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Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives
2- or 4-Substituted 3-N-benzyltriazolylmethyl-13α-oestrone derivatives were synthesised via bromination of ring A and subsequent microwave-assisted, Pd-catalysed C(sp(2))–P couplings. The antiproliferative activities of the newly synthesised brominated and phosphonated compounds against a panel of h...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Taylor & Francis
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7598997/ https://www.ncbi.nlm.nih.gov/pubmed/33121276 http://dx.doi.org/10.1080/14756366.2020.1838500 |
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author | Jójárt, Rebeka Tahaei, Seyyed Ashkan Senobar Trungel-Nagy, Péter Kele, Zoltán Minorics, Renáta Paragi, Gábor Zupkó, István Mernyák, Erzsébet |
author_facet | Jójárt, Rebeka Tahaei, Seyyed Ashkan Senobar Trungel-Nagy, Péter Kele, Zoltán Minorics, Renáta Paragi, Gábor Zupkó, István Mernyák, Erzsébet |
author_sort | Jójárt, Rebeka |
collection | PubMed |
description | 2- or 4-Substituted 3-N-benzyltriazolylmethyl-13α-oestrone derivatives were synthesised via bromination of ring A and subsequent microwave-assisted, Pd-catalysed C(sp(2))–P couplings. The antiproliferative activities of the newly synthesised brominated and phosphonated compounds against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231) were investigated by means of MTT assays. The most potent compound, the 3-N-benzyltriazolylmethyl-4-bromo-13α-oestrone derivative exerted substantial selective cell growth-inhibitory activity against A2780 cell line with a submicromolar IC(50) value. Computational calculations reveal strong interactions of the 4-bromo derivative with both colchicine and taxoid binding sites of tubulin. Disturbance of tubulin function has been confirmed by photometric polymerisation assay. |
format | Online Article Text |
id | pubmed-7598997 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Taylor & Francis |
record_format | MEDLINE/PubMed |
spelling | pubmed-75989972020-11-12 Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives Jójárt, Rebeka Tahaei, Seyyed Ashkan Senobar Trungel-Nagy, Péter Kele, Zoltán Minorics, Renáta Paragi, Gábor Zupkó, István Mernyák, Erzsébet J Enzyme Inhib Med Chem Research Paper 2- or 4-Substituted 3-N-benzyltriazolylmethyl-13α-oestrone derivatives were synthesised via bromination of ring A and subsequent microwave-assisted, Pd-catalysed C(sp(2))–P couplings. The antiproliferative activities of the newly synthesised brominated and phosphonated compounds against a panel of human cancer cell lines (A2780, MCF-7, MDA-MB 231) were investigated by means of MTT assays. The most potent compound, the 3-N-benzyltriazolylmethyl-4-bromo-13α-oestrone derivative exerted substantial selective cell growth-inhibitory activity against A2780 cell line with a submicromolar IC(50) value. Computational calculations reveal strong interactions of the 4-bromo derivative with both colchicine and taxoid binding sites of tubulin. Disturbance of tubulin function has been confirmed by photometric polymerisation assay. Taylor & Francis 2020-10-29 /pmc/articles/PMC7598997/ /pubmed/33121276 http://dx.doi.org/10.1080/14756366.2020.1838500 Text en © 2020 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. https://creativecommons.org/licenses/by/4.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Paper Jójárt, Rebeka Tahaei, Seyyed Ashkan Senobar Trungel-Nagy, Péter Kele, Zoltán Minorics, Renáta Paragi, Gábor Zupkó, István Mernyák, Erzsébet Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title | Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title_full | Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title_fullStr | Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title_full_unstemmed | Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title_short | Synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(N-benzyltriazolylmethyl)-13α-oestrone derivatives |
title_sort | synthesis and evaluation of anticancer activities of 2- or 4-substituted 3-(n-benzyltriazolylmethyl)-13α-oestrone derivatives |
topic | Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7598997/ https://www.ncbi.nlm.nih.gov/pubmed/33121276 http://dx.doi.org/10.1080/14756366.2020.1838500 |
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