Synthesis, in vitro and in vivo characterization of two novel 68Ga-labelled 5-nitroimidazole derivatives as potential agents for imaging hypoxia

Nuclear Medicine and Biology

Volumn 40, Issue 2, 2013, Pages 273-279

  Fernández, Soledad ^a   Dematteis, Sylvia ^a   Giglio, Javier ^a,b   Cerecetto, Hugo ^a   Rey, Ana ^a,b  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b Centro Uruguayo de Imagenolog a Molecular   (Uruguay)

Author keywords

5 nitroimidazole; Complex; DOTA; Gallium; Hypoxia; Imaging agent

Indexed keywords

1 FLUORO 3 (2 NITRO 1 IMIDAZOLYL) 2 PROPANOL F 18; 10 [2 (2 METHYL 5 NITRO 1H IMIDAZOLE 1 YL)ETHYLAMINOCARBONYLMETHYL] 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIACETIC ACID GA 68; 10 [N METHYL 1 [1 [2 (2 METHYL 5 NITRO 1H IMIDAZOLE 1 YL)ETHYL] 1H 1,2,3 TRIAZOLE 4 YL]METHYLAMINOCARBONYLMETHYL] 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIACETIC ACID GA 68; 5 NITROIMIDAZOLE DERIVATIVE; PENTETIC ACID; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CELL HYPOXIA; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG PROTEIN BINDING; DRUG PURITY; DRUG RETENTION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TUMOR LEVEL; DRUG UPTAKE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; LUNG CARCINOMA; MOUSE; NONHUMAN; PH;

ANIMALS; BIOLOGICAL TRANSPORT; CARCINOMA, LEWIS LUNG; CELL HYPOXIA; CELL LINE, TUMOR; CELL TRANSFORMATION, NEOPLASTIC; CHEMISTRY TECHNIQUES, SYNTHETIC; GALLIUM RADIOISOTOPES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; ISOTOPE LABELING; LIGANDS; MICE; NITROIMIDAZOLES; POSITRON-EMISSION TOMOGRAPHY;

EID: 84872955946     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.11.003     Document Type: Article

References (31)

