Thiol, disulfide, and trisulfide complexes of Ru porphyrins: Potential models for iron-sulfur bonds in heme proteins

Journal of the American Chemical Society

Volumn 134, Issue 7, 2012, Pages 3555-3570

  Rebouças, Júlio S ^a   Patrick, Brian O ^b   James, Brian R ^b  

^a FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL LIGAND; COOPERATIVITY EFFECTS; COORDINATION MODES; CRYSTAL FIELD EFFECTS; DIANIONS; DISULFIDE COMPLEX; FE-PORPHYRIN; HEME PROTEINS; IN-SITU; LINEAR CORRELATION; MESO-TETRAMESITYLPORPHYRIN; METALLOPORPHYRINS; NMR DATA; POTENTIAL MODEL; RING CURRENT EFFECTS; SOLID-STATE STRUCTURES;

BIOSYNTHESIS; IRON COMPOUNDS; LIGANDS; PORPHYRINS; SULFUR; THERMOMECHANICAL PULPING PROCESS;

SULFUR COMPOUNDS;

ACYCLIC DIALKYL DISULFIDE; DISULFIDE; HEME; IRON; PORPHYRIN DERIVATIVE; PROTON; RUTHENIUM; RUTHENIUM COMPLEX; SULFUR; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL BINDING; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DISULFIDES; HEMEPROTEINS; IRON; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PORPHYRINS; RUTHENIUM; SULFHYDRYL COMPOUNDS; SULFIDES; SULFUR;

EID: 84857418709     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211226e     Document Type: Article

References (200)

1. Mansuy, D. and Battioni, P. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., and Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 4, Chapter 26, pp 1-15.
2. Green, M. T.; Dawson, J. H.; Gray, H. B. Science 2004, 304, 1653-1656
3. Denisov, I. G.; Makris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105, 2253-2277
4. Omura, T. Biochem. Biophys. Res. Commun. 2005, 338, 404-409
5. Udit, A. K.; Gray, H. B. Biochem. Biophys. Res. Commun. 2005, 338, 470-476
6. Hofrichter, M.; Ulrich, R. Appl. Microbiol. Biotechnol. 2006, 71, 276-288
7. Aono, S. Dalton Trans. 2008, 3137-3146
8. Igarashi, J.; Kitanishi, K.; Martinkova, M.; Murase, M.; Iizuka, A.; Shimizu, T. Acta Chim. Slov. 2008, 55, 67-74
9. Green, M. T. Curr. Opin. Chem. Biol. 2009, 13, 84-88
10. Luthra, A.; Denisov, I. G.; Sligar, S. G. Arch. Biochem. Biophys. 2011, 507, 26-35
11. Du, J.; Sono, M.; Dawson, J. H. Coord. Chem. Rev. 2011, 255, 700-716
12. Du, J.; Sono, M.; Dawson, J. H. J. Porphyrins Phthalocyanines 2011, 15, 29-38
13. Dawson, J. H.; Sono, M. Chem. Rev. 1987, 87, 1255-1276
14. Dawson, J. H. Science 1988, 240, 433-439
15. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887
16. Woggon, W.-D.; Wagenknecht, H.-A.; Claude, C. J. Inorg. Biochem. 2001, 83, 289-300
17. Lochner, M.; Mu, L.; Woggon., W.-D. Adv. Synth. Catal. 2003, 345, 743-765
18. James, B. R.; Pacheco, A.; Rettig, S. J.; Thorburn, I. S.; Ball, R. G.; Ibers, J. A. J. Mol. Catal. 1987, 41, 147-161
19. James, B. R.; Pacheco, A.; Rettig, S. J.; Ibers, J. A. Inorg. Chem. 1988, 27, 2414-2421
20. Rajapakse, N.; James, B. R.; Dolphin, D. Catal. Lett. 1989, 2, 219-226
21. Rajapakse, N.; James, B. R.; Dolphin, D. In New Developments in Selective Oxidation; Centri, G.; F. Trifiro, F., Eds.; Elsevier: Amsterdam, 1990; pp 109-117.
