Energetics, conformation, and recognition of DNA duplexes modified by monodentate RuII complexes containing terphenyl arenes

Chemistry - A European Journal

Volumn 16, Issue 19, 2010, Pages 5744-5754

  Novakova, Olga ^a   Malina, Jaroslav ^a   Suchankova, Tereza ^b   Kasparkova, Jana ^a   Bugarcic, Tijana ^c   Sadler, Peter J ^c   Brabec, Viktor ^a  

^a INSTITUTE OF BIOPHYSICS   (Czech Republic)

^b PALACKÝ UNIVERSITY   (Czech Republic)

^c UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

Arenes; Calorimetry; DNA; DNA recognition; Ruthenium

Indexed keywords

ANTI-CANCER AGENTS; ARENE COMPLEXES; ARENES; BINDING MODES; CYTOTOXIC; CYTOTOXIC COMPOUNDS; CYTOTOXIC EFFECTS; DIAMINOETHANE; DNA ADDUCTS; DNA BASIS; DNA DUPLEXES; DNA POLYMERASE; DNA POLYMERIZATION; DNA RECOGNITION; DNA-BINDING MODES; DNA-BINDING PROTEIN; HUMAN TUMOR CELLS; MONODENTATES; MONOFUNCTIONAL; ORTHO-TERPHENYL; PROTEIN A; REPLICATION PROTEIN A; TERPHENYLS;

AROMATIC COMPOUNDS; BINDING ENERGY; CALORIMETRY; COMPLEXATION; COORDINATION REACTIONS; DNA; PROTEINS; RUTHENIUM; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

GENES;

ANTINEOPLASTIC AGENT; DNA; ORGANOMETALLIC COMPOUND; RUTHENIUM; TERPHENYL DERIVATIVE;

ARTICLE; CALORIMETRY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DNA ADDUCT; DNA REPAIR; DRUG EFFECT; HYDROGEN BOND; NUCLEOTIDE SEQUENCE; PROTEIN BINDING;

ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CALORIMETRY; DNA; DNA ADDUCTS; DNA REPAIR; HYDROGEN BONDING; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; ORGANOMETALLIC COMPOUNDS; PROTEIN BINDING; RUTHENIUM; TERPHENYL COMPOUNDS;

EID: 77952212731     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903078     Document Type: Article

References (78)

