New non-ionic water-soluble porphyrins: Evaluation of manganese (III) polyhydroxylamide porphyrins as MRI contrast agents

Inorganica Chimica Acta

Volumn 275-276, Issue , 1998, Pages 106-116

  Bradshaw, Joseph E ^a   Gillogly, Kelly A ^b   Wilson, Lon J ^b   Kumar, Krishan ^c   Wan, Xiaoming ^d   Tweedle, Michael F ^d   Hernandez, Griselda ^e   Bryant, Robert G ^e  

^a OUACHITA BAPTIST UNIVERSITY   (United States)

^b RICE UNIVERSITY   (United States)

^c BRISTOL MYERS SQUIBB   (United States)

^d Bracco Research USA   (United States)

^e UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Manganese complexes; MR imaging; Porphyrin complexes; Water soluble complexes

Indexed keywords

CHLORINE COMPOUNDS; IMAGE ENHANCEMENT; LIGANDS; MAGNETIC RESONANCE IMAGING; MANGANESE REMOVAL (WATER TREATMENT); NUCLEAR MAGNETIC RESONANCE; PORPHYRINS; ZINC COMPOUNDS;

GASTROINTESTINAL TRACT; MANGANESE COMPLEXES; MR IMAGING; OSMOLALITY MEASUREMENTS; PORPHYRIN COMPLEXES; VARIABLE-TEMPERATURE NMR; WATER-SOLUBLE COMPLEXES; WATER-SOLUBLE PORPHYRIN;

MANGANESE COMPOUNDS;

EID: 0001094872     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0020-1693(97)06110-0     Document Type: Article

References (71)