22. Pacheco, A.; James, B. R.; Rettig, S. J. Inorg. Chem. 1995, 34, 3477-3484
23. James, B. R.; Meng, G. G.; Posakony, J. J.; Ravensbergen, J. A.; Ware, C. J.; Skov, K. A. Metal-Based Drugs 1996, 3, 85-89
24. Pacheco, A.; James, B. R.; Rettig, S. J. Inorg. Chem. 1999, 38, 5579-5587
25. Ezhova, M. B.; James, B. R. In Advances in Catalytic Activation of Dioxygen by Metal Complexes (Ed. L. I. Simándi), Kluwer Academic Publishers: Dordrecht, 2003, Ch. 1, pp 1-77.
26. Groves, J. T.; Han, Y.; van Engen, D. J. Chem. Soc. Chem. Commun. 1990, 436-437
27. Han, Y.-Z. Ph.D. Dissertation, Princeton University, Princeton, NJ, 1992.
28. Yi, G.-B.; Khan, M. A.; Richter-Addo, G. B. Chem. Commun. 1996, 2045-2046
29. Yi, G.-B.; Khan, M. A.; Richter-Addo, G. B. Inorg. Chem. 1996, 35, 3453-3454
30. Yi, G.-B.; Khan, M. A.; Richter-Addo, G. B. Inorg. Chem. 1997, 36, 3876-3885
31. Yi, G.-B.; Khan, M. A.; Powell, D. R.; Richter-Addo, G. B. Inorg. Chem. 1998, 37, 208-214
32. Lee, J.; Yi, G.-B.; Khan, M. A.; Richter-Addo, G. B. Inorg. Chem. 1999, 38, 4578-4584
33. Cheng, L.; Richter-Addo, G. B. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 4, Chapter 33, pp 219-291.
34. Bohle, D. S.; Goodson, P. A.; Smith, B. D. Polyhedron 1996, 18, 3147-3150
35. Bohle, D. S.; Hung, C.-H.; Smith, B. D. Inorg. Chem. 1998, 37, 5798-5806
36. Yee, G. T.; Noll, B. C.; Williams, D. K. C.; Sellers, S. P. Inorg. Chem. 1997, 36, 2904-2907
37. Hopf, F. R.; O'Brien, T. P.; Scheidt, W. R.; Whitten, D. G. J. Am. Chem. Soc. 1975, 97, 277-281
38. Lushington, G. H.; Cowley, A. B.; Silchenko, S.; Lukat-Rodgers, G. S.; Rodgers, K. R.; Benson, D. R. Inorg. Chem. 2003, 42, 7550-7559
39. Baker, P. L; Freund, S. M. V. Biochemistry 1996, 35, 13627-13635
40. Le Brun., N. E.; Thomson, A. J.; Moore, G. R. Struct. Bonding (Berlin) 1997, 88, 103-138
41. Yamamoto, Y.; Terui, N.; Tachiiri, N.; Minakawa, K.; Matsuo, H.; Kameda, T.; Hasegawa, J.; Sambongi, Y.; Uchiyama, S.; Kobayashi, Y.; Igarashi., Y. J. Am. Chem. Soc. 2002, 124, 11574-11575
42. Tachiiri, N.; Hemmi, H.; Takayama, S. J.; Mita, H.; Hasegawa, J.; Sambongi, Y.; Yamamoto, Y. J. Biol. Inorg. Chem. 2004, 9, 733-742
43. Thariat, J.; Collin, F.; Marchetti, C.; Ahmed-Adrar, N. S.; Vitrac, H.; Jore, D.; Gardes-Albert, M. Biochimie 2008, 90, 1442-1451
44. Lee, B. C.; Gladyshev, V. N. Free Radical Biol. Med. 2011, 50, 221-227
45. Scheidt, W. R.; Reed, C. A. Chem. Rev. 1981, 81, 543-555
46. Moore, G. R.; Pettigrew, G. W. Cytochromes c: Evolutionary, Structural, and Physicochemical Aspects; Springer-Verlag: Berlin, 1990; pp 370-372.
