Synthesis of DOTA-pyridine chelates for 64Cu coordination and radiolabeling of αMSH peptide

Yang, Hua; Gao, Feng; McNeil, Brooke; Zhang, Chengcheng; Yuan, Zheliang; Zeisler, Stefan; Kumlin, Joel; Zeisler, Jutta; Bénard, François; Ramogida, Caterina F.; Schaffer, Paul

doi:10.1186/s41181-020-00119-4

Cited by 12 publications

(18 citation statements)

References 39 publications

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“…The lower overall basicity of H 2 BA2A1Py compared to H 3 BA3A induced a consequent decrease in the logβ of complexes with BA2A1Py 2− , although to a different degree: only 0.5 log for Cu 2+ , while 1.6 log for Pb 2+ ( Table 1 ), showing a preference towards Cu 2+ . This fact proves our suggestion about an increase in affinity for Cu 2+ of N-donor ligands and correlates with the described CuDOTAPy in vitro stability [ 9 ].…”

Section: Resultssupporting

confidence: 90%

“…Given Cu 2+ is a transition metal cation, preferring softer N-donors along with O-donor atoms, it can be effectively bound by aromatic nitrogen that is known to be less basic than aliphatic amines. Moreover, it has been recently shown that H 4 DOTA derivatives with a pyridine arm can significantly improve copper binding [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

“…To the best of our knowledge, protonation and complexation constants of such hybrid ligands with the simultaneous presence of acetic and pyridyl pendant groups have not been described in the literature yet. There are examples of substitutions of all (two or three) acetates in azacrowns by pyridines [ 3 , 6 , 10 , 11 ] and it has been shown that pyridine, as a pendant arm, can significantly improve the chelation ability and kinetics of binding towards Cu 2+ and Bi 3+ , including direct comparison with well-known H 4 DOTA [ 9 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Novel Hybrid Benzoazacrown Ligand as a Chelator for Copper and Lead Cations: What Difference Does Pyridine Make

et al. 2022

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A synthetic procedure for the synthesis of azacrown ethers with a combination of pendant arms has been developed and the synthesized ligand, characterized by various techniques, was studied. The prepared benzoazacrown ether with hybrid pendant arms and its complexes with copper and lead cations were studied in terms of biomedical applications. Similarly to a fully acetate analog, the new one binds both cations with close stability constants, despite the decrease in both constants. The calculated geometry of the complexes correlate with the data from X-ray absorption and NMR spectroscopy. Coordination of both cations differs due to the difference between the ionic radii. However, these chelation modes provide effective shielding of cations in both cases, that was shown by the stability of their complexes in the biologically relevant media towards transchelation and transmetallation.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Hybrid Benzoazacrown Ligand as a Chelator for Copper and Lead Cations: What Difference Does Pyridine Make

et al. 2022

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“…All solvents and reagents were purchased from commercial suppliers (Sigma Aldrich, Fisher Scientific, VWR) and used as received, unless otherwise noted. (7,10-bis (pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane-1,4-diyl) diacetic acid) and DOTA-3Py (2-(4,7,10-tris (pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecan-1-yl) acetic acid) were synthesized as previously described (Yang et al 2021). Instant thin layer chromatography paper impregnated with silicic acid (iTLC-SA) was purchased from Agilent Technologies (Santa Clara, CA).…”

Section: Methodsmentioning

confidence: 99%

“…We present the production of the 203 Pb and 212 Pb theranostic pair using TRIUMF's TR13 (13 MeV) and 500 MeV cyclotron, subsequent radiochemical purification and isotope characterization. The separated radioisotopes were evaluated alongside each other for radiolabeling a series of TRIUMF developed, pyridine based-DOTA analogues (Yang et al 2021) along with commercial standards DOTA and TCMC (Fig. 2), and the stability of each radiometal-complex was evaluated in vitro.…”

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confidence: 99%

Production, purification, and radiolabeling of the 203Pb/212Pb theranostic pair

McNeil

Robertson

et al. 2021

EJNMMI radiopharm. chem.

