Synthesis, characterization, and in vitro evaluation of a radio-metal organic framework composed of in vivo generator 166Dy/166Ho and DOTMP as a novel agent for bone marrow ablation
-
Sara Vosoghi
,
Ali Bahrami-Samani
Abstract
In this study, the MOF concept contributed to the preparation of a novel, bone-ablating agent composed of Cu(II) using the in vivo generator 166Dy/166Ho and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP). The product was characterized (IR, elemental analysis: CHN, ICM-MS, PIXE, DLS, XRD) and quality-controlled (radio-thin layer chromatography (RTLC)). The stability and in vitro hydroxyapatite binding was checked up to one week at 37°C in human serum. Radio-MOF crystals and colloidal radio-MOF particles were obtained by varying the synthesizing conditions (including pH and temperature), and they had similar IR patterns and similar elemental analysis results. The estimated chemical formula was [1Lu-1Cu-1Cl-1DOTMP] for both. The final product was synthesized at pH = 8 while stirring at room temperature using 166Dy/166Ho-nitrate, CuCl2, and DOTMP (yield > 99%, RTLC). Dynamic light scattering (DLS) measurements showed particles in the size range of 60 to 100 nm for the resultant radio-MOF particles (RMP). In vitro binding experiments showed acceptable bone-seeking affinity of the prepared formula even after one week of storage in human serum at 37°C. Importantly, this is the first study of the use of the MOF concept to provide a highly-stable organometallic compound containing 166Dy/166Ho in vivo generator for bone marrow ablation.
Acknowledgement:
The authors are grateful for support of this study by Nuclear Science and Technology Research Institute.
References
1. Bartlett, M. L., Webb, M., Durrant, S., Morton, J. A., Allison, R., Macfarlane, D. J.: Dosimetry and toxicity of Quadramet for bone marrow ablation in multiple myeloma and other haematological malignancies. European Journal of Nuclear Medicine and Molecular Imaging 29, 1470 (2002).10.1007/s00259-002-0934-ySuche in Google Scholar PubMed
2. Bayouth, J. E., Macey, D. J.: Dosimetry considerations of boneseeking radionuclides for marrow ablation. Medical Physics 20, 1089 (1993).10.1118/1.597005Suche in Google Scholar PubMed
3. Sohaib, M., Ahmad, M., Jehangir, M., Perveen, A.: Ethylene diamine tetramethylene phosphonic acid labeled with various β-emitting radiometals: labeling optimization and animal biodistribution. Cancer Biotherapy & Radiopharmaceuticals 26, 159 (2011).10.1089/cbr.2010.0846Suche in Google Scholar PubMed
4. Fritzberg, A. R., Abrams, P. G., Tatalick, L. M., Thoelke, K. R., Bryan, J. K., Hylarides, M. D., John, E. K.: U.S. Patent No. 6,767,531. Washington, DC: U.S. Patent and Trademark Office (2004).Suche in Google Scholar
5. Rajendran, J. G., Eary, J. F., Bensinger,W., Durack, L. D., Vernon, C., Fritzberg, A.: High-dose 166Ho-DOTMP in myeloablative treatment of multiple myeloma: pharmacokinetics, biodistribution, and absorbed dose estimation. Journal of Nuclear Medicine 43, 1383 (2002).Suche in Google Scholar
6. Turner, J.H., Claringbold, P. G., Berger, J. D., Martindale, A. A., Glancy, J. R.: 153Sm-EDTMP and melphalan chemoradiotherapy regimen for bone marrow ablation prior to marrow transplantation: an experimentalmodel in the rat. Nuclear Medicine Communications 13, 321 (1992).10.1097/00006231-199205000-00005Suche in Google Scholar PubMed
