Sensitization of ruthenium nitrosyls to visible light via direct coordination of the dye resorufin: Trackable NO donors for light-triggered NO delivery to cellular targets

Journal of the American Chemical Society

Volumn 130, Issue 27, 2008, Pages 8834-8846

  Rose, Michael J ^a   Fry, Nicole L ^a   Marlow, Rebecca ^a   Hinck, Lindsay ^a   Mascharak, Pradip K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELLULAR TARGETS; NO DONORS; RESORUFIN; VISIBLE LIGHT;

RUTHENIUM;

METAL COMPLEX; NITRIC OXIDE; NITRIC OXIDE DONOR; NITROGEN DERIVATIVE; PHENOL DERIVATIVE; PHOTOSENSITIZING AGENT; RESORUFIN; RESORUFIN DERIVATIVE; RUTHENIUM DERIVATIVE;

APOPTOSIS; ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; CONJUGATION; CONTROLLED STUDY; HUMAN; HUMAN CELL; PHOTOCHEMISTRY; PHOTOSENSITIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CELL LINE, TUMOR; FLUORESCENT DYES; HUMANS; LIGHT; NEOPLASMS; NITRIC OXIDE; NITRIC OXIDE DONORS; ORGANOMETALLIC COMPOUNDS; OXAZINES; PHOTOCHEMOTHERAPY; PHOTOLYSIS; RUTHENIUM; SKIN NEOPLASMS;

EID: 46949107841     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801823f     Document Type: Article

References (154)

1. (a) Ignarro, L. J. Nitric Oxide: Biology and Pathobiology; Academic Press: San Diego, 2000.
2. (b) Ko, G. Y.; Fang, F. C. Nitric Oxide and Infection; Kluwer Academic/Plenum Publishers: New York, 1999.
3. (c) Lincoln J.; Burnstock G. Nitric Oxide in Health and Disease; Cambridge University Press: New York, 1997.
4. (a) Ying, L.; Hofseth, L. J. Cancer Res. 2007, 67, 1407-1410.
5. (b) Li, H.; Igarashi, J.; Jamal, J.; Yang, W.; Poulos, T. L. J. Biol. Chem. 2006, 11, 753-768.
6. (c) Rosen, G. M.; Tsai, P.; Pou, S. Chem. Rev. 2002, 102, 1191-1199.
7. (d) Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Biochem. J. 2001, 357, 593-615.
8. (a) Hirst, D.; Robson, T. J. Pharm. Pharmacol. 2007, 59, 3-13.
9. (b) Bonavida, B.; Khineche, S.; Huerta-Yepez, S.; Garbán, H. Drug Res. Updates 2006, 9, 157.
10. (c) Li, C. Q.; Wogan, G. N. Cancer Lett. 2005, 226, 1-15.
11. (a) Brüne, B. Cell Death Differ. 2003, 10, 864-869.
12. (b) Brüne, B.; von Knethan, A.; Sandau, K. B. Cell. Singal. 2001, 13, 525-533.
13. (c) Abramson, S. B.; Amin, A. R.; Clancy, R. M.; Attur, M. Best Pract. Res. Clin. Rheumatol. 2001, 15, 831-845.
14. (a) Mocellin, S.; Bronte, V.; Nitti, D. Med. Res. Rev. 2007, 27, 317-352.
15. (b) Bobba, A.; Atlante, A.; Mora, L.; Calissano, P.; Marra, E. Apoptosis 2007, 12, 1597-1610.
16. (c) Wink, D. A.; Vodovotz, Y.; Laval, J.; Laval, F.; Dewhirst, M. W.; Mitchell, J. B. Carcinogenesis 1998, 19, 711-721.
17. (d) Dimmeier, S.; Zeihar, A. M. Nitric Oxide 1997, 1, 275-281.
18. (a) Tarr, J. M.; Eggleton, P.; Winyard, P. G. Curr. Pharm. Design 2006, 12, 4445-4468.
19. (b) Payne, C. M.; Waltmire, C. N.; Crowley, C.; Crowley-Weber, C. L.; Dvorakova, K.; Bernstein, H.; Bernstein, C.; Holubec, H.; Garewal, H. Cell Biol. Toxicol. 2003, 19, 373-392.
20. (c) Taylor, E. L.; Megson, I. L.; Haslett, C.; Rossi, A. G. Cell Death Differ. 2003, 10, 418-430.
