Effects of the interaction between β-carboline-3-carboxylic acid N-methylamide and polynucleotides on singlet oxygen quantum yield and DNA oxidative damage

Photochemistry and Photobiology

Volumn 83, Issue 6, 2007, Pages 1455-1464

  García Zubiri, Iñigo X ^a   Burrows, Hugh D ^b   Sergio Seixas De Melo J ^b   Pina, Joao ^b   Monteserín, María ^a   Tapia, María J ^a  

^a UNIVERSITY OF BURGOS   (Spain)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE 3 CARBOXYLIC ACID N METHYLAMIDE; BETA-CARBOLINE-3-CARBOXYLIC ACID N-METHYLAMIDE; CARBOLINE DERIVATIVE; POLYNUCLEOTIDE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DNA DAMAGE; GENETICS; OXIDATION REDUCTION REACTION; SPECTROPHOTOMETRY;

CARBOLINES; DNA DAMAGE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYNUCLEOTIDES; SINGLET OXYGEN; SPECTROPHOTOMETRY;

EID: 36248955403     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2007.00187.x     Document Type: Article

References (57)

1. Pardo, A., D. Reyman, J. M. L. Poyato F. Medina (1992) Some β-carboline derivatives as fluorescence standards. J. Lumin. 51, 269 274.
2. Ghiggino, K. P., P. F. Skilton P. J. Thistlewaite (1985) β-Carboline as a fluorescence standard. J. Photochem. 31, 113 121.
3. Chae, K. H. H. S. Ham (1986) Production of singlet oxygen and superoxide anion radicals by β-carbolines. Bull. Korean Chem. Soc. 7, 478 479.
4. Calle, P., A. Fernández-Arizpe C. Sieiro (1996) Photosensitization by harmine: An ESR spin trapping study on the generation of the superoxide anion radical. Appl. Spectrosc. 50, 1446 1451.
5. Schweitzer, C. R. Schmidt (2003) Physical mechanisms of generation and deactivation of singlet oxygen. Chem. Rev. 103, 1685 1757.
6. Cló, E., J. W. Snyder, N. V. Voigt, P. R. Ogilby K. V. Gothelf (2006) DNA-programmed control of photosensitized singlet oxygen production. J. Am. Chem. Soc. 128, 4200 4201.
7. 2. J. Am. Chem. Soc. 125, 12803 12809.
8. Varela, A. P., H. D. Burrows, P. Douglas M. da Graça Miguel (2001) Triplet state studies of β-carbolines. J. Photochem. Photobiol. A, Chem. 146, 29 36.
9. Hirakawa, K., S. Kawanishi T. Hirano (2005) The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: Activation of photosensitized singlet oxygen generation through DNA-binding interaction. Chem. Res. Toxicol. 18, 1545 1552.
10. Morin, B. J. Cadet (1994) Benzophenone photosensitization of 2′-deoxyguanosine: Characterization of the 2R and 2S diastereoisomers of 1-(2-Deoxy-Beta-D-Erythro-Pentofuranosyl)-2-methoxy-4,5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks. Photochem. Photobiol. 60, 102 109.
11. g) photosensitization. Time-resolved photoacoustic and near-IR emission studies. J. Photochem. Photobiol. A, Chem. 97, 11 18.
12. Kasai, H., Z. Yamaizumi, M. Berger J. Cadet (1992) Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′- deoxyguanosine) in DNA by riboflavin: A nonsinglet oxygen-mediated reaction. J. Am. Chem. Soc. 114, 9692 9694.
13. Cadet, J., C. Decarroz, S. Y. Wang W. R. Midden (1983) Mechanisms and production of photosensitized degradation of nucleic acids and related model compounds. Isr. J. Chem. 23, 420 429.
14. Tuite, E. M. J. M. Kelly (1993) Photochemical interactions of methylene blue and analogues with DNA and other biological substrates. J. Photochem. Photobiol. B 21, 103 124.
15. Hudson, J. B. G. H. N. Towers (1991) Therapeutic potential of plant photosensitizers. Pharmacol. Ther. 49, 181 222.
16. Hickerson, R. P., F. Prat, J. G. Muller, C. S. Foote C. J. Burrows (1999) Sequence and stacking dependence of 8-oxoguanine oxidation: Comparison of one-electron vs singlet oxygen mechanisms. J. Am. Chem. Soc. 121, 9423 9428.
17. Bohne, C., K. Faulhaber, B. Giese, A. Häfner, A. Hofmann, H. Ihmels, A.-K. Köhler, S. Perä, F. Schneider M. A. L. Sheepwash (2005) Studies on the mechanism of the photo-induced DNA damage in the presence of acridizinium salts - Involvement of singlet oxygen and an unusual source for hydroxyl radicals. J. Am. Chem. Soc. 127, 76 85.
