Synthesis and radiolabelling of DOTA-linked glutamine analogues with 67,68 ga as markers for increased glutamine metabolism in tumour cells

Molecules

Volumn 18, Issue 6, 2013, Pages 7160-7178

  Pellegrini, Paul A ^a   Howell, Nicholas R ^a   Shepherd, Rachael K ^a   Lengkeek, Nigel A ^a   Oehlke, Elisabeth ^a   Katsifis, Andrew G ^a   Greguric, Ivan ^a  

^a AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

Author keywords

67,68gallium; Amino acid transporter; DOTA; Glutamine; PET; Radiochemistry

Indexed keywords

1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; BIOLOGICAL MARKER; GALLIUM; GLUTAMINE; RADIOPHARMACEUTICAL AGENT; SINGLE HETEROCYCLIC RINGS; TRACER; DRUG DERIVATIVE; TETRAXETAN;

ANALOGS AND DERIVATIVES; CHEMISTRY; HUMAN; ISOTOPE LABELING; METABOLISM; NEOPLASM; POSITRON EMISSION TOMOGRAPHY; SYNTHESIS; TUMOR CELL LINE; ARTICLE;

BIOLOGICAL MARKERS; CELL LINE, TUMOR; GALLIUM RADIOISOTOPES; GLUTAMINE; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; ISOTOPE LABELING; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RADIOACTIVE TRACERS; RADIOPHARMACEUTICALS;

EID: 84879611149     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18067160     Document Type: Article

References (36)

