Rhenium tricarbonyl core complexes of thymidine and uridine derivatives

Inorganic Chemistry

Volumn 44, Issue 7, 2005, Pages 2198-2209

  Wei, Lihui ^a   Babich, John ^b   Eckelman, William C ^b   Zubieta, Jon ^a  

^a SYRACUSE UNIVERSITY   (United States)

^b Lantheus Medical Imaging   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [3 [BIS(PYRIDIN 2 YLMETHYL)AMINO] 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 1H PYRIMIDINE 2,4 DIONE; 1 [5 [[BIS(PYRIDIN 2 YLMETHYL)AMINO]METHYL] 4 HYDROXYTETRAHYDROFURAN 2 YL] 5 METHYL 1H PYRIMIDINE 2,4 DIONE; 1 [5 [[BIS(QUINOLIN 2 YLMETHYL)AMINO]METHYL] 4 HYDROXYTETRAHYDROFURAN 2 YL] 5 METHYL 1H PYRIMIDINE 2,4 DIONE; 5 [BIS(PYRIDIN 2 YLMETHYL)AMINO]PENTANOIC ACID; 5 [BIS(PYRIDIN 2 YLMETHYL)AMINO]PENTANOIC ACID [2 (2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 3 YL]AMIDE; 5 [BIS(PYRIDIN 2 YLMETHYL)AMINO]PENTANOIC ACID [[3 HYDROXY 5 (5 METHYL 4 OXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)TETRAHYDROFURAN 2 YL]METHYL]AMIDE; 5 [BIS(QUINOLIN 2 YLMETHYL)AMINO]PENTANOIC ACID; 5 [BIS(QUINOLIN 2 YLMETHYL)AMINO]PENTANOIC ACID [2 (2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL) 4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 3 YL]AMIDE; 5 [BIS(QUINOLIN 2 YLMETHYL)AMINO]PENTANOIC ACID [[3 HYDROXY 5 (5 METHYL 4 OXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)TETRAHYDROFURAN 2 YL]METHYL]AMIDE; ALDEHYDE; CARBONYL DERIVATIVE; CHELATING AGENT; RHENIUM; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE; VALERIC ACID DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; LUMINESCENCE; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

CHELATING AGENTS; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHENIUM; THYMIDINE; URIDINE;

EID: 16244423674     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic048301n     Document Type: Article

References (87)