47. Cheesman, M. R.; Thomson, A. J.; Grenwood, C.; Moore, G. R.; Kadir, F. Nature 1990, 346, 771-773
48. Frolow, F.; Kalb, A. J.; Yariv, J. Struct. Biol. 1994, 1, 453-460
49. Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Masciocchi, N.; Sironi, A.; Cenini, S. Inorg. Chem. 2005, 44, 2039-2049
50. Kellis, J. T., Jr.; Childers, W. E.; Robinson, C. H.; Vickery, L. E. J. Biol. Chem. 1987, 262, 4421-4426
51. Zhu, B. T.; Conney, A. H. Carcinogenesis 1998, 19, 1-27
52. Sono, M.; Stuchri, D. J.; Ikeda-Saito, M.; Dawson, J. H. J. Biol. Chem. 1995, 270, 19943-19948
53. Raman, C. S.; Martásek, P.; Masters, B. S. S. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 4, Chapter 34, pp 293-339.
54. Perera, R.; Sono, M.; Sigman, J. A.; Pfister, T. D.; Lu, Y.; Dawson, J. H. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3641-3646
55. Sono, M.; Anderson, L. A.; Dawson, J. H. J. Biol. Chem. 1982, 257, 8308-8320
56. Kraus, D. W.; Wittenberg, J. B. J. Biol. Chem. 1990, 265, 16043-16053
57. Kraus, D. W.; Wittenberg, J. B.; Lu, J. F.; Peisach, J. J. Biol. Chem. 1990, 265, 16054-16059
58. Rizzi, M.; Wittenberg, J. B.; Coda, A.; Ascenzi, P.; Bolognesi., M. J. Mol. Biol. 1996, 258, 1-5
59. Cerda-Colón, J. F.; Silfa, E.; López-Garriga, J. J. Am. Chem. Soc. 1998, 120, 9312-9317
60. James, B. R. Pure Appl. Chem. 1997, 69, 2213-2220
61. Coto, A.; de los Ríos, I.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. J. Chem. Soc., Dalton Trans. 1999, 4309-4314
62. Schwarz, D. E.; Dopke, J. A.; Rauchfuss, T. B.; Wilson, S. R. Angew. Chem., Int. Ed. 2001, 40, 2351-2353
63. McGuire, D. G.; Khan, M. A.; Ashby, M. T. Inorg. Chem. 2002, 41, 2202-2208
64. Foo, J. S.; Jones, N. D.; Patrick, B. O.; James, B. R. Chem. Commun. 2003, 988-989
65. Chatwin, S. L.; Diggle, R. A.; Jazzar, R. F. R.; Macgregor, S. A.; Mahon, M. F.; Whittlesey, M. K. Inorg. Chem. 2003, 42, 7695-7697
66. Khorasani-Motlagh, M.; Safari, N.; Pamplin, C. B.; Patrick, B. O.; James, B. R. Can. J. Chem. 2006, 84, 330-336
67. Pamplin, C. B.; Rettig, S. J.; Patrick, B. O.; James, B. R. Inorg. Chem. 2011, 50, 8094-8105 and refs therein.
68. Hughes, D. L.; Paulson, D. R. Inorg. Chim. Acta 1986, 120, 191-195
69. Jessop, P. G.; Rettig, S. J.; Lee, C.-L.; James, B. R. Inorg. Chem. 1991, 30, 4617-4627
70. Carrillo, D. Coord. Chem. Rev. 1992, 119, 137-169
71. Díaz, C.; Leal, C.; Yutronic, N. J. Organomet. Chem. 1996, 516, 59-64
72. Ju, T. D.; Capps, K. B.; Lang, R. F.; Roper, G. C.; Hoff, C. D. Inorg. Chem. 1997, 36, 614-621
73. Ju, T. D.; Capps, K. B.; Roper, G. C.; Lang, R. F.; Hoff, C. D. Inorg. Chim. Acta 1998, 270, 488-498
74. Díaz, C.; Gómez, A. J. Coord. Chem. 2001, 54, 261-266
75. Rebouças, J. S. Ph.D. Dissertation, The University of British Columbia: Vancouver, British Columbia, Canada, 2006; Chapters 8 and 9.