21. (d) Vakkala, M.; Kahlos, K.; Lakari, E.; Paakko, P.; Kinnula, V.; Soini, Y. Clin. Cancer Res. 2000, 6, 2408-2416.
22. (a) Fukumura, D.; Kashiwagi, S.; Jain, R. K. Nat. Rev. Cancer 2006, 6, 521-534.
23. (b) Lancaster, J. R.; Xie, K. P. Cancer Res. 2006, 66, 6459-6462.
24. (c) Xie, K. P.; Suyun, H. Free Radical Biol. Med. 2003, 34, 969-986.
25. (a) Brown, G. C. Frontiers Biosci. 2007, 12, 1024-1033.
26. (b) Szundi, I.; Rose, M. J.; Sen, I.; Eroy-Reveles, A. A.; Mascharak, P. K.; Einarsdóttir, Ó. Photochem. Photobiol. 2006, 82, 1377-1384.
27. (c) Zhang, J.; Jin, B.; Li, L.; Block, E. R.; Patel, J. M. Am. J. Physiol. Cell Physiol. 2005, 288, C840-C849.
28. (d) Kadenbach, B.; Arnold, S.; Lee, I.; Hüttermann, M. Biochim. Biophys. Acta 2004, 1655, 400-408.
29. (a) Boyd, C. S.; Cadenas, E. Biol. Chem. 2002, 383, 411-423.
30. (b) Brown, G. C. Biochim. Biophys. Acta 2001, 1504, 46-57.
31. (c) Brüne, B.; von Knethen, A.; Sandau, K. B. Eur. J. Pharmacol. 1998, 351, 261-272.
32. (a) Du, C.; Guan, Q.; Diao, H.; Yin, Z.; Jevnikar, A. M. Am. J. Physiol. 2006, 290, F1044-F1054.
33. (b) Chung, P.; Cook, T.; Liu, K.; Vodovotz, Y.; Zamora, R.; Finkelstein, S.; Billiar, T.; Blumberg, D. Nitric Oxide 2003, 8, 119-126.
34. (c) Chae, H. J.; Chae, S.-W.; An, N.-H.; Kim, J.-H.; Kim, C.-W.; Yoo, S.-K.; Kim, H.-H.; Lee, Z.-L.; Kim, H.-R. Biol. Pharm. Bull. 2001, 24, 453-460.
35. (d) Brüne, B.; Mohr, S. Curr. Protein Pept. Sci. 2001, 2, 61-72.
36. (a) McLaughlin, L. M.; Demple, B. Cancer Res. 2005, 65, 6097-6104.
37. (b) Martin, L. J.; Chen, K.; Liu, Z. J. Neurosci. 2005, 25, 6449-6459.
38. (c) Cook, T.; Wang, Z.; Alber, S.; Liu, K.; Watkins, S. C.; Vodovotz, Y.; Billiar, T. R.; Blumberg, D. Cancer Res. 2004, 64, 8015-8021.
39. (d) Brune, B.; Schneiderhan, N. Toxicol. Lett. 2003, 139, 119-123.
40. (a) Wang P. G.; Cai T. B.; Taniguchi N. Nitric Oxide Donors for Pharmaceutical and Biological Applications; Wiley-VCH: Weinheim, 2005.
41. (b) Gasco, A.; Fruttero, R.; Rolando, B. Rev. Med. Chem. 2005, 5, 217-229.
42. (c) Napoli, C.; Ignarro, L. J. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 97-123.
43. (d) Jia, Q. A.; Janczuk. A. J.; Cai, T. W.; Xian, M.; Wen, Z.; Wang, P. G. Expert Opin. Ther. Pat. 2002, 12, 819-826.
44. (a) Al-Sadoni, H. H.; Ferro, A. Rev. Med. Chem. 2005, 5, 247-254.
45. (b) Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, A. J. Chem. Rev. 2002, 102, 1091-1134.
46. (c) Butler, A. R.; Megson, I. L. Chem. Rev. 2002, 102, 1155-1165.
47. (a) Velazquez, C. A.; Rao, P.; Citro, M. L.; Keefer, L. K.; Knaus, E. E. Bioorg. Med. Chem. 2007, 15, 4767-4774.
48. (b) Keefer, L. K. Curr. Topics Med. Chem. 2005, 5, 625-634.