7. Macfarlane, D. J., Durrant, S., Bartlett, M. L., Allison, R., Morton, A. J.: 153Sm EDTMP for bone marrow ablation prior to stem cell transplantation for haematological malignancies. Nuclear Medicine Communications 23, 1099 (2002).10.1097/00006231-200211000-00010Suche in Google Scholar PubMed
8. Turner, J. H., Claringbold, P. G., Manning, L. S., O’Donoghue, H. L., Berger, J. D., Glancy, R. J.: Radiopharmaceutical therapy of 5T33 murine myeloma by sequential treatment with samarium-153 ethylenediaminetetramethylene phosphonate, melphalan, and bone marrow transplantation. Journal of the National Cancer Institute 85, 1508 (1993).10.1093/jnci/85.18.1508Suche in Google Scholar PubMed
9. Bayouth, J. E., Macey, D. J., Kasi, L. P., Garlich, J. R., McMillan, K., Dimopoulos, M. A., Champlin, R. E.: Pharmacokinetics, dosimetry and toxicity of holmium-166-DOTMP for bone marrow ablation in multiple myeloma. Journal of Nuclear Medicine, official publication, Society of Nuclear Medicine 36, 730 (1995).Suche in Google Scholar
10. Bayouth, J. E., Macey, D. J., Boyer, A. L., Champlin, R. E.: Radiation dose distribution within the bone marrow of patients receiving holmium-166-labeled phosphonate for marrow ablation. Medical Physics 22, 743 (1995).10.1118/1.597491Suche in Google Scholar PubMed
11. Bensinger, B., Giralt, S., Eary, J. F.: 166Holmium-DOTMP Plus Standard High Dose Chemotherapy (HDC) with Autologous Transplant Produce High Rates of Complete Remission (CR) in Multiple Myeloma (MM) Patients: An Updated Report of a Phase I/II Study. In Proceedings of the American Society of Clinical Oncology 20 (2001).Suche in Google Scholar
12. Parks, N. J., Kawakami, T. G., Avila, M. J., White, R., Cain, G. R., Raaka, S. D., Seibert, J. A.: Bone marrow transplantation in dogs after radio-ablation with a new Ho-166 amino phosphonic acid bone-seeking agent (DOTMP). Blood 82, 318 (1993).10.1182/blood.V82.1.318.bloodjournal821318Suche in Google Scholar
13. Appelbaum, F. R., Brown, P. A., Sandmaier, B.M., Storb, R., Fisher, D. R., Shulman, H.M., Graham, T. C., Schuening, F. G., Deeg, H. J., Bianco, J. A., Ketring, A. R., Kaplan, D.: Specific marrow ablation before marrow transplantation using an aminophosphonic acid conjugate 166Ho-EDTMP. Blood 80, 1608 (1992).10.1182/blood.V80.6.1608.1608Suche in Google Scholar
14. Zolghadri, S., Jalilian, A. R., Yousefnia, H., Bahrami-Samani, A., Fazaeli, Y., Pouladi, M., Ghannadi-Maragheh, M., Afarideh, H.: The synthesis, radiolabeling and first biological evaluation of a new 166Ho-complex for radiotherapy of bone metastases. Radiochimica Acta International Journal for Chemical Aspects of Nuclear Science and Technology 101, 445 (2013).10.1524/ract.2013.2042Suche in Google Scholar
15. Yousefnia, H., Zolghadri, S., Jalilian, A. R., Tajik, M., Ghannadi-Maragheh, M.: Preliminary dosimetric evaluation of 166Ho-TTHMP for human based on biodistribution data in rats. Applied Radiation and Isotopes 94, 260 (2014).10.1016/j.apradiso.2014.08.017Suche in Google Scholar
16. Ma, D., Jurisson, S. S., Ehrhardt, G. J., Yelon, W. B., Ketring, A. R.: Development of the Dy-166/Ho-166 in vivo generator for radionuclide therapy. In Proc. 40th Annual Meeting Society of Nuclear Medicine, J. Nucl. Med. 34, 231 (1992).Suche in Google Scholar
17. Mirzadeh, S., Kumar, K., Gansow, O. A.: The chemical fate of 212Bi-DOTA formed by β -decay of 212Pb (DOTA). Radiochimca Acta 60, 1 (1993).10.1524/ract.1993.60.1.1Suche in Google Scholar
