Pycup - A bifunctional, cage-like ligand for 64Cu radiolabeling

Molecular Pharmaceutics

Volumn 11, Issue 2, 2014, Pages 617-629

  Boros, Eszter ^a   Rybak Akimova, Elena ^b   Holland, Jason P ^c,d   Rietz, Tyson ^a   Rotile, Nicholas ^a   Blasi, Francesco ^a   Day, Helen ^a   Latifi, Reza ^b   Caravan, Peter ^a  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b TUFTS UNIVERSITY   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

^d AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

Author keywords

chelator; copper; fibrin; positron emission tomography

Indexed keywords

1,8 (2,6 PYRIDINEDIMETHYLENE) 1,4,8,11 TETRAAZACYCLOTETRADECANE 2,4 DIACETIC ACID; 1,8 (2,6 PYRIDINEDIMETHYLENE) 2,4 DIBENZYL 1,4,8,11 TETRAAZACYCLOTETRADECANE; 1,8 (2,6 PYRIDINEDIMETHYLENE) 4 BENZYL 1,4,8,11 TETRAAZACYCLOTETRADECANE 8 ACETIC ACID; ARGINYLGLYCYLASPARTIC ACID; BOMBESIN DERIVATIVE; COPPER 64; COPPER COMPLEX; CUPRIC ION; CYCLAM DERIVATIVE; HYDROGEN; IOPAMIDOL; PEPTIDE CONJUGATE PEP(12); TETRAXETAN; UNCLASSIFIED DRUG; 1,8-(2,6-PYRIDINEDIMETHYLENE)-1,4,8,11-TETRAAZACYCLOTETRADECANE-2,4-DIACETIC ACID; BRIDGED COMPOUND; CHELATING AGENT; COORDINATION COMPOUND; COPPER; LIGAND; SINGLE HETEROCYCLIC RINGS;

ALKYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CAROTID ARTERY THROMBOSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; COMPUTED TOMOGRAPHIC ANGIOGRAPHY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY CLEARANCE; LIGAND BINDING; MALE; MOUSE; NONHUMAN; PET SCANNER; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTEIN TARGETING; RADIOACTIVITY; RADIOCHEMISTRY; RADIONUCLIDE DOSE CALIBRATOR; RAT; RAT MODEL; SOLID PHASE EXTRACTION; X RAY CRYSTALLOGRAPHY; ANIMAL; CHEMISTRY; DRUG STABILITY; QUANTUM THEORY; WISTAR RAT;

ANIMALS; BRIDGED COMPOUNDS; CHELATING AGENTS; COORDINATION COMPLEXES; COPPER RADIOISOTOPES; CRYSTALLOGRAPHY, X-RAY; DRUG STABILITY; HETEROCYCLIC COMPOUNDS, 1-RING; LIGANDS; MALE; MODELS, MOLECULAR; POSITRON-EMISSION TOMOGRAPHY; QUANTUM THEORY; RATS; RATS, WISTAR;

EID: 84893317668     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400686z     Document Type: Article

References (48)

