Synthesis of novel 68Ga-labeled amino acid derivatives for positron emission tomography of cancer cells

Nuclear Medicine and Biology

Volumn 37, Issue 8, 2010, Pages 893-902

  Shetty, Dinesh ^a   Jeong, Jae Min ^a   Ju, Chang Hwan ^a,b   Lee, Yun Sang ^a   Jeong, Seo Young ^b   Choi, Jae Yeon ^a   Yang, Bo Yeun ^a   Lee, Dong Soo ^a,c   Chung, June Key ^a   Lee, Myung Chul ^a  

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

^b Kyung Hee University Hospital   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

Bifunctional chelating agent; DO2A; DO3A; DOTA; Gallium

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7, TRIACETIC ACID; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7, TRIACETIC ACID GA 68; 1,4,7,10 TETRAAZACYCLODODECANE 1,7 DIACETIC ACID; 1,4,7,10 TETRAAZACYCLODODECANE 1,7 DIACETIC ACID GA 68; AMINO ACID DERIVATIVE; GALLIUM 68; RADIOISOTOPE; UNCLASSIFIED DRUG; AMINO ACID; DIAGNOSTIC AGENT; GALLIUM;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; BLADDER; CATALYSIS; COLON CANCER; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG HYDROLYSIS; DRUG SPECIFICITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TUMOR LEVEL; DRUG UPTAKE; GLIOMA CELL; HEPATOMA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOTOPE LABELING; KIDNEY; MALE; MOUSE; NONHUMAN; NUCLEOPHILICITY; POSITRON EMISSION TOMOGRAPHY; PROTEIN CLEAVAGE; TUMOR XENOGRAFT; ANIMAL; CELL TRANSFORMATION; CHEMISTRY; METHODOLOGY; NEOPLASM; PATHOLOGY; RADIOCHEMISTRY; SCINTISCANNING; SYNTHESIS; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

AMINO ACIDS; ANIMALS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CELL TRANSFORMATION, NEOPLASTIC; GALLIUM RADIOISOTOPES; HUMANS; MALE; MICE; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RADIOCHEMISTRY;

EID: 78049469914     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.06.003     Document Type: Article

References (35)