76. Rosenthal, N. A.; Oster, G. J. Am. Chem. Soc. 1961, 83, 4445-4448
77. Tavarès, M.; Ramasseul, R.; Marchon, J.-C.; Vallée-Goyet, D.; Gramain, J.-C. J. Chem. Res. (S) 1994, 74-75
78. Rillema, D. P.; Nagle, J. K.; Barringer, L. F., Jr.; Meyer, T. J. J. Am. Chem. Soc. 1981, 103, 56-62
79. Rebouças, J. S.; Cheu, E. L. S.; Ware, C. J.; James, B. R.; Skov, K. A. Inorg. Chem. 2008, 47, 7894-7907
80. Groves, J. T.; Quinn, R. Inorg. Chem. 1984, 23, 3844-3846
81. Camenzind, M. J.; James, B. R.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1986, 1137-1139
82. Ohtake, H.; Higuchi, T.; Hirobe, M. Heterocycles 1995, 40, 867-903
83. Cheng, S. Y. S. Ph.D. Dissertation, The University of British Columbia, Vancouver, British Columbia, Canada, 1996.
84. Antipas, A.; Buchler, J. W.; Gouterman, M.; Smith, P. D. J. Am. Chem. Soc. 1978, 100, 3015-3024
85. Groves, J. T.; Ahn, K.-H.; Quinn, R. J. Am. Chem. Soc. 1988, 110, 4217-4220
86. d TREK: Area Detector Software, version 4.1; Molecular Structure Corporation: The Woodlands, TX, 1997.
87. Altomare, A.; Burla, M. C.; Cammalli, G.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, A. J. Appl. Crystallogr. 1999, 32, 115-119
88. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. In The DIRDIF-94 Program System, Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, Netherlands, 1994.
89. teXsan: Crystal Structure Analysis Package; Molecular Structure Corporation: The Woodlands, TX, 1985, and 1992.
90. Farrell, N.; Dolphin, D. H.; James, B. R. J. Am. Chem. Soc. 1978, 100, 324-326
91. Camenzind, M. J.; James, B. R.; Dolphin, D.; Sparapany, J. W.; Ibers, J. A. Inorg. Chem. 1988, 27, 3054-3057
92. Offord, D. A.; Sachs, S. B.; Ennis, M. S.; Eberspacher, T. A.; Griffin, J. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 1998, 120, 4478-4487
93. Collman, J. P.; Barnes, C. E.; Brothers, P. J.; Collins, T. J.; Ozawa, T.; Gallucci, J. C.; Ibers, J. A. J. Am. Chem. Soc. 1984, 106, 5151-5163
94. Groves, J. T.; Ahn, K.-H. Inorg. Chem. 1987, 26, 3831-3833
95. Groves, J. T.; Shalyaev, K.; Lee, J. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 4, Chapter 27, pp 17-40.
96. Sishta, C.; Camenzind, M. J.; James, B. R.; Dolphin, D. Inorg. Chem. 1987, 26, 1181-1182
97. Rajapakse, N.; James, B. R.; Dolphin, D. Can. J. Chem. 1990, 68, 2274-2277
98. Bailey, A. J.; James, B. R. J. Chem. Soc., Chem. Commun. 1996, 2343-2344
99. Horrocks, W. D., Jr.; Wong, C.-P. J. Am. Chem. Soc. 1976, 98, 7157-7162
100. Abraham, R. J.; Bedford, G. R.; Wright, B. Org. Magn. Reson 1982, 18, 45-52
101. Abraham, R. J.; Medforth, C. J. J. Chem. Soc., Chem. Commun. 1987, 1637-1638
102. Tong, Y.; Hamilton, D. G.; Meillon, J.-C.; Sanders, J. K. M. Org. Lett. 1999, 1, 1343-1346
103. Claeys-Bruno, M.; Bardet, M.; Marchon, J.-C. Magn. Reson. Chem. 2002, 40, 647-652
104. Che, C.-M.; Leung, W.-H.; Chung, W.-C. Inorg. Chem. 1990, 29, 1841-1846
105. Collman, J. P.; Bohle, D. S.; Powell, A. K. Inorg. Chem. 1993, 32, 4004-4011
106. Reboucas, J. S.; James, B. R. 15th International Conference of Biological Inorganic Chemistry, University of British Columbia, Vancouver, British Columbia, Canada, August 7-12, 2011; Abstract 1092769.