1. Holland, J.; Williamson, M.; Lewis, J. Unconventional nuclides for radiopharmaceuticals Mol. Imaging 2010, 9, 1-20
2. Wadas, T. J.; Wong, E. H.; Weisman, G. R.; Anderson, C. J. Copper Chelation Chemistry and its Role in Copper Radiopharmaceuticals Curr. Pharm. Des. 2007, 13, 3-16 (Pubitemid 46085298)
3. 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
4. Copper 64-ATSM and PET/CT Scan in Predicting Disease Progression in Patients With Newly-Diagnosed Stage IB, Stage II, Stage III, or Stage IVA Cervical Cancer Who Are Undergoing Radiation Therapy and Cisplatin Treatment. http://clinicaltrials.gov/show/NCT00794339 (accessed July 5, 2013).
5. 64Cu Inorg. Chem. 2012, 51, 6279-6284
6. Boswell, C. A.; Sun, X.; Niu, W.; Weisman, G. R.; Wong, E. H.; Rheingold, A. L.; Anderson, C. J. Comparative in Vivo Stability of Copper-64-Labeled Cross-Bridged and Conventional Tetraazamacrocyclic Complexes J. Med. Chem. 2004, 47, 1465-1474 (Pubitemid 38327472)
7. 177Lu Inorg. Chem. 2012, 51, 12575-12589
8. Sibbons, K. F.; Shastri, K.; Watkinson, M. The application of manganese complexes of ligands derived from 1,4,7-triazacyclononane in oxidative catalysis Dalton Trans. 2006, 5, 645-661
9. 64Cu complexes of bifunctional chelators Inorg. Chim. Acta 2012, 393, 318-323
10. Ma, M. T.; Cooper, M. S.; Paul, R. L.; Shaw, K. P.; Karas, J. A.; Scanlon, D.; White, J. M.; Blower, P. J.; Donnelly, P. S. Macrobicyclic Cage Amine Ligands for Copper Radiopharmaceuticals: A Single Bivalent Cage Amine Containing Two Lys3-bombesin Targeting Peptides Inorg. Chem. 2011, 50, 6701-6710
11. 3 Expression Bioconjugate Chem. 2010, 21, 1417-1424
12. Huang, S.; Joso, R.; Fuchs, A.; Barner, L.; Smith, S. V. Probing Solid-Liquid Interfaces Using Radiotracer Technology: Characterization of Functionalized Microspheres Chem. Mater. 2008, 20, 5375-5380
13. Wong, E. H.; Weisman, G. R.; Hill, D. C.; Reed, D. P.; Rogers, M. E.; Condon, J. P.; Fagan, M. A.; Calabrese, J. C.; Lam, K.-C.; Guzei, I. A.; Rheingold, A. L. Cross-bridged cyclams and pendant arm derivatives J. Am. Chem. Soc. 2000, 112, 10561
14. 64Cu-Labeled CB-TE2A and diamsar-conjugated RGD peptide analogs for targeting angiogenesis: comparison of their biological activity Nucl. Med. Biol. 2009, 36, 277-285
15. Tircsó, G.; Benyó, E. T.; Suh, E. H.; Jurek, P.; Kiefer, G. E.; Sherry, A. D.; Kovàcs, Z. (S)-5-(p-Nitrobenzyl)-PCTA, a Promising Bifunctional Ligand with Advantageous Metal Ion Complexation Kinetics Bioconjugate Chem. 2009, 20, 565-575
16. 64Cu-Labeled Bifunctional Chelate-Bombesin Conjugates Bioconjugate Chem. 2011, 22, 1729-1735
17. 3 Integrin Expression and Facile Radiosynthesis J. Nucl. Med. 2011, 52, 1276-1284
18. 111In via Maleimido Derivatives of DOTA and NODAGA Bioconjugate Chem. 2013, 24, 1102-1109
19. 64Cu- Complexing Bifunctional Chelators for Radioimmunoconjugation: Labeling Efficiency, Specific Activity, and in Vitro/in Vivo Stability Bioconjugate Chem. 2012, 23, 1029-1039
20. 64Cu-Radiolabeled Bioconjugate Bioconjugate Chem. 2012, 23, 330-335
21. Esteves, C. V.; Lamosa, P.; Delgado, R.; Costa, J.; Désogè re, P.; Rousselin, Y.; Goze, C.; Denat, F. Remarkable Inertness of Copper(II) Chelates of Cyclen-Based Macrobicycles with Two trans-N-Acetate Arms Inorg. Chem. 2013, 52, 5138-5153
22. Brandes, S.; Denat, F.; Lacour, S.; Rabiet, F.; Barbette, F.; Pullumbi, P.; Guilard, R. Synthesis of Macropolycyclic Ligands Based on Tetraazacycloalkanes Eur. J. Org. Chem. 1998, 11, 2349-2360 (Pubitemid 128536278)
23. 2+ Inorg. Chem. 2013, 52, 5246-5259
24. Lima, L. M. P.; Esteban-Gómez, D.; Delgado, R.; Platas-Iglesias, C.; Tripier, R. Monopicolinate Cyclen and Cyclam Derivatives for Stable Copper(II) Complexation Inorg. Chem. 2012, 51, 6916-6927
25. 64Cu-Labeling, and Bioconjugation of a New Bis(2-pyridylmethyl) Derivative of 1,4,7-Triazacyclononane Bioconjugate Chem. 2008, 19, 719-730 (Pubitemid 351436371)
26. Wynn, T.; Hegedus, L. S. Synthesis and Structural Studies of 1,8-Pyridine-Capped 5,12-Dioxocyclams J. Am. Chem. Soc. 2000, 122, 5034-5042 (Pubitemid 30354267)
