Both the N,N-(bispicolyl) (L1–L3) and N,N-bis(quinolinoyl-
methyl) (L4–L6) based bifunctional chelates can be radiolabeled
31 M. K. Levadala, S. R. Banerjee, K. P. Maresca, J. W. Babich and J.
Zubieta, Synthesis, 2004, 1159.
9
9m
32 B. de Bruin, B. Kuhnast, F. Hinnen, L. Yaouaneq, M. Amessou,
L. Johannes, A. Samson, R. Boisgard, B. Tavitian and F. Doll e´ ,
Bioconjugate Chem., 2005, 16, 406.
with
Tc in high yield to provide chemically robust com-
plexes. Consequently, this series of bifunctional chelates form
9
9m
both fluorescent Re complexes and the analogous stable Tc
complexes. These complexes are readily linked to biopolymers,
allowing images obtained on a fluorescent microscope to be
directly correlated with in vivo radioimaging studies because the
structures of the two probes are effectively identical. Preliminary
investigations indicate that the rhenium complexes are chemi-
cally robust and remain intact during extra- and intracellular
processing.
3
3
3 M. Brinkley, Bioconjugate Chem., 1992, 3, 2.
4 D. S. Wilbur, Bioconjugate Chem., 1992, 3, 433.
35 D. G. Smyth, A. Nagamatur and J. S. Fruton, J. Am. Chem. Soc.,
1960, 82, 4600.
3
3
3
6 S. R. Banerjee, J. W. Babich and J. Zubieta, Chem. Commun., 2005,
784.
1
7 S. Liu and D. S. Edwards, Chem. Rev., 1999, 99, 2235, and references
therein.
8 S. Liu, D. S. Edwards and J. A. Barrett, Bioconjugate Chem., 1997, 8,
The analogous HYNIC-maleimide was also prepared. How-
621.
ever, reactions of the [ReCl
3
(HYNIC-maleimide)
2
] complex
39 D. A. Schwartz, M. J. Abrams, M. M. Hansen, F. E. Gul, S. K.
Larsen, D. Rauh and J. Zubieta, Bioconjugate Chem., 1991, 2,
with appropriate biomolecules yielded intractable mixtures. This
observation is consistent with the persistent difficulties with the
macroscale purification of Re and Tc HYNIC complexes and
3
33.
4
0 M. J. Abrams, J. Juweid, C. I. ten Kate, D. A. Schwartz, M. M.
Hauser, F. E. Gaul, A. J. Fucello, R. H. Rubin, H. W. Strauss and
A. J. Fischman, J. Nucl. Med., 1993, 34, 1964.
9
9m
with the characterization of Tc-HYNIC reagents on the tracer
86
level.
41 J. W. Babich and A. J. Fischman, Nucl, Med. Biol., 1995, 22, 25.
4
2 Z.-F. Su, G. Liu, S. Gupta, Z. Zhu, M. Rusckowski and D. J.
Hnatowich, Bioconjugate Chem., 2002, 13, 561.
3 S. Liu, A. R. Harris, N. E. Williams and D. S. Edwards, Bioconjugate
Chem., 2002, 13, 881.
4
References
1
2
3
4
K. Schwochau, Angew. Chem., Int. Ed., 1994, 33, 2258.
S. S. Jurisson and J. D. Lydon, Chem. Rev., 1999, 99, 2205.
D. L. Nosco and B. Beaty-Nosco, Coord. Chem. Rev., 1999, 184, 91.
G. Bandoli, A. Dolmella, M. Porchia, F. Refosco and F. Tisato,
Coord. Chem. Rev., 2001, 214, 43.
44 D. J. Rose, K. P. Maresca, T. Nicholson, A. Davison, A. G. Jones, J.
Babich, A. Fischman, W. Graham, J. R. D. DeBord and J. Zubieta,
Inorg. Chem., 1998, 37, 2701, and references therein.
45 J. Blake, J. R. Tretter, G. J. Jusahz, W. Bonthrone and H. Rapoport,
J. Am. Chem. Soc., 1966, 88, 4061.
46 J. E. Bishop, J. F. O’Connell and H. Rapoport, J. Org. Chem., 1991,
56, 5079.