18. Mirzadeh, S., Ambrose, K. R., Beets, A. L., Callahan, A. P., McPherson, D.W., Hasan, A., Lambert, C. R.: ORNL Nuclear Medicine Program Progress Report, ORNL/TM-12159, 611 (1992).Suche in Google Scholar
19. Mirzadeh, S. et al.: ORNL Nuclear Medicine Program Progress Report, ORNL/TM-12485, 12 (1993b).Suche in Google Scholar
20. Mausner, L. F., Straub, R. F., Srivastava, S. C.: The in vivo generator for radioimmunotherapy. Journal of Labelled Compounds and Radiopharmaceuticals 26, 498 (1989).10.1002/jlcr.25802601213Suche in Google Scholar
21. Smith, S. V., Di Bartolo, N., Mirzadeh, S., Lambrecht, R.M., Knapp, F. F., Hetherington, E. L.: [166Dy] dysporium/[166Ho] holmium in vivo generator. Applied Radiation and Isotopes 46, 759 (1995).10.1016/0969-8043(94)00149-TSuche in Google Scholar
22. Pedraza-López, M., Ferro-Flores, G., de Murphy, C. A., Tendilla, J. I., Villanueva-Sánchez, O.: Preparation of 166Dy/166Ho-EDTMP: a potential in vivo generator system for bone marrow ablation. Nuclear Medicine Communications 25, 615 (2004).10.1097/01.mnm.0000126516.57329.07Suche in Google Scholar PubMed
23. Dadachova, E., Mirzadeh, S., Lambrecht, R. M., Hetherington, E. L., Knapp Jr, F. F.: Separation of carrier-free holmium-166 from neutron-irradiated dysprosium targets. Analytical Chemistry 66, 4272 (1994).10.1021/ac00095a024Suche in Google Scholar
24. Park, K. B., Kim, J. R., Lambrecht, R.M.: Metal macroaggregates for therapeutic purpose and the manufacturing process. Patent pending, Republic of Korea, 29 December, (1993).Suche in Google Scholar
25. Parks, N. J., Kawakami, T. G., Avila, M. J., White, R., Cain, G. R., Raaka, S. D., Hornoff, W., Fisher, p., Moore, p., Seibert, J. A.: Bone marrow transplantation in dogs after radio-ablation with a new Ho-166 amino phosphonic acid bone-seeking agent (DOTMP). Blood 82, 318 (1993).10.1182/blood.V82.1.318.bloodjournal821318Suche in Google Scholar
26. Turner, J. H., Claringbold, P.G., Klemp, P. F. B., Norman, P. E., Glancy, R. J., Hetherington, E. L., Najdovski, L., Lambrecht, R. M.: Hepatic arterial holmium-166 microsphere radiotherapy of liver metastasis: a SPECT dosimetry model in the pig. Eur. J. Nucl. Med. 20, 986 (1993).Suche in Google Scholar
27. Mumper, R. J., Ryo, U. Y., Jay, M.: Neutron-activated holmium-166-poly (L-lactic acid) microspheres: a potential agent for the internal radiation therapy of hepatic tumors. Journal of Nuclear Medicine, official publication, Society of Nuclear Medicine 32, 2139 (1991).Suche in Google Scholar
28. Shannon, R. T.:. Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallographica Section A: Crystal Physics, Diffraction, Theoretical and General Crystallography 32, 751 (1976).10.1107/S0567739476001551Suche in Google Scholar
29. Carne-Saìnchez, A., Bonnet, C. S., Imaz, I., Lorenzo, J., Tìt, E., Maspoch, D.: Relaxometry studies of a highly stable nanoscale metal–organic framework made of Cu(II), Gd(III), and the macrocyclic DOTP. Journal of the American Chemical Society 135, 17711 (2013).10.1021/ja4094378Suche in Google Scholar PubMed
30. Silva, P., Vilela, S. M., Tomé, J. P., Paz, F. A. A.: Multifunctional metal–organic frameworks: from academia to industrial applications. Chemical Society Reviews 44, 6774 (2015).10.1039/C5CS00307ESuche in Google Scholar PubMed
31. Zhou, Hong-Cai., Kitagawa, Susumu.: Metal–organic frameworks (MOFs). Chemical Society Reviews 43, 5415 (2014).10.1039/C4CS90059FSuche in Google Scholar
