Photochemical degradation of trypan blue

PURPOSE: To investigate the photochemical degradation of trypan blue (TB) and to identify decomposition products. METHODS: Defined solution samples of TB and a mixture with lutein/zeaxanthin were exposed to blue light. Thermal degradation processes were ruled out using controls not subjected to irra...

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Autores principales: Brockmann, Tobias, Blanchard, Véronique, Heretsch, Philipp, Brockmann, Claudia, Bertelmann, Eckart
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5892916/
https://www.ncbi.nlm.nih.gov/pubmed/29634764
http://dx.doi.org/10.1371/journal.pone.0195849
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author Brockmann, Tobias
Blanchard, Véronique
Heretsch, Philipp
Brockmann, Claudia
Bertelmann, Eckart
author_facet Brockmann, Tobias
Blanchard, Véronique
Heretsch, Philipp
Brockmann, Claudia
Bertelmann, Eckart
author_sort Brockmann, Tobias
collection PubMed
description PURPOSE: To investigate the photochemical degradation of trypan blue (TB) and to identify decomposition products. METHODS: Defined solution samples of TB and a mixture with lutein/zeaxanthin were exposed to blue light. Thermal degradation processes were ruled out using controls not subjected to irradiation. All samples were analyzed using optical microscopy, UV/Vis spectroscopy, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry and nuclear magnetic resonance (NMR) spectrometry. Degradation kinetics were determined based on changes in absorbance; intermediates were identified by analyzing mass differences of characteristic fragment ion peaks within the fragmentation patterns, and assignments were verified by NMR. RESULTS: TB demonstrated a photochemical degradation, which can be triggered by lutein/zeaxanthin. Intermediates vary depending on the presence of lutein/zeaxanthin. The self-sensitized photodegradation of TB occurs under generation of dimethyl sulfate and presumed formation of phenol. In contrast, within the presence of lutein/zeaxanthin the decomposition of TB indicates the formation of methoxyamine and sulfonyl arin. Thermal degradation processes were not observed. CONCLUSIONS: TB demonstrated a photodegradation that may be triggered by lutein/zeaxanthin and results in the formation of cytotoxic decomposition products. Our findings contribute to understand degradation mechanisms of TB and may elucidate previous clinical and experimental observations of cellular toxicity after TB application.
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spelling pubmed-58929162018-04-20 Photochemical degradation of trypan blue Brockmann, Tobias Blanchard, Véronique Heretsch, Philipp Brockmann, Claudia Bertelmann, Eckart PLoS One Research Article PURPOSE: To investigate the photochemical degradation of trypan blue (TB) and to identify decomposition products. METHODS: Defined solution samples of TB and a mixture with lutein/zeaxanthin were exposed to blue light. Thermal degradation processes were ruled out using controls not subjected to irradiation. All samples were analyzed using optical microscopy, UV/Vis spectroscopy, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry and nuclear magnetic resonance (NMR) spectrometry. Degradation kinetics were determined based on changes in absorbance; intermediates were identified by analyzing mass differences of characteristic fragment ion peaks within the fragmentation patterns, and assignments were verified by NMR. RESULTS: TB demonstrated a photochemical degradation, which can be triggered by lutein/zeaxanthin. Intermediates vary depending on the presence of lutein/zeaxanthin. The self-sensitized photodegradation of TB occurs under generation of dimethyl sulfate and presumed formation of phenol. In contrast, within the presence of lutein/zeaxanthin the decomposition of TB indicates the formation of methoxyamine and sulfonyl arin. Thermal degradation processes were not observed. CONCLUSIONS: TB demonstrated a photodegradation that may be triggered by lutein/zeaxanthin and results in the formation of cytotoxic decomposition products. Our findings contribute to understand degradation mechanisms of TB and may elucidate previous clinical and experimental observations of cellular toxicity after TB application. Public Library of Science 2018-04-10 /pmc/articles/PMC5892916/ /pubmed/29634764 http://dx.doi.org/10.1371/journal.pone.0195849 Text en © 2018 Brockmann et al http://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Research Article
Brockmann, Tobias
Blanchard, Véronique
Heretsch, Philipp
Brockmann, Claudia
Bertelmann, Eckart
Photochemical degradation of trypan blue
title Photochemical degradation of trypan blue
title_full Photochemical degradation of trypan blue
title_fullStr Photochemical degradation of trypan blue
title_full_unstemmed Photochemical degradation of trypan blue
title_short Photochemical degradation of trypan blue
title_sort photochemical degradation of trypan blue
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5892916/
https://www.ncbi.nlm.nih.gov/pubmed/29634764
http://dx.doi.org/10.1371/journal.pone.0195849
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