Bioorganometallic chemistry. 27. Synthetic, x-ray crystallographic, and competitive binding studies in the reactions of nucleobases, nucleosides, and nucleotides with [Cp*Rh(H2O)3](OTf)2, as a function of pH, and the utilization of several Cp*Rh-DNA base complexes in host-guest chemistry

Organometallics

Volumn 33, Issue 10, 2014, Pages 2389-2404

  Smith, David P ^a   Chen, Hong ^a   Ogo, Seiji ^a,b   Elduque, Ana I ^c   Eisenstein, Miriam ^d   Olmstead, Marilyn M ^e   Fish, Richard H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b KYUSHU UNIVERSITY   (Japan)

^c CSIC   (Spain)

^d WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMINO ACIDS; BINDING ENERGY; CHEMICAL BONDS; DIMERS; NUCLEOTIDES; PH; RHODIUM; X RAY CRYSTALLOGRAPHY;

BIO-ORGANOMETALLIC CHEMISTRY; CATIONIC COMPONENTS; HOSTGUEST CHEMISTRY; INTRAMOLECULAR H-BONDING; MONOMERIC COMPLEXES; MONONUCLEAR COMPLEXES; REDUCTIVE ELIMINATION; TRIFLUOROMETHANESULFONATE;

RHODIUM COMPOUNDS;

EID: 84901439494     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500106r     Document Type: Article

References (81)