32. Lin, Z. J., Lü, J., Hong, M., Cao, R.: Metal–organic frameworks based on flexible ligands (FL-MOFs): structures and applications. Chemical Society Reviews 43, 5867 (2014).10.1039/C3CS60483GSuche in Google Scholar PubMed
33. Lu, W., Wei, Z., Gu, Z. Y., Liu, T. F., Park, J., Park, J., Tian, J., Zhang, M., Zhang, Q., Gentle III, T., Bosch, M., Zhou, H. C.: Tuning the structure and function of metal–organic frameworks via linker design. Chemical Society Reviews 43, 5561 (2014).10.1039/C4CS00003JSuche in Google Scholar PubMed
34. Zhang, Z., Zaworotko, M. J.: Template-directed synthesis of metal–organic materials. Chemical Society Reviews 43, 5444 (2014).10.1039/C4CS00075GSuche in Google Scholar
35. Horwitz, E. P., McAlister, D. R., Bond, A. H., Barrans, R. E., Williamson, J.M.: A process for the separation of 177Lufrom neutron irradiated 176Ybtargets. Applied Radiation and Isotopes 63, 23 (2005).10.1016/j.apradiso.2005.02.005Suche in Google Scholar PubMed
36. Ma, T. Y., Zhang, X. J., Shao, G. S., Cao, J. L., Yuan, Z. Y.: Ordered macroporous titanium phosphonate materials: synthesis, photocatalytic activity, and heavy metal ion adsorption. The Journal of Physical Chemistry C 112, 3090 (2008).10.1021/jp710636xSuche in Google Scholar
37. Pavia, D., Lampman, G., Kriz, G., Vyvyan, J.: Introduction to spectroscopy. 5nd edn., Inc., Cengage Learning, Stanford (2008).Suche in Google Scholar
38. Silverstein, R.M., Webster, F. X., Kiemle, D., Bryce, D. L.: Spectrometric identification of organic compounds. 8nd edn., Inc., John Wiley and Sons, New York 2014.Suche in Google Scholar
©2016 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Solvent extraction of Th(IV) from aqueous solution with methylimidazole in ionic liquid
- Multiparametric study of thorium oxide dissolution in aqueous media
- Evaluation of consequence due to higher hydrazine content in partitioning stream of PUREX process
- Optimization of the electrochemical pre-concentration of trivalent lanthanum from aqueous media
- Synthesis, characterization, and in vitro evaluation of a radio-metal organic framework composed of in vivo generator 166Dy/166Ho and DOTMP as a novel agent for bone marrow ablation
- Development and biological evaluation of 90Y-BPAMD as a novel bone seeking therapeutic Agent
- Determination of distribution coefficients (Kd) of various radionuclides on UTEVA resin
- IonLab – a remote-controlled experiment for academic and vocational education and training on extraction chromatography and ion exchange
Artikel in diesem Heft
- Frontmatter
- Solvent extraction of Th(IV) from aqueous solution with methylimidazole in ionic liquid
- Multiparametric study of thorium oxide dissolution in aqueous media
- Evaluation of consequence due to higher hydrazine content in partitioning stream of PUREX process
- Optimization of the electrochemical pre-concentration of trivalent lanthanum from aqueous media
- Synthesis, characterization, and in vitro evaluation of a radio-metal organic framework composed of in vivo generator 166Dy/166Ho and DOTMP as a novel agent for bone marrow ablation
- Development and biological evaluation of 90Y-BPAMD as a novel bone seeking therapeutic Agent
- Determination of distribution coefficients (Kd) of various radionuclides on UTEVA resin
- IonLab – a remote-controlled experiment for academic and vocational education and training on extraction chromatography and ion exchange