107. Koch, S.; Tang, S. C.; Holm, R. H.; Frankel, R. B. J. Am. Chem. Soc. 1975, 97, 914-916
108. Nolan, K. B. J. Chem. Soc., Chem. Commun. 1986, 760-762
109. Daeid, N. N.; Atkinson, S. T.; Nolan, K. B. Pure Appl. Chem. 1993, 65, 1541-1548
110. Collman, J. P.; Sorrell, T. N.; Hoffman, B. M. J. Am. Chem. Soc. 1975, 97, 913-914
111. Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414-2434
112. Collman, J. P.; Sorrell, T. N.; Hodgson, K. O.; Kulshrestha, A. K.; Strousse, C. E. J. Am. Chem. Soc. 1977, 99, 5180-5181
113. Brault, D.; Rougee, M. Nature New Biol. 1973, 241, 19-20
114. Collman, J. P.; Brauman, J. I.; Doxsee, K. M.; Halbert, T. R.; Bunnenberg, E.; Linder, R. E.; LaMar, G. N.; Del Gaudio, J.; Lang, G.; Spartalian, K. J. Am. Chem. Soc. 1980, 102, 4182-4192
115. Collman, J. P.; Sorrell, T. N. J. Am. Chem. Soc. 1975, 97, 4133-4134
116. Kau, L.-S.; Svastits, E. W.; Dawson, J. H.; Hodgson, K. O. Inorg. Chem. 1986, 25, 4307-4309
117. Nakajima, H.; Nakagawa, E.; Kobayashi, K.; Tagawa, S.-I.; Aono, S. J. Biol. Chem. 2001, 276, 37895-37899
118. Igarashi, J.; Sato, A.; Kitagawa, T.; Yoshimuru, T.; Yamauchi, S.; Sagami, I.; Shimizu, T. J. Biol. Chem. 2004, 279, 15752-15762
119. Franzen, S.; Bailey, J.; Dyer, R. B.; Woodruff, W. H.; Hu, R. B.; Thomas, M. R.; Boxer, S. G. Biochemistry 2001, 40, 5299-5305
120. Kuehn, C. G.; Isied, S. S. Prog. Inorg. Chem. 1980, 27, 153-221
121. McKarns, P. J.; Heeg, M. J.; Winter, C. H. Inorg. Chem. 1998, 37, 4743-4747
122. Okuda, J.; Fokken, S.; Kleinhenn, T.; Spaniol, T. P. Eur. J. Inorg. Chem. 2000, 1321-1326
123. Roesky, H. W.; Gries, T.; Jones, P. G.; Weber, K.-L.; Sheldrick, G. M. J. Chem. Soc., Dalton Trans. 1984, 1781-1784
124. Adams, R. D.; Long, J. W., IV; Perrin, J. L. J. Am. Chem. Soc. 1998, 120, 1922-1923
125. Le Moustarder, S.; Mercier, N.; Hudhomme, P.; Gallego-Planas, N.; Gorgues, A.; Riou, A. Synth. Met. 2002, 130, 129-134
