Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor

Development of an efficient and scalable synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a naturally-occurring aryl hydrocarbon receptor (AhR) ligand, allowed its biological and physical properties to be studied. FICZ was shown to be the most potent among a series of 6-substituted indolo[3,2-b]c...

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Autores principales: Zhang, Cunyu, Creech, Katrina L., Zuercher, William J., Willson, Timothy M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6620467/
https://www.ncbi.nlm.nih.gov/pubmed/31292477
http://dx.doi.org/10.1038/s41598-019-46374-7
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author Zhang, Cunyu
Creech, Katrina L.
Zuercher, William J.
Willson, Timothy M.
author_facet Zhang, Cunyu
Creech, Katrina L.
Zuercher, William J.
Willson, Timothy M.
author_sort Zhang, Cunyu
collection PubMed
description Development of an efficient and scalable synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a naturally-occurring aryl hydrocarbon receptor (AhR) ligand, allowed its biological and physical properties to be studied. FICZ was shown to be the most potent among a series of 6-substituted indolo[3,2-b]carbazoles for activation of AhR in cells. Photostability studies of FICZ revealed a non-enzymatic mechanism for its conversion to a biologically active quinone. These results further support the hypothesis that FICZ is a light-dependent hormone that links sun exposure to regulation of biological pathways in peripheral tissues.
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spelling pubmed-66204672019-07-19 Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor Zhang, Cunyu Creech, Katrina L. Zuercher, William J. Willson, Timothy M. Sci Rep Article Development of an efficient and scalable synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a naturally-occurring aryl hydrocarbon receptor (AhR) ligand, allowed its biological and physical properties to be studied. FICZ was shown to be the most potent among a series of 6-substituted indolo[3,2-b]carbazoles for activation of AhR in cells. Photostability studies of FICZ revealed a non-enzymatic mechanism for its conversion to a biologically active quinone. These results further support the hypothesis that FICZ is a light-dependent hormone that links sun exposure to regulation of biological pathways in peripheral tissues. Nature Publishing Group UK 2019-07-10 /pmc/articles/PMC6620467/ /pubmed/31292477 http://dx.doi.org/10.1038/s41598-019-46374-7 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as 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 images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Zhang, Cunyu
Creech, Katrina L.
Zuercher, William J.
Willson, Timothy M.
Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title_full Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title_fullStr Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title_full_unstemmed Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title_short Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
title_sort gram-scale synthesis of ficz, a photoreactive endogenous ligand of the aryl hydrocarbon receptor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6620467/
https://www.ncbi.nlm.nih.gov/pubmed/31292477
http://dx.doi.org/10.1038/s41598-019-46374-7
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