Synthesis of 68Ga-labeled DOTA-nitroimidazole derivatives and their feasibilities as hypoxia imaging PET tracers

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 7, 2011, Pages 2176-2181

  Hoigebazar, Lathika ^a   Jeong, Jae Min ^a   Hong, Mee Kyung ^a   Kim, Young Ju ^a   Lee, Ji Youn ^a   Shetty, Dinesh ^a   Lee, Yun Sang ^a   Lee, Dong Soo ^a,b   Chung, June Key ^a   Lee, Myung Chul ^a  

^a Seoul National University College of Medicine   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

68Ga; Ga 68; Gallium; Nitroimidazole

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 2 (2 NITROIMIDAZOLYL)ETHANAMINE; 2 (2 NITROIMIDAZOLYL)ETHYLAMINE; AMIDE; GALLIUM 68; NITROIMIDAZOLE DERIVATIVE; TERT N BUTYL 2 (2 NITROIMIDAZOLYL)ETHYLCARBAMATE; THIOUREA; UNCLASSIFIED DRUG; 1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; DIAGNOSTIC AGENT; GALLIUM; RADIOPHARMACEUTICAL AGENT; SINGLE HETEROCYCLIC RINGS;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER CELL; COLON CANCER; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG STABILITY; DRUG STRUCTURE; DRUG UPTAKE; FEASIBILITY STUDY; HUMAN; HUMAN CELL; HYDROPHILICITY; HYPOXIA; ISOTOPE LABELING; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; TUMOR XENOGRAFT; ANIMAL; CELL HYPOXIA; CHEMISTRY; CHO CELL; COLON TUMOR; CRICETULUS; HAMSTER; HELA CELL; METABOLISM; METHODOLOGY; PHYSIOLOGY; PROTEIN BINDING; SCINTISCANNING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TISSUE DISTRIBUTION; TUMOR CELL LINE; XENOGRAFT;

ANIMALIA; MUS;

ANIMALS; CELL HYPOXIA; CELL LINE, TUMOR; CHO CELLS; COLONIC NEOPLASMS; CRICETINAE; CRICETULUS; GALLIUM RADIOISOTOPES; HELA CELLS; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; MICE; NITROIMIDAZOLES; POSITRON-EMISSION TOMOGRAPHY; PROTEIN BINDING; RADIOPHARMACEUTICALS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TRANSPLANTATION, HETEROLOGOUS;

EID: 79953222548     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.041     Document Type: Article

References (37)

