Mild and efficient 64Cu labeling of perhydro-1, 4-diazepine derivatives for potential use with large peptides, proteins and antibodies
-
Lukas Greifenstein
Abstract
DATA (6-Amino-1,4-diazapine-triacetate) and AAZTA (6-Amino-1,4-diazapine-tetracetate) chelators represent a novel approach representing hybrid-chelates: possessing significant cyclic and acyclic character. It is believed that flexibility of the acyclic part facilitates rapid complexation, whilst the preorganized cyclic part minimizes the energy barrier to complexation and inhibits decomplexation processes. So far, these chelators have been used exclusively with 44Sc and 68Ga only. Recent results with natCu predict high stabilities for Cu-AAZTA, yet no radioactive labeling of AAZTA or DATA with 64Cu or any additional radioactive isotope has been reported. We present the one pot synthesis of the bifunctional derivatives AAZTA5OMe and DATA5mOMe and their labeling with 64Cu. In addition, in vitro stability of the respective complexes are presented.
References
1. Anderson, C. J., Ferdani, R.: Copper-64 radiopharmaceuticals for PET imaging of cancer: advances in preclinical and clinical research. Cancer Biother. Radiopharm. 24, 379 (2009).10.1089/cbr.2009.0674Suche in Google Scholar PubMed PubMed Central
2. Niccoli Asabella, A., Cascini, G. L., Altini, C., Paparella, D., Notaristefano, A., Rubini, G.: The copper radioisotopes: a systematic review with special interest to 64Cu. Biomed. Res. Int. 2014, 786463 (2014).10.1155/2014/786463Suche in Google Scholar PubMed PubMed Central
3. Shokeen, M., Anderson, C. J.: Molecular imaging of cancer with copper-64 radiopharmaceuticals and positron emission tomography (PET). Acc. Chem. Res. 42, 832 (2009).10.1021/ar800255qSuche in Google Scholar PubMed PubMed Central
4. Wu, N., Kang, C. S., Sin, I., Ren, S., Liu, D., Ruthengael, V. C., Lewis, M. R., Chong, H.-S.: Promising bifunctional chelators for copper 64-PET imaging: practical 64Cu radiolabeling and high in vitro and in vivo complex stability. J. Biol. Chem. 21, 177 (2015).10.1007/s00775-015-1318-7Suche in Google Scholar PubMed PubMed Central
5. Kumar, A., Hao, G., Liu, L., Ramezani, S., Hsieh, J.-T., Öz, O. K., Sun, X.: Click-chemistry strategy for labeling antibodies with copper-64 via a cross-bridged tetraazamacrocyclic chelator scaffold. Bioconj. Chem. 26, 782 (2015).10.1021/acs.bioconjchem.5b00102Suche in Google Scholar PubMed PubMed Central
6. Banerjee, S. R., Pullambhatla, M., Foss, C. A., Nimmagadda, S., Ferdani, R., Anderson, C. J., Mease, R. C., Pomper, M. G.: 64Cu-labeled inhibitors of prostate-specific membrane antigen for PET imaging of prostate cancer. J. Med. Chem. 57, 2657 (2014).10.1021/jm401921jSuche in Google Scholar PubMed PubMed Central
7. Novak-Hofer, I., Schubiger, P. A.: Copper-67 as a therapeutic nuclide for radioimmunotherapy. EJNMMI 29, 821 (2002).10.1007/s00259-001-0724-ySuche in Google Scholar PubMed
8. Smith, N. A., Bowers, D. L., Ehst, D. A.: The production, separation, and use of 67Cu for radioimmunotherapy: a review. Appl. Radiat. Isot. 70, 2377 (2012).10.1016/j.apradiso.2012.07.009Suche in Google Scholar PubMed
9. Ahmedova, A., Todorov, B., Burdzhiev, N., Goze, C.: Copper radiopharmaceuticals for theranostic applications. Eur. J. Med. Chem. 157, 1406 (2018).10.1016/j.ejmech.2018.08.051Suche in Google Scholar PubMed
10. Conry, R. R.: Copper: inorganic & coordination chemistry based in part on the article copper: inorganic & coordination chemistry by Rebecca R. Conry & Kenneth D. Karlin which appeared in the encyclopedia of inorganic chemistry, First Edition. In: R. B. King, R. H. Crabtree, C. M. Lukehart, D. A. Atwood, R. A. Scott (Eds.), Encyclopedia of Inorganic Chemistry (2006), John Wiley & Sons, Ltd, Chichester, UK, p. 2309.10.1002/0470862106.ia052Suche in Google Scholar
11. Wadas, T. J., Wong, E. H., Weisman, G. R., Anderson, C. J.: Copper chelation chemistry and its role in copper radiopharmaceuticals. Curr. Pharm. Res. 13, 3 (2007).10.2174/138161207779313768Suche in Google Scholar PubMed
