Evaluation of nitrogen-rich macrocyclic ligands for the chelation of therapeutic bismuth radioisotopes
Abstract
The use of α-emitting isotopes for radionuclide therapy is a promising treatment strategy for small micro-metastatic disease. The radioisotope ²¹³Bi is a nuclide that has found substantial use for targeted α-therapy (TAT). The relatively unexplored aqueous chemistry of Bi³⁺, however, hinders the development of bifunctional chelating agents that can successfully deliver these Bi radioisotopes to the tumor cells. Here, a novel series of nitrogen-rich macrocyclic ligands is explored for their potential use as Bi-selective chelating agents. The ligands, 1,4,7,10-tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane (Lpy), 1,4,7,10-tetrakis(3-pyridazylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyd), 1,4,7,10-tetrakis(4-pyrimidylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyr), and 1,4,7,10-tetrakis(2-pyrazinylmethyl)-1,4,7,10-tetraazacyclododecane (Lpz), were prepared by a previously reported method and investigated here for their abilities to bind Bi radioisotopes. The commercially available and commonly used ligands 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) and N-[(R)-2-amino-3-(p-isothiocyanato-phenyl)propyl]-trans-(S,S)- cyclohexane-1,2-diamine-N,N,N',N",N"-pentaacetic acid (CHX-A''-DTPA) were also explored for comparative purposes. Radio-thin-layer chromatography (TLC) was used to measure the binding kinetics and stabilities of the complexes formed. The long-lived isotope, ²⁰⁷Bi (t1/2 = 32 years), was used for these studies. Density functional theory (DFT) calculations were also employed to probe the ligand interactions with Bi³⁺ and the generator parent ion Ac³⁺.In contrast to DOTA and CHX-A''-DTPA, these nitrogen-rich macrocycles selectively chelate Bi³⁺ in the presence of the parent isotope Ac³⁺. Among the four tested, Lpy wasmore »
- Authors:
-
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
- Publication Date:
- Research Org.:
- Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1193399
- Alternate Identifier(s):
- OSTI ID: 1359705
- Report Number(s):
- LA-UR-14-28015
Journal ID: ISSN 0969-8051; PII: S0969805114005721; TRN: US1600595
- Grant/Contract Number:
- AC52-06NA25396
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nuclear Medicine and Biology
- Additional Journal Information:
- Journal Volume: 42; Journal Issue: 5; Journal ID: ISSN 0969-8051
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 62 RADIOLOGY AND NUCLEAR MEDICINE; targeted α-therapy; bismuth-213; actinium-225; radiolabeling; radio-thin-layer chromatography; macrocycles
Citation Formats
Wilson, Justin J., Ferrier, Maryline, Radchenko, Valery, Maassen, Joel R., Engle, Jonathan W., Batista, Enrique R., Martin, Richard L., Nortier, Francois M., Fassbender, Michael E., John, Kevin D., and Birnbaum, Eva R. Evaluation of nitrogen-rich macrocyclic ligands for the chelation of therapeutic bismuth radioisotopes. United States: N. p., 2015.
Web. doi:10.1016/j.nucmedbio.2014.12.007.
Wilson, Justin J., Ferrier, Maryline, Radchenko, Valery, Maassen, Joel R., Engle, Jonathan W., Batista, Enrique R., Martin, Richard L., Nortier, Francois M., Fassbender, Michael E., John, Kevin D., & Birnbaum, Eva R. Evaluation of nitrogen-rich macrocyclic ligands for the chelation of therapeutic bismuth radioisotopes. United States. https://doi.org/10.1016/j.nucmedbio.2014.12.007
Wilson, Justin J., Ferrier, Maryline, Radchenko, Valery, Maassen, Joel R., Engle, Jonathan W., Batista, Enrique R., Martin, Richard L., Nortier, Francois M., Fassbender, Michael E., John, Kevin D., and Birnbaum, Eva R. Fri .
"Evaluation of nitrogen-rich macrocyclic ligands for the chelation of therapeutic bismuth radioisotopes". United States. https://doi.org/10.1016/j.nucmedbio.2014.12.007. https://www.osti.gov/servlets/purl/1193399.
@article{osti_1193399,
title = {Evaluation of nitrogen-rich macrocyclic ligands for the chelation of therapeutic bismuth radioisotopes},
author = {Wilson, Justin J. and Ferrier, Maryline and Radchenko, Valery and Maassen, Joel R. and Engle, Jonathan W. and Batista, Enrique R. and Martin, Richard L. and Nortier, Francois M. and Fassbender, Michael E. and John, Kevin D. and Birnbaum, Eva R.},
abstractNote = {The use of α-emitting isotopes for radionuclide therapy is a promising treatment strategy for small micro-metastatic disease. The radioisotope ²¹³Bi is a nuclide that has found substantial use for targeted α-therapy (TAT). The relatively unexplored aqueous chemistry of Bi³⁺, however, hinders the development of bifunctional chelating agents that can successfully deliver these Bi radioisotopes to the tumor cells. Here, a novel series of nitrogen-rich macrocyclic ligands is explored for their potential use as Bi-selective chelating agents. The ligands, 1,4,7,10-tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane (Lpy), 1,4,7,10-tetrakis(3-pyridazylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyd), 1,4,7,10-tetrakis(4-pyrimidylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyr), and 1,4,7,10-tetrakis(2-pyrazinylmethyl)-1,4,7,10-tetraazacyclododecane (Lpz), were prepared by a previously reported method and investigated here for their abilities to bind Bi radioisotopes. The commercially available and commonly used ligands 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) and N-[(R)-2-amino-3-(p-isothiocyanato-phenyl)propyl]-trans-(S,S)- cyclohexane-1,2-diamine-N,N,N',N",N"-pentaacetic acid (CHX-A''-DTPA) were also explored for comparative purposes. Radio-thin-layer chromatography (TLC) was used to measure the binding kinetics and stabilities of the complexes formed. The long-lived isotope, ²⁰⁷Bi (t1/2 = 32 years), was used for these studies. Density functional theory (DFT) calculations were also employed to probe the ligand interactions with Bi³⁺ and the generator parent ion Ac³⁺.In contrast to DOTA and CHX-A''-DTPA, these nitrogen-rich macrocycles selectively chelate Bi³⁺ in the presence of the parent isotope Ac³⁺. Among the four tested, Lpy was found to exhibit optimal Bi³⁺-binding kinetics and complex stability. Lpy complexes Bi³⁺ more rapidly than DOTA, yet the resulting complexes are of similar stability. DFT calculations corroborate the experimentally observed selectivity of these ligands for Bi³⁺ over Ac³⁺. Taken together, these data implicate Lpy as a valuable chelating agent for the delivery of ²¹³Bi. Its selectivity for Bi³⁺ and rapid and stable labeling properties warrant further investigation and biological studies.},
doi = {10.1016/j.nucmedbio.2014.12.007},
journal = {Nuclear Medicine and Biology},
number = 5,
volume = 42,
place = {United States},
year = {Fri May 01 00:00:00 EDT 2015},
month = {Fri May 01 00:00:00 EDT 2015}
}
Web of Science
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