Physiologically relevant concentrations of NaCl and KCl increase DNA photocleavage by an N-substituted 9-aminomethylanthracene dye

Biochemistry

Volumn 50, Issue 47, 2011, Pages 10375-10389

  Terry, Carla A ^a   Fernández, María José ^b   Gude, Lourdes ^b   Lorente, Antonio ^b   Grant, Kathryn B ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CELL NUCLEUS; CIRCULAR DICHROISM SPECTRA; DNA BINDING; DNA FRAGMENT; DNA HELIX; DNA PHOTO-CLEAVAGE; DNA-BINDING MODES; EXPECTED EFFECTS; FLUORESCENCE EMISSION; HIGH IONIC STRENGTH; METHYLENE BLUE; MICROMOLAR CONCENTRATION; PHOTOCLEAVAGE REACTION; PHOTOCLEAVAGES; REACTIVE OXYGEN SPECIES; SIDE-CHAINS; SUPERCOILED; THERMAL DENATURATIONS; UV-VIS ABSORPTIONS;

BINDING ENERGY; COMPLEXATION; DICHROISM; IONIC STRENGTH; ORGANIC POLYMERS; PHOTOSENSITIZERS; PYROLYSIS; SODIUM CHLORIDE; SUBSTITUTION REACTIONS;

DNA;

ANTHRACENE DERIVATIVE; DNA FRAGMENT; DYE; METHYLENE BLUE; N (ANTHRACEN 9 YLMETHYL) N' ((6 ((DIMETHYLAMINO)METHYL)PYRIDIN 2 YL)METHYL) N,N' DIMETHYLETHANE 1,2 DIAMINE; PLASMID DNA; POTASSIUM CHLORIDE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CELL NUCLEUS; CIRCULAR DICHROISM; CONTROLLED STUDY; DENATURATION; DNA BINDING; DNA HELIX; FLUORESCENCE; INTERCALATION COMPLEX; IONIC STRENGTH; PHOTODEGRADATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN INTERACTION; SYNTHESIS; ULTRAVIOLET RADIATION;

ANTHRACENES; COLORING AGENTS; DNA; INTERCALATING AGENTS; MOLECULAR STRUCTURE; OSMOLAR CONCENTRATION; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; PLASMIDS; POTASSIUM CHLORIDE; SODIUM CHLORIDE;

EID: 81855172178     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi200972c     Document Type: Article

References (63)