12. Nurchi, V. M., Crisponi, G., Crespo-Alonso, M., Lachowicz, J. I., Szewczuk, Z., Cooper, G. J. S.: Complex formation equilibria of Cu(II) and Zn(II) with triethylenetetramine and its mono- and di-acetyl metabolites. Dalton Trans. 42, 6161 (2013).10.1039/C2DT32252HSuche in Google Scholar
13. 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. 110, 2858 (2010).10.1021/cr900325hSuche in Google Scholar PubMed PubMed Central
14. Cai, Z., Anderson, C. J.: Chelators for copper radionuclides in positron emission tomography radiopharmaceuticals. J. Labed. Compd. Radiopharm. 57, 224 (2013).10.1002/jlcr.3165Suche in Google Scholar PubMed PubMed Central
15. Aime, S., Calabi, L., Cavallotti, C., Gianolio, E., Giovenzana, G. B., Losi, P., Maiocchi, A., Palmisano, G., Sisti, M.: Gd-AAZTA: a new structural entry for an improved generation of MRI contrast agents. Inorg. Chem. 43, 7588 (2004).10.1021/ic0489692Suche in Google Scholar PubMed
16. Sengar, R. S., Nigam, A., Geib, S. J., Wiener, E. C.: Syntheses and crystal structures of gadolinium and europium complexes of AAZTA analogues. Polyhedron. 28, 1525 (2009).10.1016/j.poly.2009.03.005Suche in Google Scholar
17. Baranyai, Z., Uggeri, F., Maiocchi, A., Giovenzana, G. B., Cavallotti, C., Takács, A., Tóth, I., Bányai, I., Bényei, A., Brucher, E., Aime, S.: Equilibrium, kinetic and structural studies of AAZTA complexes with Ga3+ In3+ and Cu2+. Eur. J. Inorg. Chem. 2013, 147 (2013).10.1002/ejic.201201108Suche in Google Scholar
18. Tei, L., Gugliotta, G., Fekete, M., Kálmán, F. K., Botta, M.: Mn(II) complexes of novel hexadentate AAZTA-like chelators: a solution thermodynamics and relaxometric study. Dalton Trans. 40, 2025 (2011).10.1039/c0dt01114bSuche in Google Scholar PubMed
19. Vágner, A., D’Alessandria, C., Gambino, G., Schwaiger, M., Aime, S., Maiocchi, A., Tóth, I., Baranyai, Z., Tei, L.: A rigidified AAZTA-like ligand as efficient chelator for 68Ga radiopharmaceuticals. Chemistry Select. 1, 163 (2016).10.1002/slct.201500051Suche in Google Scholar
20. Farkas, E., Nagel, J., Waldron, B. P., Parker, D., Tóth, I., Brücher, E., Rösch, F., Baranyai, Z.: Equilibrium, kinetic and structural properties of gallium(III) and some divalent metal complexes formed with the new DATAm and DATA5m ligands. Chemistry 23, 10358 (2017).10.1002/chem.201701508Suche in Google Scholar PubMed
21. Nagy, G., Szikra, D., Trencsényi, G., Fekete, A., Garai, I., Giani, A. M., Negri, R., Masciocchi, N., Maiocchi, A., Uggeri, F., Tóth, I., Aime, S., Giovenzana, G. B., Baranyai, Z.: AAZTA: An ideal chelating agent for the development of 44 Sc PET imaging agents. Angew. Chem. 129, 2150 (2017).10.1002/ange.201611207Suche in Google Scholar
22. Seemann, J., Waldron, B., Parker, D., Roesch, F.: DATATOC: a novel conjugate for kit-type 68Ga labelling of TOC at ambient temperature. EJNMMI Radiopharm. Chem. 1, 4 (2016).10.1186/s41181-016-0007-3Suche in Google Scholar
23. Nock, B. A., Kaloudi, A., Nagel, J., Sinnes, J.-P., Roesch, F., Maina, T.: Novel bifunctional DATA chelator for quick access to site-directed PET 68Ga-radiotracers: preclinical proof-of- principle with Tyr3octreotide. Dalton Trans. 46, 14584–14590 (2017).10.1039/C7DT01684KSuche in Google Scholar
24. Bass, L. A., Wang, M., Welch, M. J., Anderson, C. J.: In vivo transchelation of copper-64 from TETA-octreotide to superoxide dismutase in rat liver. Bioconj. Chem. 11, 527 (2000).10.1021/bc990167lSuche in Google Scholar
25. Moi, M. K., Meares, C. F., McCall, M. J., Cole, W. C., DeNardo, S. J.: Copper chelates as probes of biological systems: Stable copper complexes with a macrocyclic bifunctional chelating agent. Anal. Biochem. 148, 249 (1985).10.1016/0003-2697(85)90653-0Suche in Google Scholar
26. McQuade, P., Miao, Y., Yoo, J., Quinn, T. P., Welch, M. J., Lewis, J. S.: Imaging of melanoma using 64Cu- and 86Y-DOTA-ReCCMSH(Arg11), a cyclized peptide analogue of alpha-MSH. J. Med. Chem. 48, 2985 (2005).10.1021/jm0490282Suche in Google Scholar PubMed
27. Chen, X., Hou, Y., Tohme, M., Park, R., Khankaldyyan, V., Gonzales-Gomez, I., Bading, J. R., Laug, W. E., Conti, P. S.: Pegylated Arg-Gly-Asp peptide: 64Cu labeling and PET imaging of brain tumor alphavbeta3-integrin expression. J. Nucl. Med. 45, 1776 (2004).Suche in Google Scholar