18. Duarte, V., D. Gasparutto, L. F. Yamaguchi, J.-L. Ravanat, G. R. Martinez, M. H. G. Medeiros, P. D. Mascio J. Cadet (2000) Oxaluric acid as the major product of singlet oxygen-mediated oxidation of 8-oxo-7,8-dihydroguanine in DNA. J. Am. Chem. Soc. 122, 12622 12628.
19. Schneider, J. E., S. Price, L. Maidt, J. M. C. Gutteridge R. A. Floyd (1990) Methylene blue plus light mediates 8-hydroxy 2′-deoxyguanosine formation in DNA preferentially over strand breakage. Nucleic Acids Res. 18, 631 635.
20. Devasagayam, T. P. A., S. Steenken, M. S. W. Obendorf, W. A. Schulz 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.
21. Dougherty, T. J., C. J. Gomer, B. W. Henderson, D. Kessel, M. Korbelik, J. Moan Q. Peng (1998) Photodynamic therapy. J. Natl. Cancer Inst. 90, 889 905.
22. Meester, C. (1995) Genotoxic potential of β-carbolines: A review. Mutat. Res. 339, 139 153.
23. Boeira, J. M., A. F. Viana, J. N. Picada J. A. P. Henriques (2002) Genotoxic and recombinogenic activities of the two β-carboline alkaloids harman and harmine in Saccharomyces cerevisiae. Mutat. Res. 500, 39 48.
24. Majer, B. J., F. Kassie, Y. Sasaki, W. Pfau, H. Glatt, W. Meinl, F. Darroudi S. Knasmüller (2004) Investigation of the genotoxic effects of 2-amino-9H-pyrido[2,3-b]indole in different organs of rodents and in human derived cells. J. Chromatogr. B 802, 167 173.
25. Picada, J. N., K. V. C. L. da Silva, B. Erdtmann, A. T. Henriques J. A. P. Henriques (1997) Genotoxic effects of structurally related β-carboline alkaloids. Mutat. Res. 379, 135 149.
26. Wakabayashi, K., Y. Totsuka, K. Fukutome, A. Oguri, H. Ushiyama T. Sugimura (1997) Human exposure to mutagenic/carcinogenic heterocyclic amines and comutagenic β-carbolines. Mutat. Res. 376, 253 259.
27. Sasaki, Y. F., H. Yamada, K. Shimoi, N. Kinae, I. Tomita, H. Matsumura, T. Ohta Y. Shirasu (1992) Enhancing effects of heterocyclic amines and β-carbolines on the induction of chromosome aberrations in cultured mammalian cells. Mutat. Res. 269, 79 95.
28. Guan, H., X. Liu, W. Peng, R. Cao, Y. Ma, H. Chen A. Xu (2006) β-Carboline derivatives: Novel photosensitizers that intercalate into DNA to cause direct DNA damage in photodynamic therapy. Biochem. Biophys. Res. Commun. 342, 894 901.
29. Laronze, M., M. Boisbrun, S. Léonce, B. Pfeiffer, O. Lozach, L. Meijer, A. Lansiaux, C. Bailly, J. Sapi J.-Y. Laronze (2005) Synthesis and anticancer activity of new pyrrolocarbazoles and pyrrolo-β-carbolines. Bioorg. Med. Chem. 13, 2263 2283.
30. Boursereau, Y. I. Coldham (2004) Synthesis and biological studies of 1-amino β-carbolines. Bioorg. Med. Chem. Lett. 14, 5841 5844.
31. Nguyen, C. H., E. Bisagni, F. Lavelle, M.-C. Bissery C. Huel (1992) Synthesis and antitumor properties of new 4-methyl-substituted-pyrido [4,3-b] indoles (γ-carbolines). Anti Cancer Drug Design 7, 219 233.
32. Toshima, K., Y. Okuno, Y. Nakajima S. Matsumura (2002) β-Carboline-carbohydrate hybrids: Molecular design, chemical synthesis and evaluation of novel DNA photocleavers. Bioorg. Med. Chem. Lett. 12, 671 673.
33. Nii, H. (2003) Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA. Mutat. Res. 541, 123 136.
34. Cao, R., W. Peng, H. Chen, Y. Ma, X. Liu, X. Hou, H. Guan A. Xu (2005) DNA binding properties of 9-substituted harmine derivatives. Biochem. Biophys. Res. Commun. 338, 1557 1563.
35. Todorović, N., T. B. Phuong, P. Langer K. Weisz (2006) DNA triplex stabilization by a δ-carboline derivative tethered to third strand oligonucleotides. Bioorg. Med. Chem. Lett. 16, 1647 1650.
36. Duportail, G. (1981) Linear and circular dichroism of harmine and harmaline interacting with DNA. Int. J. Biol. Macromol. 3, 188 192.
