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Switching on Cytotoxicity of Water-Soluble Diiron Organometallics by UV Irradiation
[Image: see text] The diiron compounds [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CSEt)]CF(3)SO(3), [1]CF(3)SO(3), K[Fe(2)Cp(2)(CO)(3)(CNCH(2)CO(2))], K[2], [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CNMe(2))]NO(3), [3]NO(3), [Fe(2)Cp(2)(CO)(2)(PTA){μ-CNMe(Xyl)}]CF(3)SO(3), [4]CF(3)SO(3), and [Fe(2)Cp(2)(CO)(μ-CO){μ–η:(1)η(3)-C(4-...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9951222/ https://www.ncbi.nlm.nih.gov/pubmed/35537207 http://dx.doi.org/10.1021/acs.inorgchem.2c00504 |
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author | Biancalana, Lorenzo Kubeil, Manja Schoch, Silvia Zacchini, Stefano Marchetti, Fabio |
author_facet | Biancalana, Lorenzo Kubeil, Manja Schoch, Silvia Zacchini, Stefano Marchetti, Fabio |
author_sort | Biancalana, Lorenzo |
collection | PubMed |
description | [Image: see text] The diiron compounds [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CSEt)]CF(3)SO(3), [1]CF(3)SO(3), K[Fe(2)Cp(2)(CO)(3)(CNCH(2)CO(2))], K[2], [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CNMe(2))]NO(3), [3]NO(3), [Fe(2)Cp(2)(CO)(2)(PTA){μ-CNMe(Xyl)}]CF(3)SO(3), [4]CF(3)SO(3), and [Fe(2)Cp(2)(CO)(μ-CO){μ–η:(1)η(3)-C(4-C(6)H(4)CO(2)H)CHCNMe(2)}]CF(3)SO(3), [5]CF(3)SO(3), containing a bridging carbyne, isocyanoacetate, or vinyliminium ligand, were investigated for their photoinduced cytotoxicity. Specifically, the novel water-soluble compounds K[2], [3]NO(3), and [4]CF(3)SO(3) were synthesized and characterized by elemental analysis and IR and multinuclear NMR spectroscopy. Stereochemical aspects concerning [4]CF(3)SO(3) were elucidated by (1)H NOESY NMR and single-crystal X-ray diffraction. Cell proliferation studies on human skin cancer (A431) and nontumoral embryonic kidney (HEK293) cells, with and without a 10-min exposure to low-power UV light (350 nm), highlighted the performance of the aminocarbyne [3]NO(3), nicknamed NIRAC (Nitrate-Iron-Aminocarbyne), which is substantially nontoxic in the dark but shows a marked photoinduced cytotoxicity. Spectroscopic (IR, UV–vis, NMR) measurements and the myoglobin assay indicated that the release of one carbon monoxide ligand represents the first step of the photoactivation process of NIRAC, followed by an extensive disassembly of the organometallic scaffold. |
format | Online Article Text |
id | pubmed-9951222 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-99512222023-02-25 Switching on Cytotoxicity of Water-Soluble Diiron Organometallics by UV Irradiation Biancalana, Lorenzo Kubeil, Manja Schoch, Silvia Zacchini, Stefano Marchetti, Fabio Inorg Chem [Image: see text] The diiron compounds [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CSEt)]CF(3)SO(3), [1]CF(3)SO(3), K[Fe(2)Cp(2)(CO)(3)(CNCH(2)CO(2))], K[2], [Fe(2)Cp(2)(CO)(2)(μ-CO)(μ-CNMe(2))]NO(3), [3]NO(3), [Fe(2)Cp(2)(CO)(2)(PTA){μ-CNMe(Xyl)}]CF(3)SO(3), [4]CF(3)SO(3), and [Fe(2)Cp(2)(CO)(μ-CO){μ–η:(1)η(3)-C(4-C(6)H(4)CO(2)H)CHCNMe(2)}]CF(3)SO(3), [5]CF(3)SO(3), containing a bridging carbyne, isocyanoacetate, or vinyliminium ligand, were investigated for their photoinduced cytotoxicity. Specifically, the novel water-soluble compounds K[2], [3]NO(3), and [4]CF(3)SO(3) were synthesized and characterized by elemental analysis and IR and multinuclear NMR spectroscopy. Stereochemical aspects concerning [4]CF(3)SO(3) were elucidated by (1)H NOESY NMR and single-crystal X-ray diffraction. Cell proliferation studies on human skin cancer (A431) and nontumoral embryonic kidney (HEK293) cells, with and without a 10-min exposure to low-power UV light (350 nm), highlighted the performance of the aminocarbyne [3]NO(3), nicknamed NIRAC (Nitrate-Iron-Aminocarbyne), which is substantially nontoxic in the dark but shows a marked photoinduced cytotoxicity. Spectroscopic (IR, UV–vis, NMR) measurements and the myoglobin assay indicated that the release of one carbon monoxide ligand represents the first step of the photoactivation process of NIRAC, followed by an extensive disassembly of the organometallic scaffold. American Chemical Society 2022-05-10 /pmc/articles/PMC9951222/ /pubmed/35537207 http://dx.doi.org/10.1021/acs.inorgchem.2c00504 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Biancalana, Lorenzo Kubeil, Manja Schoch, Silvia Zacchini, Stefano Marchetti, Fabio Switching on Cytotoxicity of Water-Soluble Diiron Organometallics by UV Irradiation |
title | Switching on Cytotoxicity of Water-Soluble Diiron
Organometallics by UV Irradiation |
title_full | Switching on Cytotoxicity of Water-Soluble Diiron
Organometallics by UV Irradiation |
title_fullStr | Switching on Cytotoxicity of Water-Soluble Diiron
Organometallics by UV Irradiation |
title_full_unstemmed | Switching on Cytotoxicity of Water-Soluble Diiron
Organometallics by UV Irradiation |
title_short | Switching on Cytotoxicity of Water-Soluble Diiron
Organometallics by UV Irradiation |
title_sort | switching on cytotoxicity of water-soluble diiron
organometallics by uv irradiation |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9951222/ https://www.ncbi.nlm.nih.gov/pubmed/35537207 http://dx.doi.org/10.1021/acs.inorgchem.2c00504 |
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