1. Zhang, Y. and Galoppini, E. (2010) Organic polyaromatic hydrocarbons as sensitizing model dyes for semiconductor nanoparticles ChemSusChem 3, 410-428
2. Jarikov, V. V. (2008) Quantum efficiency improvement in anthracene-based organic light-emitting diodes codoped with a hole-trapping material Appl. Phys. Lett. 92, 244103/1-244103/3
3. Gunnlaugsson, T., Ali, H. D. P., Glynn, M., Kruger, P. E., Hussey, G. M., Pfeffer, F. M., Santos, C. M. G., and Tierney, J. (2005) Fluorescent photoinduced electron transfer (PET) sensors for anions; from design to potential application J. Fluoresc. 15, 287-299 (Pubitemid 40952243)
4. Lodeiro, C., Lippolis, V., and Mameli, M. (2010) From Macrocyclic Ligands to Fluorescent Molecular Sensors for Metal Ions: Recent Results and Perspectives, in Macrocyclic Chemistry: New Research Developments (Fitzpatrick, D. W. and Ulrich, H. J., Eds.) pp 159-212, Nova Publishers, Hauppauge, NY.
5. Bowden, G. T., Roberts, R., Alberts, D. S., Peng, Y. M., and Garcia, D. (1985) Comparative molecular pharmacology in leukemic L1210 cells of the anthracene anticancer drugs mitoxantrone and bisantrene Cancer Res. 45, 4915-4920 (Pubitemid 16236172)
6. Iyengar, B. S., Dorr, R. T., Alberts, D. S., Sólyom, A. M., Krutzsch, M., and Remers, W. A. (1997) 1,4-disubstituted anthracene antitumor agents J. Med. Chem. 40, 3734-3738 (Pubitemid 27481718)
7. Wilson, W. D., Wang, Y. H., Kusuma, S., Chandrasekaran, S., and Boykin, D. W. (1986) The effect of intercalator structure on binding strength and base-pair specificity in DNA interactions Biophys. Chem. 24, 101-109
8. Modukuru, N. K., Snow, K. J., Perrin, B. S., Jr., Bhambhani, A., Duff, M., and Kumar, C. V. (2006) Tuning the DNA binding modes of an anthracene derivative with salt J. Photochem. Photobiol. A 177, 43-54 (Pubitemid 41794155)
9. Tan, W. B., Bhambhani, A., Duff, M. R., Rodger, A., and Kumar, C. V. (2006) Spectroscopic identification of binding modes of anthracene probes and DNA sequence recognition Photochem. Photobiol. 82, 20-30 (Pubitemid 43343033)
10. Holmes, F. A., Esparza, L., Yap, H. Y., Buzdar, A. U., Blumenschein, G. R., and Hortobagyi, G. N. (1986) A comparative study of bisantrene given by two dose schedules in patients with metastatic breast cancer Cancer Chemother. Pharmacol. 18, 157-161 (Pubitemid 17121431)
11. Morschhauser, F., Mounier, N., Sebban, C., Brice, P., Solal-Celigny, P., Tilly, H., Feugier, P., Fermé, C., Copin, M. C., and Lamy, T. (2010) Efficacy and safety of the combination of rituximab, fludarabine, and mitoxantrone for rituximab-naive, recurrent/refractory follicular non-Hodgkin lymphoma with high tumor burden: a multicenter phase 2 trial by the Groupe d'Etude des Lymphomes de l'Adulte (GELA) and Groupe Ouest Est des Leucémies et Autres Maladies du Sang (GOELAMS) Cancer 116, 4299-4308
12. Parker, C., Waters, R., Leighton, C., Hancock, J., Sutton, R., Moorman, A. V., Ancliff, P., Morgan, M., Masurekar, A., Goulden, N., Green, N., Révész, T., Darbyshire, P., Love, S., and Saha, V. (2010) Effect of mitoxantrone on outcome of children with first relapse of acute lymphoblastic leukaemia (ALL R3): an open-label randomised trial Lancet 376, 2009-2017
13. de Bono, J. S., Oudard, S., Ozguroglu, M., Hansen, S., Machiels, J. P., Kocak, I., Gravis, G., Bodrogi, I., Mackenzie, M. J., Shen, L., Roessner, M., Gupta, S., and Sartor, A. O. (2010) Prednisone plus cabazitaxel or mitoxantrone for metastatic castration-resistant prostate cancer progressing after docetaxel treatment: a randomised open-label trial Lancet 376, 1147-1154
14. Tuveson, R. W., Wang, G. R., Wang, T. P., and Kagan, J. (1990) Light-dependent cytotoxic reactions of anthracene Photochem. Photobiol. 52, 993-1002
15. Huang, Y., Zhang, Y., Zhang, J., Zhang, D. W., Lu, Q.-S., Liu, J.-L., Chen, S.-Y., Lin, H.-H., and Yu, X.-Q. (2009) Synthesis, DNA binding and photocleavage study of novel anthracene-appended macrocyclic polyamines Org. Biomol. Chem. 7, 2278-2285
16. Bernal, M. E., Varon, J., Acosta, P., and Montagnier, L. (2010) Oxidative stress in critical care medicine Int. J. Clin. Pract. 64, 1480-1488