1. (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
2. (b) Eaton, B. E.; Pieken, W. A. Annu. Rev. Biochem. 1995, 64, 837.
3. (c) Limbach, P. A.; Grain, P. F.; McClosky, J. A. Nucleic Acids Res. 1994, 22, 2183.
4. Townsend, L. B. Chemistry of Nucleosides and Nucleotides; New York, 1988.
5. Schwartz, J. L.; Tamura, Y.; Jordan, R.; Grierson, J. R.; Krohn, K. A. J. Nucl. Med. 2003, 44, 2027.
6. Alauddin, M. M.; Shahinian, A.; Park, R.; Tohme, M.; Fisseks, J. D.; Conti, P. S. Nucl. Med. Biol. 2004, 31, 399.
7. Steigman, J.; Eckelman, W. C. The Chemistry of Technetium in Medicine; National Academy Press: Washington, DC, 1992.
8. Ehrhardt, J.; Ketring, A. R.; Turpin, T. A.; Razavi, M. S.; Vanderheyden, J. L.; Su, F. M.; Feitzberg, A. R. In Technetium and Rhenium in Chemistry and Nuclear Medicine; Nicolini, M., Bandoli, G., Mazzi, U., Eds.; Cortina International: Verona, Italy, 1990; p 3.
9. (a) Wentworth, P., Jr.; Janda, K. D. Chem. Commun. 1996, 2097.
10. (b) Hosain, P.; Zeichner, S. J.; Brody, K. R.; Hosain, F.; Spencer, R. P. Int. J. Nucl. Med. Biol. 1980, 7, 46.
11. (c) Kim, J. Y.; Oh, S. J.; Kang, S. H.; Ryn, J. S.; Kim, J. S.; Yeo, S. J.; Choi, S. J.; Park, K. B.; Moon, D. H. Presented at the 51th Annual SNM Meeting, Philadelphia, PA, June 19-23, 2004, No. 313; J. Nucl. Med. 2004, 45, 113P:
12. (c) Kim, J. Y.; Oh, S. J.; Kang, S. H.; Ryn, J. S.; Kim, J. S.; Yeo, S. J.; Choi, S. J.; Park, K. B.; Moon, D. H. Presented at the 51th Annual SNM Meeting, Philadelphia, PA, June 19-23, 2004, No. 313; J. Nucl. Med. 2004, 45, 113P:
13. Schibli, R.; Natter, M.; Scapozza; L.; Birringer, M.; Schelling; P.; Dumas, C.; Schoch, J.; Schubiger, P. A. J. Organomet. Chem. 2003, 668, 67.
14. (a) Alberto, R.; Schibli,R.; Angst; D.; Schubiger, P. A.; Abram, U.; Abram, S.; Kaden, T. L. A. Trans. Mater. Chem. 1997, 22, 597.
15. (b) Alberto, R.; Schibli, R.; Egli, A.; Schubiger, P. A. J. Am. Chem. Soc. 1998, 120, 7987.
16. (c) Alberto, R.; Shibli, R.; Schubiger, P. A. J. Am. Chem. Soc. 1999, 121, 6076.
17. (d) Waibie, R.; Alberto, R.; Willude, J.; Finnern, R.; Schibli, R. Stichelberger, A.; Egli, A.; Abram, U.; Mach, J. P.; Pluckthern, A.; Schubiger, P. A. Nat. Biotechnol. 1999, 17, 897.
18. (a) Amann, A.; Decristoforo; C.; Ott, I.; Wenger, M.; Bader, D.; Alberto, R.; Putz, G. Nucl. Med. Biol. 2001, 28, 243.
19. (b) Schibli, R.; LaBelle, R.; Alberto, R.; Garcia-Garayoa, L.; Ortner, K.; Abram, U.; Schubiger, P. A. Bioconjugate Chem. 2000, 11, 345.
20. (c) Wald, J.; Alberto, R.; Ortner, K.; Andreia, L. Angew. Chem., Int. Ed. 2001, 40, 3062.
21. (d) Petrig, R.; Schibli, R.; Dumas, C.; Alberto, R.; Schubiger, P. A. Chem.-Eur. J. 2001, 7, 1868.
22. Banerjee, S. R.; Levadala, M. K.; Lazarova, N.; Wei, L.; Valliant, J. F.; Stephenson, K. A.; Babich, J. W.; Maresca, K. P.; Zubieta, J. Inorg. Chem. 2002, 41, 6417.
23. Stephenson, K. A.; Valliant, J. F.; Zubieta, J.; Banerjee, S. R.; Levadala, M. K.; Taggan, L.; Ryan, L.; MaFarlane, N.; Boreham, D. R.; Babich, J. W.; Maresca, K. P. Presented at the 50th Annual SNM Meeting, New Orleans, LA, June 22-25, 2003, No. 154; J. Nucl. Med. 2003, 44, 48p.
24. Stephenson, K. A.; Valliant, J. F.; Zubieta, J.; Banerjee, S. R.; Levadala, M. K.; Taggan, L.; Ryan, L.; MaFarlane, N.; Boreham, D. R.; Babich, J. W.; Maresca, K. P. Presented at the 50th Annual SNM Meeting, New Orleans, LA, June 22-25, 2003, No. 154; J. Nucl. Med. 2003, 44, 48p.
