RGD conjugates of the H 2dedpa scaffold: Synthesis, labeling and imaging with 68Ga

Nuclear Medicine and Biology

Volumn 39, Issue 6, 2012, Pages 785-794

  Boros, Eszter ^a,b   Ferreira, Cara L ^c   Yapp, Donald T T ^d   Gill, Rajanvir K ^d   Price, Eric W ^a,b   Adam, Michael J ^b   Orvig, Chris ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b TRIUMF   (Canada)

^c MDS Inc   (Canada)

^d BRITISH COLUMBIA CANCER AGENCY   (Canada)

Author keywords

v 3 integrin; 67Ga; 68Ga; Bifunctional chelates; CRGDyK; Transferrin

Indexed keywords

CHELATE; DIMERIC H2RGD 2; H2DP BB NCS; H2DP N NCS; MONOMERIC H2RGD 1; PENTAPEPTIDE; RADIOISOTOPE; RGD 1 GA 68; RGD 2 GA 68; TRANSFERRIN; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR; ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; CHELATING AGENT; CROSS LINKING REAGENT; DIAGNOSTIC AGENT; ETHYLENEDIAMINE DERIVATIVE; GALLIUM; OLIGOPEPTIDE; PICOLINIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG BINDING; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; DRUG TISSUE LEVEL; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; LIGAND BINDING; MOUSE; NONHUMAN; PROTEIN STABILITY; PROTEIN TARGETING; ROOM TEMPERATURE; SUBCUTANEOUS TISSUE TUMOR; TUMOR XENOGRAFT; ANIMAL; BINDING COMPETITION; CHEMISTRY; HUMAN; MALE; METABOLISM; RADIOCHEMISTRY; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; BINDING, COMPETITIVE; CELL LINE, TUMOR; CHELATING AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; CROSS-LINKING REAGENTS; ETHYLENEDIAMINES; GALLIUM RADIOISOTOPES; HUMANS; INTEGRIN ALPHAVBETA3; ISOTOPE LABELING; MALE; MICE; OLIGOPEPTIDES; PICOLINIC ACIDS; RADIOCHEMISTRY;

EID: 84864026040     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.01.003     Document Type: Article

References (27)

1. Wadas T.J., Wong E.H., Weisman G.R., Anderson C.J. Coordinating radiometals of copper, gallium, indium, yttrium, and zirconium for PET and SPECT imaging of disease. Chem Rev 2010, 110:2858-2902.
2. Bandoli G., Dolmella A., Porchia M., Refosco F., Tisato F. Structural overview of technetium compounds (1993-1999). Coord Chem Rev 2001, 214:43-90.
3. Wadas T.J., Wong E.H., Weisman G.R., Anderson C.J. Chem Rev 2010, 110:2858-2902.
4. Bartholomä M.D., Louie A.S., Valliant J.F., Zubieta J. Technetium and gallium derived radiopharmaceuticals: comparing and contrasting the chemistry of two important radiometals for the molecular imaging era. Chem Rev 2010, 110:2903-2920.
5. Harris W.R., Pecoraro V.L. Thermodynamic binding constants for gallium transferrin. Biochemistry 1983, 22:292-299.
6. 111In] for SPECT, PET, and targeted therapeutic applications of somatostatin receptor (hsst2) expressing tumors. Bioconjug Chem 2002, 13:530-541.
7. 3 integrin expression and facile radiosynthesis. J Nucl Med 2011, 52:1276-1284.
8. Singh A.N., Liu W., Hao G., Kumar A., Gupta A., Öz O.K., et al. Multivalent bifunctional chelator scaffolds for gallium-68 based positron emission tomography imaging probe design: signal amplification via multivalency. Bioconjug Chem 2011, 22:1650-1662.
9. 68Ga tracers for positron emission tomography. Chem Eur J 2010, 16:7174-7185.
10. Tircsó G., Benyó E.T., Suh E.H., Jurek P., Kiefer G.E., Sherry A.D., et al. (S)-5-(p-nitrobenzyl)-PCTA, a promising bifunctional ligand with advantageous metal ion complexation kinetics. Bioconjug Chem 2009, 20:565-575.
11. Ferreira C.L., Lamsa E., Woods M., Duan Y., Fernando P., Bensimon C., et al. Evaluation of bifunctional chelates for the development of gallium-based radiopharmaceuticals. Bioconjug Chem 2010, 21:531-536.
12. 64Cu-labeled bifunctional chelate-bombesin conjugates. Bioconjug Chem 2011, 22:1729-1735.
13. Berry D.J., Ma Y., Ballinger J.R., Tavare R., Koers A., Sunassee K., et al. Efficient bifunctional gallium-68 chelators for positron emission tomography: Tris(hydroxypyridinone) ligands. Chem Commun 2011, 47:7068-7070.
14. 68Ga PET imaging agent elaboration. J Am Chem Soc 2010, 132:15726-15733.
15. Eliceiri B.P., Cheresh D.A. The role of αv integrins during angiogenesis: insights into potential mechanisms of action and clinical development. J Clin Invest 1999, 103:1227-1230.
16. DeNardo S.J., Liu R., Albrecht H., Natarajan A., Sutcliffe J.L., Anderson C., et al. 111In-LLP2A-DOTA polyethylene glycol-targeting 4β1 integrin: comparative pharmacokinetics for imaging and therapy of lymphoid malignancies. J Nucl Med 2009, 50:625-634.
17. Liu W., Hao G., Long M.A., Anthony T., Hsieh J.T., Sun X. Imparting multivalency to a bifunctional chelator: a scaffold design for targeted PET imaging probes. Angew Chem Int Ed 2009, 48:7346-7349.
18. Platas-Iglesias C., Mato-Iglesias M., Djanashvili K., Muller R.N., Elst L.V., Peters J.A., et al. Lanthanide chelates containing pyridine units with potential application as contrast agents in magnetic resonance imaging. Chem Eur J 2004, 10:3579-3590.
19. Zeng X., Coquiere D., Alenda A., Garrier E., Prange T., Li Y., et al. Efficient synthesis of calix[6]tmpa: a new calix[6]azacryptand with unique conformational and host-guest properties. Chem Eur J 2006, 12:6393-6402.
20. Ali M.S., Quadri S.Y. Maleimido derivatives of diethylenetriaminepentaacetic acid and triethylenetetraaminehexaacetic acid: their synthesis and potential for specific conjugation with biomolecules. Bioconjug Chem 1996, 7:576-583.
21. 3-positive breast cancer. Bioconjug Chem 2007, 18:438-446.
22. Wieholt C., Hsiao I., Lin K., Chung Y., Chen C., Yen T. Performance evaluation of small animal PET system using NEMA standards. J Nucl Med 2008, 49.
23. Corson D.T., Meares C.F. Efficient multigram synthesis of the bifunctional chelating agent (S)-1-p-isothiocyanatobenzyl-diethylene-tetraaminepentaacetic acid. Bioconjug Chem 2000, 11:292-299.
24. 3-targeted radiotracers: maximizing binding affinity via bivalency. Bioconjug Chem 2009, 20:2199-2213.
25. Chen K., Xie J., Chen X. RGD-human serum albumin conjugates as efficient tumor targeting probes. Mol Imaging 2009, 8:65-73.
26. 3 expression. Eur J Nucl Med Mol Imaging 2008, 35:1100-1108.
27. 2dedpa scaffold with improved clearance and persistent heart uptake. Nucl Med Biol 2011, 38:1165-1174.