A red-shifted two-photon-only caging group for three-dimensional photorelease

Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visual...

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Autores principales: Becker, Yvonne, Unger, Erik, Fichte, Manuela A. H., Gacek, Daniel A., Dreuw, Andreas, Wachtveitl, Josef, Walla, Peter J., Heckel, Alexander
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5914290/
https://www.ncbi.nlm.nih.gov/pubmed/29732066
http://dx.doi.org/10.1039/c7sc05182d
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author Becker, Yvonne
Unger, Erik
Fichte, Manuela A. H.
Gacek, Daniel A.
Dreuw, Andreas
Wachtveitl, Josef
Walla, Peter J.
Heckel, Alexander
author_facet Becker, Yvonne
Unger, Erik
Fichte, Manuela A. H.
Gacek, Daniel A.
Dreuw, Andreas
Wachtveitl, Josef
Walla, Peter J.
Heckel, Alexander
author_sort Becker, Yvonne
collection PubMed
description Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized via double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected strands. While being an excellent 2P-cage, DMA-NDBF is surprisingly stable under visible-light one-photon excitation (1PE). This case of excitation-specific photochemistry enhances the scope of orthogonal photoregulation.
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spelling pubmed-59142902018-05-04 A red-shifted two-photon-only caging group for three-dimensional photorelease Becker, Yvonne Unger, Erik Fichte, Manuela A. H. Gacek, Daniel A. Dreuw, Andreas Wachtveitl, Josef Walla, Peter J. Heckel, Alexander Chem Sci Chemistry Based on nitrodibenzofuran (NDBF) a new photocage with higher two-photon action cross section and red-shifted absorption was developed. Due to calculations, a dimethylamino functionality (DMA) was added at ring position 7. The uncaging of nucleobases after two-photon excitation (2PE) could be visualized via double-strand displacement in a hydrogel. With this assay we achieved three-dimensional photorelease of DMA-NDBF-protected DNA orthogonal to NDBF-protected strands. While being an excellent 2P-cage, DMA-NDBF is surprisingly stable under visible-light one-photon excitation (1PE). This case of excitation-specific photochemistry enhances the scope of orthogonal photoregulation. Royal Society of Chemistry 2018-02-09 /pmc/articles/PMC5914290/ /pubmed/29732066 http://dx.doi.org/10.1039/c7sc05182d Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Becker, Yvonne
Unger, Erik
Fichte, Manuela A. H.
Gacek, Daniel A.
Dreuw, Andreas
Wachtveitl, Josef
Walla, Peter J.
Heckel, Alexander
A red-shifted two-photon-only caging group for three-dimensional photorelease
title A red-shifted two-photon-only caging group for three-dimensional photorelease
title_full A red-shifted two-photon-only caging group for three-dimensional photorelease
title_fullStr A red-shifted two-photon-only caging group for three-dimensional photorelease
title_full_unstemmed A red-shifted two-photon-only caging group for three-dimensional photorelease
title_short A red-shifted two-photon-only caging group for three-dimensional photorelease
title_sort red-shifted two-photon-only caging group for three-dimensional photorelease
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5914290/
https://www.ncbi.nlm.nih.gov/pubmed/29732066
http://dx.doi.org/10.1039/c7sc05182d
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