17. Rai, S., Kasturi, C., Grayzar, J., Platz, M. S., Goodrich, R. P., Yerram, N. R., Wong, V., and Tay-Goodrich, B. H. (1993) Dramatic improvements in viral inactivation with brominated psoralens, naphthalenes and anthracenes Photochem. Photobiol. 58, 59-65
18. Kumar, C. V., Tan, W. B., and Betts, P. W. (1997) Hexamminecobalt(III) chloride assisted, visible light induced, sequence dependent cleavage of DNA J. Inorg. Biochem. 68, 177-181 (Pubitemid 27459386)
19. Kumar, C. V., Punzalan, E. H. A., and Tan, W. B. (2000) Adenine-thymine base pair recognition by an anthryl probe from the DNA minor groove Tetrahedron 56, 7027-7040
20. Gude, L., Fernández, M.-J., Grant, K. B., and Lorente, A. (2002) Anthracene and naphthalene (2,2′-bipyridine)platinum(II) conjugates: synthesis and DNA photocleavage Tetrahedron Lett. 43, 4723-4727 (Pubitemid 34634008)
21. Gude, L., Fernández, M.-J., Grant, K. B., and Lorente, A. (2005) Syntheses and copper(II)-dependent DNA photocleavage by acridine and anthracene 1,10-phenanthroline conjugate systems Org. Biomol. Chem. 3, 1856-1862 (Pubitemid 40751356)
22. Naora, H., Naora, H., Izawa, M., Allfrey, V. G., and Mirsky, A. E. (1962) Some observations on differences in composition between the nucleus and cytoplasm of the frog oocyte Proc. Natl. Acad. Sci. U. S. A. 48, 853-859
23. Billett, M. A. and Barry, J. M. (1974) Role of histones in chromatin condensation Eur. J. Biochem. 49, 477-484
24. Hooper, G. and Dick, D. A. T. (1976) Nonuniform distribution of sodium in the rat hepatocyte J. Gen. Physiol. 67, 469-474
25. Moore, R. D. and Morrill, G. A. (1976) A possible mechanism for concentrating sodium and potassium in the cell nucleus Biophys. J. 16, 527-533
26. Schelhorn, T., Kretz, S., and Zimmermann, H. W. (1992) Reinvestigation of the binding of proflavine to DNA. Is intercalation the dominant binding effect? Cell. Mol. Biol. 38, 345-365
27. Bhattacharya, S. and Mandal, S. S. (1997) Interaction of surfactants with DNA. Role of hydrophobicity and surface charge on intercalation and DNA melting Biochim. Biophys. Acta 1323, 29-44 (Pubitemid 27051431)
28. 2 duplex: calorimetric and spectroscopic studies J. Mol. Biol. 271, 244-257 (Pubitemid 27344746)
29. Manning, G. S. (1972) Application of polyelectrolyte "limiting laws" to the helix-coil transition of DNA. I. Excess univalent cations Biopolymers 11, 937-949
30. Baase, W. A. and Johnson, W. C. (1979) Circular dichroism and DNA secondary structure Nucleic Acids Res. 6, 797-813
31. Belintsev, B. N., Gagua, A. V., and Nedospasov, S. A. (1979) The effect of the superhelicity on the double helix twist angle in DNA Nucleic Acids Res. 6, 983-992
32. Bednar, J., Furrer, P., Stasiak, A., Dubochet, J., Egelman, E. H., and Bates, A. D. (1994) The twist, writhe and overall shape of supercoiled DNA change during counterion-induced transition from a loosely to a tightly interwound superhelix. Possible implications for DNA structure in vivo J. Mol. Biol. 235, 825-847
33. Hamelberg, D., Williams, L. D., and Wilson, W. D. (2001) Influence of the dynamic positions of cations on the structure of the DNA minor groove: sequence-dependent effects J. Am. Chem. Soc. 123, 7745-7755 (Pubitemid 32899339)
34. OhUigin, C., McConnell, D. J., Kelly, J. M., and van der Putten, W. J. (1987) Methylene blue photosensitised strand cleavage of DNA: effects of dye binding and oxygen Nucleic Acids Res. 15, 7411-7427
35. Munson, B. and Fiel, R. J. (1992) DNA intercalation and photosensitization by cationic meso substituted porphyrins Nucleic Acids Res. 24, 1080-1090
36. Åckerman, B. and Tuite, E. (1996) Single- and double-strand photocleavage of DNA by YO, YOYO and TOTO Nucleic Acids Res. 20, 1315-1319
37. Grant, K. B., Terry, C. A., Gude, L., Fernández, M.-J., and Lorente, A. (2011) Synthesis and DNA photocleavage by a pyridine-linked bis-acridine chromophore in the presence of copper(II): ionic strength effects Bioorg. Med. Chem. Lett. 21, 1047-1051
38. Newcomb, M., Timko, J. M., Walba, D. M., and Cram, D. J. (1977) Host-guest complexation. 3. Organization of pyridyl binding sites J. Am. Chem. Soc. 99, 6392-6398
39. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2 nd ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, New York.