49. (c) Saavedra, J. E.; Shami, P. J.; Wang, L. Y.; Davies, K. M.; Booth, M. N.; Citro, M. L.; Keefer, L. K. J. Med. Chem. 2000, 43, 261-269.
50. (a) Castano, A. P.; Mroz, P.; Hamblin, M. R. Nat. Rev. Cancer 2006, 6, 535-545.
51. (b) Pandey, R. K. J. Porph. Pthal. 2006, 4, 368-373.
52. (c) Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med. Chem. 2004, 47, 3897-3915.
53. (d) Dolmans, D. E. J. G.; Fukumora, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380-387.
54. (a) Pavlos, C. M.; Xu, H.; Toscano, J. P. Curr. Top. Med. Chem. 2005, 5, 635-645.
55. (b) Bigio, I. J.; Bown, S. G. Cancer Biol. Therapy 2004, 3, 259-267.
56. (a) Srinivasan, A.; Kebede, N.; Saavedra, J. E.; Nikolaitchik, A. V.; Brady, D. A.; Yourd, E.; Davies, K. M.; Keefer, L. K.; Toscano, J. P. J. Am. Chem. Soc. 2001, 123, 5465-5472.
57. (b) Zhelyaskov, V. R.; Gee, K. R.; Godwin, D. W. Photochem. Photobiol. 1998, 67, 282-288.
58. (c) Wood, P. D.; Mutus, B.; Redmond, R. W. Photochem. Photobiol. 1996, 64, 518-524.
59. (a) Rose, M. J.; Mascharak, P. K. Curr. Opin. Chem. Biol. 2008, 12, 238-244.
60. (b) Ford, P. C.; Bourassa, J.; Miranda, K.; Lee, B.; Lorkovic, I.; Boggs, S.; Kudo, S.; Laverman, L. Coord. Chem. Rev. 1998, 171, 185-202.
61. (c) Richter-Addo, G. B.; Legzdins, P. Metal Nitrosyls; Oxford University Press: Oxford, UK 1992.
62. (a) Szacilowski, K.; Wacyk, W.; Stochel, G.; Stasicka, Z.; Sostero, S.; Traverso, O. Coord. Chem. Rev. 2000, 208, 277-297.
63. (b) Stochel, G.; Wanat, A.; Kulis, E.; Stasicka, Z. Coord. Chem. Rev. 1998, 171, 203-220.
64. (c) Singh, R. J.; Hogg, N.; Neese, F.; Joseph, J.; Kalyanaraman, B. Photochem. Photobiol. 1995, 61, 325-330.
65. (d) Wolfe, S. K.; Swinehart, J. H. Inorg. Chem. 1975, 14, 1049-1053.
66. (a) Alaniz, C.; Watts, B. Ann. Pharmacother. 2005, 39, 388-389.
67. (b) Ryu, J.-S.; Lloyd, D. FEMS Microbiol. Letts. 1995, 130, 183-188.
68. Conrado, C.; Bourassa, J. L.; Egler, C.; Wecksler, S.; Ford, P. C. Inorg. Chem. 2003, 42, 2288-2293.
69. (a) Bourassa, J. L.; Ford, P. C. Coord. Chem. Rev. 2000, 200-202, 887-900.
70. (b) Bourassa, J.; Lee, B.; Bernard, S.; Schoonover, J.; Ford, P. C. Inorg. Chem. 1999, 38, 2947-2952.
71. (a) Janczyk, A.; Wolnicka-Glubisz, A.; Chmura, A.; Elas, M.; Matuszak, Z.; Stochel, G.; Urbanska, K. Nitric Oxide 2004, 10, 42-50.
72. (b) Bourassa, J.; DeGraff, W.; Kudo, S.; Wink, D. A.; Mitchell, J. B.; Ford, P. C. J. Am. Chem. Soc. 1997, 119, 2853-2860.
73. (a) Lim, M. D.; Lorkovic, I. M.; Wedeking, K.; Zanella, A. W.; Works, C. F.; Massick, S. M.; Ford, P. C. J. Am. Chem. Soc. 2002, 124, 9737-9743.
74. (b) Hoshino, M.; Laverman, L.; Ford, P. C. Coord. Chem. Rev. 1999, 187, 75-102.
