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A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers
Lipid messengers exert their function on short time scales at distinct subcellular locations, yet most experimental approaches for perturbing their levels trigger cell‐wide concentration changes. Herein, we report on a coumarin‐based photocaging group that can be modified with organelle‐targeting mo...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6175159/ https://www.ncbi.nlm.nih.gov/pubmed/30048020 http://dx.doi.org/10.1002/anie.201807497 |
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author | Wagner, Nicolai Stephan, Milena Höglinger, Doris Nadler, André |
author_facet | Wagner, Nicolai Stephan, Milena Höglinger, Doris Nadler, André |
author_sort | Wagner, Nicolai |
collection | PubMed |
description | Lipid messengers exert their function on short time scales at distinct subcellular locations, yet most experimental approaches for perturbing their levels trigger cell‐wide concentration changes. Herein, we report on a coumarin‐based photocaging group that can be modified with organelle‐targeting moieties by click chemistry and thus enables photorelease of lipid messengers in distinct organelles. We show that caged arachidonic acid and sphingosine derivatives can be selectively delivered to mitochondria, the ER, lysosomes, and the plasma membrane. By comparing the cellular calcium transients induced by localized uncaging of arachidonic acid and sphingosine, we show that the precise intracellular localization of the released second messenger is crucial for the signaling outcome. Ultimately, we anticipate that this new class of caged compounds will greatly facilitate the study of cellular processes on the organelle level. |
format | Online Article Text |
id | pubmed-6175159 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-61751592018-10-15 A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers Wagner, Nicolai Stephan, Milena Höglinger, Doris Nadler, André Angew Chem Int Ed Engl Communications Lipid messengers exert their function on short time scales at distinct subcellular locations, yet most experimental approaches for perturbing their levels trigger cell‐wide concentration changes. Herein, we report on a coumarin‐based photocaging group that can be modified with organelle‐targeting moieties by click chemistry and thus enables photorelease of lipid messengers in distinct organelles. We show that caged arachidonic acid and sphingosine derivatives can be selectively delivered to mitochondria, the ER, lysosomes, and the plasma membrane. By comparing the cellular calcium transients induced by localized uncaging of arachidonic acid and sphingosine, we show that the precise intracellular localization of the released second messenger is crucial for the signaling outcome. Ultimately, we anticipate that this new class of caged compounds will greatly facilitate the study of cellular processes on the organelle level. John Wiley and Sons Inc. 2018-09-03 2018-10-01 /pmc/articles/PMC6175159/ /pubmed/30048020 http://dx.doi.org/10.1002/anie.201807497 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Wagner, Nicolai Stephan, Milena Höglinger, Doris Nadler, André A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title | A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title_full | A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title_fullStr | A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title_full_unstemmed | A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title_short | A Click Cage: Organelle‐Specific Uncaging of Lipid Messengers |
title_sort | click cage: organelle‐specific uncaging of lipid messengers |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6175159/ https://www.ncbi.nlm.nih.gov/pubmed/30048020 http://dx.doi.org/10.1002/anie.201807497 |
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