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Background Lead-212 (212Pb, t1/2 = 10.6 h) and lead-203 (203Pb, t1/2 = 51.9 h) are an element-equivalent, or a matched theranostic radioisotope pair that show great potential for application in targeted radionuclide therapy (TRT) and single-photon emission computed tomography (SPECT), respectively. At TRIUMF we have produced both 203Pb and 212Pb using TRIUMF’s TR13 (13 MeV) and 500 MeV cyclotrons, and subsequently purified and evaluated both radioisotopes using a series of pyridine-modified DOTA analogues in comparison to the commercially available chelates DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) and TCMC (1,4,7,10-tetraaza-1,4,7,10-tetra(2-carbamoylmethyl)cyclododecane). Results Proton irradiation (12.8 MeV) of natural and enriched thallium-203 (203Tl) targets gave 203Pb saturation yields of 134 ± 25 and 483 ± 3 MBq/μA, respectively. Thorium-228 (228Th, t1/2 = 1.9 y), a by-product of 232Th proton spallation on TRIUMF’s main 500 MeV beamline (beamline 1A, BL1A), was recovered to build a 228Th/212Pb generator with the ability to deliver up to 9–10 MBq of 212Pb daily. Both lead isotopes were purified via solid phase extraction chromatography (Pb resin), and isolated in an acetate form ([203/212Pb]Pb(OAc)2) suitable for direct radiolabeling of chelators and bioconjugates. A series of cyclen-based chelators (herein referred to as DOTA-1Py, -2Py, and -3Py) along with established chelates DOTA and TCMC were evaluated for their ability to complex both 203Pb and 212Pb. All chelates incorporated 212Pb/203Pb efficiently, with higher radiolabeling yields observed for the 212Pb-complexes. Conclusion The production of 203Pb and 212Pb was established using TRIUMF 13 MeV and 500 MeV cyclotrons, respectively. Both production methods provided radiometals suitable for subsequent radiolabeling reactions using known and novel chelates. Furthermore, the novel chelate DOTA-3Py may be a good candidate for biomolecule conjugation and further theranostic 212Pb/203Pb studies.

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An Overview of Structural Framework and Classification of Theranostic Radiopharmaceuticals

Kaur,

Mukherjee

2024

ChemistrySelect

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Radiopharmaceuticals constitute the backbone of nuclear medicine research and have been commonly used in diagnostic imaging and radionuclide therapy. In the past, there has been a strong emphasis on the meticulous design and development of radiotheranostics for targeted molecular imaging and therapy of different types of tumors. Theranostic radiopharmaceuticals offer synergistic advantages of simultaneous molecular imaging and radionuclide therapy all in one molecule. Owing to their successful pre‐clinical and clinical applications, many new theranostic radiopharmaceuticals have been explored in recent years. This review aims to provide a comprehensive overview of the design and the structural framework of theranostic radiopharmaceuticals. In this review, we have primarily focused on the different types of chelating agents, linkers, and radionuclides used for the development of potential radiotheranostics. In addition, this review also summarizes the classification and the different categories of theranostic radiopharmaceuticals such as molecular radiotheranostics and nano‐radiotheranostics along with their pre‐clinical and clinical theranostic applications. The recent developments and the theranostic applications of small molecule‐based radiotheranostics, antibody‐based radiotheranostics, peptide‐based radiotheranostics, and nanoparticle‐based radiotheranostics have also been reviewed for inspiring research efforts towards the development of efficient radiotheranostics.

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Synthesis of DOTA-pyridine chelates for 64Cu coordination and radiolabeling of αMSH peptide

Cited by 12 publications

References 39 publications

Novel Hybrid Benzoazacrown Ligand as a Chelator for Copper and Lead Cations: What Difference Does Pyridine Make

Novel Hybrid Benzoazacrown Ligand as a Chelator for Copper and Lead Cations: What Difference Does Pyridine Make

Production, purification, and radiolabeling of the 203Pb/212Pb theranostic pair

An Overview of Structural Framework and Classification of Theranostic Radiopharmaceuticals

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