75. (a) Patra, A. K.; Rowland, J. M.; Marlin, D. S.; Bill, E.; Olmstead, M. M.; Mascharak, P. K. Inorg. Chem. 2003, 42, 6812-6823.
76. (b) Patra, A. K.; Afshar, R. K.; Olmstead, M. M.; Mascharak, P. K. Angew. Chem., Intl. Ed. 2002, 41, 2512-2515.
77. (a) Afshar, R. K.; Eroy-Reveles, A. A.; Olmstead, M. M.; Mascharak, P. K. Inorg. Chem. 2006, 45, 10347-10354.
78. (b) Patra, A. K.; Afshar, R. K.; Rowland, J. M.; Olmstead, M. M.; Mascharak, P. K. Angew. Chem., Int. Ed. 2003, 42, 4517-4521.
79. (c) Ford, P. C.; Lorkovic, I. M. Chem. Rev. 2002, 102, 993-1018.
80. (d) Bottomley, F. Acc. Chem. Res. 1978, 11, 158-163.
81. (a) Patra, A. K.; Rose, M. J.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 2004, 126, 4780-4781.
82. (b) Lim, M. D.; Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 2002, 41, 1026-1028.
83. (c) Lin, R.; Farmer, P. J. J. Am. Chem. Soc. 2001, 123, 1143-1150.
84. (d) Lorkovic, I. M.; Ford, P. C. Inorg. Chem. 1999, 38, 1467-1473.
85. (e) Franz, K. J.; Lippard, S. J. J. Am. Chem. Soc. 1998, 120, 9034-9040.
86. Rose, M. J.; Mascharak, P. K. Coord. Chem. Rev. 2008, in press, doi:10.1016/j.ccr.2007.11.011.
87. (a) Nikol'skii, A. B.; Popov, A. M.; Vasilevskii, I. V. Koord. Khimiya. 1976, 2, 671-677.
88. (b) Cox, A. B.; Wallace, R. M. Inorg. Nucl. Chem. Letts. 1971, 7, 1191-1194.
89. Toledo, J. C.; Ledo, B. D. S. L.; Franco, D. W. Coord. Chem. Rev. 2005, 249, 419-431.
90. Patra, A. K.; Rose, M. J.; Murphy, K. M.; Olmstead, M. M.; Mascharak, P. K. Inorg. Chem. 2004, 43, 4487-4495.
91. (a) Afshar, R. K.; Eroy-Reveles, A. A.; Olmstead, M. M.; Mascharak, P. K. Inorg. Chem. 2006, 45, 10347-10354.
92. (b) Patra, A. K.; Rose, M. J.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 2004, 126, 4780-4781.
93. (a) Sizova, O. V.; Lyubimova, O. O. Russ. J. Gen. Chem. 2004, 74, 996-1000.
94. (b) Greene, S. N.; Richards, N. G. J. Inorg. Chem. 2004, 43, 7030-7041.
95. (a) Zollinger, H. Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, 3rd Ed.; Wiley-VCH and Verlag Helvetica Chimica Acta: Zurich, Switzerland, 2003.
96. (b) Griffith, J. Ed. Developments in the Chemistry and Technology of Organic Dyes; Blackwell Scientific: Oxford, 1984.
97. Rose, M. J.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 2007, 129, 5342-5343.
98. Ford, P. C.; Wecksler, S. Coord. Chem. Rev. 2005, 249, 1382-1395.
99. Rosa, D. T.; Reynolds, R. A.; Malinak, S. M.; Coucouvanis, D. Inorg. Synth. 2002, 33, 112-119.
100. (a) Schmidt, R.; Brauer, H.-D. J. Photochem. 1984, 25, 489-499.
101. (b) Murov, S. Handbook of Photochemistry; Marcel Dekker: New York, 1973.
102. (a) Rose, M. J.; Patra, A. K.; Alcid. E. A.; Olmstead, M. M.; Mascharak, P. K. Inorg. Chem. 2007, 46, 2328-2338.
103. (b) Patra, A. K.; Mascharak, P. K. Inorg. Chem. 2003, 42, 7363-7365.
104. (a) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728-3739.
105. (b) Bordini, J.; Hughes, D. L.; da Motto Neto, J. D.; da Cunha, C. J. Inorg. Chem. 2002, 41, 5410-5416.
106. (c) Works, C. F.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 7592-7593.