1. S. Rockwell, I.T. Dobrucki, E.Y. Kim, S.T. Marrison, and V.T. Vu Curr. Mol. Med. 9 2009 442
2. F. Dehdashti, P.W. Grigsby, J.S. Lewis, R. Laforest, B.A. Siegel, and M.J. Welch J. Nucl. Med. 49 2008 201
3. S. Shimizu, Y. Eguchi, W. Kamiike, Y. Itoh, J. Hasegawa, K. Yamabe, Y. Otsuki, H. Matsuda, and Y. Tsujimoto Cancer Res. 56 1996 2161
4. J.P. Steinbach, H. Wolburg, A. Klumpp, H. Probst, and M. Weller Cell Death Differ. 10 2003 823
5. A.L. Vavere, and J.S. Lewis J. Chem. Soc., Dalton Trans. 2007 4893
6. S.T. Lee, and A.M. Scott Semin. Nucl. Med. 37 2007 451
7. P. Kumar, S. Emami, Z. Kresolek, J. Yang, A.J. McEwan, and L.I. Wiebe Med. Chem. 5 2009 118
8. P. Kumar, E. Naimi, A.J. McEwan, and L.I. Wiebe Bioorg. Med. Chem. 18 2010 2255
9. M. Piert, H.J. Machulla, M. Picchio, G. Reischl, S. Ziegler, P. Kumar, H.J. Wester, R. Beck, A.J. McEwan, L.I. Wiebe, and M. Schwaiger J. Nucl. Med. 46 2005 106
10. T.J. Tewson Nucl. Med. Biol. 24 1997 755
11. M.B. Mallia, S. Subramanian, A. Mathur, H.D. Sarma, M. Venkatesh, and S. Banerjee Bioorg. Med. Chem. Lett. 18 2008 5233
12. F. Riche, A.D. d'Hardemare, S. Sepe, L. Riou, D. Fagret, and M. Vidal Bioorg. Med. Chem. Lett. 11 2001 71
13. K.E. Linder, Y.W. Chan, J.E. Cyr, M.F. Malley, D.P. Nowotnik, and A.D. Nunn J. Med. Chem. 37 1994 9
14. E.O. Aboagye, A.D. Lewis, A. Johnson, P. Workman, M. Tracy, and I.M. Huxham Br. J. Cancer 72 1995 312
15. A. Nunn, K. Linder, and H.W. Strauss Eur. J. Nucl. Med. 22 1995 265
16. M. Takasawa, R.R. Moustafa, and J.C. Baron Stroke 39 2008 1629
17. R. Bejot, V. Kersemans, C. Kelly, L. Carroll, R.C. King, and V. Gouverneur Nucl. Med. Biol. 37 2010 565
18. R.A. Cairns, K.L. Bennewith, E.E. Graves, A.J. Giaccia, D.T. Chang, and N.C. Denko Clin. Cancer Res. 15 2009 7170
19. D. Stypinski, L.I. Wiebe, and J.R. Mercer J. Pharm. Biomed. Anal. 16 1998 1067
20. P. Rigo, P. Paulus, B.J. Kaschten, R. Hustinx, T. Bury, G. Jerusalem, and T. Benoit Eur. J. Nucl. Med. 23 1996 1641
21. K. Kaira, M. Endo, M. Abe, K. Nakagawa, Y. Ohde, T. Okumura, T. Takahashi, H. Murakami, A. Tsuya, Y. Nakamura, T. Naito, I. Hayashi, M. Serizawa, Y. Koh, H. Hanaoka, H. Tominaga, N. Oriuchi, H. Kondo, T. Nakajima, and N. Yamamoto J. Clin. Oncol. 28 2010 3746
22. M. Hasebe, K. Yoshikawa, S. Ohashi, S. Toubaru, K. Kawaguchi, J. Sato, J. Mizoe, and H. Tsujii Mol. Imaging Biol. 12 2010 554
23. K. Van Laere, K. Clerinx, E. D'Hondt, T. de Groot, and W. Vandenberghe J. Nucl. Med. 51 2010 588
24. H. Herzog, F. Rosch, G. Stocklin, C. Lueders, S.M. Qaim, and L.E. Feinendegen J. Nucl. Med. 34 1993 2222
25. M.L. Thakur, M.R. Aruva, J. Gariepy, P. Acton, S. Rattan, S. Prasad, E. Wickstrom, and A. Alavi J. Nucl. Med. 45 2004 1381
26. J.M. Jeong, M.K. Hong, Y.S. Chang, Y.S. Lee, Y.J. Kim, G.J. Cheon, D.S. Lee, J.K. Chung, and M.C. Lee J. Nucl. Med. 49 2008 830
27. D. Shetty, J.M. Jeong, C.H. Ju, Y.J. Kim, J.Y. Lee, Y.S. Lee, D.S. Lee, J.K. Chung, and M.C. Lee Bioorg. Med. Chem. 18 2010 7338
28. D. Shetty, J.M. Jeong, C.H. Ju, Y.S. Lee, S.Y. Jeong, J.Y. Choi, B.Y. Yang, D.S. Lee, J.K. Chung, and M.C. Lee Nucl. Med. Biol. 37 2010 893
29. B.Y. Yang, J.M. Jeong, Y.J. Kim, J.Y. Choi, Y.S. Lee, D.S. Lee, J.K. Chung, and M.C. Lee Nucl. Med. Biol. 37 2010 149
30. D. Shetty, Y.S. Lee, and J.M. Jeong Nucl. Med. Mol. Imaging 44 2010 233
31. W.A. Breeman, and A.M. Verbruggen Eur. J. Nucl. Med. Mol. Imaging 34 2007 978
32. D. Shetty, S.Y. Choi, J.M. Jeong, L. Hoigebazar, Y.S. Lee, D.S. Lee, M.C. Lee, and J.K. Chung Eur. J. Inorg. Chem. 2010 5432
33. I. Velikyan, G.J. Beyer, and B. Langstrom Bioconjugate Chem. 15 2004 554
34. J.M. Jeong, Y.J. Kim, Y.S. Lee, D.S. Lee, J.K. Chung, and M.C. Lee Nucl. Med. Mol. Imaging 43 2009 330
35. F. Benetollo, G. Bombieri, L. Calabi, S. Aime, and M. Botta Inorg. Chem. 42 2003 148
36. L. Hoigebazar, J.M. Jeong, S.Y. Choi, J.Y. Choi, D. Shetty, Y.S. Lee, D.S. Lee, J.K. Chung, M.C. Lee, and Y.K. Chung J. Med. Chem. 53 2010 6378
37. T. Mukai, J. Suwada, K. Sano, M. Okada, F. Yamamoto, and M. Maeda Bioorg. Med. Chem. 17 2009 4285