Tracing the Photoaddition of Pharmaceutical Psoralens to DNA

The psoralens 8-methoxypsoralen (8-MOP), 4,5′,8-trimethylpsoralen (TMP) and 5-methoxypsoralen (5-MOP) find clinical application in PUVA (psoralen + UVA) therapy. PUVA treats skin diseases like psoriasis and atopic eczema. Psoralens target the DNA of cells. Upon photo-excitation psoralens bind to the...

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Autores principales: Diekmann, Janina, Theves, Isabell, Thom, Kristoffer A., Gilch, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7696755/
https://www.ncbi.nlm.nih.gov/pubmed/33182821
http://dx.doi.org/10.3390/molecules25225242
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author Diekmann, Janina
Theves, Isabell
Thom, Kristoffer A.
Gilch, Peter
author_facet Diekmann, Janina
Theves, Isabell
Thom, Kristoffer A.
Gilch, Peter
author_sort Diekmann, Janina
collection PubMed
description The psoralens 8-methoxypsoralen (8-MOP), 4,5′,8-trimethylpsoralen (TMP) and 5-methoxypsoralen (5-MOP) find clinical application in PUVA (psoralen + UVA) therapy. PUVA treats skin diseases like psoriasis and atopic eczema. Psoralens target the DNA of cells. Upon photo-excitation psoralens bind to the DNA base thymine. This photo-binding was studied using steady-state UV/Vis and IR spectroscopy as well as nanosecond transient UV/Vis absorption. The experiments show that the photo-addition of 8-MOP and TMP involve the psoralen triplet state and a biradical intermediate. 5-MOP forms a structurally different photo-product. Its formation could not be traced by the present spectroscopic technique.
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spelling pubmed-76967552020-11-29 Tracing the Photoaddition of Pharmaceutical Psoralens to DNA Diekmann, Janina Theves, Isabell Thom, Kristoffer A. Gilch, Peter Molecules Article The psoralens 8-methoxypsoralen (8-MOP), 4,5′,8-trimethylpsoralen (TMP) and 5-methoxypsoralen (5-MOP) find clinical application in PUVA (psoralen + UVA) therapy. PUVA treats skin diseases like psoriasis and atopic eczema. Psoralens target the DNA of cells. Upon photo-excitation psoralens bind to the DNA base thymine. This photo-binding was studied using steady-state UV/Vis and IR spectroscopy as well as nanosecond transient UV/Vis absorption. The experiments show that the photo-addition of 8-MOP and TMP involve the psoralen triplet state and a biradical intermediate. 5-MOP forms a structurally different photo-product. Its formation could not be traced by the present spectroscopic technique. MDPI 2020-11-10 /pmc/articles/PMC7696755/ /pubmed/33182821 http://dx.doi.org/10.3390/molecules25225242 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
Diekmann, Janina
Theves, Isabell
Thom, Kristoffer A.
Gilch, Peter
Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title_full Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title_fullStr Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title_full_unstemmed Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title_short Tracing the Photoaddition of Pharmaceutical Psoralens to DNA
title_sort tracing the photoaddition of pharmaceutical psoralens to dna
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7696755/
https://www.ncbi.nlm.nih.gov/pubmed/33182821
http://dx.doi.org/10.3390/molecules25225242
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