1. Tullius, T. D. In Metal-DNA Chemistry; Tullius, T. D., Ed.; American Chemical Society: Washington, DC, 1989; ACS Symposium Series 402, Chapter 1 and references therein.
2. Barton, J. K. Comments Inorg. Chem. 1985, 3, 321 and references therein
3. Pyle, A. M.; Barton, J. K. in Progress in Inorganic Chemistry, Bioinorganic Chemistry, Lippard, S. J., Ed.; J. Wiley and Sons: New York, 1990, vol 38, p 413 and references therein.
4. Marzilli, L. G. In Progress in Inorganic Chemistry; Lippard, S. J., Ed.; Wiley: New York, 1977; Vol. 23, p 255, and references therein.
5. Howe-Grant, M. E.; Lippard, S. J. Met. Ions Biol. Syst. 1980, 11, 63 and references therein
6. Raudaschl-Sieber, G.; Schollhorn, H.; Thewalt, U.; Lippert, B. J. Am. Chem. Soc. 1985, 107, 3591
7. Reily, M. D.; Hambley, T. W.; Marzilli, L. G. J. Am. Chem. Soc. 1988, 110, 2999
8. Alink, M. A.; Nakahara, H.; Hirano, T.; Inagaki, K.; Hakanishi, M.; Kidani, Y.; Reedijk, J. Inorg. Chem. 1991, 30, 1236 and references therein
9. Reily, M. D.; Marzilli, L. G. J. Am. Chem. Soc. 1986, 108, 8299
10. Qu, Y.; Farrell, N. J. Am. Chem. Soc. 1991, 113, 4851 and references therein
11. Caradonna, J. P.; Lippard, S. J.; Gait, M. J.; Singh, M. J. Am. Chem. Soc. 1982, 104, 5793
12. Marcelis, A. T. M.; den Hartog, J. H. J.; Reedijk, J. J. Am. Chem. Soc. 1982, 104, 2664
13. Sherman, S. E.; Gibson, D.; Wang, A. H.-J.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 7368
14. Mukundan, S., Jr; Xu, Y.; Zon, G.; Marzilli, L. G. J. Am. Chem. Soc. 1991, 113, 3021
15. Pneumatikakis, G.; Hadjiliadis, H. J. Chem. Soc., Dalton Trans. 1979, 596
16. Rainen, L.; Howard, R. A.; Kimball, A. P.; Bear, J. L. Inorg. Chem. 1975, 14, 2752
17. Torres, L. M.; Marzilli, L. G. J. Am. Chem. Soc. 1991, 113, 4678
18. Scheller, K. H.; Mitchell, P. R.; Prijs, B.; Sigel, H. J. Am. Chem. Soc. 1981, 103, 247
19. Sigel, H. In Metal-DNA Chemistry; Tullius, T. D., Ed.; American Chemical Society: Washington, DC, 1989; ACS Symposium Series 402, Chapter 11 and references therein.
20. Hodgson, D. J. In Progress in Inorganic Chemistry; Lippard, S. J., Ed.; Wiley: New York, 1977; Vol. 23, p 211.
21. Muller, J. G.; Zheng, P.; Rokita, S. E.; Burrows, C. J. J. Am. Chem. Soc. 1996, 118, 2320 and references therein
22. Fish, R. H.; Jaouen, G. Organometallics 2003, 22, 2166 and references therein
23. Fish, R. H. Aus. J. Chem. 2010, 63, 1505 and references therein
24. Eisen, M. S.; Haskel, A.; Chen, H.; Olmstead, M. M.; Smith, D. P.; Maestre, M. F.; Fish, R. H. Organometallics 1995, 14, 2806 and references therein
25. Ogo, S.; Chen, H.; Olmstead, M. M.; Fish, R. H. Organometallics 1996, 15, 2009
26. Ogo, S.; Buriez, O.; Kerr, J. B.; Fish, R. H. J. Organomet. Chem. 1999, 589, 66
27. Kramer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415
28. Severin, K.; Bergs, R.; Beck, W. Angew. Chem., Int. Ed. 1998, 37, 1086 and references therein
29. Beck, W.; Kottmair, N. Chem. Ber. 1976, 109, 970
30. Singh, M. M.; Rosopulos, Y.; Beck, W. Chem. Ber. 1983, 116, 1364
31. Krämer, R.; Polborn, K.; Beck, W. J. Organomet. Chem. 1991, 410, 111
32. Fish, R. H.; Kimmel, E. C.; Casida, J. E. J. Organomet. Chem. 1975, 93, C1
33. Fish, R. H.; Kimmel, E. C.; Casida, J. E. J. Organomet. Chem. 1976, 118, 41
34. Fish, R. H.; Casida, J. E.; Kimmel, E. C. ACS Symp. Ser. 1978, 82, 82
35. Fish, R. H.; Price, R. T. Organometallics 1989, 8, 225
36. Parvin, B. A.; Maestre, M. F.; Fish, R. H.; Johnston, W. E. A Method and Apparatus for Accurately Manipulating an Object During Microelectrophoresis. U. S. Patent No. US5671086(A), University of California, September 23, 1997.
37. Toney, J. H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 947
38. Kuo, L. Y.; Kanatzdis, M. G.; Marks, T. J. J. Am. Chem. Soc. 1987, 109, 7207
39. Toney, J. H.; Brock, C. P.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 7263
40. Kuo, L. Y.; Kanatzdis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027
41. Ang, W. H.; Daldini, E.; Scolaro, C.; Scopelliti, R.; Juillerat-Jeannerat, L.; Dyson, P. J. Inorg. Chem. 2006, 45, 9006
