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2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes

Investigations on the antitumor activity of metallacarboranes are sparse in the literature and limited to a handful of ruthena‐ and molybdacarboranes. In this study, the molybdacarborane fragment [3‐(CO)(2)‐closo‐3,1,2‐MoC(2)B(9)H(11)] was combined with a vector molecule, inspired by the well‐known...

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Autores principales: Schwarze, Benedikt, Jelača, Sanja, Welcke, Linda, Maksimović‐Ivanić, Danijela, Mijatović, Sanja, Hey‐Hawkins, Evamarie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972990/
https://www.ncbi.nlm.nih.gov/pubmed/31677361
http://dx.doi.org/10.1002/cmdc.201900554
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author Schwarze, Benedikt
Jelača, Sanja
Welcke, Linda
Maksimović‐Ivanić, Danijela
Mijatović, Sanja
Hey‐Hawkins, Evamarie
author_facet Schwarze, Benedikt
Jelača, Sanja
Welcke, Linda
Maksimović‐Ivanić, Danijela
Mijatović, Sanja
Hey‐Hawkins, Evamarie
author_sort Schwarze, Benedikt
collection PubMed
description Investigations on the antitumor activity of metallacarboranes are sparse in the literature and limited to a handful of ruthena‐ and molybdacarboranes. In this study, the molybdacarborane fragment [3‐(CO)(2)‐closo‐3,1,2‐MoC(2)B(9)H(11)] was combined with a vector molecule, inspired by the well‐known drug tamoxifen or 4,4′‐dihydroxytamoxifen (TAM‐diOH). The molybdacarborane derivative [3,3‐{4‐[1,1‐bis(4‐hydroxyphenyl)but‐1‐en‐2‐yl]‐2,2′‐bipyridine‐κ(2) N,N′}‐3‐(CO)(2)‐closo‐3,1,2‐MoC(2)B(9)H(11)] (10), as well as the ligand itself 4‐[1,1‐bis(4‐hydroxyphenyl)but‐1‐en‐2‐yl]‐2,2′‐bipyridine (6) showed cytotoxic activities in the low micromolar range against breast adenocarcinoma (MDA‐MB‐231, MDA‐MB‐361 and MCF‐7), human glioblastoma (LN‐229) and human glioma (U‐251) cell lines. In addition, compounds 6 and 10 were found to induce senescence and cytodestructive autophagy, lower ROS/RNS levels, but only the molybdacarborane 10 induced a strong increase of nitric oxide (NO) concentration in the MCF‐7 cells.
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spelling pubmed-69729902020-01-27 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes Schwarze, Benedikt Jelača, Sanja Welcke, Linda Maksimović‐Ivanić, Danijela Mijatović, Sanja Hey‐Hawkins, Evamarie ChemMedChem Full Papers Investigations on the antitumor activity of metallacarboranes are sparse in the literature and limited to a handful of ruthena‐ and molybdacarboranes. In this study, the molybdacarborane fragment [3‐(CO)(2)‐closo‐3,1,2‐MoC(2)B(9)H(11)] was combined with a vector molecule, inspired by the well‐known drug tamoxifen or 4,4′‐dihydroxytamoxifen (TAM‐diOH). The molybdacarborane derivative [3,3‐{4‐[1,1‐bis(4‐hydroxyphenyl)but‐1‐en‐2‐yl]‐2,2′‐bipyridine‐κ(2) N,N′}‐3‐(CO)(2)‐closo‐3,1,2‐MoC(2)B(9)H(11)] (10), as well as the ligand itself 4‐[1,1‐bis(4‐hydroxyphenyl)but‐1‐en‐2‐yl]‐2,2′‐bipyridine (6) showed cytotoxic activities in the low micromolar range against breast adenocarcinoma (MDA‐MB‐231, MDA‐MB‐361 and MCF‐7), human glioblastoma (LN‐229) and human glioma (U‐251) cell lines. In addition, compounds 6 and 10 were found to induce senescence and cytodestructive autophagy, lower ROS/RNS levels, but only the molybdacarborane 10 induced a strong increase of nitric oxide (NO) concentration in the MCF‐7 cells. John Wiley and Sons Inc. 2019-11-18 2019-12-17 /pmc/articles/PMC6972990/ /pubmed/31677361 http://dx.doi.org/10.1002/cmdc.201900554 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Schwarze, Benedikt
Jelača, Sanja
Welcke, Linda
Maksimović‐Ivanić, Danijela
Mijatović, Sanja
Hey‐Hawkins, Evamarie
2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title_full 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title_fullStr 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title_full_unstemmed 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title_short 2,2′‐Bipyridine‐Modified Tamoxifen: A Versatile Vector for Molybdacarboranes
title_sort 2,2′‐bipyridine‐modified tamoxifen: a versatile vector for molybdacarboranes
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972990/
https://www.ncbi.nlm.nih.gov/pubmed/31677361
http://dx.doi.org/10.1002/cmdc.201900554
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