A gadolinium chelate for detection of β-glucuronidase: A self-immolative approach

Journal of the American Chemical Society

Volumn 127, Issue 37, 2005, Pages 12847-12855

  Duimstra, Joseph A ^a,b   Femia, Frank J ^a,c   Meade, Thomas J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b California Institute of Technology   (United States)

^c A Subsidiary of Lantheus Holdings   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD; ENZYMES; LIQUID CHROMATOGRAPHY; MAGNETIC RESONANCE; MASS SPECTROMETRY; PH EFFECTS; PROTONS; SYNTHESIS (CHEMICAL); WATER;

BICARBONATE ANIONS; BUFFER MIMICKING; MICHAELIS-MENTEN MODEL; SYNTHETIC PROCEDURES;

GADOLINIUM;

2 AMINOETHYLGADOLINIUM 1,4,7 TRICARBOXYMETHYLENE 1,4,7,10 TETRAAZACYCLODODECANE; BETA GLUCURONIDASE; BICARBONATE; CONTRAST MEDIUM; GADOLINIUM; GADOLINIUM 1,4,7 TRICARBOXYMETHYLENE 1,4,7,10 TETRAAZACYCLODODECANE; GLUCURONIC ACID; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG HYDROLYSIS; DRUG SYNTHESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICHAELIS MENTEN KINETICS; NUCLEAR MAGNETIC RESONANCE IMAGING; PH; TEMPERATURE;

ANIMALS; CATTLE; CHELATING AGENTS; GADOLINIUM; GLUCURONIDASE; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; TIME FACTORS;

EID: 25144512977     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042162r     Document Type: Article

References (61)

