Photoactivated DNA cleavage and anticancer activity of pyrenyl-terpyridine lanthanide complexes

European Journal of Medicinal Chemistry

Volumn 50, Issue , 2012, Pages 319-331

  Hussain, Akhtar ^a   Gadadhar, Sudarshan ^a   Goswami, Tridib K ^a   Karande, Anjali A ^a   Chakravarty, Akhil R ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Cellular imaging; Crystal structure; Lanthanide complexes; Medicinal chemistry; Photocytotoxicity; Pyrenyl terpyridine photosensitizer

Indexed keywords

ANTINEOPLASTIC AGENT; LANTHANIDE; PHOTOSENSITIZING AGENT; PYRENYL TERPYRIDINE LANTHANIDE COMPLEX; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL DEATH; CONFOCAL MICROSCOPY; CYTOTOXICITY; DNA BINDING; DNA CLEAVAGE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; PHOTOACTIVATION; PHOTODYNAMIC THERAPY; ULTRAVIOLET A RADIATION; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL NUCLEUS; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DNA; DNA CLEAVAGE; HELA CELLS; HUMANS; LANTHANOID SERIES ELEMENTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBCELLULAR FRACTIONS; ULTRAVIOLET RAYS;

EID: 84858443650     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.011     Document Type: Article

References (80)

