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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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
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.
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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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