126. S-S-C and C-S-S-C angles (not given in ref 50a) were disclosed by Mercier, N.; personal communication.
127. Beagley, B.; McAloon, K. T. Trans. Faraday Soc. 1971, 67, 3216-3222
128. Yokozeki, A.; Bauer, S. H. J. Phys. Chem. 1976, 80, 618-625
129. Krebs, B.; Lindner, T.; Stork, L. Z. Kristallogr. 1986, 174, 125-127
130. MeSSMe crystallographic data (not given in ref 51c) were disclosed by Krebs, B.; personal communication.
131. Sacerdoti, M.; Gilli, G.; Domiano, P. Acta Crystallogr., Sect. B 1975, 31, 327-329
132. Freeman, F.; Lee, C.; Po, H. N.; Hehre, W. J. J. Comput. Chem. 1998, 19, 1064-1071
133. Le Moustarder, S.; Hudhomme, P.; Illien, B.; Halet, J.-F.; Gorgues, A.; Riou, A. Mol. Cryst. Liq. Cryst. 2000, 338, 61-74
134. Le Moustarder, S.; Mercier, N.; Hudhomme, P.; Gorgues, A.; Riou, A. Synth. Met. 1999, 102, 1671-1672
135. Boyd, D. J. J. Am. Chem. Soc. 1972, 94, 8799-8804
136. Dezarnaud-Dandine, C.; Bournel, F.; Tronc, M.; Jones, D.; Modelli, A. J. Phys. B: At. Mol. Opt. Phys. 1998, 31, L497-L502
137. Redman, J. E.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. Inorg. Chem. 2001, 40, 3217-3221
138. Khun, N.; Schumann, H. J. Organomet. Chem. 1985, 287, 345-356
139. Abel, E. W.; Bhargava, S. K.; Mittal, P. K.; Orrell, K. G.; Šik, V. J. Chem. Soc., Chem. Commun. 1982, 535-536
140. Abel, E. W.; Bhargava, S. K.; Orrell, K. G. Prog. Inorg. Chem. 1984, 32, 1-118
141. Abel, E. W.; Mittal, P. K.; Orrell, K. G.; Šik, V. J. Chem. Soc., Dalton Trans. 1985, 1569-1575
142. Abel, E. W.; Moss, I.; Orrell, K. G.; Qureshi, K. B.; Šik, V.; Stephenson, D. J. Chem. Soc., Dalton Trans. 1988, 1489-1492
143. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967
144. Domazetis, G.; James, B. R.; Dolphin, D. Inorg. Chim. Acta 1981, 54, L47-L49
145. Ball, R. G.; Domazetis, G.; Dolphin, D.; James, B. R.; Trotter, J. Inorg. Chem. 1981, 20, 1556-1562
146. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
147. The van der Waals radius of Ru is not available, but it has been estimated to be 2.30 Å. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
148. Walker, F. A. J. Am. Chem. Soc. 1973, 95, 1150-1153
149. Stynes, D. V.; Stynes, H. C.; James, B. R.; Ibers, J. A. J. Am. Chem. Soc. 1973, 95, 1796-1801
150. Mahmood, A.; Liu, H.-L.; Jones, J. G.; Edwards, J. O.; Sweigart, D. A. Inorg. Chem. 1988, 27, 2149-2154
151. Ašperger, S.; Cetina-Čižmek, B. Croat. Chem. Acta 1996, 69, 1305-1328
152. Brault, D.; Rougee, M. Biochem. Biophys. Res. Commun. 1974, 57, 654-659
153. Brault, D.; Rougee, M. Biochemistry 1974, 13, 4591-4597
154. Ellis, P. E., Jr.; Linard, J. E.; Szymanski, T.; Jones, R. D.; Budge, F.; Basolo, J. R. J. Am. Chem. Soc. 1980, 102, 1889-1896
155. Morgan, B.; Dolphin, D. Struct. Bonding (Berlin) 1987, 64, 115-201
156. Hunter, E. P.; Lias, S. G. J. Phys. Chem. Ref. Data. 1998, 27, 413-656
157. Ezhova, M. B.; James, B. R. To be published.
158. Block, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1135-1178
159. Clennan, E. L.; Stensaas, K. L. Org. Prep. Proced. Int. 1998, 30, 551-600
160. Steudel, R. Chem. Rev. 2002, 102, 3905-3945
161. Nielsen, R. W.; Tachibana, C.; Hansen, N. E.; Winther, J. R. Antioxid. Redox Signaling 2011, 15, 67-75
162. Furuhashi, A.; Kawano, M.; Tashiro, N.; Ouchi, A. J. Inorg. Nucl. Chem. 1972, 34, 2960-2962
163. Brodersen, K.; Jordan, G. Chem. Ber 1978, 111, 1221-1222