1. R. E. Morris, R. E. Aird, P. D. Murdoch, H. M. Chen, J. Cummings, N. D. Hughes, S. Parsons, A. Parkin, G. Boyd, D. I. Jodrell, P. J. Sadler, J. Med. Chem. 2001, 44, 3616-3621.
2. R. Aird, J. Cummings, A. Ritchie, M. Muir, R. Morris, H. Chen, P. Sadler, D. Jodrell, British J. Cancer 2002, 86, 1652-1657.
3. Y. K. Yan, M. Melchart, A. Habtemariam, P. J. Sadler, Chem. Commun.(Cambridge) 2005, 4764-4776.
4. S. J. Dougan, P. J. Sadler, Chimia 2007, 61, 704-715.
5. V. Brabec, O. Novakova, Drug Resist. Updates 2006, 9, 111-122.
6. M. A. Jakupec, E. Reisner, A. Eichinger, M. Pongratz, V. B. Arion, M. Galanski, C. G. Hartinger, B. K. Keppler, J. Med. Chem. 2005, 48, 2831-2837.
7. P. J. Dyson, G. Sava, Dalton Trans. 2006, 1929-1933.
8. H. Chen, J. A. Parkinson, O. Novakova, J. Bella, F. Wang, A. Dawson, R. Gould, S. Parsons, V. Brabec, P. J. Sadler, Proc. Natl. Acad. Sci. USA 2003, 100, 14623-14628.
9. O. Novakova, H. Chen, O. Vrana, A. Rodger, P. J. Sadler, V. Brabec, Biochemistry 2003, 42, 11544-11554.
10. O. Novakova, J. Kasparkova, V. Bursova, C. Hofr, M. Vojtiskova, H. Chen, P. J. Sadler, V. Brabec, Chem. Biol. 2005, 12, 121-129.
11. M. Melchart, A. Habtemariam, O. Novakova, S. A. Moggach, F. P. A. Fabbiani, S. Parsons, V. Brabec, P. J. Sadler, Inorg. Chem. 2007, 46, 8950-8962.
12. S. W. Magennis, A. Habtemariam, O. Novakova, J. B. Henry, S. Meier, S. Parsons, I. D. H. Oswald, V. Brabec, P. J. Sadler, Inorg. Chem. 2007, 46, 5059-5068.
13. T. Bugarcic, O. Novakova, A. Halamikova, L. Zerzankova, O. Vrana, J. Kasparkova, A. Habtemariam, S. Parsons, P. J. Sadler, V. Brabec, J. Med Chem. 2008, 51, 5310-5319.
14. T. Bugarcic, A. Habtemariam, J. Stepankova, P. Heringova, J. Kasparkova, R. J. Deeth, R. D. L. Johnstone, A. Prescimone, A. Parkin, S. Parsons, V. Brabec, P. J. Sadler, Inorg. Chem. 2008, 47, 11470-11486.
15. O. Nováková, A. A. Nazarov, C. G. Hartinger, B. K. Keppler, V. Brabec, Biochem. Pharmacol. 2009, 77, 364-374.
16. N. Poklar, D. S. Pilch, S. J. Lippard, E. A. Redding, S. U. Dunham, K. J. Breslauer, Proc. Natl. Acad. Sci. USA 1996, 93, 7606-7611.
17. D. S. Pilch, S. U. Dunham, E. R. Jamieson, S. J. Lippard, K. J. Breslauer, J. Mol. Biol. 2000, 296, 803-812.
18. C. Hofr, N. Farrell, V. Brabec, Nucleic Acids Res. 2001, 29, 2034-2040.
19. C. Hofr, V. Brabec, J. Biol. Chem. 2001, 276, 9655-9661.
20. J. Malina, O. Novakova, B. K. Keppler, E. Alessio, V. Brabec, J. Biol. Inorg. Chem 2001, 6, 435-445.
21. C. Hofr, V. Brabec, Biopolymers 2005, 77, 222-229.
22. V. Bursova, J. Kasparkova, C. Hofr, V. Brabec, Biophys. J. 2005, 88, 1207-1214.
23. V. Brabec, K. Stehlikova, J. Malina, M. Vojtiskova, J. Kasparkova, Arch. Biochem Biophys. 2006, 446, 1-10.
24. J. Malina, O. Novakova, M. Vojtiskova, G. Natile, V. Brabec, Biophys. J. 2007, 93, 3950-3962.
25. O. Nováková, J. Malina, J. Kašpárková, A. Halámiková, V. Bernard, F. Intini, G. Natile, V. Brabec, Chem. Eur. J. 2009, 15, 6211-6221.
26. H. K. Liu, S. J. Berners-Price, F. Y. Wang, J. A. Parkinson, J. J. Xu, J. Bella, P. J. Sadler, Angew. Chem. 2006, 118, 8333-8336;
27. Angew. Chem. Int. Ed. 2006, 45, 8153-8156.
28. P. E. Nielsen, J. Mol. Recognit. 1990, 3, 1-24.
29. V. Brabec, M. Sip, M. Leng, Biochemistry 1993, 32, 11676-11681.
30. H. Kostrhunova, V. Brabec, Biochemistry 2000, 39, 12639-12649.
31. S. M. Patrick, J. J. Turchi, Biochemistry 1998, 37, 8808-8815.
32. K. M. Comess, J. N. Burstyn, J. M. Essigmann, S. J. Lippard, Biochemistry 1992, 31, 3975-3990.
33. Z. Suo, K. Johnson, J. Biol Chem. 1998, 273, 27259-27267.
34. A. Vaisman, M. W. Warren, S. G. Chaney, J. Biol. Chem. 2001, 276, 18999-19005.
35. E. Bassett, A. Vaisman, J. M. Havener, C. Masutani, F. Hanaoka, S. G. Chaney, Biochemistry 2003, 42, 14197-14206.
36. J. Kasparkova, O. Novakova, V. Marini, Y. Najajreh, D. Gibson, J.-M. Perez, V. Brabec, J. Biol. Chem. 2003, 278, 47516-47525.
