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[Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity
A series of metallosupramolecular [Fe(2)L(3)](BF(4))(4) “click” cylinders have been synthesized in excellent yields (90%–95%) from [Fe(H(2)O)(6)](BF(4))(2) and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, (1)H-, (13)C- and DOSY-NM...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6290563/ https://www.ncbi.nlm.nih.gov/pubmed/23760034 http://dx.doi.org/10.3390/molecules18066383 |
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author | Vellas, Sreedhar K. Lewis, James E. M. Shankar, Madhu Sagatova, Alia Tyndall, Joel D. A. Monk, Brian C. Fitchett, Christopher M. Hanton, Lyall R. Crowley, James D. |
author_facet | Vellas, Sreedhar K. Lewis, James E. M. Shankar, Madhu Sagatova, Alia Tyndall, Joel D. A. Monk, Brian C. Fitchett, Christopher M. Hanton, Lyall R. Crowley, James D. |
author_sort | Vellas, Sreedhar K. |
collection | PubMed |
description | A series of metallosupramolecular [Fe(2)L(3)](BF(4))(4) “click” cylinders have been synthesized in excellent yields (90%–95%) from [Fe(H(2)O)(6)](BF(4))(2) and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, (1)H-, (13)C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these “click” complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the “click” complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe(2)L(3)](BF(4))(4) “click” cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the “click” complexes in DMSO and biological media. |
format | Online Article Text |
id | pubmed-6290563 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62905632018-12-17 [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity Vellas, Sreedhar K. Lewis, James E. M. Shankar, Madhu Sagatova, Alia Tyndall, Joel D. A. Monk, Brian C. Fitchett, Christopher M. Hanton, Lyall R. Crowley, James D. Molecules Article A series of metallosupramolecular [Fe(2)L(3)](BF(4))(4) “click” cylinders have been synthesized in excellent yields (90%–95%) from [Fe(H(2)O)(6)](BF(4))(2) and bis(bidentate) pyridyl-1,2,3-triazole ligands. All complexes were characterized by elemental analysis, IR, UV-vis, (1)H-, (13)C- and DOSY-NMR spectroscopies and, in four cases, the structures confirmed by X-ray crystallography. Molecular modeling indicated that some of these “click” complexes were of similar size and shape to related biologically active pyridylimine-based iron(II) helicates and suggested that the “click” complexes may bind both duplex and triplex DNA. Cell-based agarose diffusion assays showed that the metallosupramolecular [Fe(2)L(3)](BF(4))(4) “click” cylinders display no antifungal activity against S. cerevisiae. This observed lack of antifungal activity appears to be due to the poor stability of the “click” complexes in DMSO and biological media. MDPI 2013-05-29 /pmc/articles/PMC6290563/ /pubmed/23760034 http://dx.doi.org/10.3390/molecules18066383 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Vellas, Sreedhar K. Lewis, James E. M. Shankar, Madhu Sagatova, Alia Tyndall, Joel D. A. Monk, Brian C. Fitchett, Christopher M. Hanton, Lyall R. Crowley, James D. [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title | [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title_full | [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title_fullStr | [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title_full_unstemmed | [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title_short | [Fe(2)L(3)](4+) Cylinders Derived from Bis(bidentate) 2-Pyridyl-1,2,3-triazole “Click” Ligands: Synthesis, Structures and Exploration of Biological Activity |
title_sort | [fe(2)l(3)](4+) cylinders derived from bis(bidentate) 2-pyridyl-1,2,3-triazole “click” ligands: synthesis, structures and exploration of biological activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6290563/ https://www.ncbi.nlm.nih.gov/pubmed/23760034 http://dx.doi.org/10.3390/molecules18066383 |
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