164. Jeannin, S.; Jeannin, Y.; Lavigne, G. Inorg. Chem. 1979, 18, 3528-3535
165. Emsley, J.; Griffiths, D. W. J. Chem. Res., Synop. 1979, 251
166. Emsley, J.; Griffiths, D. W. J. Chem. Res., Miniprints 1979, 2966-2983
167. Wang, S.; Fackler, J. P., Jr. J. Chem. Soc., Chem Commun. 1988, 22-24
168. Ruiz, E.; Alvarez, S. New. J. Chem. 1993, 17, 147-152
169. Ingham, S. L.; Long, N. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1752-1753
170. Ohba, Y.; Ito, K.; Nagasawa, T. Heterocycl. Commun. 1998, 4, 529-534
171. Salivon, N. F.; Olijnik, V. V.; Shkurenko, A. A. Russ. J. Coord. Chem. 2007, 33, 908-913
172. Lee, M. D.; Dunne, T. S.; Siegel, M. M.; Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3464-3466
173. Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.-I.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462-3464
174. Cramer, K. D.; Townsend, C. A. Tetrahedron Lett. 1991, 32, 4635-4638
175. Mulhearn, D. C.; Bacharach, S. M. J. Am. Chem. Soc. 1996, 118, 9415-9421
176. Chatterji, T.; Gates, K. S. Bioorg. Med. Chem. Lett. 1998, 8, 535-538
177. Greer, A. J. Am. Chem. Soc. 2001, 123, 10379-10386
178. Xiao, D.; Lew, K. L.; Kim, Y. A.; Zeng, Y.; Hahm, E. R.; Dhir, R.; Singh, S. V. Clin. Cancer Res. 2006, 12, 6836-6843
179. Shukla, Y.; Kalra, N. Cancer Lett. 2007, 247, 167-181
180. Kim, Y. A.; Xiao, D.; Xiao, H.; Powolny, A. A.; Lew, K. L.; Reilly, M. L.; Zeng, Y.; Wang, Z.; Singh, S. V. Mol. Cancer Ther. 2007, 6, 1599-1609
181. Munchberg, U.; Anwar, A.; Mecklenburg, S.; Jacob, C. Org. Biomol. Chem. 2007, 5, 1505-1508
182. Powolny, A. A.; Singh, S. V. Cancer Lett. 2008, 269, 305-314
183. Iciek, M.; Kwiecien, I.; Wlodek, L. Environ. Mol. Mutagen. 2009, 50, 247-265
184. Karmakar, S.; Choudhury, S. R.; Banik, N. L.; Ray, S. K. Anti-Cancer Agents Med. Chem. 2011, 11, 398-407 and refs therein.
185. Chun, H. S.; Kim, H. J.; Choi, E. H. Biosci. Biotechnol. Biochem. 2001, 65, 2205-2212
186. Wu, C.-C.; Sheen, L.-Y.; Chen, H.-W.; Kuo, W.-K.; Tsai, S.-J.; Lii, C.-K. J. Agric. Food Chem. 2002, 50, 378-383
187. Kim, H. J.; Chun, H. S. Biotechnol. Lett. 2002, 24, 2041-2046
188. Kim, H. J.; Chun, H. S. Food Sci. Biotechnol. 2005, 14, 297-300
189. Lii, C. K.; Tsai, C. W.; Wu, C. C. J. Agric. Food Chem. 2006, 54, 5191-5196
190. Hosono-Fukao, T.; Hosono, T.; Seki, T.; Ariga, T. J. Nutr. 2009, 139, 2252-2256
191. Zeng, T.; Xie, K.-Q. Food Rev. Int. 2010, 26, 353-363
192. Wang, Y.; Zou, M. J.; Zhao, N.; Ren, J. G.; Zhou, H.; Cheng, G. J. Food Sci. 2011, 76, T30-T40
193. Tsao, S.-M.; Yin, M.-C. J. Antimicrob. Chemother. 2001, 47, 665-670
194. Tsao, S.-M.; Yin, M.-C. J. Med. Microbiol. 2001, 50, 646-649
195. Lew, K.; Xiao, D.; Zeng, Y.; Singh, S. V. Proc. Am. Assoc. Cancer Res. 2003, 44, 862
196. Rattanachaikunsopon, P.; Phumkhachorn, P. Biosci. Biotechnol. Biochem. 2008, 72, 2987-2991
197. Seki, T.; Hosono, T.; Hosono-Fukao, T.; Inada, K.; Tanaka, R.; Ogihara, J.; Ariga, T. Asia Pac. J. Clin. Nutr. 2008, 17, 249-252
198. Hosono, T.; Hosono-Fukao, T.; Inada, K.; Tanaka, R.; Yamada, H.; Iitsuka, Y.; Seki, T.; Hasegawa, I.; Ariga, T. Carcinogenesis 2008, 29, 1400-1406
199. Iitsuka, Y.; Tanaka, Y.; Hosono-Fukao, T.; Hosono, T.; Seki, T.; Ariga, T. Oncol. Res. 2010, 18, 575-582
200. Field, L. In Organic Chemistry of Sulfur; Oae, S., Ed.; Plenum Press: New York, 1977; Chapter 7, pp 303-382.