1. Warburg, O. On the origin of cancer cells. Science 1956, 123, 309-314.
2. Vander Heiden, M.G.; Locasale, J.W.; Swanson, K.D.; Sharfi, H.; Heffron, G.J.; Amador-Noguez, D.; Christofk, H.R.; Wagner, G.; Rabinowitz, J.D.; Asara, J.M.; et al. Evidence for an alternative glycolytic pathway in rapidly proliferating cells. Science 2010, 329, 1492-1499.
3. 18F-FDG uptake by cells involved in pannus formation in rheumatoid arthritis. J. Nucl. Med. 2009, 50, 920-926.
4. Robey, I.F.; Stephen, R.M.; Brown, K.S.; Baggett, B.K.; Gatenby, R.A.; Gillies, R.J. Regulation of the Warburg effect in early-passage breast cancer cells. Neoplasia 2008, 10, 745-756.
5. 18F]fluorotyrosine, a new PET tracer of protein synthesis. J. Nucl. Med. 1989, 30, 1367-1372.
6. Klasner, B.D.; Krause, B.J.; Beer, A.J.; Drzezga, A. PET imaging of gliomas using novel tracers: a sleeping beauty waiting to be kissed. Exp. Rev. Anticancer Ther. 2010, 10, 609-613.
7. 11C-methyl-L-cysteine: a new amino acid PET tracer for cancer imaging. J. Nucl. Med. 2011, 52, 287-293.
8. 11C]-glutamine for metabolic imaging of tumors. J. Nucl. Med. 2012, 53, 98-105.
9. Qu, W.; Zha, Z.; Ploessl, K.; Lieberman, B.P.; Zhu, L.; Wise, D.R.; Thompson, C.B.; Kung, H.F. Synthesis of optically pure 4-fluoro-glutamines as potential metabolic imaging agents for tumors. J. Am. Chem. Soc. 2011, 133, 1122-1133.
10. McDonald, J.M.; Gelbard, A.S.; Clarke, L.P.; Christie, T.R.; Laughlin, J.S. Imaging of tumors involving bone with 13N-glutamic acid. Radiol. 1976, 120, 623-626.
11. 68Ga-PET: a powerful generator-based alternative to cyclotron-based PET radiopharmaceuticals. 2008, 3, 67-77.
12. Stasiuk, G.J.; Long, N.J. The ubiquitous DOTA and its derivatives: the impact of 1,4,7,10- tetraazacyclododecane-1,4,7,10-tetraacetic acid on biomedical imaging. Chem. Comm. 2013, 49, 2732-2746.
13. Blom, E.; Velikyan, I.; Estrada, S.; Hall, H.; Muhammad, T.; Ding, C.; Nair, M.; Langstrom, B. (68)Ga-Labeling of RGD peptides and biodistribution. Int. J. Clin. Exp. Med. 2012, 5, 165-172.
14. 68Ga-DOTA-TATE. Eur. J. Nucl. Med. Mol. Imag. 2010, 37, 2004-2010.
15. 68Ga-DOTATOC. J. Nucl. Med. 2011, 52, 123-131.
16. Craig, A.S.; Parker, D.; Adams, H.; Bailey, N.A. Stability, 71Ga NMR, and crystal structure of a neutral gallium(III) complex of 1,4,7- triazacyclononanetriacetate: a potential radio-pharmaceutical? J. Chem. Soc. Chem. Comm. 1989, 1793-1794.
17. 68Ga BAPEN kit for myocardial positron emission tomography imaging and biodistribution study. Nucl. Med.Biol. 2010, 37, 149-155.
18. Fellner, M.; Baum, R.P.; Kubicek, V.; Hermann, P.; Lukes, I.; Prasad, V.; Rosch, F. PET/CT imaging of osteoblastic bone metastases with (68)Ga-bisphosphonates: first human study. Eur. J. Nucl. Med. Mol. Imag. 2010, 37, 834.
19. Shetty, D.; Jeong, J.M.; Ju, C.H.; Kim, Y.J.; Lee, J.Y.; Lee, Y.S.; Lee, D.S.; Chung, J.K.; Lee, M.C. Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography. Bioorg. Med. Chem. 2010, 18, 7338-7347.
20. 68Ga-labeled amino acid derivatives for positron emission tomography of cancer cells. Nucl. Med. Biol. 2010, 37, 893-902.
21. Burchardt, C.; Riss, P.J.; Zoller, F.; Maschauer, S.; Prante, O.; Kuwert, T.; Roesch, F. [(68)Ga]Ga-DO(2)A-(OBu-l-tyr)(2): synthesis, (68)Ga-radiolabeling and in vitro studies of a novel (68)Ga-DO(2)A-tyrosine conjugate as potential tumor tracer for PET. Bioorg. Med. Chem. Lett. 2009, 19, 3498-3501.
22. 68Ga: practical aspects of radiolabelling. Contrast Med. Mol. Imag. 2011, 6, 492-498.
23. Bode, B.P. Recent molecular advances in mammalian glutamine transport. J. Nutrit. 2001, 131, 2475S-2485S.
24. DeBerardinis, R.J.; Mancuso, A.; Daikhin, E.; Nissim, I.; Yudkoff, M.; Wehrli, S.; Thompson, C.B. Beyond aerobic glycolysis: transformed cells can engage in glutamine metabolism that exceeds the requirement for protein and nucleotide synthesis. Proc. Natl. Acad. Sci. USA 2007, 104, 19345-19350.
25. Geninatti Crich, S.; Cabella, C.; Barge, A.; Belfiore, S.; Ghirelli, C.; Lattuada, L.; Lanzardo, S.; Mortillaro, A.; Tei, L.; Visigalli, M.; Forni, G.; Aime, S. In vitro and in vivo magnetic resonance detection of tumor cells by targeting glutamine transporters with Gd-based probes. J. Med. Chem. 2006, 49, 4926-4936.
26. Kim, C.S.; Cho, S.H.; Chun, H.S.; Lee, S.Y.; Endou, H.; Kanai, Y.; Kim do, K. BCH, an inhibitor of system L amino acid transporters, induces apoptosis in cancer cells. Biol. Pharm. Bull. 2008, 31, 1096-1100.
27. Ennis, S.R.; Ren, X.D.; Betz, A.L. Transport of alpha-aminoisobutyric acid across the blood-brain barrier studied with in situ perfusion of rat brain. Brain Res. 1994, 643, 100-107.
28. Martins, A.F.; Prata, M.I.; Rodrigues, S.P.; Geraldes, C.F.; Riss, P.J.; Amor-Coarasa, A.; Burchardt, C.; Kroll, C.; Roesch, F. Spectroscopic, radiochemical, and theoretical studies of the Ga(3+) -N-2-hydroxyethyl piperazine-N'-2-ethanesulfonic acid (HEPES buffer) system: Evidence for the formation of Ga(3+) - HEPES complexes in (68) Ga labeling reactions. Contrast Med. Mol. Imag. 2013, 8, 265-273.
29. Mukai, T.; Suwada, J.; Sano, K.; Okada, M.; Yamamoto, F.; Maeda, M. Design 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, 4285-4289.
30. 68Ga-DOTA-glutamine. Ann. Nuc. Med. Sci. 2009, 22, 35-42.
31. Ščasnár, V.; Lier, J. The use of SEP-PAK Sl cartridges for the preparation of gallium chloride from the citrate solution. Eur. J. Nucl. Med. 1993, 20, 273-273.
32. 18F]fluoropropyl)homocysteine for tumor imaging using positron emission tomography. J. Med. Chem. 2011, 54, 1860-1870.
33. Lattuada, L.; Demattio, S.; Vincenzi, V.; Cabella, C.; Visigalli, M.; Aime, S.; Crich, S.G.; Gianolio, E. Magnetic resonance imaging of tumor cells by targeting the amino acid transport system. Bioorg. Med. Chem. Lett. 2006, 16, 4111-4114.
34. Stefania, R.; Tei, L.; Barge, A.; Geninatti Crich, S.; Szabo, I.; Cabella, C.; Cravotto, G.; Aime, S. Tuning glutamine binding modes in Gd-DOTA-based probes for an improved MRI visualization of tumor cells. Chemistry 2009, 15, 76-85.
35. Le, V.S. (68)Ga generator integrated system: elution-purification- concentration integration. Rec. Res. Can. Res. 2013, 194, 43-75.
36. Hahn, Gary Scott, Immunoregulatory Peptides. PCT Int. Appl 1986/004334, 31 July 1987. Ltd