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Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications
BACKGROUND: Re(I) tricarbonyl complexes exhibit immense potential as fluorescence imaging agents. However, only a handful of rhenium complexes have been utilized in biological imaging. The present study describes the synthesis of four novel rhenium complexes, their characterization and preliminary b...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5123207/ https://www.ncbi.nlm.nih.gov/pubmed/27942267 http://dx.doi.org/10.1186/s13065-016-0218-4 |
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author | Ranasinghe, Kokila Handunnetti, Shiroma Perera, Inoka C. Perera, Theshini |
author_facet | Ranasinghe, Kokila Handunnetti, Shiroma Perera, Inoka C. Perera, Theshini |
author_sort | Ranasinghe, Kokila |
collection | PubMed |
description | BACKGROUND: Re(I) tricarbonyl complexes exhibit immense potential as fluorescence imaging agents. However, only a handful of rhenium complexes have been utilized in biological imaging. The present study describes the synthesis of four novel rhenium complexes, their characterization and preliminary biological studies to assess their potential as biological imaging agents. RESULTS: Four facial rhenium tricarbonyl complexes containing a pyridyl triazine core, (L1 = 5,5′(3-(2-pyridyl)-1,2,4-triazine-5,6-diyl)-bis-2-furansulfonic acid disodium salt and L2 = (3-(2- pyridyl)-5,6-diphenyl-1,2,4-triazine-4′,4′′-disulfonic acid sodium salt) have been synthesized by utililzing two different Re metal precursors, Re(CO)(5)Br and [Re(CO)(3)(H(2)O)(3)]OTf in an organic solvent mixture and water, respectively. The rhenium complexes [Re(CO)(3)(H(2)O)L1](+) (1), Re(CO)(3)L1Br (2), [Re(CO)(3)(H(2)O)L2](+) (3), and Re(CO)(3)L2Br (4), were obtained in 70–85% yield and characterized by (1)H NMR, IR, UV, and luminescence spectroscopy. In both H(2)O and acetonitrile, complexes display a weak absorption band in the visible region which can be assigned to a metal to ligand charge transfer excitation and fluorescent emission lying in the 650–710 nm range. Cytotoxicity assays of complexes 1, 3, and 4 were carried out for rat peritoneal cells. Both plant cells (Allium cepa bulb cells) and rat peritoneal cells were stained using the maximum non-toxic concentration levels of the compounds, 20.00 mg ml(−1) for 1 and 3 and 5.00 mg ml(−1) for 4 to observe under the epifluorescence microscope. In both cell lines, compound concentrated specifically in the nuclei region. Hence, nuclei showed red fluorescence upon excitation at 550 nm. CONCLUSIONS: Four novel rhenium complexes have been synthesized and characterized. Remarkable enhancement of fluorescence upon binding with cells and visible range excitability demonstrates the possibility of using the new complexes in biological applications. [Figure: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-016-0218-4) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-5123207 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-51232072016-12-09 Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications Ranasinghe, Kokila Handunnetti, Shiroma Perera, Inoka C. Perera, Theshini Chem Cent J Research Article BACKGROUND: Re(I) tricarbonyl complexes exhibit immense potential as fluorescence imaging agents. However, only a handful of rhenium complexes have been utilized in biological imaging. The present study describes the synthesis of four novel rhenium complexes, their characterization and preliminary biological studies to assess their potential as biological imaging agents. RESULTS: Four facial rhenium tricarbonyl complexes containing a pyridyl triazine core, (L1 = 5,5′(3-(2-pyridyl)-1,2,4-triazine-5,6-diyl)-bis-2-furansulfonic acid disodium salt and L2 = (3-(2- pyridyl)-5,6-diphenyl-1,2,4-triazine-4′,4′′-disulfonic acid sodium salt) have been synthesized by utililzing two different Re metal precursors, Re(CO)(5)Br and [Re(CO)(3)(H(2)O)(3)]OTf in an organic solvent mixture and water, respectively. The rhenium complexes [Re(CO)(3)(H(2)O)L1](+) (1), Re(CO)(3)L1Br (2), [Re(CO)(3)(H(2)O)L2](+) (3), and Re(CO)(3)L2Br (4), were obtained in 70–85% yield and characterized by (1)H NMR, IR, UV, and luminescence spectroscopy. In both H(2)O and acetonitrile, complexes display a weak absorption band in the visible region which can be assigned to a metal to ligand charge transfer excitation and fluorescent emission lying in the 650–710 nm range. Cytotoxicity assays of complexes 1, 3, and 4 were carried out for rat peritoneal cells. Both plant cells (Allium cepa bulb cells) and rat peritoneal cells were stained using the maximum non-toxic concentration levels of the compounds, 20.00 mg ml(−1) for 1 and 3 and 5.00 mg ml(−1) for 4 to observe under the epifluorescence microscope. In both cell lines, compound concentrated specifically in the nuclei region. Hence, nuclei showed red fluorescence upon excitation at 550 nm. CONCLUSIONS: Four novel rhenium complexes have been synthesized and characterized. Remarkable enhancement of fluorescence upon binding with cells and visible range excitability demonstrates the possibility of using the new complexes in biological applications. [Figure: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-016-0218-4) contains supplementary material, which is available to authorized users. Springer International Publishing 2016-11-25 /pmc/articles/PMC5123207/ /pubmed/27942267 http://dx.doi.org/10.1186/s13065-016-0218-4 Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. |
spellingShingle | Research Article Ranasinghe, Kokila Handunnetti, Shiroma Perera, Inoka C. Perera, Theshini Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title | Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title_full | Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title_fullStr | Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title_full_unstemmed | Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title_short | Synthesis and characterization of novel rhenium(I) complexes towards potential biological imaging applications |
title_sort | synthesis and characterization of novel rhenium(i) complexes towards potential biological imaging applications |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5123207/ https://www.ncbi.nlm.nih.gov/pubmed/27942267 http://dx.doi.org/10.1186/s13065-016-0218-4 |
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