1. R.B. Lauffer, Chem. Rev., 87 (1987) 901-927.
2. S.H. Koenig and R.D. Brown, in G. Berthon (ed.), Handbook of Metal-Ligand Interactions in Biological Fluids: Bioinorganic Chemistry, Vol. 2, Marcel Dekker, New York, 1995.
3. J.F. Desreux and B. Jacques, in G. Berthon (ed.), Handbook of Metal-Ligand Interactions in Biological Fluids: Bioinorganic Chemistry, Vol. 2, Marcel Dekker, New York, 1995.
4. S.E. Matthews, C.W. Pouton and M.D. Threadgill, Adv. Drug Delivery Rev., 18(2) (1996) 219-267.
5. B. Misselwitz, A. Muehler and H.-J. Weinmann, Invest. Radiol., 30 (10) (1995) 611-620.
6. J.S. Mann and R.C. Brasch, in G. Berthon (ed.), Handbook of Metal-Ligand Interactions in Biological Fluids, Bioinorganic Chemistry, Vol. 2, Marcel Dekker, New York, 1995.
7. P. Niemi, in V.P. Torchilin (ed.), Handbook Targeted Delivery Imaging Agents, CRC Press, Boca Raton, FL, 1995.
8. R. Weissleder, A.A. Bogdanov, Jr. and M. Papisov, in V.P. Torchilin (ed.), Handbook Targeted Delivery Imaging Agents, CRC Press, Boca Raton, FL, 1995.
9. A.D. Watson, J. Alloys Compd., 207-208 (1994) 14-19.
10. M.J. Abrams and B.A. Murrer, Science, 261 (5122) (1993) 725-730.
11. M.F. Tweedle, Invest. Radiol., 27 ( 1992) S2-S6.
12. M.F. Tweedle, J. Alloys Compd., 180 (1992) 317-323.
13. L. Lex, ActaBiochim. Biophys. Hung., 24 (3) (1989) 265-281.
14. H. Goldstein, W. Lumma and A. Rudzik, Annu. Rep. Med. Chem., 24 (1989) 265-276.
15. A.D. Sherry, J. Less-Common Met., 149 (1989) 133-141.
16. M.H. Mendonca Dias and P.C. Lauterbur, Biol. Trace Elem. Res., 13 (1987) 229-239.
17. M.F. Tweedle, in J.C.G. Bunzli and G.R. Choppin (eds.), Lanthanide Probes in Life, Chemical and Earth Sciences, Theory and Practice, Elsevier, New York, 1989, p. 142, Fig. 5.9.
18. D.R. Doiron and C.J. Gomer (eds.), Porphyrin Localization and Treatment of Tumors, Alan R. Liss, New York, 1984.
19. J.A. Nelson, U. Schmiedl and E.G. Shankland, Invest. Radiol., 25 (1990) S71-S73.
20. D. A. Place, P.J. Faustino, P.C.M. van Ziji, A. Chesnick and J.S. Cohen, Invest. Radiol., 25 (1990) S69-S70.
21. J. Winkleman, Cancer Res., 22 (1962) 589-596.
22. W.C. Chen, J.S. Cohen, C.E. Myers and M. Sohn, FEBS, 168 (1984) 70-74.
23. N.J. Patronas, J.S. Cohen, R.H. Knop, A.J. Dwyer, D. Colcher, J. Lundy, F. Mornex, P. Hambright, M. Sohn and C.E. Myers, Cancer Treat. Rep., 70 (1986) 391-395.
24. R.J. Fiel, T.M. Button, S. Gilani, E.H. Mark, D.A. Musser, R.M. Henkelman, M.J. Bronskill and J.G. van Heteren, Magn. Reson. Imaging, 5 (1987) 149-156.
25. R.J. Fiel, D.A. Musser, E.H. Mark, R. Mazurchuk and J.J. Alletto, Magn. Reson. Imaging, 8 (1990) 255-259.
26. D.A. Place, J.P. Faustino, K.K. Berghmans, P.C.M. van Ziji, A.S. Chesnick and J.S. Cohen, Magn. Reson. Imaging, 10 (1992) 919-928.
27. F. Megnin, P.J. Faustino, R.C. Lyon, P.I. Lelkes and J.S. Cohen, Biochim. Biophys. Acta, 929 (1987) 173-181.
28. M.D. Ogan, D. Revel and R.C. Brasch, Invest. Radiol., 22 (1987) 822-828.
29. R.C. Lyon, P.J. Faustino, J.S. Cohen, A. Katz, F. Mornex, D. Colcher, C. Baglin, S.H. Koenig and P. Hambright, Magn. Reson. Med., 4 (1987) 24-33.
30. S.W. Young, F. Qing, A. Harriman, J.L. Sessler, W.C. Dow, Tarak D. Mody, G.W. Hemmi, Y. Hao and R.A. Miller, Proc. Natl. Acad. Sci. U.S.A., 93 (1996) 6610-6615.
31. S.K. Sur and R.G. Bryant, J. Phys. Chem., 99 (1995) 7172-7179.
32. K. Bockhorst, M. Höhn-Berlage, M. Kocher and K.-A. Hossmann, Magn. Reson. Imaging, 8 (4) (1990) 499-504.
33. S.H. Koenig, R.D. Brown III and M. Spiller, Magn. Reson. Med., 4 (1987) 252-260.
