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Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol

9-HC≡CCH(2)Me(2)N-nido-7,8-C(2)B(9)H(11), a previously described carboranyl terminal alkyne, was used for the copper(I)-catalyzed azide-alkyne cycloaddition with azido-3β-cholesterol to form a novel zwitter-ionic conjugate of nido-carborane with cholesterol, bearing a 1,2,3-triazol fragment. The con...

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Autores principales: Druzina, Anna A., Zhidkova, Olga B., Dudarova, Nadezhda V., Nekrasova, Natalia A., Suponitsky, Kyrill Yu., Timofeev, Sergey V., Bregadze, Vladimir I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588508/
https://www.ncbi.nlm.nih.gov/pubmed/34771096
http://dx.doi.org/10.3390/molecules26216687
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author Druzina, Anna A.
Zhidkova, Olga B.
Dudarova, Nadezhda V.
Nekrasova, Natalia A.
Suponitsky, Kyrill Yu.
Timofeev, Sergey V.
Bregadze, Vladimir I.
author_facet Druzina, Anna A.
Zhidkova, Olga B.
Dudarova, Nadezhda V.
Nekrasova, Natalia A.
Suponitsky, Kyrill Yu.
Timofeev, Sergey V.
Bregadze, Vladimir I.
author_sort Druzina, Anna A.
collection PubMed
description 9-HC≡CCH(2)Me(2)N-nido-7,8-C(2)B(9)H(11), a previously described carboranyl terminal alkyne, was used for the copper(I)-catalyzed azide-alkyne cycloaddition with azido-3β-cholesterol to form a novel zwitter-ionic conjugate of nido-carborane with cholesterol, bearing a 1,2,3-triazol fragment. The conjugate of nido-carborane with cholesterol, containing a charge-compensated group in the linker, can be used as a precursor for the preparation of liposomes for BNCT (Boron Neutron Capture Therapy). The solid-state molecular structure of a nido-carborane derivative with the 9-Me(2)N(CH(2))(2)Me(2)N-nido-7,8-C(2)B(9)H(11) terminal dimethylamino group was determined by single-crystal X-ray diffraction.
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spelling pubmed-85885082021-11-13 Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol Druzina, Anna A. Zhidkova, Olga B. Dudarova, Nadezhda V. Nekrasova, Natalia A. Suponitsky, Kyrill Yu. Timofeev, Sergey V. Bregadze, Vladimir I. Molecules Article 9-HC≡CCH(2)Me(2)N-nido-7,8-C(2)B(9)H(11), a previously described carboranyl terminal alkyne, was used for the copper(I)-catalyzed azide-alkyne cycloaddition with azido-3β-cholesterol to form a novel zwitter-ionic conjugate of nido-carborane with cholesterol, bearing a 1,2,3-triazol fragment. The conjugate of nido-carborane with cholesterol, containing a charge-compensated group in the linker, can be used as a precursor for the preparation of liposomes for BNCT (Boron Neutron Capture Therapy). The solid-state molecular structure of a nido-carborane derivative with the 9-Me(2)N(CH(2))(2)Me(2)N-nido-7,8-C(2)B(9)H(11) terminal dimethylamino group was determined by single-crystal X-ray diffraction. MDPI 2021-11-05 /pmc/articles/PMC8588508/ /pubmed/34771096 http://dx.doi.org/10.3390/molecules26216687 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
Druzina, Anna A.
Zhidkova, Olga B.
Dudarova, Nadezhda V.
Nekrasova, Natalia A.
Suponitsky, Kyrill Yu.
Timofeev, Sergey V.
Bregadze, Vladimir I.
Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title_full Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title_fullStr Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title_full_unstemmed Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title_short Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol
title_sort synthesis of zwitter-ionic conjugate of nido-carborane with cholesterol
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8588508/
https://www.ncbi.nlm.nih.gov/pubmed/34771096
http://dx.doi.org/10.3390/molecules26216687
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