1. N.J. Farrer, L. Salassa, and P.J. Sadler Dalton Trans. 2009 10690 10701
2. H.T. Chifotides, and K.R. Dunbar Acc. Chem. Res. 38 2005 146 156
3. N.L. Fry, and P.K. Mascharak Acc. Chem. Res. 44 2011 289 298
4. A.D. Ostrowski, and P.C. Ford Dalton Trans. 2009 10660 10669
5. U. Schatzschneider Eur. J. Inorg. Chem. 2010 1451 1467
6. R. Bonnett Chemical Aspects of Photodynamic Therapy 2000 Gordon & Breach London, U.K
7. M. Ethirajan, Y. Chen, P. Joshi, and R.K. Pandey Chem. Soc. Rev. 40 2011 340 362
8. M.R. Detty, S.L. Gibson, and S.J. Wagner J. Med. Chem. 47 2004 3897 3915
9. A.P. Castano, P. Mroz, and M.R. Hamblin Nat. Rev. Cancer 6 2006 535 545
10. M.C. DeRosa, and R.J. Crutchley Coord. Chem. Rev. 233-234 2002 351 371
11. I.J. MacDonald, and T.J. Dougherty J. Porphyrins Phthalocyanines 5 2001 105 129
12. K. Szacilowski, W. Macyk, A. Drzewiecka-Matuszek, M. Brindell, and G. Stochel Chem. Rev. 105 2005 2647 2694
13. S.I. Moriwaki, J. Misawa, Y. Yoshinari, I. Yamada, M. Takigawa, and Y. Tokura Photodermatol. Photoimmunol. Photomed. 17 2001 241 243
14. M. Ochsner, and J. Photochem Photobiol. B. Biol. 32 1996 3 9
15. F.S. Mackay, J.A. Woods, P. Heringová, J. Kašpá rková, A.M. Pizarro, S.A. Moggach, S. Parsons, V. Brabec, and P.J. Sadler Proc. Natl. Acad. Sci. U.S.A. 104 2007 20743 20748
16. A.M. Angeles-Boza, H.T. Chifotides, J.D. Aguirre, A. Chouai, P.K.-L. Fu, K.R. Dunbar, and C. Turro J. Med. Chem. 49 2006 6841 6847
17. M.J. Rose, N.L. Fry, R. Marlow, L. Hinck, and P.K. Mascharak J. Am. Chem. Soc. 130 2008 8834 8846
18. S. Swavey, and K.J. Brewer Inorg. Chem. 41 2002 6196 6198
19. A.A. Holder, S. Swavey, and K.J. Brewer Inorg. Chem. 43 2004 303 308
20. D.A. Lutterman, P.K.-L. Fu, and C. Turro J. Am. Chem. Soc. 128 2006 738 739
21. D. Loganathan, and H. Morrison Curr. Opin. Drug Discov. Devel. 8 2005 478 486
22. N.J. Farrer, J.A. Woods, L. Salassa, Y. Zhao, K.S. Robinson, G. Clarkson, F.S. Mackay, and P.J. Sadler Angew. Chem. Int. Ed. 49 2010 8905 8908
23. S. Saha, D. Mallick, R. Majumdar, M. Roy, R.R. Dighe, E.D. Jemmis, and A.R. Chakravarty Inorg. Chem. 50 2011 2975 2987
24. S. Saha, R. Majumdar, M. Roy, R.R. Dighe, and A.R. Chakravarty Inorg. Chem. 48 2009 2652 2663
25. B. Banik, P.K. Sasmal, S. Roy, R. Majumdar, R.R. Dighe, and A.R. Chakravarty Eur. J. Inorg. Chem. 9 2011 1425 1435
26. P.K. Sasmal, S. Saha, R. Majumdar, R.R. Dighe, and A.R. Chakravarty Chem. Commun. 2009 1703 1705
27. P.K. Sasmal, A.K. Patra, M. Nethaji, and A.R. Chakravarty Inorg. Chem. 46 2007 11112 11121
28. J.L. Sessler, and R.A. Miller Biochem. Pharmacol. 59 2000 733 939
29. W.-H. Wei, Z. Wang, T. Mizuno, C. Cortez, L. Fu, M. Sirisawad, L. Naumovski, D. Magda, and J.L. Sessler Dalton Trans. 2006 1934 1942
30. J.C. Frias, G. Bobba, M.J. Cann, C.J. Hutchison, and D. Parker Org. Biomol. Chem. 1 2003 905 907
31. E.J. New, D. Parker, D.G. Smith, and J.W. Walton Curr. Opin. Chem. Biol. 14 2010 238 246
32. E.J. New, and D. Parker Org. Biomol. Chem. 7 2009 851 855
33. J.C.G. Bunzli Chem. Rev. 110 2010 2729 2755
34. A. Datta, and K.N. Raymond Acc. Chem. Res. 42 2009 938 947
35. P. Caravan Acc. Chem. Res. 42 2009 851 862
36. M. Bottrill, L. Kwok, and N.J. Long Chem. Soc. Rev. 35 2006 557 571
37. A. Hussain, D. Lahiri, M.S.A. Begum, S. Saha, R. Majumdar, R.R. Dighe, and A.R. Chakravarty Inorg. Chem. 49 2010 4036 4045
38. A. Hussain, S. Saha, R. Majumdar, R.R. Dighe, and A.R. Chakravarty Ind. J. Chem. Sec. A 50A 2011 519 530
39. R.A. Gatenby, and R.J. Gillies Nat. Rev. Cancer 4 2004 891 899