28. Anderson, C. J., Jones, L. A., Bass, L. A., Sherman, E. L., McCarthy, D. W., Cutler, P. D., Lanahan, M. V., Cristel, M. E., Lewis, J. S., Schwarz, S. W.: Radiotherapy, toxicity and dosimetry of copper-64-TETA-octreotide in tumor-bearing rats. J. Nucl. Med. 39, 1944 (1998).Suche in Google Scholar
29. Chen, X., Park, R., Tohme, M., Shahinian, A. H., Bading, J. R., Conti, P. S.: MicroPET and autoradiographic imaging of breast cancer alpha v-integrin expression using 18F- and 64Cu-labeled RGD peptide. Bioconj. Chem. 15, 41 (2004).10.1021/bc0300403Suche in Google Scholar PubMed
30. Chen, X., Sievers, E., Hou, Y., Park, R., Tohme, M., Bart, R., Bremner, R., Bading, J. R., Conti, P. S.: Integrin αvβ3-targeted imaging of lung cancer. Neoplasia 7, 271 (2005).10.1593/neo.04538Suche in Google Scholar PubMed PubMed Central
31. Anderson, C. J., Dehdashti, F., Cutler, P. D., Schwarz, S. W., Laforest, R., Bass, L. A., Lewis, J. S., McCarthy, D. W.: 64Cu-TETA-octreotide as a PET imaging agent for patients with neuroendocrine tumors. J. Nucl. Med. 42, 213 (2001).Suche in Google Scholar
©2020 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Editorial
- Editorial
- Original papers
- Integral measurement of spectrum-averaged cross sections of a few threshold reactions induced by fast neutrons of a TRIGA reactor: comparison with integrated data from excitation functions given in various data libraries
- Quantum chemical studies of selective back-extraction of Am(III) from Eu(III) and Cm(III) with two hydrophilic 1,10-phenanthroline-2,9-bis-triazolyl ligands
- Luminescence of uranium(VI) after liquid-liquid extraction from HCl by Aliquat® 336 in n-dodecane:1-decanol by time-resolved laser-induced luminescence spectroscopy
- Volume oxidation of uranium mononitride and uranium monocarbide in the dry NOX-gaseous atmosphere
- Interference of Zr(IV) during the extraction of trivalent Nd(III) from the aqueous waste generated from metallic fuel reprocessing
- Mild and efficient 64Cu labeling of perhydro-1, 4-diazepine derivatives for potential use with large peptides, proteins and antibodies
- 68Ga CdTe/CdS fluorescent quantum dots for detection of tumors: investigation on the effect of nanoparticle size on stability and in vivo pharmacokinetics
- Natural radioactivity, radon emanating power and mass exhalation rate of environmental soil samples from Karabük province, Turkey
- Enhancing the physico-mechanical properties of irradiated rubber/waste plastic blend via incorporation of different fillers for industrial applications
- Corrigendum
- Corrigendum to: Effect of humic acid, fulvic acid, pH, ionic strength and temperature on 63Ni(II) sorption to MnO2
Artikel in diesem Heft
- Frontmatter
- Editorial
- Editorial
- Original papers
- Integral measurement of spectrum-averaged cross sections of a few threshold reactions induced by fast neutrons of a TRIGA reactor: comparison with integrated data from excitation functions given in various data libraries
- Quantum chemical studies of selective back-extraction of Am(III) from Eu(III) and Cm(III) with two hydrophilic 1,10-phenanthroline-2,9-bis-triazolyl ligands
- Luminescence of uranium(VI) after liquid-liquid extraction from HCl by Aliquat® 336 in n-dodecane:1-decanol by time-resolved laser-induced luminescence spectroscopy
- Volume oxidation of uranium mononitride and uranium monocarbide in the dry NOX-gaseous atmosphere
- Interference of Zr(IV) during the extraction of trivalent Nd(III) from the aqueous waste generated from metallic fuel reprocessing
- Mild and efficient 64Cu labeling of perhydro-1, 4-diazepine derivatives for potential use with large peptides, proteins and antibodies
- 68Ga CdTe/CdS fluorescent quantum dots for detection of tumors: investigation on the effect of nanoparticle size on stability and in vivo pharmacokinetics
- Natural radioactivity, radon emanating power and mass exhalation rate of environmental soil samples from Karabük province, Turkey
- Enhancing the physico-mechanical properties of irradiated rubber/waste plastic blend via incorporation of different fillers for industrial applications
- Corrigendum
- Corrigendum to: Effect of humic acid, fulvic acid, pH, ionic strength and temperature on 63Ni(II) sorption to MnO2