5
S. Banerjee, M. R. Pillai and N. Ramamoorthy, Semin. Nucl. Med.,
2
001, 31, 260.
6
7
8
R. Schibli and P. A. Schubiger, Eur. J. Nucl. Med., 2002, 29, 1529.
R. Alberto and U. Abram, Handb. Nucl. Chem., 2003, 4, 211.
R. Alberto, in Comprehensive Coordination Chemistry II, ed. J.
McCleverty and T. Meyer, Elsevier Ltd., Oxford, UK, 2004, vol. 5,
p. 127.
47 J. N. Demas and G. A. Crosby, J. Phys. Chem., 1971, 75, 991.
48 K. Nakamaru, Bull. Chem. Soc. Jpn., 1982, 55, 2697.
49 A. J. Fischman, M. F. Solomon, J. W. Babich, M. J. Abrams, R. J.
Callahan, H. W. Strauss and R. H. Rubin, J. Nucl. Med., 1994, 34,
1964.
9
S. R. Banerjee, L. Francesconi, J. F. Valliant, J. W. Babich and J.
Zubieta, J. Nucl. Med. Biol., 2005, 32, 1.
50 N. Lazarova, S. James, J. W. Babich and J. Zubieta, Inorg. Chem.
Commun., 2004, 7, 1023.
1
1
1
1
1
0 W. A. Volkert and S. Jurisson, Top. Curr. Chem., 1996, 176, 123.
1 J. R. Dilworth and S. J. Parrott, Chem. Soc. Rev., 1998, 27, 43.
2 K. Hashimoto and K. Yoskihara, Top. Curr. Chem., 1996, 176, 275.
3 W. A. Volkert and T. J. Hoffman, Chem. Rev., 1999, 99, 2269.
4 X. Guo, F. N. Castellano, L. Li and J. R. Lakowicz, Anal. Chem.,
51 SMART, Data Collection Software, version 4.050, Siemens Analytical
Instruments Inc., Madison, WI, 1996.
52 SAINT, Data Reduction Software, Version 4.050, Siemens Analytical
Instruments Inc., Madison, WI, 1996.
53 G. M. Sheldrick, SADABS, University of G o¨ ttingen, 1996.
54 SHELXTL PC, Siemens Analytical X-Ray Instruments Inc., Madi-
son, WI, 1993.
55 M. A. Walker, J. Org. Chem., 1995, 60, 5352.
56 R. Y. Reddy, S. Kondo, T. Toru and U. Ueno, J. Org. Chem., 1996,
61, 2652.
1
998, 70, 632.
1
1
5 X. guo, F. N. Castellano, L. Li, H. Szmacinski, J. R. Lakowicz and J.
Sipior, Anal. Biochem., 1997, 254, 179.
6 Y. Shen, B. P. Malival and J. R. Lakowicz, J. Fluoresc., 2001, 11,
3
15.
1
1
7 K. K.-W. Lo and W.-K. Hui, Inorg. Chem., 2005, 44, 1992.
8 K. A. Stephenson, S. R. Banerjee, T. Besanger, O. O. Sogebin,
M. K. Levadala, N. McFarlane, J. A. Lemon, D. R. Boreham, K. P.
Maresca, J. D. Brennan, J. W. Babich, J. Zubieta and J. F. Valliant,
J. Am. Chem. Soc., 2004, 126, 8598.
57 H. D. King, G. M. Dubowchik and M. A. Walker, Tetrahedron Lett.,
2002, 43, 1987.
58 F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen
and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1–S19.
59 P. J. Cox and S. F. Parker, Acta Crystallogr., Sect. C, 1996, 52,
2578.
1
9 W. M. Yeh, D. G. Sherman and C. F. Meares, Anal. Biochem., 1979,
1
00, 152.
