Selective photocleavage of DNA and RNA by anthraquinone derivatives: Targeting the single-strand region of hairpin structures

Photochemistry and Photobiology

Volumn 70, Issue 6, 1999, Pages 847-852

  Fernandez Saiz, Maria ^a   Henderson, Paul T ^a   Wilson, W David ^b   Schuster, Gary B ^a,b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE; INTERCALATING AGENT; N,N,N',N' TETRAKIS(3 AMINOPROPYL) 2,7 ANTHRAQUINONESULFONAMIDE TETRAHYDROCHLORIDE; N,N,N',N'-TETRAKIS(3-AMINOPROPYL)-2,7-ANTHRAQUINONESULFONAMIDE TETRAHYDROCHLORIDE; PHOTOSENSITIZING AGENT; RNA; SINGLE STRANDED DNA;

ARTICLE; CHEMISTRY; CONFORMATION; DNA DAMAGE; DRUG EFFECT; METABOLISM; PHOTOLYSIS; RADIATION EXPOSURE; ULTRAVIOLET RADIATION;

ANTHRAQUINONES; DNA DAMAGE; DNA, SINGLE-STRANDED; INTERCALATING AGENTS; NUCLEIC ACID CONFORMATION; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; RNA; ULTRAVIOLET RAYS;

EID: 0033250747     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb08292.x     Document Type: Article

References (26)

1. Armitage, B. (1998) Photocleavage of nucleic acids. Chem. Rev. 98, 1171-1200.
2. Breslin, D. T., J. E. Coury, J. R. Anderson, L. McFail-Isom, Y. Kan, L. D. Williams, L. A. Bottomley and G. B. Schuster (1997) Anthraquinone photonuclease structure determines its mode of binding to DNA and the cleavage chemistry observed. J. Am. Chem. Soc. 119, 5043-5044.
3. Siriam, M. and A. H.-J. Wang (1996) Structure of DNA and RNA. In Biorganic Chemistry: Nucleic Acids (Edited by S. M. Hecht), pp. 105-143. Oxford University Press, New York.
4. Perez-Ruiz, M., D. Sievers, P. A. Garcia-Lopez and A. Berzal-Herranz (1999) The antisense sequence of the HIV-1 TAR stem-loop structure covalently linked to the hairpin ribozyme enhances its catalytic activity against two artificial substrates. Antisense Nucleic Acid Drug Dev. 9, 33-42.
5. Suo, Z. and K. A. Johnson (1998) DNA secondary structure effects on DNA synthesis catalyzed by HIV-1 reverse transcriptase. J. Biol. Chem. 273, 27259-27267.
6. Hope, T. J. (1999) The ins and outs of HIV Rev. Arch. Biochem. Biophys. 365, 186-191.
7. Carter, P. J., K. M. Breiner and H. H. Thorp (1998) Effects of secondary structure on DNA and RNA cleavage by diplatinum(II). Biochemistry 37, 13736-13743.
8. Breslin, D. T., C. Yu, D. Ly and G. B. Schuster (1997) Structural modification changes the DNA binding mode of cationsubstituted anthraquinone photonucleases: association by intercalation or minor groove binding determines the DNA cleavage efficiency. Biochemistry 36, 10463-10473.
9. Henderson, P. T., B. Armitage and G. B. Schuster (1998) Selective photocleavage of DNA by unthraquinone derivatives: targeting the single strand region of hairpin structures. Biochemistry 37, 2991-3001.
10. Armitage, B. A., C. Yu, C. Devadoss and G. B. Schuster (1994) Cationic anthraquinone derivatives as catalytic DNA photonucleases: mechanisms for DNA damage and quinone recycling. J. Am. Chem. Soc. 116, 9847-9859.
11. Hilbers, C. W., C. A. G. Haasnoot, S. H. de Bruin, J. J. M. Joordens, G. A. Van Der Marel and J. H. Van Boom (1985) Hairpin formation in synthetic oligonucleotides. Biochimie 67, 685-695.
12. Mitas, M. (1997) Trinucleotide repeats associated with human disease. Nucleic Acids Res. 25, 2245-2253.
13. Sambrook, J., E. F. Fritsch and T. Maniatis (1989) Molecular Cloning. A Laboratory Manual. 2nd ed. Cold Spring Harbor Press, Cold Spring Harbor, NY.
14. Peattie, D. A. (1979) Expression and characterization of human FKBP52, an immunophilin that associates with the 90-kDa heatshock protein and is a component of steroid-receptor complexes. Proc. Natl. Acad. Sci. USA 76, 1760-1764.
15. Knapp, G. (1989) Enzymatic approaches to probing of RNA secondary and tertiary structure. Methods Enzymol. 180, 192-212.
16. Armitage, B. and G. B. Schuster (1997) Anthraquinone photonucleases: a surprising role for chloride in the sequence-neutral cleavage of DNA and the footprinting of minor groove-bound ligands. Photochem. Photobiol. 66, 164-170.
17. Devasagayam, T. P. A., S. Steenken, M. S. W. Obendorf, W. A. Schulz and H. Sies (1991) Formation of 8-hydroxy(deoxy) guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen. Biochemistry 30, 6283-6289.
18. Moore, J. N., D. Phillips, N. Nakashima and K. Yoshihara (1987) Photophysics and photochemistry of sulphonated derivatives of 9,10-amhraquinone. J. Chem. Soc. Faraday Trans. 2 83, 1487-1508.
19. Arkin, M. R., E. D. Stemp, S. C. Pulver and J. K. Barton (1997) Long-range oxidation of guanine by Ru(III) in duplex DNA. Chem. Biol. 4, 389-400.
20. Gasper, S. M. and G. B. Schuster (1997) Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: the effects of gaps and traps on long range radical migration. J. Am. Chem. Soc. 119, 12762-12771.
21. Hail, D. B. and J. K. Barton (1997) Sensitivity of DNA-mediated electron transfer to the intervening pi-stack. A probe for the integrity of the DNA base stack. J. Am. Chem. Soc. 119, 5045-5046.
22. Henderson, P. T., D. Jones, G. Hampikian, Y. Kan and G. B. Schuster (1999) Long-distance charge transport in duplex DNA: the phonon-assisted polaron-like hopping mechanism. Proc. Nail. Acad. Sci. USA 96, 8353-8358.
23. Cadet, J. and R. Teoule (1978) Comparative study of oxidation of nucleic acid components hydroxyl radicals, singlet oxygen and superoxide anion radicals. Photochem. Pholobiol. 28, 661.
24. Kawanishi, S., S. Inoue and S. Sano (1986) Photodynamic modification by hematoporphyrin is specific for single-stranded DNA with singlet oxygen as a mediator. J. Biol. Chem. 261, 6090-6095.
25. Lee, P. C. C. and M. A. Rogers (1987) Laser flash photokinetic studies of Rose-Bengal sensitized photodynamic interactions of nucleotides and DNA. Photochem. Photobiol. 45, 79.
26. Schulman, L. H. (1971) Laser flash studies of rose bengal sensitized photodynamic interactions of nucleotides and DNA. J. Mol. Biol. 58, 117-131.