1. 68Ga-labelled tracers in clinical routine?. Eur J Nucl Med Mol Imaging 2007, 34:978-981.
2. Ehrhardt G.J., Welch M.J. A new germanium-63/gallium-68 generator. J Nucl Med 1978, 19:925-929.
3. 68Ga for medical application. J Nucl Med 2007, 48:1741-1748.
4. Chen W. Clinical applications of PET in brain tumors. J Nucl Med 2007, 48:1468-1481.
5. 18F-FDG PET as a cancer screening test. Nucl Med Mol Imaging 2008, 42:444-450.
6. 11C]l-Methionine uptake in gliomas. Neurosurgery 1989, 25:720-728.
7. 18F]fluoromethyl-cyclobutane-1-carboxylic acid (FMACBC), potential PET ligands for tumor detection. J Med Chem 2002, 45:2250-2259.
8. McConathy J., Goodman M.M. Non-natural amino acids for tumor imaging using positron emission tomography and single photon emission computed tomography. Cancer Metastasis Rev 2008, 27:555-573.
9. 18F-FDG PET. Eur J Nucl Med Mol Imaging 2005, 32:52-59.
10. Shoup T.M., Goodman M.M. Synthesis of [F-18]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC): a PET tracer for tumor delineation. J Label Compd Radiopharm 1999, 42:215-225.
11. 18F]fluoroethyl)-l-tyrosine for tumor imaging. J Nucl Med 1999, 40:205-212.
12. 11C)-methionine in brain tumors studied with positron emission tomography. Acta Radiol 1987, 28:225-229.
13. 11C-methionine in cerebral glioma patients studied with PET. Acta Neurochir (Wien) 1990, 104:8-12.
14. 11C-methionine and positron emission tomography. AJNR Am J Neuroradiol 1985, 6:505-514.
15. 11C-methionine and computed tomography of intracranial tumours compared with histopathologic examination of multiple biopsies. Acta Radiol 1987, 28:673-681.
16. Hatazawa J., Ishiwata K., Itoh M., Kameyama M., Kubota K., Ido T., et al. Quantitative evaluation of l-[methyl-C-11] methionine uptake in tumor using positron emission tomography. J Nucl Med 1989, 30:1809-1813.
17. 11C]methionine in human plasma. Eur J Nucl Med 1989, 15:665-669.
18. 68Ga-labeled c(RGDyK)-isothiocyanatobenzyl-1,4,7-triazacyclononane-1,4,7-triacetic acid and feasibility studies in mice. J Nucl Med 2008, 49:830-836.
19. 68Ga-labelled DOTA-derivatised peptide ligands. Eur J Nucl Med Mol Imaging 2004, 31:1097-1104.
20. Chen X., Li L., Liu F., Liu B. Synthesis and biological evaluation of technetium-99m-labeled deoxyglucose derivatives as imaging agents for tumor. Bioorg Med Chem Lett 2006, 16:5503-5506.
21. Storr T., Obata M., Fisher C., Bayly S., Green D., Brudzinska I., et al. Novel carbohydrate-appended metal complexes for potential use in molecular imaging. Chem Eur J 2005, 11.
22. + and recognized by the L-type amino acid transporter LAT1. J Am Chem Soc 2006, 128:15996-15997.
23. 68Ga and investigation of in vitro properties. Nucl Med Mol Imaging 2009, 43:336.
24. Kneifel S., Cordier D., Good S., Ionescu M.C., Ghaffari A., Hofer S., et al. Local targeting of malignant gliomas by the diffusible peptidic vector 1,4,7,10-tetraazacyclododecane-1-glutaric acid-4,7,10-triacetic acid-substance P. Clin Cancer Res 2006, 12:3843-3850.
25. 2) and its Gd(III) complex. Bioorg Med Chem 2007, 15:4714-4721.
26. Chang C.A., Wu B.H., Kuan B.Y. Macrocyclic lanthanide complexes as artificial nucleases and ribonucleases: effects of pH, metal ionic radii, number of coordinated water molecules, charge, and concentrations of the metal complexes. Inorg Chem 2005, 44:6646-6654.
27. Huskens J., Torres D.A., Kovacs Z., Andre J.P., Geraldes C.F., Sherry A.D. Alkaline earth metal and lanthanide(III) complexes of ligands based upon 1,4,7,10-tetraazacyclododecane-1,7-bis(acetic acid). Inorg Chem 1997, 36:1495-1503.
28. Elaref S.R., John C.V. Reaction of trimethylsilylamines with N-Cbz-l-serine-β-lactone: a convenient route to optically pure β-amino-l-alanine derivatives. Tetrahedron Lett 1994, 35:7605-7608.
29. Kucharczyk N., Badet B., Legoffic F. Quantitative synthesis of l or d N-2-tert-butoxycarbonyl-2,3-diaminopropanoic acid from protected l-serine-beta-lactone or d-serine-beta-lactone. Synth Commun 1989, 19:1603-1609.
30. Alvydas J.O., Gerald A.R. Synthesis of l-canaline and γ-functional 2-aminobutyric acid derivatives. J Org Chem 1986, 51:5047-5050.
31. Kuwahara M., Arimitsu M., Sisido M. Novel peptide nucleic acid that shows high sequence specificity and all-or-none-type hybridization with the complementary DNA. J Am Chem Soc 1999, 121:256-257.
32. Chong H.S., Song H.A., Dadwal M., Sun X., Sin I., Chen Y.W. Efficient synthesis of functionalized aziridinium salts. J Org Chem 2010, 75:219-221.
33. Viola N., Rarig R., Ouellette W., Doyle R. Synthesis, structure and thermal analysis of the gallium complex of 1,4,7,10-tetraazacyclo-dodecane-N,N,N,N-tetraacetic acid (DOTA). Polyhedron 2006, 25:3457-3462.
34. 68Ga BAPEN kit for myocardial positron emission tomography imaging and biodistribution study. Nucl Med Biol 2010, 37:149-155.
35. 68Ga-DO(2)A-tyrosine conjugate as potential tumor tracer for PET. Bioorg Med Chem Lett 2009, 19:3498-3501.