37. B. Moriarity, O. Novakova, N. Farrell, V. Brabec, J. Kasparkova, Arch. Biochem Biophys. 2007, 459, 264-272.
38. A. Alt, K. Lammens, C. Chiocchini, A. Lammens, J. C. Pieck, D. Kuch, K. P. Hopfner, T. Carell, Science 2007, 318, 967-970.
39. Y. Jung, S. J. Lippard, Chem. Rev. 2007, 107, 1387-1407.
40. V. Brabec, J. Kasparkova in Role of DNA Repair in Antitumor Effects of Platinum Drugs (Eds.: N. Hadjiliadis, E. Sletten), Wiley, New York, 2009, pp. 175-208.
41. G. E. Plum, C. A. Gelfand, K. J. Breslauer in Physicochemical Approaches to Structural Elucidation: Effects of 3, N4-Ethenodeoxycytidine on Duplex Stability and Energetics (Eds.: B. Singer, H. Bartsch), International Agency for Research on. Cancer, Lyon, 1999, pp. 169-177.
42. N. E. Geacintov, S. Broyde, T. Buterin, H. Naegeli, M. Wu, S. X. Yan, D. J. Patel, Biopolymers 2002, 65, 202-210.
43. Y. Maeda, K. Nunomura, E. Ohtsubo, J. Mol. Biol. 1990, 215, 321-329.
44. M. T. Bjorndal, D. K. Fygenson, Biopolymers 2002, 65, 40-44.
45. J. M. Sturtevant, Proc. Natl. Acad. Sci. USA 1977, 74, 2236-2240.
46. R. S. Spolar, M. T. Record, Jr., Science 1994, 263, 777-784.
47. P. J. Mikulecky, A. L. Feig, Nucleic Acids Res. 2004, 32, 3967-3976.
48. W. B. Peters, S. P. Edmondson, J. W. Shriver, Biochemistry 2005, 44, 4794-4804.
49. Y. Zhang, Z. Xi, R. S. Hegde, Z. Shakked, D. M. Crothers, Proc. Natl. Acad. Sci. USA 2004, 101, 8337-8341.
50. J. Malina, J. Kasparkova, G. Natile, V. Brabec, Chem. Biol. 2002, 9, 629-638.
51. R. E. Dickerson, T. K. Chiu, Biopolymers 1997, 44, 361-403.
52. S. M. Cohen, E. R. Jamieson, S. J. Lippard, Biochemistry 2000, 39, 8259-8265.
53. M. Missura, T. Buterin, R. Hindges, U. Hubscher, J. Kasparkova, V. Brabec, H. Naegeli, EMBO J. 2001, 20, 3554-3564.
54. R. Dip, U. Camenisch, H. Naegeli, DNA Repair 2004, 3, 1409-1423.
55. Y. Liu, Y. Liu, Z. Yang, C. Utzat, G. Wang, A. K. Basu, Y. Zou, Biochemistry 2005, 44, 7361-7368.
56. S. F. Bellon, S. J. Lippard, Biophys. Chem. 1990, 35, 179-188.
57. C. Iftode, Y. Daniely, J. A. Borowiec, Crit. Rev. Biochem. Mol. Biol. 1999, 34, 141-180.
58. Y. Zou, Y. Liu, X. Wu, S. M. Shell, J. Cell. Physiol. 2006, 208, 267-273.
59. J. Kasparkova, J. Zehnulova, N. Farrell, V. Brabec, J. Biol Chem. 2002, 277, 48076-48086.
60. V. Brabec, Prog. Nucleic Acid Res. Mol. Biol. 2002, 71, 1-68.
61. E. L. Mamenta, E. E. Poma, W. K. Kaufmann, D. A. Delmastro, H. L. Grady, S. G. Chaney, Cancer Res. 1994, 54, 3500-3505.
62. S. W. Johnson, P. B. Laub, J. S. Beesley, R. F. Ozols, T. C. Hamilton, Cancer Res. 1997, 57, 850-856.
63. U. Hübscher, H. P. Nasheuer, J. E. Syvaoja, Trends Biochem. Sci. 2000, 25, 143-147.
64. W. C. Lam, E. J. C. Van der Schans, L. C. Sowers, D. P. Millar, Biochemistry 1999, 38, 2661-2668.
65. T. A. Steitz, J. Biol. Chem. 1999, 274, 17395-17398.
66. S. Lone, L. J. Romano, Biochemistry 2003, 42, 3826-3834.
67. L. Ronconi, P. J. Sadler, Coord. Chem. Rev. 2007, 251, 1633-1648.
68. P. C. Bruijnincx, P. J. Sadler, Curr. Opin. Chem. Biol, 2008, 12, 197-206.
69. N. P. Johnson, J.-L. Butour, G. Villani, F. L. Wimmer, M. Defais, V. Pierson, V. Brabec, Prog. Clin. Biochem. Med. 1989, 6, 1-24.
70. E. R. Jamieson, S. J. Lippard, Chem. Rev. 1999, 99, 2467-2498.
71. E. Alessio, G. Mestroni, A. Bergamo, G. Sava, Curr. Top. Med. Chem. 2004, 4, 1525-1535.
72. V. Brabec, J. Reedijk, M. Leng, Biochemistry 1992, 31, 12397-12402.
73. C. J. Jones, R. D. Wood, Biochemistry 1993, 32, 12096-12104.
74. I. L. Hermanson-Miller, J. J. Turchi, Biochemistry 2002, 41, 2402-2408.
75. J. L. Manley, A. Fire, A. Cano, P. A. Sharp, M. L. Gefter, Proc. Natl. Acad. Sci, USA 1980, 77, 3855-3859.
76. J. T. Reardon, A. Vaisman, S. G. Chaney, A. Sanear, Cancer Res. 1999, 59, 3968-3971.
77. V. Brabec, M. Leng, Proc. Natl. Acad. Sci. USA 1993, 90, 5345-5349.
78. O. Novakova, J. Kasparkova, J. Malina, G. Natile, V. Brabec, Nucleic Acids Res. 2003, 31, 6450-6460.