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In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer

Photodynamic therapy (PDT) is a skin cancer treatment alternative to chemotherapy and radiotherapy. This method exploits three elements: a phototoxic compound (photosensitizer), light source and oxygen. Upon irradiation by light of a specific wavelength, the photosensitizer generates reactive oxygen...

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Autores principales: Sztandera, Krzysztof, Marcinkowska, Monika, Gorzkiewicz, Michał, Janaszewska, Anna, Laurent, Regis, Zabłocka, Maria, Mignani, Serge, Majoral, Jean Pierre, Klajnert-Maculewicz, Barbara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7352946/
https://www.ncbi.nlm.nih.gov/pubmed/32585884
http://dx.doi.org/10.3390/ijms21124456
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author Sztandera, Krzysztof
Marcinkowska, Monika
Gorzkiewicz, Michał
Janaszewska, Anna
Laurent, Regis
Zabłocka, Maria
Mignani, Serge
Majoral, Jean Pierre
Klajnert-Maculewicz, Barbara
author_facet Sztandera, Krzysztof
Marcinkowska, Monika
Gorzkiewicz, Michał
Janaszewska, Anna
Laurent, Regis
Zabłocka, Maria
Mignani, Serge
Majoral, Jean Pierre
Klajnert-Maculewicz, Barbara
author_sort Sztandera, Krzysztof
collection PubMed
description Photodynamic therapy (PDT) is a skin cancer treatment alternative to chemotherapy and radiotherapy. This method exploits three elements: a phototoxic compound (photosensitizer), light source and oxygen. Upon irradiation by light of a specific wavelength, the photosensitizer generates reactive oxygen species triggering the cascade of reactions leading to cell death. The positive therapeutic effect of PDT may be limited due to low solubility, low tumor specificity and inefficient cellular uptake of photosensitizers. A promising approach to overcome these obstacles involves the use of nanocarrier systems. The aim of this initial study was to determine the potential of the application of phosphorus dendrimers as carriers of a photosensitizer—rose bengal (RB). The primary goal involved the synthesis and in vitro studies of covalent drug–dendrimer conjugates. Our approach allowed us to obtain RB–dendrimer conjugates with the use of tyramine as an aromatic linker between the carrier and the drug. The compounds were characterized by FT-IR, (1)H NMR, (13)C NMR, (31)P NMR, size and zeta potential measurements and spectrofluorimetric analysis. The dialysis to check the drug release from the conjugate, flow cytometry to specify intracellular uptake, and singlet oxygen generation assay were also applied. Finally, we used MTT assay to determine the biological activity of the tested compounds. The results of our experiments indicate that the conjugation of RB to phosphorus dendrimers via the tyramine linker decreases photodynamic activity of RB.
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spelling pubmed-73529462020-07-15 In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer Sztandera, Krzysztof Marcinkowska, Monika Gorzkiewicz, Michał Janaszewska, Anna Laurent, Regis Zabłocka, Maria Mignani, Serge Majoral, Jean Pierre Klajnert-Maculewicz, Barbara Int J Mol Sci Article Photodynamic therapy (PDT) is a skin cancer treatment alternative to chemotherapy and radiotherapy. This method exploits three elements: a phototoxic compound (photosensitizer), light source and oxygen. Upon irradiation by light of a specific wavelength, the photosensitizer generates reactive oxygen species triggering the cascade of reactions leading to cell death. The positive therapeutic effect of PDT may be limited due to low solubility, low tumor specificity and inefficient cellular uptake of photosensitizers. A promising approach to overcome these obstacles involves the use of nanocarrier systems. The aim of this initial study was to determine the potential of the application of phosphorus dendrimers as carriers of a photosensitizer—rose bengal (RB). The primary goal involved the synthesis and in vitro studies of covalent drug–dendrimer conjugates. Our approach allowed us to obtain RB–dendrimer conjugates with the use of tyramine as an aromatic linker between the carrier and the drug. The compounds were characterized by FT-IR, (1)H NMR, (13)C NMR, (31)P NMR, size and zeta potential measurements and spectrofluorimetric analysis. The dialysis to check the drug release from the conjugate, flow cytometry to specify intracellular uptake, and singlet oxygen generation assay were also applied. Finally, we used MTT assay to determine the biological activity of the tested compounds. The results of our experiments indicate that the conjugation of RB to phosphorus dendrimers via the tyramine linker decreases photodynamic activity of RB. MDPI 2020-06-23 /pmc/articles/PMC7352946/ /pubmed/32585884 http://dx.doi.org/10.3390/ijms21124456 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Sztandera, Krzysztof
Marcinkowska, Monika
Gorzkiewicz, Michał
Janaszewska, Anna
Laurent, Regis
Zabłocka, Maria
Mignani, Serge
Majoral, Jean Pierre
Klajnert-Maculewicz, Barbara
In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title_full In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title_fullStr In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title_full_unstemmed In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title_short In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer
title_sort in search of a phosphorus dendrimer-based carrier of rose bengal: tyramine linker limits fluorescent and phototoxic properties of a photosensitizer
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7352946/
https://www.ncbi.nlm.nih.gov/pubmed/32585884
http://dx.doi.org/10.3390/ijms21124456
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