25. Stephenson, K. A.; Zubieta, J.; Banerjee, S. R.; Levadala, M. K.; Taggart, L.; Ryan, L.; McFarlane, N.; Boreham, D. R.; Maresca, K. P.; Babich, J. W.; Valliant, J. F. Bioconjugate Chem. 2004, 15, 128.
26. Lo, K. K. W.; Hui, W. K.; Ng, D. C. M.; Cheung, K. K. Inorg. Chem. 2002, 41, 40.
27. (a) Wrighton, M.; Morse, D. L. J. Am. Chem. Soc. 1974, 96, 998.
28. (b) Sullivan, B. P. J. Phys. Chem. 1989, 93, 24.
29. (c) Tapolsky, G.; Duesing, R.; Meyer, T. J. Inorg. Chem. 1990, 29, 2285.
30. (d) Zipp, A. P.; Sacksteder, L.; Streich, J.; Cook, A.; Demas, J. N.; DeGraff, B. A. Inorg. Chem. 1993, 32, 5629.
31. (e) Stufkens, D. J.; Vlcek, A. Coord. Chem. Rev. 1998, 177, 127.
32. (a) Chen, P.; Curry, M.; Meyer, T. J. Inorg. Chem. 1989, 28, 2771.
33. (b) Yam, V. W. W.; Lau, V. C. Y.; Cheung, K. K. J. Chem. Soc., Chem. Commum. 1995, 259.
34. (c) Wallace, L.; Woods, C.; Rillema, D. P. Inorg. Chem. 1995, 34, 2875.
35. (d) Lucia, L. A.; Abbous, K.; Schanze, K. S. Inorg. Chem. 1997, 36, 6224.
36. (e) Yam, V. W. W.; Lo, K. K. W.; Cheung, K. K.; Kong, R. Y. C. J. Chem. Soc., Dalton Trans. 1997, 2067.
37. (f) Kunkely, H.; Vogler, A. Inorg. Chem. Commun. 2000, 3, 188.
38. (g) Yam, V. W. W.; Lo, K. K. W.; Cheung, K. K.; Kong, R. Y. C. J. Chem. Soc., Chem. Commun. 1995, 1191.
39. (h) Thornton, N. B.; Schanze, K. S. Inorg. Chem. 1993, 32, 4994.
40. (i) Stoeffler, H. D.; Thornton, N. B.; Temkin, S. L.; Schanze, K. S. J. Am. Chem. Soc. 1995, 117, 7119.
41. (a) Di Bilio, A. J.; Crane, B. R.; Wehbi, W. A.; Kiser, C. N.; Abu-Omar, M. M.; Carlos, R. M.; Richards, J. H.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 2001, 123, 3181.
42. (b) Guo, X. Q.; Castellano, F. N.; Li, L.; Szmacinski, H.; Lakowicz, J. R.; Sipior, J. Anal. Biochem. 1997, 254, 179.
43. (c) Guo, X. Q.; Castellano, F. N.; Li, L.; Lakowicz, J. R. Anal. Chem. 1998, 70, 632.
44. (d) Dattelbaum, J. D.; Abugo, O. O.; Lakowicz, J. R. Bioconjugate Chem. 2000, 11, 533.
45. Alberto, R.; Egli, A.; Abram, U.; Hegetschweiler, K.; Gramlich, V.; Schubiger, P. A. J. Chem. Soc., Dalton Trans. 1994, 2815.
46. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
47. Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697.
48. Bannwarth, W. Helv. Chim. Acta. 1988, 71, 1517.
49. Levadala, M. K.; Banerjee, S. R.; Maresca, K. P.; Babich, J. W.; Zubieta, J. Synthesis 2004, 1179.
50. McGee, D.; Vaughn-Settle, A.; Vargeese, C.; Zhai, Y. J. Org. Chem. 1996, 61, 781.
51. Smart Software Reference Manual; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1994.
52. Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction; University of Göttingen: Göttingen, Germany, 1996.
53. Sheldrick, G. M. SHELXL96: Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1996.
54. (a) Suhadolnik, R. J. Nucleoside Antibiotics; New York, 1970.
55. (b) Suhadolnik, R. J. Nucleoside as Biological Probes; New York, 1979.
56. (c) Chen, Y. C. J.; Janda, K. D. J. Am. Chem. Soc. 1992, 114, 1488.
57. (a) Frank, N. L.; Meade, T. J. Inorg. Chem. 2003, 42, 1039.