60 K. K.-W. Lo, W.-Ki. Hui, C.-M. Ng and K.-K. Cheung, Inorg. Chem.,
2
2
0 C. F. Meares and T. G. Wensel, Acc. Chem. Res., 1984, 17, 202.
1 R. Alberto, R. Schibli, D. Angst, P. A. Schubiger, U. Abram, S.
Abram and T. L. A. Kaden, Transition Met. Chem., 1997, 22, 597.
2 R. Alberto, A. Schibli, A. Egli and P. A. Schubiger, J. Am. Chem.
Soc., 1998, 120, 7987.
2002, 41, 40.
61 J. N. Demas and G. A. Crosby, J. Phys. Chem., 1971, 75, 991.
62 K. Nakamaru, Bull. Chem. Soc. Jpn., 1982, 55, 2697.
63 W. Bannwarth, Helv. Chim. Acta, 1988, 71, 1517.
64 J. D. Dattelbaum, O. O. Abugo and J. R. Lakowicz, Bioconjugate
Chem., 2000, 11, 533.
2
2
2
3 R. Alberto, R. Schibli and P. A. Schubiger, J. Am. Chem. Soc., 1999,
1
21, 6076.
65 K. K. W. Lo, W. K. Hui, D. C. M. Ng and K. K. Cheung, Inorg.
Chem., 2002, 41, 40.
66 M. Wrighton and D. L. Morse, J. Am. Chem. Soc., 1974, 96, 998.
67 B. P. Sullivan, J. Phys. Chem., 1989, 93, 24.
68 G. Tapolsky, R. Duesing and T. J. Meyer, Inorg. Chem., 1990, 29,
2285.
69 A. P. Zipp, L. Sacksteder, J. Streich, A. Cook, J. N. Demas and B. A.
DeGraff, Inorg. Chem., 1993, 32, 5629.
70 D. J. Stufkens and A. Vlcek, Coord. Chem. Rev., 1998, 177, 127.
71 P. Chen, M. Curry and T. J. Meyer, Inorg. Chem., 1989, 28, 2771.
72 V. W. W. Yam, V. C. Y. Lau and K. K. Cheung, J. Chem. Soc., Chem.
Commun., 1995, 259.
4 R. Wabei, R. Alberto, J. Wielude, R. Finneru, R. Schibli, A.
Stichelberger, A. Egli, U. Abram, J. P. Mach, A. Pluckthern and
P. A. Schubiger, Nat. Biotechnol., 1999, 17, 897.
2
2
2
2
2
5 A. Amman, C. Decristoforo, I. Ott, M. Wenger, D. Bader, R. Alberto
and G. Putz, Nucl. Med. Biol., 2001, 28, 243.
6 J. Wald, R. Alberto, K. Ortner and L. Andreai, Angew. Chem., Int.
Ed., 2001, 40, 3062.
7 R. Alberto, A. Egli, K. Hegetschweiler, V. Gamlich and P. A.
Schubiger, J. Chem. Soc., Dalton Trans., 1994, 2815.
8 R. Alberto, K. Ortner, N. Wheatley, R. Schibli and P. A. Schubiger,
J. Am. Chem. Soc., 2001, 123, 3135.
9 K. A. Stephenson, J. Zubieta, S. R. Banerjee, M. K. Levadala, L.
Taggart, L. Ryan, N. McFarlane, D. R. Boreham, K. P. Maresca,
J. W. Babich and J. F. Valliant, Bioconjugate Chem., 2004, 15, 128.
0 S. R. Banerjee, M. K. Levadala, N. Lazarova, L. Wei, J. F. Valliant,
K. A. Stephenson, J. W. Babich, K. P. Maresca and J. Zubieta, Inorg.
Chem., 2002, 41, 6417.
73 L. Wallace, C. Woods and D. P. Rillema, Inorg. Chem., 1995, 34,
2875.
74 L. A. Lucia, K. Abbous and K. S. Schanze, Inorg. Chem., 1997, 36,
3
6224.
75 V. W. W. Yam, K. K. W. Lo, K. K. Cheung and R. Y. C. Kong,
J. Chem. Soc., Dalton Trans., 1997, 2067.
3
8 9 6
D a l t o n T r a n s . , 2 0 0 5 , 3 8 8 6 – 3 8 9 7