107. (a) Prakash, R.; Czaja, A. U.; Heinemann, F. W.; Sellmann, D. J. Am. Chem. Soc. 2005, 127, 13758-13759.
108. (b) Sellmann, D.; Prakash, R.; Heinemann, F. W.; Moll, M.; Klimowicz, M. Angew. Chem., Int. Ed. 2004, 43, 1877-1880.
109. (a) Pipes, D. W.; Meyer, T. J. Inorg. Chem. 1984, 23, 2466-2472.
110. (b) Callahan, R. W.; Meyer, T. J. Inorg. Chem. 1977, 16, 574-581.
111. (a) de Lima, R. G.; Sauaia, M. G.; Bonaventura, D.; Tedesco, A. C. Inorg. Chim. Acta 2006, 359, 2543-2549.
112. (b) de Lima, R. G.; Sauaia, M. G.; Bonaventura, D.; Tedesco, A. C.; Lopez, R. F. V.; Bendhack, L. M.; da Silva, R. S. Inorg. Chim. Acta 2005, 358, 2643-2650.
113. (c) Carlos, R. M.; Cordoso, D. R.; Castellano, E. E.; Osti, R. Z.; Camargo, A. J.; Macedo, L. G.; Franco, D. W. J. Am. Chem. Soc. 2004, 126, 2546-2555.
114. (d) Sugimori, A.; Uchida, H.; Akiyama, T.; Mukaida, M.; Shimuzu, K. Chem. Lett. 1982, 1135-1138.
115. (a) Montejano, H. A.; Gervaldo, M.; Bertolotti, S. G. Dyes Pigments. 2005, 64, 117-124.
116. (b) Bueno, C.; Villegas, M. L.; Bertolotti, S. G.; Previtali, C. M.; Neumann, M. G.; Encinas, M. V. Photochem. Photobiol. 2002, 76, 385-390.
117. (c) Flamigni, L.; Venuti, E.; Camaioni, N.; Barigelleti, F. J. Chem. Soc., Faraday Trans. 1989, 85, 1935-1943.
118. (d) Fabian, J.; Hartmann, H. Light Absorption of Organic Colorants: Theoretical Treatment and Empirical Rules; Springer-Verlag: Heidelberg, Germany, 1980.
119. The ε-value of unbound Resorufin (as sodium salt) was determined in DMF for the sake of comparison to the complexes described in this work.
120. (a) Sizova, O. V.; Ivanova, N. V.; Sizov, W.; Nikol'skii, A. B. Russ. J. Gen. Chem. 2004, 74, 481-485.
121. (b) Sizova, O. V.; Lyubimova, O. O.; Sizov, W. Russ. J. Gen. Chem. 2004, 74, 317-322.
122. (c) Sizova, O. V.; Ivanova, N. V.; Lyubimova, O. O.; Nikol'skii, A. B. Russ. J. Gen. Chem. 2004, 74, 155-163.
123. (d) Gorelsky, S. I.; da Silva, S. C.; Lever, A. B. P.; Franco, D. W. Inorg. Chim. Acta 2000, 300-302, 698-708.
124. (e) Schreiner, A. F.; Lin, S. W.; Hauser, P. J.; Hopcus, E. A.; Hamm, D. J.; Gunter, J. D. Inorg. Chem. 1972, 11, 880-888.
125. (a) Sauaia, M. G.; de Lima, R. G.; Tedesco, A. C.; da Silva, R. S. Inorg. Chem. 2005, 44, 9946-9951.
126. (b) Sauaia, M. G.; de Lima, R. G.; Tedesco, A. C.; da Silva, R. S. J. Am. Chem. Soc. 2003, 125, 14718-14719.
127. (a) Wecksler, S. R.; Mikhailovsky, A.; Korystov, D.; Ford, P. C. J. Am. Chem. Soc. 2006, 128, 3831-3837.
128. (b) Wecksler, S. R.; Hutchinson, J.; Ford, P. C. Inorg. Chem. 2006, 45, 1192-1200.
129. (a) Baker, E. S.; Bushnell, J. E.; Wecksler, S. R.; Lim, M. D.; Manard, M. J.; Dupuis, N. F.; Ford, P. C.; Bowers, M. T. J. Am. Chem. Soc. 2005, 127, 18222-18228.
130. (b) Conrado, C. L.; Wecksler, S.; Egler, C.; Magde, D.; Ford, P. C. Inorg. Chem. 2004, 43, 5543-5549.
