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Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates
The development of novel, tumor-selective and boron-rich compounds as potential agents for use in boron neutron capture therapy (BNCT) represents a very important field in cancer treatment by radiation therapy. Here, we report the design and synthesis of two promising compounds that combine meta-car...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8038343/ https://www.ncbi.nlm.nih.gov/pubmed/33916755 http://dx.doi.org/10.3390/molecules26072057 |
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author | Kellert, Martin Friedrichs, Jan-Simon Jeshua Ullrich, Nadine Anke Feinhals, Alexander Tepper, Jonas Lönnecke, Peter Hey-Hawkins, Evamarie |
author_facet | Kellert, Martin Friedrichs, Jan-Simon Jeshua Ullrich, Nadine Anke Feinhals, Alexander Tepper, Jonas Lönnecke, Peter Hey-Hawkins, Evamarie |
author_sort | Kellert, Martin |
collection | PubMed |
description | The development of novel, tumor-selective and boron-rich compounds as potential agents for use in boron neutron capture therapy (BNCT) represents a very important field in cancer treatment by radiation therapy. Here, we report the design and synthesis of two promising compounds that combine meta-carborane, a water-soluble monosaccharide and a linking unit, namely glycine or ethylenediamine, for facile coupling with various tumor-selective biomolecules bearing a free amino or carboxylic acid group. In this work, coupling experiments with two selected biomolecules, a coumarin derivative and folic acid, were included. The task of every component in this approach was carefully chosen: the carborane moiety supplies ten boron atoms, which is a tenfold increase in boron content compared to the l-boronophenylalanine (l-BPA) presently used in BNCT; the sugar moiety compensates for the hydrophobic character of the carborane; the linking unit, depending on the chosen biomolecule, acts as the connection between the tumor-selective component and the boron-rich moiety; and the respective tumor-selective biomolecule provides the necessary selectivity. This approach makes it possible to develop a modular and feasible strategy for the synthesis of readily obtainable boron-rich agents with optimized properties for potential applications in BNCT. |
format | Online Article Text |
id | pubmed-8038343 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-80383432021-04-12 Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates Kellert, Martin Friedrichs, Jan-Simon Jeshua Ullrich, Nadine Anke Feinhals, Alexander Tepper, Jonas Lönnecke, Peter Hey-Hawkins, Evamarie Molecules Article The development of novel, tumor-selective and boron-rich compounds as potential agents for use in boron neutron capture therapy (BNCT) represents a very important field in cancer treatment by radiation therapy. Here, we report the design and synthesis of two promising compounds that combine meta-carborane, a water-soluble monosaccharide and a linking unit, namely glycine or ethylenediamine, for facile coupling with various tumor-selective biomolecules bearing a free amino or carboxylic acid group. In this work, coupling experiments with two selected biomolecules, a coumarin derivative and folic acid, were included. The task of every component in this approach was carefully chosen: the carborane moiety supplies ten boron atoms, which is a tenfold increase in boron content compared to the l-boronophenylalanine (l-BPA) presently used in BNCT; the sugar moiety compensates for the hydrophobic character of the carborane; the linking unit, depending on the chosen biomolecule, acts as the connection between the tumor-selective component and the boron-rich moiety; and the respective tumor-selective biomolecule provides the necessary selectivity. This approach makes it possible to develop a modular and feasible strategy for the synthesis of readily obtainable boron-rich agents with optimized properties for potential applications in BNCT. MDPI 2021-04-03 /pmc/articles/PMC8038343/ /pubmed/33916755 http://dx.doi.org/10.3390/molecules26072057 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Kellert, Martin Friedrichs, Jan-Simon Jeshua Ullrich, Nadine Anke Feinhals, Alexander Tepper, Jonas Lönnecke, Peter Hey-Hawkins, Evamarie Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title | Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title_full | Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title_fullStr | Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title_full_unstemmed | Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title_short | Modular Synthetic Approach to Carboranyl‒Biomolecules Conjugates |
title_sort | modular synthetic approach to carboranyl‒biomolecules conjugates |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8038343/ https://www.ncbi.nlm.nih.gov/pubmed/33916755 http://dx.doi.org/10.3390/molecules26072057 |
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