42. Allardyce, C. S.; Dyson, P. J.; Ellis, D. J.; Heath, S. L. Chem. Commun. 2001, 1396
43. Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietto, M.; Laurenczy, G.; Geldbach, T. J.; Sava, G.; Dyson, P. J. J. Med. Chem. 2005, 48, 4161
44. Scolaro, C.; Chaplin, A. B.; Hartinger, C. G.; Bergamo, A.; Cocchietto, M.; Keppler, B. K.; Sava, G.; Dyson, P. J. Dalton Trans. 2007, 43, 5065
45. Dorcier, A.; Hartinger, C. G.; Scopelliti, R.; Fish, R. H.; Keppler, B. K.; Dyson, P. J. Inorg. Biochem. 2008, 102, 1066 and references therein
46. Annen, P.; Schildberg, S.; Sheldrick, W. S. Inorg. Chim. Acta 2000, 307, 115
47. Korn, S.; Sheldrick, W. S. Inorg. Chem. Acta 1997, 254, 85
48. Korn, S.; Sheldrick, W. S. J. Chem. Soc., Dalton Trans. 1997, 2191
49. Sheldrick, W. S.; Hagen-Eckard, H. S.; Heeb, S. Inorg. Chim. Acta 1993, 206, 15
50. Yamanari, K.; Yamamoto, S.; Ito, R.; Kushi, Y.; Fuyuhiro, A.; Kubota, N.; Fukuo, T.; Arakawa, R. Angew. Chem., Int. Ed. 2001, 40, 2268
51. Smith, D. P.; Baralt, E.; Morales, B.; Olmstead, M. M.; Maestre, M. F.; Fish, R. H. J. Am. Chem. Soc. 1992, 114, 10647
52. Smith, D. P.; Olmstead, M. M.; Noll, B. C.; Maestre, M. F.; Fish, R. H. Organometallics 1993, 12, 593
53. Smith, D. P.; Griffin, M. T.; Olmstead, M. M.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677
54. Chen, H.; Olmstead, M. M.; Smith, D. P.; Maestre, M. F.; Fish, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1514
55. Chen, H.; Olmstead, M. M.; Maestre, M. F.; Fish, R. H. J. Am. Chem. Soc. 1995, 117, 9097
56. Gagnon, P. C.; Beauchamp, A. L. Acta Crystallogr., Sect. B 1977, 33, 1448
57. De Meester, P.; Goodgame, D. M. L.; Skapski, A. C.; Warkne, Z. Biochim. Biophys. Acta 1973, 324, 301
58. Fish, R. H.; Kim, H.-S.; Babin, J. E.; Adams, R. D. Organometallics 1988, 7, 2250
59. Dunbar, K. R.; Matonic, J. H.; Saharan, V. P.; Crawford, C. A.; Christou, G. J. Am. Chem. Soc. 1994, 116, 2201 and references therein
60. Chifotides, H. T.; Koshlap, K. M.; Pérez, L. M.; Dunbar, K. R. J. Am. Chem. Soc. 2003, 125, 10703 and references therein
61. Johnson, D. A. Some Thermodynamic Aspects of Inorganic Chemistry; Cambridge University Press: Cambridge, U.K., 1982.
62. Munns, A. R. I.; Tollin, P. Acta Crystallogr., Sect. B 1970, 26, 1101
63. Frommer, G.; Mutikainen, I.; Pesch, F. J.; Hillgeris, E. C.; Preut, H.; Lippert, B. Inorg. Chem. 1992, 31, 2429
64. Faggiani, R.; Lippert, B.; Lock, C. J. L.; Speranzini, R. A. J. Am. Chem. Soc. 1981, 103, 1111
65. Schollhorn, H.; Thewalt, U.; Lippert, B. J. Am. Chem. Soc. 1986, 108, 3680
66. Kosturko, L. D.; Folzer, C.; Stewart, R. F. Biochemistry 1974, 13, 3949
67. Raudaschi-Sieber, G.; Lippert, B. Inorg. Chem. 1985, 24, 2426
68. Kickham, J. E.; Loeb, S. J.; Murphy, S. L. J. Am. Chem. Soc. 1993, 115, 7031 and references therein
69. Kickham, J. E.; Loeb, S. J. Inorg. Chem. 1995, 34, 5656
70. Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993
71. Power, P. P. Comments Inorg. Chem. 1989, 8, 177 and references therein
72. Bartlett, R. A.; Chen, H.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1989, 28, 316
73. Chen, H.; Bartlett, R. A.; Dias, H. V. R.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1989, 111, 4338
74. Chen, H.; Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1990, 112, 1048
75. Bartlett, R. A.; Power, P. P. J. Am. Chem. Soc. 1987, 109, 7563
76. Andersen, R. A.; Faegri, K., Jr.; Green, J. C.; Haaland, A.; Lappert, M. F.; Leung, W.-P.; Rypdal, K. Inorg. Chem. 1988, 27, 1782
77. Lappert, M. F.; Power, P. P.; Sanger, A. R.; Srivastava, R. C. Metal and Metalloid Amides; Ellis-Horwood: Chichester, U.K., 1980.
78. Paneque, M.; Maitlis, P. J. Chem. Soc., Chem. Commun. 1989, 105
79. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119
80. For a preliminary communication using 11 as a host: Elduque, A. I.; Carmona, D.; Oro, L. A.; Eisenstein, M.; Fish, R. H. J. Organomet. Chem. 2003, 668, 123
81. Ogo, S.; Nakamura, S.; Chen, H.; Isobe, K.; Watanabe, Y.; Fish, R. H. J. Org. Chem. 1998, 63, 7151