40. Schmid, N. and Behr, J. P. (1991) Location of spermine and other polyamines on DNA as revealed by photoaffinity cleavage with poly(amino)benzenediazonium salts Biochemistry 30, 4357-4361
41. Vedernikov, A. N., Wu, P., Huffman, J. C., and Caulton, K. G. (2002) Cu(I) and Cu(II) complexes of a pyridine-based pincer ligand Inorg. Chim. Acta 330, 103-110
42. 3-6, in complex with 5′-TGACT-3′ sites by two-dimensional NMR J. Am. Chem. Soc. 115, 9900-9906
43. Blackburn, G. M. and Taussig, P. E. (1975) The photocarcinogenicity of anthracence: photochemical binding to deoxyribonucleic acid in tissue culture Biochem. J. 149, 289-291
44. Sinha, B. K. and Chignell, C. F. (1983) Binding of anthracene to cellular macromolecules in the presence of light Photochem. Photobiol. 37, 33-37
45. de Silva, A. P. and de Silva, S. A. (1986) Fluorescent signalling crown ethers; switching on' of fluorescence by alkali metal ion recognition and binding in situ J. Chem. Soc., Chem. Commun. 1709-1710
46. Kubo, K., Sakurai, T., and Mori, A. (1999) Complexation and fluorescence behavior of 9,10-bis[bis(beta-hydroxyethyl)aminomethyl]anthracene Talanta 50, 73-77
47. Wilson, B., Gude, L., Fernández, M.-J., Lorente, A., and Grant, K. B. (2005) Tunable DNA photocleavage by an imidazole-acridine conjugate Inorg. Chem. 44, 6159-6173 (Pubitemid 41323462)
48. Fernández, M.-J., Wilson, B., Palacios, M., Rodrigo, M. M., Grant, K. B., and Lorente, A. (2007) Copper-activated DNA photocleavage by a pyridine-linked bis-acridine intercalator Bioconjugate Chem. 18, 121-129 (Pubitemid 46146001)
49. Oikawa, S. and Kawanishi, S. (1998) Distinct mechanisms of site-specific DNA damage induced by endogenous reductants in the presence of iron(III) and copper(II) Biochim. Biophys. Acta 1399, 19-30 (Pubitemid 28374911)
50. Sinden, R. R. (1994) DNA Structure and Function, pp 109-110, Academic Press, Inc., San Diego.
51. Duff, M., Mudhivarthi, V. M., and Kumar, C. V. (2009) Rational design of anthracene-based DNA binders J. Phys. Chem. B 113, 1710-1721
52. Modukuru, N. K., Snow, K. J., Perrin, B. S., Jr., Thota, J., and Kumar, C. V. (2005) Contributions of a long side chain to the binding affinity of an anthracene derivative to DNA J. Phys. Chem. B 109, 11810-11818 (Pubitemid 40925642)
53. Cantor, C. and Schimmel, P. R. (1980) Biophysical Chemistry, p 398, W.H. Freeman, San Francisco.
54. Tuite, E. M. and Kelly, J. M. (1993) Photochemical interactions of methylene blue and analogues with DNA and other biological substrates J. Photochem. Photobiol. B 21, 103-124 (Pubitemid 24011420)
55. Dixon, D. W. and Steullet, V. (1998) Dimerization of tetracationic porphyrins: ionic strength dependence J. Inorg. Biochem. 69, 25-32 (Pubitemid 28231618)
56. Bolte, J., Demuynck, C., Lhomme, M. F., Lhomme, J., Barbet, J., and Roques, B. P. (1982) Synthetic models related to DNA intercalating molecules: comparison between quinacrine and chloroquine in their ring-ring interaction with adenine and thymine J. Am. Chem. Soc. 104, 760-765 (Pubitemid 12145838)
57. Kumar, C. V. and Asuncion, E. H. (1993) DNA binding studies and site selective fluorescence sensitization of an anthryl probe J. Am. Chem. Soc. 115, 8547-8553
58. Wilson, W. D., Tanious, F. A., and Fernández-Saiz, M. (1997) Evaluation of Drug-Nucleic Acid Interactions by Thermal Melting Curves, in Drug-DNA Interaction Protocols (Fox, K. R., Ed.) pp 219-240, Humana Press, Clifton, NJ.
59. Gotoh, O., Wada, A., Tada, M., and Tada, M. (1978) Base and base sequence specificity of the binding of 4-hydroxyaminoquinoline 1-oxide to DNA Gann 69, 61-66
60. 2+ Biophys. J. 69, 2623-2641
61. Novakova, O., Chen, H., Vrana, O., Rodger, A., Sadler, P. J., and Brabec, V. (2003) DNA interactions of monofunctional organometallic ruthenium(II) antitumor complexes in cell-free media Biochemistry 42, 11544-11554 (Pubitemid 37205749)
62. Khan, A. U. (1976) Singlet molecular oxygen. A new kind of oxygen J. Phys. Chem. 80, 2219-2228
63. Poulos, A. T., Kuzmin, V., and Geacintov, N. E. (1982) Probing the microenvironment of benzo[a]pyrene diol epoxide-DNA adducts by triplet excited state quenching methods J. Biochem. Biophys. Methods 6, 269-281 (Pubitemid 13205232)