58. (b) Martin, J. A.; Lambert, R. W.; Merrett, J. H.; Parkes, K. E. B.; Thomas, G. J.; Baker, S. J.; Bushnell, D. J.; Cansfield, J. E.; Dunsdon, S. J.; Freeman, A. C.; Hopkins, R. A.; Johns, I. R.; Keech, E.; Simmonite, H.; Walmsley, A.; Kai-In, P. W.; Holland, M. Bioorg. Med. Chem. Lett. 2001, 11, 1655.
59. (a) Anderson, P. A.; Keene, F. R.; Horn, E.; Tiekink, E. R. T. Appl. Organomet. Chem. 1990, 4, 523.
60. (b) Abel, E. W.; Ouell, K. G.; Osborne, A. G.; Pain, H. M.; Sik, V.; Hursthouse, M. B.; Malik, K. M. A. J. Chem. Soc., Dalton Trans. 1994, 3441.
61. (c) Gamelin, D. R.; George, M. W.; Glyn, P.; Grevek, F. W.; Schaffner, K.; Turner, J. J. Inorg. Chem. 1995, 33, 3246.
62. (d) Granifo, J. Polyhedron 1999, 18, 1061.
63. Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Tables of Spectral Data; Springer-Verlag: Berlin, 2000.
64. (a) Wei, L.; Banerjee, S. R.; Levadala, M. K.; Babich, J.; Zubieta, J. Inorg. Chim. Acta 2004, 357, 1499.
65. (b) Wei, L.; Banerjee, S. R.; Levadala, M. K.; Babich, J.; Zubieta, J. Inorg. Chem. Commun. 2003, 6, 1099.
66. Moya, S. A.; Guerrero, J.; Pastene, R.; Schmidt, R.; Sariego, R.; Sartori, R.; Sanz-Aparicio, J.; Fonseca, I.; Martinez-Ripoll, M. Inorg. Chem. 1994, 33, 2341.
67. Lo, K. K. W.; Tsang, K. H. K.; Hui, W. K.; Zhu, N. Chem. Commun. 2003, 2704.
68. (a) Koike, K.; Tanabe, J.; Toyama, S.; Tsubaki, H.; Sakmoto, K.; Westwell, J. R.; Johnson, F. P. A.; Hori, H.; Saitoh, H.; Ishitani, O. Inorg. Chem. 2000, 39, 2777.
69. (b) Breikss, A. I.; Abruna, H. D. J. Electroanal. Chem. 1986, 347.
70. (c) Moya, S. A.; Guerrero, J.; Pastene, R.; Schmidt, R.; Sanz-Aparicio, J.; Fonseca, I.; Martinez-Ripoll, M. Inorg. Chem. 1994, 33, 2341.
71. (d) Moya, S. A.; Pastene, R.; Schmidt, R.; Guerrero, J.; Sartori, R. Polyhedron 1992, 11, 1665.
72. (e) Christesen, P.; Hammet, A.; Muir, A. V. G.; Timney, J. A. J. Chem. Soc., Dalton Trans. 1992, 1455.
73. (f) Sun, S. S.; Lees, A. J. J. Am. Chem. Soc. 2000, 122, 8956.
74. (g) Otsuki, J.; Tsujino, M.; Lizaki, T.; Araki, K.; Seno, M.; Takatera, K.; Watabnabe, T. J. Am. Chem. Soc. 1992, 119, 7895.
75. (a) Wong, K. M. C.; Lam, S. C. F.; Ko, C. C.; Zhu, N.; Yam, V. W. W.; Roué, S.; Lapinte, C.; Fathallah, S.; Costuas, K.; Kahlal, S.; Halet, J. F. Inorg. Chem. 2003, 42, 7086.
76. (b) Yam, V. W. W.; Wong, K. M. C.; Chong, S. H. F.; Lau, V. C. Y.; Lam, S. C. F.; Zhang, L.; Cheng K. K. J. Organomet. Chem. 2003, 670, 205.
77. (c) Yam, V. W. W.; Chong, S. H. F.; Ko, C. C.; Cheung, K. K. Organometallics 2000, 19, 5092.
78. (a) Hu, X.; Smith, G. D.; Sykora, M.; Lee, S. J.; Grinstaff, M. W. Inorg. Chem. 2000, 39, 2500.
79. (b) Beilstein, A. E.; Tierney, M. T.; Grinstaff, M. W. Comments Inorg. Chem. 2000, 22, 105, part A.
80. (c) Kahn, S. I.; Beilstein, A. E.; Grinstaff, M. W. Inorg. Chem. 1999, 38, 418.
81. (d) Krider, E. S.; Rack, J. J.; Frank, N. L.; Meade, T. J. Inorg. Chem. 2001, 40, 4002.
82. Rack, J. J.; Kirder, E. S.; Meade, T. J. J. Am. Chem. Soc. 2000, 122, 6287.
83. (b) Krider, E. S.; Miller, J. E. Meade, T. J. Bioconjugate Chem. 2002, 13, 155.
84. (a) Bannwarth, W.; Schmidt, D. Tetrahedron Lett. 1989, 30, 1513.
85. (b) Magda, D.; Crofts, S.; Lin, A.; Miles, D.; Wright, M.; Sessler, J. L. J. Am. Chem. Soc. 1997, 119, 2293.
86. (c) Meggers, E.; Kusch, D.; Giese, B. Helv. Chim. Acta 1997, 80, 640.
87. (d) Khan, S. I.; Beilstein, A. E.; Smith, G. D.; Sykoram, M.; Grinstaff, M. W. Inorg. Chem. 1999, 38, 3922.