1. Deleted in proof.
2. J. Magn. Reson. Imaging. Special Issue: Molecular Imaging 2002, 4, 333-483.
3. Li, K.; Pandit, S.; Guccione, S.; Bednarski, M. Biomed. Microdev. 2004, 6, 113-116.
4. J. Cell. Biochem., Supplement: Molecular Imaging 2002, 87, supplement 39, 1-248.
5. Nordberg, A. Lancet Neurol. 2004, 3, 519-527.
6. Choy, G.; Choyke, P.; Libutti, S. K. Mol. Imaging 2003, 2, 303-312.
7. Rooseboom, M.; Commandeur, J. N. M.; Vermeulen, N. P. E. Pharmacol. Rev. 2004, 56, 53-102.
8. Brusselbach, S. Methods Mol. Med. 2004, 90, 303-330.
9. Papot, S.; Tranoy, I.; Tillequin, F.; Florent, J. C.; Gesson, J. P. Curr. Med. Chem.: Anti-Cancer Agents 2002, 2, 155-185.
10. Xu, G.; McLeod, H. L. Clin. Cancer Res. 2001, 7, 3314-3324.
11. Tietre, L. F.; Feuerstein, T. Aust. J. Chem. 2003, 56, 841-854.
12. Bosslet, K.; Straub, R.; Blumrich, M.; Czech, J.; Gerken, M.; Sperker, B.; Kroemer, H. K.; Gesson, J.-P.; Koch, M.; Monneret, C. Cancer Res. 1998, 58, 1195-1201.
13. Guerquin-Kern, J.-L.; Volk, A.; Chenu, E.; Lougerstay-Madec, R.; Monneret, C.; Florent, J.-C.; Carrez, D.; Croisy, A. NMR Biomed. 2000, 13, 306-310.
14. Pedley, R. B.; Sharma, S. K.; Hawkins, R. E.; Chester, K. A. Methods Mol. Med. 2004, 90, 491-514.
15. Biela, B. H.; Khawli, L. A.; Hu, P.; Epstein, A. L. Can. Biother. Radiopharm. 2003, 18, 339-353.
16. Heine, D.; Muller, R.; Brusselbach, S. Gene Therapy 2001, 8, 1005-1010.
17. Merbach, A. E.; Toth, E. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging; John Wiley and Sons: West Sussex, New York, 2001.
18. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293-2352.
19. Caravan, P. et al. J. Am. Chem. Soc. 2002, 124, 3152-3162.
20. Aime, S.; Botta, M.; Fasano, M.; Crich, S. G.; Terreno, E. J. Biol. Inorg. Chem. 1996, 1, 312-319.
21. Doble, D. M. J.; Botta, M.; Wang, J.; Aime, S.; Barge, A.; Raymond, K. N. J. Am. Chem. Soc. 2001, 123, 10758-10759.
22. Moats, R. A.; Fraser, S. E.; Meade, T. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 726-728.
23. Louie, A. Y.; Huber, M. M.; Ahrens, E. T.; Rothbacher, U.; Moats, R.; Jacobs, R. E.; Fraser, S. E.; Meade, T. J. Nat. Biotechnol. 2000, 18, 321-325.
24. Alauddin, M. M.; Louie, A. Y.; Shahinian, A.; Meade, T. J.; Conti, P. S. Nucl. Med. Biol. 2003, 30, 261-265.
25. Allen, M. J.; Meade, T. J. Metal Ions Biol. Syst. 2004, 42, 1-38.
26. Morawski, A. M.; Winter, P. M.; Crowder, K. C.; Caruthers, S. D.; Fuhrhop, R. W.; Scott, M. J.; Robertson, J. D.; Abendschein, D. R.; Lanza, G. M.; Wiekline, S. A. Magn. Reson. Med. 2004, 51, 480-486.
27. Nivorozhkin, A. L.; Kolodziej, A. F.; Caravan, P.; Greenfield, M. T.; Lauffer, R. B.; McMurry, T. J. Angew. Chem., Int. Ed. 2001, 40, 2903-2906.
28. Sakai, N.; Gerard, D.; Matile, S. J. Am. Chem. Soc. 2001, 123, 2517-2524.
29. Parker, D. In Crown Compounds: Towards Future Applications; Cooper, S. R., Ed.; VCH: New York, 1992; pp 51-67.
30. (a) Supkowski, R. M.; Horrocks, W. D., Jr. Inorg. Chim. Acta 2002, 340, 44-48.
31. (b) Beeby, A.; Clarkson, I. M.; Dickins, R. S.; Faulkner, S.; Parker, D.; Royle, L.; de Sousa, A. S.; Williams, J. A. G.; Woods, M. J. Chem. Soc., Perkin Trans. 2 1999, 493-504.
32. Bollenback, G. N.; Long, J. W.; Benjamin, D. G.; Lindquist, J. A. J. Am. Chem. Soc. 1955, 77, 3310-3315.
33. Florent, J.-C. et al. J. Med. Chem. 1998, 41, 3572-3581.
34. Leu, Y. L.; Roffler, S. R.; Chern, J. W. J. Med. Chem. 1999, 42, 3623-3628.
35. Eckert, H.; Forster, B. Angew. Chem. 1987, 99, 922-923.
36. Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937-1938.
37. Dadabhoy, A.; Faulkner, S.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 2 2002, 348-357.
38. Schmidt, H. W. H.; Neukom, H. Tetrahedron Lett. 1969, 2011-2012.
39. Stachulski, A. V.; Jenkins, G. N. Nat. Prod. Rep. 1998, 15, 173-186.
40. Duimstra, J. A. Carbohydrate-Based Gadolinium(III) Magnetic Resonance Imaging Contrast Agents: A Synthetic Retrospective. M.S. Thesis, California Institute of Technology, Pasadena, 2002.
41. Bretonniere, Y.; Cann, M. J.; Parker, D.; Slater, R. Chem. Commun. 2002, 1930-1931.
42. Bretonniere, Y.; Cann, M. J.; Parker, D.; Slater, R. Org. Biomol. Chem. 2004, 2, 1624-1632.
43. Bruce, J. I. et al. J. Am. Chem. Soc. 2000, 122, 9674-9684.
44. 1 approximately twice that of a q = 1 complex, such as GdHP-DO3A
45. Messeri, D.; Lowe, M. P.; Parker, D.; Botta, M. Chem. Commun. 2001, 2742-2743.
46. Lowe, M. P.; Parker, D.; Reany, O.; Aime, S.; Botta, M.; Castellano, G.; Gianolio, E.; Pagliarin, R. J. Am. Chem. Soc. 2001, 123, 7601-7609.
47. The q values at elevated temperatures must be viewed with caution since the empirically observed relationship between phosphorescence lifetime and coordination number was evaluated at room temperature. It is unlikely that the empirical parameters will be independent of temperature.
48. Aime, S.; Gianolio, E.; Terreno, E.; Giovenzana, G. B.; Pagliarin, R.; Sisti, M.; Palmisano, G.; Botta, M.; Lowe, M. P.; Parker, D. J. Biol. Inorg. Chem. 2000, 5, 488-497.
49. Dickins, R. S. et al. J. Am. Chem. Soc. 2002, 124, 12697-12705.
50. Supkowski, R. M.; Horrocks, W. D., Jr. Inorg. Chem. 1999, 38, 5616-5619.
51. Vander Elst, L.; Van Haverbeke, Y.; Goudemant, J. F.; Muller, R. N. Magn. Reson. Med. 1994, 31, 437-444.
52. Himeno, M.; Hashiguchi, Y.; Kato, K. J. Biochem. (Tokyo) 1974, 76, 1243-1252.
53. A search of the CSD returned no structures containing a lanthanide coordinated to both a pyridyl and aquo ligand.
54. Aime, S.; Terreno, E.; Botta, M.; Bruce, J. I.; Parker, D.; Mainero, V. Chem. Commun. 2001, 115-116.
55. 44
56. Azoulay, M.; Chalard, F.; Gesson, J. P.; Florent, J. C.; Monneret, C. Carbohydr. Res. 2001, 332, 151-156.
57. Brot, F. E.; Bell, C. E., Jr.; Sly, W. S. Biochemistry 1978, 17, 385-391.
58. Jain, S.; Drendel, W. B.; Chen, Z.-w.; Mathews, F. S.; Sly, W. S.; Grubb, J. H. Nat. Struct. Biol. 1996, 3, 375-381.
59. Jefferson, R. A.; Burgess, S. M.; Hirsh, D. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8447-8451.
60. Aich, S.; Delbaere, L. T. J.; Chen, R. BioTechniques 2001, 30, 846-850.
61. O'Leary, K. A.; Day, A. J.; Needs, P. W.; Sly, W. S.; O'Brien, N. M.; Williamson, G. FEBS Lett. 2001, 503, 103-106.