1. Caramelo P., Peña J., Castilla A., Justo S., De Solís A.J., Neira F., et al. Respuesta a la hipoxia. Medicina 2006, 66:155.
2. Nunn A., Linder K., Strauss H.W. Nitroimidazoles and imaging hypoxia: a review. Eur J Nucl Med 1995, 22:265-280.
3. Liu R., Kiess M.C., Okada R.D., Block P.C., Strauss H.W., Pohost G.M., et al. The persistent defect on exercise thallium imaging and its fate after myocardial revascularization: does it represent scar or ischemia?. J Am Heart Assoc 1985, 110:996.
4. Straub N.C. Transport of oxygen and carbon dioxide tissue oxygenation 1993, Mosby Yearbook, St. Louis. 3rd. ed.
5. 2. J Cereb Blood Flow Metab 1987, 7:709-719.
6. Olive P.L., Durand R.E. Misonidazole binding in SCCVII tumours in relation to the tumour blood supply. Int J Rad Onc Biol Phys 1989, 16:755-761.
7. 2. J Appl Phys 1990, 68:833-842.
8. Kabayashi M., Nakagawa K. Metastasis and hypoxia-inducible factor. Gan To Kagaku Ryoho 2010, 37:2047-2051.
9. Brizel D.M., Scully S.P., Harrelson J.M., Layfield L.J., Bean J.M., Prosnitz L.R., et al. Tumor oxygenation predicts for the likelihood of distant metastases in human soft tissue sarcoma. Cancer Res 1996, 56:941-943.
10. Gray L.H., Conger A.D., Ebert M., Hornsey S., Scott O.C. The concentration of oxygen dissolved in tissues at the time of irradiation as a factor in radiotherapy. Br J Radiol 1953, 26:638-648.
11. Vaupel P., Mayer A. Hypoxia in cancer: significance and impact on clinical outcome. Cancer Metastasis Rev 2007, 26:225-239.
12. Mukai T., Suwada J., Sano K., Okada M., Yamamoto F., Maeda M. Designed of Ga-DOTA-based bifunctional radiopharmaceuticals: two functional moieties can be conjugated to radiogallium-DOTA without reducing the complex stability. Bioorg Med Chem 2009, 17:4285-4290.
13. 18F-fluoromisonidazole. Semin Nucl Med 2007, 37:451-461.
14. Bourgeois M., Rajerison H., Guerard F., Mougin-Degraef M., Barbet J., Michel N., et al. Nucl Med Rev Cent East Eur 2011, 14:90-95.
15. Chitneni S.K., Palmer G.M., Zalutsky M.R., Dewhirst M.W. Molecular imaging of hypoxia. J Nucl Med 2011, 52:165-168.
16. Takasawa M., Moustafa R.R., Baron J.C. Applications of nitroimidazole in vivo hypoxia imaging in ischemic stroke. Stroke 2008, 39:1629-1637.
17. Hoigebazar L., Jeong J.M. Hypoxia imaging agents labeled with positron emitters. Rec Res Can Res 2012, 194:285-299.
18. 68Ga-Labeling and testing in tumor xenografted mice. J Med Chem 2010, 53:6378-6385.
19. 68Ga-labeled DOTA-nitroimidazole derivatives and their feasibilities as hypoxia imaging PET tracers. Bioorg Med Chem 2011, 19:2176-2181.
20. Cerecetto H., González M., Lavaggi M.L. Development of hypoxia selective cytotoxins for cancer treatment: an update. Med Chem 2006, 2:315-327.
21. Cerecetto H., González M., Onetto S., Risso M., Rey A., Giglio J., et al. Synthesis and characterization of thiol containing furoxan derivatives as coligands for the preparation of potential bioreductive radiopharmaceuticals. Arch Pharm 2006, 339:59-66.
22. Giglio J., Rey A., Cerecetto H., Pirmettis I., Papadopoulos M., León E., et al. Design and evaluation of "3+1" mixed ligand oxorhenium and oxotechnetium complexes bearing a nitroaromatic group with potential application in nuclear medicine oncology. Eur J Med Chem 2006, 41:1144-1152.
23. Giglio J., Patsis G., Pirmettis I., Papadopoulos M., Raptopoulou C., Pelecanou M., et al. Preparation and characterization of technetium and rhenium tricarbonyl complexes bearing the 4-nitrobenzyl moiety as potential bioreductive diagnostic radiopharmaceuticals. In vitro and in vivo studies. Eur J Med Chem 2008, 43:741-748.
24. 99mTc-complexes as potential agents for targeting hypoxia. Bioorg Med Chem Lett 2011, 21:394-397.
25. 99mTc(I)-carbonyl complexes. Application to the development of radiopharmaceuticals for imaging hypoxic tissue. Bioorg Med Chem 2012, 20:4040-4048.
26. 99mTc-'4+1'-labeled 5-nitroimidazole derivatives as potential agents for imaging hypoxia. Nucl Med Biol 2012, 39:679-686.
27. Suzuki T., Fujikura K., Higashiyama T., Takata K. DNA staining for fluorescence and laser confocal microscopy. J Histochem Cytochem 1997, 45:49-53.
28. Huang H., Mei L., Chu T. Synthesis, radiolabeling and biological evaluation of propylene amine oxime complexes containing nitrotriazoles as hypoxia markers. Molecules 2012, 17:6808-6820.
29. Lewis S., Welch M.J. PET imaging of hypoxia. Q J Nucl Med 2001, 45:183-188.
30. Nunn A., Linder K., Strauss H.W. Nitroimidazoles and imaging hypoxia. Eur J Nucl Med 1995, 22:265-280.
31. 18F]fluoromisonidazole. Appl Radiat Isot 1993, 44:1085-1091.