. Kubota, Y., Motoda, Y., Shigemune, Y., and Fujisaki, Y. (1979) Fluorescence quenching of 10-methylacridinium chloride by nucleotides. Photochem. Photobiol. 29, 1099-1106.
16. Georghiou, S. (1977) Interaction of acridine drugs with DNA and nucleotides. Photochem. Photobiol. 26, 59-68.
17. Murphy, C. J., Arkin, M. R., Jenkins. Y., Ghatlia, N. D., Bossmann. S. H., Turro, N. J., and Barton. J. K. (1993) Long-range photoinduced electron transfer through a DNA helix. Science 262, 1025-1029.
18. Brun, A. M., and Harriman, A. (1994) Energy-and electron-transfer processes involving palladium porphyrins bound to DNA. J. Am. Chem. Soc. 116, 10383-10393.
19. Thuong, N. T., and Chassignol, M. (1988) Solid phase synthesis of oligo-α- and oligo-β-deoxynucleotides covalently linked to an acridine. Tetrahedron Lett. 29, 5905-5908.
20. Bertrand, J.-R., Vasseur, J.-J., Rayner, B., Imbach, J.-L., Paoletti, J., Paoletti, C., and Malvy, C. (1989) Synthesis. thermal stability and reactivity toward 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site. Nucleic Acids Res. 17, 10307-10319.
21. Baldini, G. Doglia, S., Dolci, S., and Sassi, G. (1981) Biophys. J. 36, 465-477.
22. Sun, J.-S., Rougée, M., Delarue, M., Montenay-Garestier. T., and Héléne, C (1990) Solvent relaxation around excited 2-methoxy-6-chloro-9-aminoacridine in aqueous solvent. J. Phys. Chem. 94, 968-977.