131. (a) DeRosa, F.; Bu, X.; Ford, P. C. Inorg. Chem. 2005, 44, 4157-4165.
132. (b) DeRosa, F.; Bu, X.; Pohaku, K.; Ford, P. C. Inorg. Chem. 2005, 44, 4166-4174.
133. (c) DeRosa, F.; Bu, X.; Ford, P. C. Inorg. Chem. 2003, 42, 4171-4178.
134. (a) Eroy-Reveles, A. A.; Leung, Y.; Beavers, C.; Olmstead, M. M.; Mascharak, P. K. J. Am. Chem. Soc. 2008,
135. (b) Eroy-Reveles, A. A.; Hoffman-Luca, C. G.; Mascharak, P. K. Dalton Trans. 2007, 5268-5274.
136. Turro, N. J. Modern Molecular Photochemistry; University Science: Mill Valley, USA, 1991.
137. (a) Sapsford, K. E.; Berti, L.; Medintz, I. L. Angew. Chem., Int. Ed. 2006, 45, 4562-4588.
138. (b) Raymo, F. M.; Tomasulo, M. Chem. Soc. Rev. 2005, 34, 327-336.
139. (c) Huynh, M. H. V.; Dattelbaum, D. M.; Meyer, T. J. Coord. Chem. Rev. 2005, 249, 457-483.
140. (d) Faure, S.; Stern, C.; Guillard, R.; Harvey, P. D. J. Am. Chem. Soc. 2004, 126, 1253-1261.
141. Simeone, A.-M.; Colella, S.; Krahe, R.; Johnson, M. M.; Mora, E.; Tari, A. M. Carcinogenesis. 2006, 27, 568-577.
142. Kang, J. X.; Liu, J.; Wang, J. D.; He, C. W.; Li, F. P. Carcinogenesis. 2005, 26, 1934-1939.
143. (a) Thangapazham, R. L.; Singh, A. K.; Sharma, A.; Warren, J.; Gaddpati, J. P.; Maheshwari, R. K. Cancer Letts. 2007, 245, 232-241.
144. (b) Kim, M.; Katayose, Y.; Rojanala, L.; Shah, S.; Sgagias, M.; Jang, L.; Jung, Y.-L.; Lee, S.-H.; Hwang, S.-G.; Cowan, K. H. Cell Death Differ. 2000, 7, 706-711.
145. (a) Viale, M.; Mariggio, M. A.; Ottone, M.; Chiavarina, B.; Vinella, A.; Prevesto, C.; Dell'Arba, C.; Petrillo, G.; Novi, M. Invest. New Drugs. 2004, 22, 359-267.
146. (b) Meßner, U. K.; Brüne, B. Arch. Biochem. Biophys. 1996, 327, 1-10.
147. (a) Tannous, M.; Hutnik, C. M. L.; Tingey, D. P.; Mutus, B. Invest. Opthamol. Vis. Sci. 2000, 41, 749-755.
148. (b) Saavedra, J. E.; Booth, M. N.; Hrabie, J. A.; Davies, K. M.; Keefer, L. K. J. Org. Chem. 1999, 64, 5124.
149. (a) Kamiya, M.; Kobayashi, H.; Hama, Y.; Koyama, Y.; Bernardo, M.; Nagano, T.; Choyke, P. L.; Urano, Y. J. Am. Chem. Soc. 2007, 129, 3918-3929.
150. (b) Leevy, W. M.; Gammon, S. T.; Jiang, H.; Johnson, J. R.; Maxwell, D. J.; Jackson, E. N.; Marquez, M.; Piwnica-Worms, D.; Smith, B. D. J. Am. Chem. Soc. 2006, 128, 16476-16477.
151. (c) Bogaards, A.; Zhang, K.; Zach, D.; Bisland, S. K.; Moriyama, E. H.; Lilge, L.; Muller, P. J.; Wilson, B. C. Photochem. Photobiol. Sci. 2005, 4, 438-442.
152. (a) Korbelik, M. Lasers Surg. Med. 2006, 38, 500-508.
153. (b) Castano, A. P.; Mroz, P.; Hamblin, M. R. Nat. Rev. Cancer. 2006, 6, 535-545.
154. (c) Lilge, L.; Portnoy, M.; Wilson, B. C. Br. J. Cancer 2000, 83, 1110-1117.