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Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification

A straightforward modification route to obtain mono‐ and di‐substituted anthroyl ester bridge functionalized dinuclear Au(I) bis‐N‐heterocyclic carbene complexes is presented. The functionalization can be achieved starting from a hydroxyl‐functionalized ligand precursor followed by transmetallation...

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Autores principales: Jakob, Christian H. G., Dominelli, Bruno, Schlagintweit, Jonas F., Fischer, Pauline J., Schuderer, Franziska, Reich, Robert M., Marques, Fernanda, Correia, João D. G., Kühn, Fritz E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756789/
https://www.ncbi.nlm.nih.gov/pubmed/33405335
http://dx.doi.org/10.1002/asia.202001104
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author Jakob, Christian H. G.
Dominelli, Bruno
Schlagintweit, Jonas F.
Fischer, Pauline J.
Schuderer, Franziska
Reich, Robert M.
Marques, Fernanda
Correia, João D. G.
Kühn, Fritz E.
author_facet Jakob, Christian H. G.
Dominelli, Bruno
Schlagintweit, Jonas F.
Fischer, Pauline J.
Schuderer, Franziska
Reich, Robert M.
Marques, Fernanda
Correia, João D. G.
Kühn, Fritz E.
author_sort Jakob, Christian H. G.
collection PubMed
description A straightforward modification route to obtain mono‐ and di‐substituted anthroyl ester bridge functionalized dinuclear Au(I) bis‐N‐heterocyclic carbene complexes is presented. The functionalization can be achieved starting from a hydroxyl‐functionalized ligand precursor followed by transmetallation of the corresponding Ag complex or via esterification of the hydroxyl‐functionalized gold complex. The compounds are characterized by NMR‐spectroscopy, ESI‐MS, elemental analysis and SC‐XRD. The mono‐ester Au complex shows quantum yields around 18%. In contrast, the corresponding syn‐di‐ester Au complex, exhibits significantly lower quantum yields of around 8%. Due to insufficient water solubility of the di‐ester, only the mono‐ester complex has been tested regarding its antiproliferative activity against HeLa‐ (cervix) and MCF‐7‐ (breast) cancer cell lines and a healthy fibroblast cell line (V79). IC(50) values of 7.26 μM in the HeLa cell line and 7.92 μM in the MCF‐7 cell line along with selectivity indices of 8.8 (HeLa) and 8.0 (MCF‐7) are obtained. These selectivity indices are significantly higher than those obtained for the reference drugs cisplatin or auranofin.
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spelling pubmed-77567892020-12-28 Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification Jakob, Christian H. G. Dominelli, Bruno Schlagintweit, Jonas F. Fischer, Pauline J. Schuderer, Franziska Reich, Robert M. Marques, Fernanda Correia, João D. G. Kühn, Fritz E. Chem Asian J Communications A straightforward modification route to obtain mono‐ and di‐substituted anthroyl ester bridge functionalized dinuclear Au(I) bis‐N‐heterocyclic carbene complexes is presented. The functionalization can be achieved starting from a hydroxyl‐functionalized ligand precursor followed by transmetallation of the corresponding Ag complex or via esterification of the hydroxyl‐functionalized gold complex. The compounds are characterized by NMR‐spectroscopy, ESI‐MS, elemental analysis and SC‐XRD. The mono‐ester Au complex shows quantum yields around 18%. In contrast, the corresponding syn‐di‐ester Au complex, exhibits significantly lower quantum yields of around 8%. Due to insufficient water solubility of the di‐ester, only the mono‐ester complex has been tested regarding its antiproliferative activity against HeLa‐ (cervix) and MCF‐7‐ (breast) cancer cell lines and a healthy fibroblast cell line (V79). IC(50) values of 7.26 μM in the HeLa cell line and 7.92 μM in the MCF‐7 cell line along with selectivity indices of 8.8 (HeLa) and 8.0 (MCF‐7) are obtained. These selectivity indices are significantly higher than those obtained for the reference drugs cisplatin or auranofin. John Wiley and Sons Inc. 2020-10-30 2020-12-14 /pmc/articles/PMC7756789/ /pubmed/33405335 http://dx.doi.org/10.1002/asia.202001104 Text en © 2020 The Authors. Chemistry – An Asian Journal published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Jakob, Christian H. G.
Dominelli, Bruno
Schlagintweit, Jonas F.
Fischer, Pauline J.
Schuderer, Franziska
Reich, Robert M.
Marques, Fernanda
Correia, João D. G.
Kühn, Fritz E.
Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title_full Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title_fullStr Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title_full_unstemmed Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title_short Improved Antiproliferative Activity and Fluorescence of a Dinuclear Gold(I) Bisimidazolylidene Complex via Anthracene‐Modification
title_sort improved antiproliferative activity and fluorescence of a dinuclear gold(i) bisimidazolylidene complex via anthracene‐modification
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756789/
https://www.ncbi.nlm.nih.gov/pubmed/33405335
http://dx.doi.org/10.1002/asia.202001104
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