37. Tamura, S., T. Konakahara, H. Komatsu, T. Ozaki, Y. Ohta H. Takeuchi (1998) Synthesis of β-carboline derivatives and their interaction with duplex-DNA. Heterocycles 12, 2477 2480.
38. Yang, M., K. Wang, Ch-B. Zang, B.-H. Wang Y.-M. Zhang (1994) Binding of carboline derivatives to calf thymus DNA - Determination of binding mode and binding strength. J. Chin. Pharm. Sci. 3, 51 58.
39. Tapia, M. J., D. Reyman, M. H. Viñas, A. Arroyo J. M. L. Poyato (2003) An experimental and theoretical approach to the acid-base and photophysical properties of 3-substituted β-carbolines in aqueous solutions. J. Photochem. Photobiol. 156, 1 7.
40. Costa, D., H. D. Burrows M. da Graça Miguel (2005) Changes in hydration of lanthanide ions on binding to DNA in aqueous solution. Langmuir 21, 10492 10496.
41. Rosa, M., R. Dias, M. da Graça Miguel B. Lindman (2005) DNA-cationic surfactant interactions are different for double- and single-stranded DNA. Biomacromolecules 6, 2164 2171.
42. King, A. M. Q. B. H. Nicholson (1969) The interaction of aflatoxin B1 with polynucleotides and its effect on ribonucleic acid polymerase. Biochem. J. 114, 679 687.
43. Kononov, A. I. V. M. Bakulev (1996) Red-shifted fluorescence from polyguanylic acid in aqueous solution at room temperature. J. Photochem. Photobiol. B, Biol. 34, 211 216.
44. Polak, M. N. V. Hud (2002) Complete disproportionation of duplex poly(dT)-poly(dA) into triplexpoly(dT)-poly(dA)-poly(dT) and poly(dA) by coralyne. Nucleic Acids Res. 30, 983 992.
45. Quinlan, G. J. J. M. C. Gutteridge (1987) Oxygen radical damage to DNA by rifamycin SV and copper ions. Biochem. Pharmacol. 36, 3629 3633.
46. Dias, A., A. P. Varela, M. da G. Miguel, A. L. Mançanita R. S. Becker (1992) β-Carboline photosensitizers. 1. Photophysics, kinetics and excited-state equilibria in organic solvents, and theoretical calculations. J. Phys. Chem. 96, 10290 10296.
47. Seixas de Melo, J. P. F. Fernandes (2001) Spectroscopy and photophysics of 4- and 7-hydroxycoumarins and their thione analogs. J. Mol. Struct. 565-566, 69 78.
48. Striker, G., V. Subramaniam, C. A. M. Seidel A. Volkmer (1999) Photochromicity and fluorescence lifetimes of green fluorescent protein. J. Phys. Chem. B 103, 8612 8617.
49. g) photosensitization. Time-resolved photoacoustic and near-IR emission studies. J. Photochem. Photobiol. 97, 11 18.
50. Benesi, H. A. J. H. Hildebrand (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703 2707.
51. Balón, M., M. A. Muñoz, C. Carmona, P. Guradado M. Galán (1999) A fluorescence study of the molecular interactions of harmane with the nucleobases, their nucleosides and mononucleotides. Biophys. Chem. 80, 41 52.
52. Abdel-Shafi, A. A. (2001) Effect of β-cyclodextrin on the excited state proton transfer in 1-naphthol-2-sulfonate. Spectrochim. Acta [A] 57, 1819 1828.
53. Behravan, G., M. Leijon, U. Sechlstedt, B. Nordén, H. Vallberg, J. Bergman A. Gräslund (1994) The interaction of ellipticine derivatives with nucleic acids studied by optical and [1]H-NMR spectroscopy: effect of size of the heterocyclic ring system. Biopolymers 34, 599 609.
54. Rock, C., P. A. Shamlou M. S. Levy (2003) An automated microplate-based method for monitoring DNA strand breaks in plasmids and bacterial artificial chromosomes. Nucleic Acids Res. 31, e65.
55. Feigon, J., A. D. William, L. Werner D. R. Kearns (1984) Interactions of antitumor drugs with natural DNA: Proton NMR study of binding mode and kinetics. J. Med. Chem. 27, 450 465.
56. Xiao, S., W. Lin, C. Wang M. Yang (2001) Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives. Bioorg. Med. Chem. Lett. 11, 437 441.
57. Becker, R. S., L. F. V. Ferreira, F. Elisei, I. Machado L. Latterini (2005) Comprehensive photochemistry and photophysics of land- and marine-based β-carbolines employing time-resolved emission and flash transient spectroscopy. Photochem. Photobiol. 81, 1195 1204.