34. V.E. Yushmanov, T.T. Tominaga, I.E. Borissevitch, H. Imasato and M. Tabak, Magn. Reson. Imaging, 14 (3) (1996) 255-261.
35. L.S. Jackson, J.A. Nelson, T.A. Case and B.F. Burnham, Invest. Radiol., 20 (1985) 226-229.
36. J.H. McMillan, G.G. Cox, B.F. Kimler, J.S. Spicer and S. Batnitzky, Magn. Reson. Imaging, 9 (1991) 553-558.
37. T. La, R. Richards and G.M. Miskelly, Inorg. Chem., 22 (1994) 3159-3163.
38. (a) M. Sovak, in M. Sovak (ed.), Radio Contrast Agents, Springer, Berlin, 1984, Ch. 'Introduction';
39. (b) G.B. Hoey and K.R. Smith, in M. Sovak (ed.), Radio Contrast Agents, Springer, Berlin, 1984, pp. 23-114.
40. M.F. Tweedle, L.J. Wilson, J.E. Bradshaw and D.W. Lee, US Patent No. 5 262 532 (16 Nov. 1993).
41. P.A. Miran and F.A. Bovey, in F.A. Bovey (ed.), Nuclear Magnetic Resonance Spectrsocopy, Academic Press, San Diego, 2nd edn., 1988, Ch. 9.3.
42. M.F. Tweedle and L.J. Wilson, Rev. Sci. Instrum., 49 (7) (1978) 1001-1004.
43. G. Hernandez, H.G. Brittain, M.F. Tweedle and R.G. Bryant, Inorg. Chem., 29 (5) (1990) 985-988.
44. C.C. Lester and R.G. Bryant, Magn. Reson. Med., 22 (1) (1991) 143-153.
45. (a) S.H. Koenig and W.S. Schillinger, J. Biol. Chem., 244 (1969) 3283-3289;
46. (b) A.G. Redfield, W. Fite II and H.E. Bleich, Rev. Sci. Instrum., 39 (1968) 710-715.
47. C.C. Lester, Ph.D. Thesis, University of Rochester, 1990.
48. A.D. Adler, F.R. Longo, F. Kampas and J. Kim, J. Inorg. Nucl. Chem., 32 (1970) 2443-2445.
49. N.O. Sonntag, Chem. Rev., 52 (1953) 237-416.
50. M. Nappa and J.S. Valentine, J. Am. Chem. Soc., 100 (16) (1978) 5075-5080.
51. L.J. Boucher, Coord. Chem. Rev., 7 (3) (1972) 289-329.
52. M.M. Williamson and C.L. Hill, Inorg. Chem., 26 (1987) 4155-4160.
53. S.M. Eaton, H.M. Tsay, F.H. Yost and M.F. Tweedle, Invest. Radiol., 25 (1990) 789.
54. S.S. Eaton and G.R. Eaton, J. Am. Chem. Soc., 99 (1977) 1601-1604.
55. K. Kano, T. Nakajima, M. Takei and S. Hashimoto, Bull. Chem. Soc. Jpn., 60 (1987) 1281-1287.
56. (a) T. La, R.A. Richards, R.S. Lu, R. Bau and G.M. Miskelly, Inorg. Chem., 34 (22) (1995) 5632-5640;
57. (b) F.J. Vergeldt, R.B.M. Koehorst, A. van Hoek and T.J. Schaafsma, J. Phys. Chem., 99 (13) (1995) 4397-4405.
58. I. Bertini and C. Luchinat, NMR of Paramagnetic Molecules in Biological Systems, Benjamin-Cummings, Redwood City, CA, 1986, Chs. 3 and 4.
59. L.H. Bryant, Jr., M. Whaley and R.G. Bryant, Inorg. Chem., submitted for publication.
60. (a) I. Solomon, Physiol. Rev., 99 (1955) 559;
61. (b) N. Bloembergen, J. Chem. Phys., 27 (1957) 572-573.
62. (a) R.R. Sharp, J. Chem. Phys., 98 (1993) 912-921;
63. (b) J. Chem. Phys., 98 (1993) 2507-2515;
64. (c) J.M. Bovet and R.R. Sharp, J. Chem. Phys., 99 (1993) 18-26;
65. (d) R.R. Sharp, J. Chem. Phys., 98 (1993) 6092-6101.
66. G. Hernandez and R.G. Bryant, Bioconj. Chem., 2 (1991) 394-397.
67. M.F. Tweedle, G.T. Gaughan, J. Hagan, P.W. Wedeking, P. Sibley, L.J. Wilson and D.W. Lee, Nucl. Med. Biol., 15 (1) (1988) 31-36.
68. J.S. Cohen and R. Lyon, in V.M. Ringe, C. Claussen, R. Felix and A.E. James (eds.), Contrast Agents in Magnetic Resonance Imaging, Excerpta Medica, Amsterdam, 1986.
69. M. Schaeffer, D. Meyer, S. Beaute and D. Doucet, Mag. Res. Med., 22 (1991) 238.
70. G .B. Hoey and K.R. Smith, in M. Sovak (ed.), Radio Contrast Agents, Springer, Berlin, 1984, p. 49.
71. M.F. Tweedle, in J.C.G. Bunzli and G.R. Choppin (eds.), Lanthanide Probes in Life, Chemical and Earth Sciences, Theory and Practice, Elsevier, New York, 1989, p. 142.