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The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties
In order to compare the coordination properties of 1,4,7-triazacyclononane (tacn) derivatives bearing varying numbers of phosphinic/carboxylic acid pendant groups towards (68)Ga, 1,4,7-triazacyclononane-7-acetic-1,4-bis(methylenephosphinic) acid (NOPA) and 1,4,7-triazacyclononane-4,7-diacetic-1-[met...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331800/ https://www.ncbi.nlm.nih.gov/pubmed/26197305 http://dx.doi.org/10.3390/molecules200713112 |
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author | Máté, Gábor Šimeček, Jakub Pniok, Miroslav Kertész, István Notni, Johannes Wester, Hans-Jürgen Galuska, László Hermann, Petr |
author_facet | Máté, Gábor Šimeček, Jakub Pniok, Miroslav Kertész, István Notni, Johannes Wester, Hans-Jürgen Galuska, László Hermann, Petr |
author_sort | Máté, Gábor |
collection | PubMed |
description | In order to compare the coordination properties of 1,4,7-triazacyclononane (tacn) derivatives bearing varying numbers of phosphinic/carboxylic acid pendant groups towards (68)Ga, 1,4,7-triazacyclononane-7-acetic-1,4-bis(methylenephosphinic) acid (NOPA) and 1,4,7-triazacyclononane-4,7-diacetic-1-[methylene(2-carboxyethyl)phosphinic] acid (NO2AP) were synthesized using Mannich reactions with trivalent or pentavalent forms of H-phosphinic acids as phosphorus components. Stepwise protonation constants logK(1–3) 12.06, 3.90 and 1.95, and stability constants with Ga(III) and Cu(II), logK(GaL) 24.01 and logK(CuL) 16.66, were potentiometrically determined for NOPA. Both ligands were labelled with (68)Ga and compared with NOTA (tacn-N,N′,N″-triacetic acid) and NOPO, a TRAP-type [tacn-N,N′,N″-tris(methylenephosphinic acid)] chelator. At pH 3, NOPO and NOPA showed higher labelling efficiency (binding with lower ligand excess) at both room temperature and 95 °C, compared to NO2AP and NOTA. Labelling efficiency at pH = 0–3 correlated with a number of phosphinic acid pendants: NOPO >> NOPA > NO2AP >> NOTA; however, it was more apparent at 95 °C than at room temperature. By contrast, NOTA was found to be labelled more efficiently at pH > 4 compared to the ligands with phosphinic acids. Overall, replacement of a single phosphinate donor with a carboxylate does not challenge (68)Ga labelling of TRAP-type chelators. However, the presence of carboxylates facilitates labelling at neutral or weakly acidic pH. |
format | Online Article Text |
id | pubmed-6331800 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-63318002019-01-24 The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties Máté, Gábor Šimeček, Jakub Pniok, Miroslav Kertész, István Notni, Johannes Wester, Hans-Jürgen Galuska, László Hermann, Petr Molecules Article In order to compare the coordination properties of 1,4,7-triazacyclononane (tacn) derivatives bearing varying numbers of phosphinic/carboxylic acid pendant groups towards (68)Ga, 1,4,7-triazacyclononane-7-acetic-1,4-bis(methylenephosphinic) acid (NOPA) and 1,4,7-triazacyclononane-4,7-diacetic-1-[methylene(2-carboxyethyl)phosphinic] acid (NO2AP) were synthesized using Mannich reactions with trivalent or pentavalent forms of H-phosphinic acids as phosphorus components. Stepwise protonation constants logK(1–3) 12.06, 3.90 and 1.95, and stability constants with Ga(III) and Cu(II), logK(GaL) 24.01 and logK(CuL) 16.66, were potentiometrically determined for NOPA. Both ligands were labelled with (68)Ga and compared with NOTA (tacn-N,N′,N″-triacetic acid) and NOPO, a TRAP-type [tacn-N,N′,N″-tris(methylenephosphinic acid)] chelator. At pH 3, NOPO and NOPA showed higher labelling efficiency (binding with lower ligand excess) at both room temperature and 95 °C, compared to NO2AP and NOTA. Labelling efficiency at pH = 0–3 correlated with a number of phosphinic acid pendants: NOPO >> NOPA > NO2AP >> NOTA; however, it was more apparent at 95 °C than at room temperature. By contrast, NOTA was found to be labelled more efficiently at pH > 4 compared to the ligands with phosphinic acids. Overall, replacement of a single phosphinate donor with a carboxylate does not challenge (68)Ga labelling of TRAP-type chelators. However, the presence of carboxylates facilitates labelling at neutral or weakly acidic pH. MDPI 2015-07-21 /pmc/articles/PMC6331800/ /pubmed/26197305 http://dx.doi.org/10.3390/molecules200713112 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Máté, Gábor Šimeček, Jakub Pniok, Miroslav Kertész, István Notni, Johannes Wester, Hans-Jürgen Galuska, László Hermann, Petr The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title | The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title_full | The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title_fullStr | The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title_full_unstemmed | The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title_short | The Influence of the Combination of Carboxylate and Phosphinate Pendant Arms in 1,4,7-Triazacyclononane-Based Chelators on Their (68)Ga Labelling Properties |
title_sort | influence of the combination of carboxylate and phosphinate pendant arms in 1,4,7-triazacyclononane-based chelators on their (68)ga labelling properties |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331800/ https://www.ncbi.nlm.nih.gov/pubmed/26197305 http://dx.doi.org/10.3390/molecules200713112 |
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