40. M. Hanif, S.M. Meier, W. Kandioller, A. Bytzek, M. Hejl, C.G. Hartinger, A.A. Nazarov, V.B. Arion, M.A. Jakupec, P.J. Dyson, and B.K. Keppler J. Inorg. Biochem. 105 2011 224 231
41. S.J. Franklin Curr. Opin. Chem. Biol. 5 2001 201 208
42. S.A. Moya, R. Pastene, H.L. Bozec, P.J. Baricelli, A.J. Pardey, and J. Gimeno Inorg. Chim. Acta 312 2001 7 14
43. W. Leslie, R.A. Poole, P.R. Murray, L.J. Yellowlees, A. Beeby, and J.A.G. Williams Polyhedron 23 2004 2769 2777
44. B. Arezzini, M. Ferrali, E. Ferrari, C. Frassineti, S. Lazzari, G. Marverti, F. Spagnolo, and M. Saladini Eur. J. Med. Chem. 43 2008 2549 2556
45. T. Mosmann J. Immunol. Methods 65 1983 55 63
46. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds third ed. 1978 John Wiley & Sons New York
47. K. Mohri, Y. Watanabe, Y. Yoshida, M. Satoh, K. Isobe, N. Sugimoto, and Y. Tsuda Chem. Pharm. Bull. 51 2003 1268 1272
48. S. Roy, S. Saha, R. Majumdar, R.R. Dighe, E.D. Jemmis, and A.R. Chakravarty Dalton Trans. 40 2011 1233 1242
49. D.J. Toffoli, L. Gomes, N.D. Vieira Jr., and L.C. Courrol J. Opt. A: Pure Appl. Opt. 10 2008 104026 (8pp)
50. J.R. Lakowicz Principles of Fluorescence Spectroscopy third ed. 2006 Springer New York
51. Y. Fukuda, A. Nakao, and K. Hayashi J. Chem. Soc. Dalton Trans. 2002 527 533
52. H. Krass, E.A. Plummer, J.M. Haider, P.R. Barker, N.W. Alcock, Z. Pikramenou, M.J. Hannon, and D.G. Kurth Angew. Chem. Int. Ed. 40 2001 3862 3865
53. A.M. Angeles-Boza, P.M. Bradley, P.K.-L. Fu, S.E. Wicke, J. Bacsa, K.R. Dunbar, and C. Turro Inorg. Chem. 43 2004 8510 8519
54. Y. An, S.-D. Liu, S.-Y. Deng, L.-N. Ji, and Z.-W. Mao J. Inorg. Biochem. 100 2006 1586 1593
55. J.M. Veal, and R.L. Rill Biochemistry 30 1991 1132 1340
56. P.A. Pellegrini, and J.R. Aldrich-Wright Dalton Trans. 2003 176 183
57. K.E. Erkkila, D.T. Odom, and J.K. Barton Chem. Rev. 99 1999 2777 2795
58. A.U. Khan J. Phys. Chem. 80 1976 2219 2227
59. M. Tanaka, K. Ohkubo, and S. Fukuzumi J. Phys. Chem. A 110 2006 11214 11218
60. E. Delaey, F. Van Laar, D. De Vos, A. Kamuhabwa, P. Jacobs, and P. De Witte J. Photochem. Photobiol. B. 55 2000 27 36
61. J. Portugal BMC Pharmacol. 9 2009 11
62. N.J. Wheate, C.R. Brodie, J.G. Collins, S. Kemp, and J.R. Aldrich-Wright Mini Rev. Med. Chem. 7 2007 627 648
63. T. Storr, K.H. Thompson, and C. Orvig Chem. Soc. Rev. 35 2006 534 544
64. K.H. Thompson, and C. Orvig Dalton Trans. 2006 761 764
65. R.A. Madina, and G.I. Owen Biol. Res. 35 2002 9 26
66. M.-W. Louie, H.-W. Liu, M.H.-C. Lam, Y.-W. Lam, and K.K.-W. Lo Chem. Eur. J. 17 2011 8304 8308
67. D.D. Perrin, W.L.F. Armarego, and D.R. Perrin Purification of Laboratory Chemicals 1980 Pergamon Press Oxford
68. D.F. Evans J. Chem. Soc. 1959 2003 2005
69. D.F. Evans, and T.A. James J. Chem. Soc. Dalton Trans. 1979 723 726
70. A.T.R. Williams, S.A. Winfield, and J.N. Miller Analyst 108 1983 1067 1071
71. N. Walker, and D. Stuart Acta Crystallogr. Sect. A 39 1983 158 166
72. G.M. Sheldrick Acta Cryst. A64 2008 112 122
73. C.K. Johnson ORTEP-III, Report ORNL-5138 1976 Oak Ridge National Laboratory Oak Ridge, TN
74. L.J. Farrugia J. Appl. Cryst. 30 1997 565 566
75. M.E. Reichmann, S.A. Rice, C.A. Thomas, and P. Doty J. Am. Chem. Soc. 76 1954 3047 3053
76. J.D. McGhee, and P.H. von Hippel J. Mol. Biol. 86 1974 469 489
77. M.T. Carter, M. Rodriguez, and A.J. Bard J. Am. Chem. Soc. 111 1989 8901 8911
78. M.L. Kopka, C. Yoon, and D. Goodsell Proc. Natl. Acad. Sci. U.S.A. 82 1985 1376 1380
79. S.K. Kim, and B. Norden FEBS Lett. 315 1993 61 64
80. J. Bernadou, G. Pratviel, F. Bennis, M. Girardet, and B. Meunier Biochemistry 28 1989 7268 7275