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First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays
In this work, the synthesis, characterization and photophysical assays of a new trans-A(2)B-corrole derivative from the naturally occurring quinone are described. β-Lapachone is a naturally occurring quinoidal compound that provides highly fluorescent heterocyclic compounds such as lapimidazoles. Th...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10089255/ https://www.ncbi.nlm.nih.gov/pubmed/37056965 http://dx.doi.org/10.1039/d3ra00823a |
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author | Rodrigues, Bruna M. Diniz, Carlos C. da Rocha, Vinicius N. Köhler, Mateus H. Brandão, Guilherme P. Machado, Luana A. da Silva Júnior, Eufranio N. Iglesias, Bernardo A. |
author_facet | Rodrigues, Bruna M. Diniz, Carlos C. da Rocha, Vinicius N. Köhler, Mateus H. Brandão, Guilherme P. Machado, Luana A. da Silva Júnior, Eufranio N. Iglesias, Bernardo A. |
author_sort | Rodrigues, Bruna M. |
collection | PubMed |
description | In this work, the synthesis, characterization and photophysical assays of a new trans-A(2)B-corrole derivative from the naturally occurring quinone are described. β-Lapachone is a naturally occurring quinoidal compound that provides highly fluorescent heterocyclic compounds such as lapimidazoles. The new trans-A(2)B-corrole compound was obtained from the reaction between 2,3,4,5,6-(pentafluorophenyl)dipyrromethane and the lapimidazole bearing an aldehyde group. The dyad was characterized by high-resolution mass spectrometry (HRMS), NMR spectroscopy ((1)H, COSY 2D, HMBC, (19)F), FT-IR, UV-vis, steady-state and time-resolved fluorescence, electrochemical studies (CV), TD-DFT analysis and photobiological experiments, in which includes aggregation, stability in solution, photostability and partition coefficients assays. Finally, ROS generation assays were performed using 1,3-diphenylisobenzofuran (DPBF) method and the presented compound showed significant photostability and singlet oxygen production. |
format | Online Article Text |
id | pubmed-10089255 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-100892552023-04-12 First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays Rodrigues, Bruna M. Diniz, Carlos C. da Rocha, Vinicius N. Köhler, Mateus H. Brandão, Guilherme P. Machado, Luana A. da Silva Júnior, Eufranio N. Iglesias, Bernardo A. RSC Adv Chemistry In this work, the synthesis, characterization and photophysical assays of a new trans-A(2)B-corrole derivative from the naturally occurring quinone are described. β-Lapachone is a naturally occurring quinoidal compound that provides highly fluorescent heterocyclic compounds such as lapimidazoles. The new trans-A(2)B-corrole compound was obtained from the reaction between 2,3,4,5,6-(pentafluorophenyl)dipyrromethane and the lapimidazole bearing an aldehyde group. The dyad was characterized by high-resolution mass spectrometry (HRMS), NMR spectroscopy ((1)H, COSY 2D, HMBC, (19)F), FT-IR, UV-vis, steady-state and time-resolved fluorescence, electrochemical studies (CV), TD-DFT analysis and photobiological experiments, in which includes aggregation, stability in solution, photostability and partition coefficients assays. Finally, ROS generation assays were performed using 1,3-diphenylisobenzofuran (DPBF) method and the presented compound showed significant photostability and singlet oxygen production. The Royal Society of Chemistry 2023-04-11 /pmc/articles/PMC10089255/ /pubmed/37056965 http://dx.doi.org/10.1039/d3ra00823a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Rodrigues, Bruna M. Diniz, Carlos C. da Rocha, Vinicius N. Köhler, Mateus H. Brandão, Guilherme P. Machado, Luana A. da Silva Júnior, Eufranio N. Iglesias, Bernardo A. First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title | First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title_full | First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title_fullStr | First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title_full_unstemmed | First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title_short | First report of trans-A(2)B-corrole derived from a lapachone derivative: photophysical, TD-DFT and photobiological assays |
title_sort | first report of trans-a(2)b-corrole derived from a lapachone derivative: photophysical, td-dft and photobiological assays |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10089255/ https://www.ncbi.nlm.nih.gov/pubmed/37056965 http://dx.doi.org/10.1039/d3ra00823a |
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