27. Achmatowicz, M.; Hegedus, L. S.; David, S. Synthesis and Structural Studies of 5,12-Dioxocyclams Capped by 4-Substituted Pyridines Across the Amine Nitrogens J. Org. Chem. 2003, 68, 7661-7666 (Pubitemid 37203346)
28. Gil, J. M.; David, S.; Reiff, A. L.; Hegedus, L. S. Synthesis and Complexation of "Back-to-Back" Capped Bis-dioxocyclams Inorg. Chem. 2005, 44, 5858-5865 (Pubitemid 41174552)
29. 111In] for SPECT, PET and Targeted Therapeutic Applications of Somatostatin Receptor (hsst2) Expressing Tumors Bioconjugate Chem. 2002, 13, 530-541 (Pubitemid 34535940)
30. Krenning, E. P.; Kwekkeboom, D. J.; Bakker, W. H.; Breeman, W. A. P.; Kooij, P. P. M.; Oei, H. Y.; Vanhagen, M.; Postema, P. T. E.; Dejong, M.; Reubi, J. C.; Visser, T. J.; Reijs, A. E. M.; Hofland, L. J.; Koper, J. W.; Lamberts, S. W. J. Somatostatin Receptor Scintigraphy with [In-111-Dtpa-D-Phe(1)]- and [I-123-Tyr(3)]-Octreotide-the Rotterdam Experience with More Than 1000 Patients Eur. J. Nucl. Med. 1993, 20, 716-731 (Pubitemid 23284773)
31. Guo, Y.; Ferdani, R.; Anderson, C. J. Preparation and Biological Evaluation of 64Cu Labeled Tyr3-Octreotate Using a Phosphonic Acid-Based Cross-Bridged Macrocyclic Chelator Bioconjugate Chem. 2012, 23, 1470-1477
32. 111In-Labeled Bombesin Homodimer for Improved Imaging of GRPR-Positive Prostate Cancer Mol. Pharmaceutics 2013, 10, 1716-1724
33. 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 (Pubitemid 351717550)
34. Ciesienski, K. L.; Yang, Y.; Ay, I.; Chonde, D. B.; Loving, G. S.; Rietz, T. A.; Catana, C.; Caravan, P. Fibrin-Targeted PET Probes for the Detection of Thrombi Mol. Pharmaceutics 2013, 10, 1100-1110
35. Sheldrick, G. M. Phase annealing in SHELX-90: direct methods for larger structures Acta Crystallogr. 1990, A46, 467
36. Sheldrick, G. M. SHELXL 97, Program for Crystal Structure Analysis (Release 97-2); University Göttingen: Göttingen, 1997.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
38. Becke, A. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
39. Lee, C.; Yang, W.; Parr, R. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37, 785-789
40. Loening, A. M.; Gambhir, S. S. AMIDE: A Free Software Tool for Multimodality Medical Image Analysis Mol. Imaging 2003, 2, 131
41. Heroux, K. J.; Woodin, K. S.; Tranchemontagne, D. J.; Widger, P. C. B.; Southwick, E.; Wong, E. H.; Weisman, G. R.; Tomellini, S. A.; Wadas, T. J.; Anderson, C. J.; Kassel, S.; Golen, J. A.; Rheingold, A. L. The long and short of it: the influence of N-carboxyethyl versus N-carboxymethyl pendant arms on in vitro and in vivo behavior of copper complexes of cross-bridged tetraamine macrocycles Dalton Trans. 2007, 21, 2150-2162 (Pubitemid 46791134)
42. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2[prime or minute]-yl)-2,6-dithiaheptane] copper(II) perchlorate J. Chem. Soc., Dalton Trans. 1984, 7, 1349-1356
43. Kolodziej, A. F.; Nair, S. A.; Graham, P.; McMurry, T. J.; Ladner, R. C.; Wescott, C.; Sexton, D. J.; Caravan, P. Fibrin Specific Peptides Derived by Phage Display: Characterization of Peptides and Conjugates for Imaging Bioconjugate Chem. 2012, 23, 548-556
44. Botnar, R. M.; Buecker, A.; Wiethoff, A. J.; Parsons, E. C.; Katoh, M.; Katsimaglis, G.; Weisskoff, R. M.; Lauffer, R. B.; Graham, P. B.; Gunther, R. W.; Manning, W. J.; Spuentrup, E. In vivo magnetic resonance imaging of coronary thrombosis using a fibrin-binding molecular magnetic resonance contrast agent Circulation 2004, 110, 1463-1466 (Pubitemid 39238024)
45. Monroe, D. M.; Hoffman, M. What Does It Take to Make the Perfect Clot? Arterioscler. Thromb. Vasc. Biol. 2006, 26, 41-48 (Pubitemid 43732226)
46. Overoye-Chan, K.; Koerner, S.; Looby, R.; Kolodziej, A.; Zech, S.; Deng, Q.; Chasse, J.; McMurry, T.; Caravan, P. EP-2104R: a fibrin-specific gadolinium-Based MRI contrast agent for detection of thrombus J. Am. Chem. Soc. 2008, 130, 6025-6039 (Pubitemid 351620850)
47. Uppal, R.; Ciesienski, K. L.; Chonde, D. B.; Loving, G. S.; Caravan, P. Discrete Bimodal Probes for Thrombus Imaging J. Am. Chem. Soc. 2012, 134, 10799-10802
48. Uppal, R.; Ay, I.; Dai, G.; Kim, Y.; Sorensen, A.; Caravan, P. Molecular MRI of intracranial thrombus in a rat ischemic stroke model Stroke 2010, 41, 1271-1277