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Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivativ...

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Autores principales: Lewkowski, Jarosław, Rodriguez Moya, Maria, Wrona-Piotrowicz, Anna, Zakrzewski, Janusz, Kontek, Renata, Gajek, Gabriela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979872/
https://www.ncbi.nlm.nih.gov/pubmed/27559373
http://dx.doi.org/10.3762/bjoc.12.117
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author Lewkowski, Jarosław
Rodriguez Moya, Maria
Wrona-Piotrowicz, Anna
Zakrzewski, Janusz
Kontek, Renata
Gajek, Gabriela
author_facet Lewkowski, Jarosław
Rodriguez Moya, Maria
Wrona-Piotrowicz, Anna
Zakrzewski, Janusz
Kontek, Renata
Gajek, Gabriela
author_sort Lewkowski, Jarosław
collection PubMed
description A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (Φ(F) = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC(50) = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC(50) = 230.8 µM).
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spelling pubmed-49798722016-08-24 Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates Lewkowski, Jarosław Rodriguez Moya, Maria Wrona-Piotrowicz, Anna Zakrzewski, Janusz Kontek, Renata Gajek, Gabriela Beilstein J Org Chem Full Research Paper A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20–97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (Φ(F) = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC(50) = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC(50) = 230.8 µM). Beilstein-Institut 2016-06-16 /pmc/articles/PMC4979872/ /pubmed/27559373 http://dx.doi.org/10.3762/bjoc.12.117 Text en Copyright © 2016, Lewkowski et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Lewkowski, Jarosław
Rodriguez Moya, Maria
Wrona-Piotrowicz, Anna
Zakrzewski, Janusz
Kontek, Renata
Gajek, Gabriela
Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title_full Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title_fullStr Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title_full_unstemmed Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title_short Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
title_sort synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979872/
https://www.ncbi.nlm.nih.gov/pubmed/27559373
http://dx.doi.org/10.3762/bjoc.12.117
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